new england road trip 1 week

New England Summer Road Trip (One Week Itinerary)

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My mother grew up in a small lake town in Western Connecticut. I suppose that’s how it all started, the annual family New England road trip. 

I was born and raised in NJ, but really, m y brothers and I grew up New England. Our summer and holiday weekends were often spent on that grueling strip of I-95 that stretches between New Jersey and the northern part of the country.

Between my grandparent’s house in Connecticut, a beach house in a small fishing village on the coast of Rhode Island, and my father’s annual meeting in Bar Harbor, Maine, I got to know New England intimately. It has some of my happiest childhood (and later, adulthood) memories.

Long after my family had drifted apart and those road trips stopped I continued to explore, taking my own family (AKA Joe and Della pup) along this very route.

New England is downright gorgeous.

It’s allll the cliches. Small cities filled with charming cobblestone streets, tiny, snow covered homes, and old-school Main Streets. 

It’s also small geographically. Like, you can drive from the tip of Connecticut to the tip of Maine in half a day, small. 

Though we won’t be doing that here. Here, we’re showing you how to take your time and absorb some of the most scenic spots — filled with the best food, obviously — in a week’s time.

In this one week New England road trip itinerary we’re sticking to the New England coast, perfect for cruising in the Summer or Fall months.

P.S. Going for longer than a week? Check the end of the post for suggestions on how to extend your road trip through other New England hot spots.

Table of Contents

Steps to Plan the Best Road Trip in New England

1. Plot your route

Where are you leaving from? What are your “can’t misses?” Where do you want to stay? Our itinerary below is a guide…you can follow it exactly (because it’s freaking awesome) or you can pick and choose which works best for you to form your own path.

2. Check your route against the weather. 

This is so often overlooked! Plan your route as loosely as possible. This way, you can quickly pivot if the weather is threatening to ruin your plans. It allows you more flexibility, so when there is rain forecast on the day you want to go to Acadia National Park, you can easily switch it to another.

Obviously take this with a grain of salt…weather is weather, and in New England, weather is usually unpredictable, so bring a sense of humor. As they say up around here:

“There’s no such thing as bad weather, just bad clothing” or, my personal favorite, “If you don’t like the weather, wait 15 minutes” 

3. Follow your heart

This applies to every travel experience. If you plan an activity and it sucks, BAIL. If you find a local seafood restaurant on the side of the road where a grandma-looking lady is frying fish …slam on those breaks immediately. 

When should you go on a new england road trip?

I’m going to say that SUPER annoying thing we all hate and say…it depends! Road trips in New England can vary depending on the weather. Let’s break it down by season:

How does this itinerary work?

This itinerary leaves from the New York City metro area, but you can hop on or off at any point along the way. 

If you’re in upstate New York simply head west until you reach I-95 (or check out these New York day trips instead.

Leaving from further South? Trying extending the road trip through Philadelphia– stopping for a pizza break –or go for a scenic run on the New Jersey shore .

One Week New England Road Trip Itinerary

Day 1 Connecticut

Start your New England road trip off by cruising north from New York City and into Connecticut, possibly the most underrated of the New England states. The southern part of the state is mostly made up of wealthy New York City suburbs, so we’ll skip right over that. 

The first stop will be a welcome break from the traffic you’ll likely be sitting in on I-95. New Haven is known for two things:

1. Yale and–more importantly in our book– 2. P izza

We’re the type of people who took a train to Naples just to eat pizza for 6 hours straight, so you know we couldn’t miss the opportunity to explore what folks claim to be the best Napoli style pizza this side of the Atlantic.

The best pizza in New Haven is debated with a ferocity that you probably don’t need to involve yourself in as a brief visitor.

Instead, just trust us and head to Modern Apizza for the best pie in the city. 

Or, if you want to do the tourist thing, check out the clam pies at Frank Pepe Pizzeria Napoletana. It wasn’t our favorite, but its been around for almost 100 years (which earns lots of respect in its own right).

Expect to wait in line for hours if you choose this spot.

If you’re one of THOSE people who don’t like pizza, there’s a great selection of taco trucks in a parking lot next to I-95. This is the spot to sample actual Mexican food, like beef tongue and tripe. 

And if you don’t like pizza or tacos…you’re honestly on the wrong blog.

Once you’re done consuming your body weight in pizza and/or tacos, hop back in the car and drive an hour north to Mystic, Connecticut. 

This little seaside town is a straight charmer. Fun fact: it’s also where the ultra-80’s classic Mystic Pizza was filmed, much to my mother’s delight. It’s worth spending a night here to tuck into one of the many B & B’s and snuggle up next to your boo.

Mystic Aquarium is great for all you fellow marine nerds (good for the kiddos and rainy days, too). When you wake up in the morning, head to Kitchen Little at Mystic River Marina, order the Lobster Benedict, and then call me immediately to thank me for starting your day off with such a marvelous treat on your tongue.

Where to Eat in New England

• Pizza at Modern Apizza , 874 State St, (203) 776-5306 http://modernapizza.com/
• Tacos at T aco trucks , 351 Long Wharf Dr in Long Wharf Park, varied
• Lobsters Benedict at Kitchen Little , 36 Quarry Rd, (860) 536-2122 https://kitchenlittle.org/

Where to Stay in Mystic, Connecticut

We’ve actually never stayed in Mystic ourselves so can’t personally recommend anything, but taking a dip in the gorgeous looking pool at House of 1833 Bed and Breakfast feels like something we’d be very into.

Days 2-3 Narragansett, Rhode Island

The smallest state in the union is also one of our favorites. Rhode Island is not, in fact, an island as I’m sure you’re all aware. However, thanks to its 400 miles of coastline, it still lives up to its “Ocean State” nickname. 

Rhode Island beaches are the main thing that draws us here every summer, though you could easily spend time praising the marshy and wooded trail walks as well.

Up north near Newport, beaches are steep rocky cliffs lined with old mansions. Down in the southern edge of the state–our fave–beaches are soft, sandy strips backed by grassy dunes.

Specifically, it’s the beaches in Rhode Island’s South County that have captured our hearts. They’re the reason we go back year after year, aside from the fact that we have family there.

Plus, this area is filled with some of our favorite seafood restaurants of all time.

These are some of our favorite South County beaches:

• Galilee Beach – little bit more of a local scene on a GORGEOUS beach
• Narragansett town beach – go surfing (or hang and watch!)
• Point Judith Lighthouse – rocky cliff facing out to the sea, can catch sunset views here depending on the time of year

Narragansett is a great little town to use as your home base here. It’s the home of URI and has a smattering of chill beach bars and delicious food.

Between beach trips, h ead into town for a fresh juice or smoothie at the hole-in-the-wall Crazy Burger , or do a fancy pants date night over at Coast Guard House , where you can sip on chowder while watching the Atlantic Ocean crash into the rocks outside the oversized glass windows.

If you really want to enjoy the scenery and the locavore seafood here, though, hop in the car and ride over to Matunuck Oyster Bar . 

Perched on the marsh where the oysters are grown, owner and aquaculturist Perry Rasso has grown this restaurant into a gorgeous indoor-outdoor space, serving up oysters as soon as they’re pulled from the water.

Our trips to Matunuck Oyster Bar usually consist of us waiting two hours for a table outside, cracking open a bottle of champagne, and watching the tide roll in and out while we slurp down dozens of our favorite salty little bivalves.

Honestly, I could (and usually do) spend a week here in Rhode Island and go nowhere else. It is the ultimate combination of rest, sweet salt air, and ultra-fresh seafood that my body craves after a long winter.

But you’re on a mission to explore New England on this road trip, so stop off for a night or two and then head North.

Where to Eat in Narragansett, Rhode Island

• Oysters at Matunuck Oyster Bar , 629 Succotash Rd, Wakefield, RI (401) 783-4202 https://www.rhodyoysters.com/
• Chowder and clam cakes at Iggy’s Doughboys , 1151 Point Judith Rd, Narragansett, RI (401) 783-5608 https://www.iggysri.com/chowda
• Coast Guard House , 40 Ocean Rd, Narragansett, RI (401) 789-0700 https://thecoastguardhouse.com/
• Crazy Burger , 144 Boon St, Narragansett, RI (401) 783-1810 http://www.crazyburger.com/

Where to Stay in Narragansett, Rhode Island

We’ve stayed at the Aqua Blue Hotel before which was ok (the location is AMAZING literally steps from the beach and Coast Guard House for dinner, although you pay for that) but we’ve heard GREAT things about The Break Hotel .

Days 3-4 Massachusetts

Hop back on I-95 and head north until you hit Boston, your next stop on this New England road trip.

Boston is a little city that feels like a little city, but with a bunch of strangely aggressive folks who drink a lot. I don’t mean that as an insult…Boston is a lot of fun. And being from New Jersey where people also tend to be angry at random times, these are my kind of people.

In all seriousness, Boston epitomizes so much of what is great about New England in an urban setting. The cobblestone streets are crammed with history and lined with tiny row houses that look straight out of a Charles Dickens novel. 

Fenway Park , the oldest operating baseball stadium in the country, sits in a charming downtown neighborhood with great food.

Boston’s Little Italy in the North End still has pasta cooking grannies rolling out dough by hand, and there are a delightful craft beer and food options everywhere you look.

The harbor is kept shockingly clean (coming from New York) and love it or hate it, Cambridge and Harvard are downright stunning.

Spend a full day exploring the historical sites, catching a Red Sox game, or touring the eclectic Harpoon brewery on the harbor. 

I’m also a sucker for the original Legal Sea Foods, though it’s recently moved and I’m not sure it’s worth it without the nostalgia factor.

Before you continue on your New England road trip, make time for a quick pit stop in Ipswich, MA.

It’s an adorable little town jutting out into the Atlantic Ocean that also happens to have some of the best fried clams EVER! Argue it…I dare you.

Then, continue North… 

Where to Eat in Massachusetts:

• Clam Box , 246 High St, Ipswich, MA (978) 356-9707 http://www.clamboxipswich.com/
• Legal Sea Foods , 55 Boylston St., Chestnut Hill, (617) 277-7300 https://www.legalseafoods.com/
• Giacomo’s , 355 Hanover St (617) 523-9026

Where to Stay in Boston, Massachusetts:

There’s literally an option for anyone when it comes to hotels in Boston. Click here to see a full hotel list with 100’s of options in every budget and style.

Day 4-6 Maine

Maine, you crafty, beautiful genius! How did you get to be so wild and stunning?

The lobsters…the pine trees…the rocky majestic coast…Maine is the epitome of when you just can’t even.

Here’s how you spend 2 days in Maine.

First off, go to Acadia National Park . Just go right there. Because as beautiful and amazing as much of the rest of the state is…Acadia is the masterpiece of it all.

Plus, with only a couple of days to explore, it’s the easiest way to see the best of what Maine has to offer.

Camp inside the park (Blackwoods Campground is the best if you can get in) or head downtown to Bar Harbor for a home base. Hotels here aren’t cheap, though, so plan ahead for this.

Take whale watching trips off the coast, hike the winding ocean-view hugging trials, scramble up rock faces, or just eat lobster rolls every hour on the hour.

One time, Joe ate lobster for every single meal for a week straight in Bar Harbor…it wasn’t cheap or particularly healthy, but it was impressive. And, he was happy. 

You can see the first sunrise hitting the continental US from Cadillac mountain (note: this gets really crowded) and head down for early morning blueberry pancakes at Jordan’s Restaurant.

Or, head out to pick wild blueberries yourself. They’re much smaller than the traditional grocery store ones, all the easier to pop them in your mouth like candy.  In season, you can find them hugging the trails, or you can stop by a local farm.

Where to Eat in Maine:

• Fresh boiled lobsters at Thurston’s Lobster Pound , 9 Thurston Rd, Bernard, ME (207) 244-7600 https://www.thurstonforlobster.com/
• Lobster rolls at Thirsty Whale , 40 Cottage St, Bar Harbor, ME (207) 288-9335 https://www.thirstywhaletavern.com/
• Blueberry pancakes at Jordan’s Restaurant , 80 Cottage St, Bar Harbor, ME (207) 288-3586 http://www.jordansbarharbor.com

Where to Stay in Bar Harbor, Maine:

Bar Harbor Inn is where I stayed every time growing up. Even after decades in use, it’s managed to stay modern and refined. I love the charming rooms, elegant feel, and actually good breakfasts here. Oh, and it just so happens to be on the ocean (think listening to the waves crashing on the rocks beneath you…DREAMY). Granted…my parents were floating the bill then, it’s not cheap, but SO worth it if you can swing it.

Click here to book The Bar Harbor Inn if you want to ball out on some luxury.

Or try Camping at Acadia National Park .

Day 7 On the road back home.. .

Head home, OR just never leave, We won’t judge.

Not sure where to stay? Use the search box below to find the best hotels in Connecticut, Rhode Island, and everywhere else in gorgeous New England.

Options to extend your New England road trip:

Add a night, day, or as long as you’d like on through some of these great additions:

• Portsmouth, NH – this trendy little harbor town gets its fair share of local tourists but isn’t often on the radar for outsiders. Be in the know and visit.
• Portland, Maine – one of our all-time favorite cities, Portland feels more like a small town, albeit one on the rugged Maine coast that happens to have exceptional dining.
• Burlington, Vermont – a hippy college town at it’s finest, lake-front Burlington is a bit out there but well worth the segway.
• Cape Cod, MA – come for pictures of the wood-shingled beachfront mansions, stay for the local pubs serving up piping hot seafood chowder and freshly fried, fish.
• Block Island , RI – this reminds us a lot of Ireland, it shares the romantic feelings and rolling, green hills. We like to take the ferry over and rent a bike, which will easily take you around the entire island.
• Kennebunk, Maine – Which we hit up on a different new England road trip (also where that lobster roll pic was born!!)

Road Trip Destinations in New England

It’s worth time to come up to New England just to stop at any one of these spots.

• Acadia National Park – For the unreal, oceanfront hiking.
• South County Beaches – For pristine, sandy beaches.
• New Haven – For the pizza and tacos.
• Boston seaport – For the charming, small city feel.

What is there to do in New England in Summer?

Soooo many things! 

• Bake your skin on the sandy beaches
• Hiking! Best in the Northern parts in my opinion (Vermont, New Hampshire, and Maine) but there are still great forested trails in Connecticut and marshland walks in Rhode Island
• Kayaking, canoeing, and stand up paddleboarding on lakes, rivers, marshes, and the Atlantic Ocean…oh my!
• Eating all of the fresh, local seafood like a maniac

New England Road Trip Map

We are the dynamic running duo that run this site. Lovers of new places, bridges, and all the food.

Returning to NYC / New England for first time in 20 years for family road trip. . Grew up on Pepe’s and Modern Pizza, and many other things you mentioned about Connecticut were spot on, love the recommendations throughout your articles. Will be using a lot of this information to help plan out our New England Summer vacation. Thank you for taking the time to share.

Thanks Frank! So glad you found it helpful

Should we travel on over to Plymouth since we’d be so close?

Hey Charlene, that’s a great idea! We’ve actually never visited Plymouth but from what I’ve heard about it I’m sure it would make a great addition

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Are you planning the ultimate New England road trip? Let me help! After exploring New England for more than 20 years, I have put together this comprehensive guide to exploring this charming region. The best way to see New England is by car, and this 2-3 week itinerary offers a grand tour of New England, covering the best places to visit , especially for first-time visitors.

Spanning Connecticut, Massachusetts, Maine, Vermont, New Hampshire, and Rhode Island, this itinerary shows you the best of New England, from quaint coastal towns to lush mountain landscapes. The itinerary is also well-paced to allow you to spend time seeing the sites, enjoy local activities, and cross items off your New England bucket list . And, the itinerary is flexible and can be adapted to your needs, interests, and desired trip length.

Whether you’re in for the full journey or seeking shorter road trip variations (I’ve included those, too!), this guide caters to your wanderlust, ensuring a memorable and personalized exploration of New England’s beauty. Let’s go!

PS: Pop this New England playlist on—it’s perfect for a road trip!

Table of Contents

New England Road Trip FAQ

When’s the best time of year to road trip new england.

New England is gorgeous in all seasons, but for the easiest driving (and best New England road tripping experiences), summer and fall are ideal.

If you want the fall foliage experience, late September and early October are the key weeks to plan for. Of course, these times of years are also peak tourist season, so expect more traffic and higher hotel prices.

(PS: If you want to do a shorter road trip or a route that’s perfect for fall, check out my 7 day New England Fall Road Trip itinerary!

One of my favorite times of the year in New England is mid to late May. The weather is beautiful, and the region’s roads and attractions are generally less busy. The budding greenery is especially gorgeous and fresh, too.

Early September can also be lovely, just after kids have returned to school and summer has ended. Expect crisp temperatures and leaves just beginning to change colors.

A winter road trip may be doable, but remember, New England can be quite snowy, so you’ll want to have a reliable vehicle outfitted with snow tires, and you’ll need to stay aware of changing weather conditions and road closures.

How many days do you need for a road trip to New England?

You need 2-3 weeks for a comprehensive road trip around New England. This is the ideal amount of time needed to cover the major highlights of all six New England states.

If you don’t have that much time, you can still pack a lot into a shorter trip. A minimum of 7 to 10 days is ideal for a thorough yet relaxed New England road trip. For a 7-10 day trip, consider my Southern or Northern New England itineraries, or do shorter segments of the full 2-3 week itinerary.

Where should I start my road trip through New England?

I’ve started this New England travel itinerary in Boston, as it’s the biggest city in New England and home to a major airport, Boston Logan International. This airport is easy to fly into and rent a vehicle. Boston is also a great destination on its own, so my itinerary includes a couple days exploring the city.

Ps: Ready to rent a car for your New England drive? Click here to find the best rates on rental cars !

The Perfect New England Road Trip Itinerary

Days 1 & 2: boston, massachusetts.

You’ll start your New England excursion from Boston, Massachusetts: an absolutely fantastic city.

Boston is a well-known place that’s filled to the brim with history. From famous historical events like the Boston Tea Party to its reputation as a modern-day sports town, you’ll never be bored here.

Some great things to do in Boston :

• Visit the North End and dine on amazing Italian food . Don’t miss grabbing cannoli from Mike’s Pastry and Modern Pastry.
• Stroll around quaint Beacon Hill
• Tempt your taste buds with a Boston Food Tour
• Go shopping on classy Newbury Street
• Follow the Freedom Trail to learn Boston’s revolutionary history
• Join an expert-led walking tour for a more in-depth experience of the city
• Check out one of the many great Boston museums, including the Museum of Science which I especially love
• Join a Boston Duck Tour and ride in one of the famous amphibious vehicles

Hotel Suggestion in Boston: Fairmont Copley Plaza

Need more guidance for Boston? Check out my post on The Top Things to Do in Boston for first timers , and I’ve also got some recommendations on where to grab coffee, breakfast , a beer, or a bite to eat in Boston , too !

PS: Looking for a shorter road trip from Boston? Check out my New England trip itinerary focusing on the journey from Boston to Acadia National Park .

Days 3 & 4: Newport, Rhode Island

On Day 3, drive from Boston to Newport. This is a straightforward route, with about 2 hours of drive time. Glitz and glamour. That’s what you’ll find in Newport, Rhode Island. This town is perhaps best known for its iconic Gilded Age mansions . These opulent buildings were once the summer cottages of America’s rich and famous families.

Today, many of them have been converted into museums that you can wander through and admire some of New England’s opulence past.

Some of my favorite things to do in Newport:

• Visit a mansion or two. I recommend The Breakers if you only have time for one of Newport’s mansions
• Hop on this fun Gilded Age Mansions Tour, which takes you around via trolley
• Stroll along the scenic Cliff Walk
• Dine at the White Horse Tavern, America’s oldest operating restaurant

Hotel Suggestion in Newport: Hotel Viking

For further Newport ideas : Click here to read more about the top things to do in Newport, including beaches, restaurants, hotels , and vacation rentals too!

READ NEXT   15 Festive Things to Do for Christmas in Newport RI

Day 5: Mystic, Connecticut

Mystic, Connecticut is a wonderful little seaside town that feels like a must-do on a New England adventure. It is one of my favorite places in New England, and there is plenty to do here: history, culture, art, sailing. And, for seafood lovers, Mystic’s coastal location offers a variety of delicious seafood dining options

Like pretty much every other scenic New England town, there’s a cute little downtown area with great shopping, dining, and activities.

A few terrific things to do in Mystic:

• Explore Mystic Seaport , a historic shipyard and museum destination you could spend hours touring
• Watch the Mystic drawbridge (the Mystic River Bascule Bridge) go up, especially while enjoying some Mystic Drawbridge Ice Cream !
• See the adorable beluga whales at Mystic Aquarium
• Browse the epic shops in Olde Mystick Village including my personal favorite: Alice’s Haunted Little Bookshop

Hotel recommendation for Mystic: The Whaler’s Inn

Further reading on Mystic: Check out my tips for all the fun things to do , best restaurants to eat at , and the best places to stay in Mystic!

READ NEXT   25 Best Beach Towns in New England for Coastal Fun

Day 6: Litchfield Hills, Connecticut

As you roadtrip New England, your next destination is the enchanting Litchfield Hills . This is another easy drive day, as the distance from Mystic to the Litchfield region is a short 2 hours. And if you’re traveling in the fall, the Connecticut fall foliage along this route creates a magical backdrop. To me, this area in the northwest corner of the state is a hidden gem .

Here you’ll find all the classic New England pastimes you know and love. In particular, there is an abundance of outdoor activities (hiking, paddling, fishing) as well as exceptional antique shops.

The Litchfield Hills make up a large portion of this region, and include towns such as Torrington, Woodbury, Kent, Cornwall, and Washington (very English sounding names, aren’t they?)

A few excellent things to do in the Litchfield Hills:

• Live out your Gilmore Girls Dreams. This region is well known for being the inspiration for the iconic tv show that perfectly encapsulates New England small town charm .
• Grab ice cream from Arethusa Farm
• Go covered bridge chasing – Bulls Bridge in Kent has a worthwhile nearby hiking trail
• Hike to Campbell Falls, a beautiful waterfall (this trail technically takes you over the border into Massachusetts, too, so it’s a 2-for-1!)

Recommended hotel in the Litchfield Hills: The Mayflower Inn & Spa : legend has it that it was the inspiration for Lorelei Gilmore’s inn, the Dragonfly.

READ NEXT   18 Wonderful Weekend Getaways from Boston

Day 7: Lenox, Massachusetts

Continue on your New England road trip into the Berkshires of Massachusetts . Here you will encounter art, nature, and culture combined. This region has been very popular among vacationers for many years.  And the town of Lenox is the center of it all.

Best things to do in Lenox:

• Enjoy a concert at the famous Tanglewood (these are a staple in summer, and you can hear everything from leading symphonies to folk singers like James Taylor
• Take in a performance at Shakespeare & Company. This theatre produces excellent shows; I’ve been twice!
• Take a hike on one of the area’s many scenic trails
• Step back in time at the Ventfort Hall Mansion and Gilded Age Museum, a 1890s home that’s open for tours.
• If you are interested in literature, you may also wish to stop by the Mount, Edith Wharton’s turn-of-the-century estate.

Where to stay in Lenox:

More resources for your trip to Lenox and the Berkshires: 🍁 Best Restaurants in Lenox 🍁 10 Charming Cabins in the Berkshires 🍁 Best Hikes in the Berkshires

Day 8: Manchester, Vermont

Finally, you’ve made it into the spectacular state of Vermont (my personal favorite, if you couldn’t tell). It’s a fairly easy drive from the Berkshires in Massachusetts up to Manchester in the southwestern corner of Vermont, only a couple of hours. And this is another route that is especially glorious if you opt to do a New England fall road trip .

Manchester is one of the most beautiful places in Vermont, marrying quaint village charm with touches of modern luxury. It’s no surprise that it’s very popular among travelers.

Some of my favorite things to do in Manchester:

• Tour Hildene , the beautiful Lincoln family home (Yes, some of Abraham Lincoln’s children lived here!)
• Drive to the top of Mt. Equinox on Skyline Drive (or consider hiking the trail up to the summit)
• In the fall, pick pumpkins from the patch at Equinox Valley Nursery (and don’t miss the cider donuts!)
• Shop til you drop at Manchester’s many outlet stores
• Dine at the stately Ye Olde Tavern
• Pop into Northshire Bookstore , one of the leading independent bookstores in New England

Hotel Recommendation for Manchester: Kimpton Taconic Hotel

More resources on Manchester: Read my entire Manchester VT travel guide for more of the top Manchester activities, as well as these articles on the best restaurants , breakfast spots , and hotels in Manchester .

READ NEXT   25 Best Hikes in New England: New England Hiking Options for Everyone

PS: If you’re very interested in exploring Vermont, a trip through Manchester, Burlington, and Stowe make the ideal Vermont road trip itinerary .

Day 9: Burlington, Vermont

Just around 2 hours north of Manchester (taking the beautiful and scenic Route 7) you’ll find yourself in Burlington: Vermont’s biggest city. It’s also often mislabeled as Vermont’s capital, but that honor goes to Montpelier. Still, you’re likely to run into Bernie Sanders in either town!

Burlington is where my husband and I lived for several years. It’s a fantastic town that is hip, artsy, and full of good, local food . Seriously, in Vermont, you need to eat. There’s so much delicious cheese, coffee, beer, maple syrup, and much, much more.

To get you started on your culinary adventures, check out this post on my favorite Burlington breweries and bars , and this one on my beloved coffee shops. Oh, and don’t forget to enjoy brunch in BTV . We do breakfast here right.

The gem of Burlington is Lake Champlain, the sprawling, sparkling lake that the city overlooks. Here is the chance to go sailing, stand-up paddleboarding, or take a ferry across to New York state.

If you’d prefer to stay on dry land, visit one of the many beautiful parks and natural areas. Burlington is amazing for outdoor activities. If you want to get moving, the Burlington Bike Path stretches for miles, hugging the lake’s edge. This is ideal for running or cycling. You can even rent bikes right on the bike path.

More epic things to do in Burlington VT:

• Sail on Lake Champlain on the Spirit of Ethan Allen cruise
• Walk down Church Street for shopping, eats, people-watching, and more
• Hike Mt. Philo, a nearby easy hike with the payoff of a fantastic view

Hotel recommendation in Burlington: Hotel Vermont

Even more resources for your Burlington trip:  🍁 21 Hikes Near Burlington VT to Add to Your Bucket List  🍁 10 Can’t-Miss Free Things to do in Burlington VT  🍁 9 Incredible Day Trips from Burlington VT 🍁 Where to Stay in Burlington VT in 2023: Best Burlington Hotels

PS: Considering visiting Burlington in 2024? It’s one of the cities that the total solar eclipse will pass fully over on April 8, 2024, so start planning ASAP!

Days 10 & 11: Stowe, Vermont

From Burlington, head south on I89 to Exit 10. From there, you’ll take the scenic Route 100 past Waterbury and out to Stowe. When people think of the classic Vermont places, they’re likely thinking of Stowe.

It’s absolutely gorgeous: a charming town surrounded by mountains. The short Main Street and its side streets boast a white-steepled church, an old-timey general store, and a ski museum.

Simply put, Stowe is adorable. I have been to Stowe countless times and I highly recommend it as one of the premier New England road trip destinations!

Wonderful things to do in Stowe:

• Traverse the trails and property at the Trapp Family Lodge , and grab a beer afterwards at their European-style brewery and Bierhall
• Shop the adorable shops on Main Street
• Visit a haunted covered bridge if you dare (Emily’s Bridge)
• Spend a day skiing on one of the area’s fantastic ski mountains
• One of my number one tips: on your way to Stowe, stop by Cold Hollow Cider Mill for all things apple (a must-visit in the fall) and the Ben & Jerry’s Ice Cream Factory tour .

Where to stay in Stowe: Field Guide Lodge , Topnotch Resort , or the Trapp Family Lodge

More on Stowe: I have an entire post dedicated to Things to Do in Stowe, Vermont, the best restaurants , the best breakfast , the best hikes , the best hotels , everything!

READ NEXT   15 Gorgeous VRBO & Airbnb Stowe VT Vacation Rentals (2023)

READ NEXT   Stowe Vermont in Summer: 11 Fun Things to do for All Ages

Days 12 & 13: The White Mountains, New Hampshire

No adventure in New England could be complete without some mountain time. And this is especially true if you’re planning a New England fall road trip .

New Hampshire’s White Mountains are impressive and exciting. They’re the tallest in New England (with Mount Washington tallest of all) and offer spectacular hiking and more. There are several places you could base yourself during this portion of the road trip, but I recommend North Conway, Lincoln, or North Woodstock, as they each offer lots of amenities and accommodations, and are a reasonable distance from the most popular attractions in the region.

Unmissable things to do in the White Mountains:

• Take in some of the coolest natural wonders of the White Mountains , such as the Basin, a granite “pothole” that is found at the base of a waterfall in Franconia Notch State Park
• Go hiking! This is the #1 item on any New Hampshire bucket list . And here is a guide to some of the best hikes in New Hampshire .
• Meander through Flume Gorge. This is a natural ravine that formed over many years and now a hiking trail with a boardwalk passes through it. This is a wonderful hike with some amazing scenery. Another spot that is extra special with the fall foliage
• Clark’s Trading Post in Lincoln, an old-fashioned New Hampshire classic
• A scenic drive along The Kancamangus Highway. This epic stretch of road runs 26 miles between Lincoln and Conway and is one of New Hampshire’s most scenic roads . There are many great spots to stop and explore further and this is undoubtedly one of the best places to see New England fall foliage.
• Shop in North Conway, and don’t miss Zeb’s General Store for a taste of pure nostalgia.
• Tube or paddle in the Saco River. On a friend’s recent bachelorette party trip, we used Saco River Tubing and had an absolute blast!
• Near Bartlett you can stop by Diana’s Baths, a beautiful area of cascading waterfalls and gentle pools. On a hot summer’s day, it’s the perfect place to cool off.

Where to Stay in the White Mountains: Lumen Nature Retreat

More White Mountains travel guides:  🍁  Best Things to Do in North Conway, NH  🍁  Best Things to Do in Lincoln, NH  🍁  Best Things to Do in Franconia, NH  🍁  15 Amazing Cabins in the White Mountains, NH

READ NEXT   Your Guide to Mt Washington NH: The Highest Peak in the Northeast!

Days 14 & 15: Portland, Maine

Finally, the last state on the great New England road trip. This is Maine, “the way life should be.”

Maine is massive so there’s no way to do the state justice in this itinerary; I’m essentially covering a few of the must-see areas. You could spend weeks on a road trip of Maine alone. (See also these  8 autumn scenic drives in Maine delivering up insane fall colors).

If you do wish to explore the rest of Maine (and you absolutely should) I recommend taking a look at my epic list of 50+ Fun Things to Do in Maine , as well as this guide to the top places to visit in Maine . But let’s continue with our amazing road trip!

Stop for a bit in Portland, a modern portside town that may surprise you. There’s a hip city right on the water in Portland, Maine, and this is a hot spot for restaurants, coffee shops, breweries, bakeries , and entertainment .

Fun things to do in Portland:

• Visit a brewery. Beer lovers will be happy to know that Portland has 18 breweries all its own .
• Check out one of several lighthouses in the area . There are 5 less than 20 minutes’ drive from Portland, including the iconic Portland Head Light.
• Grab some of that famous Maine lobster.
• Stuff your face with Maine potato donuts from local staple The Holy Donut
• Walk the pretty Old Port and patronize the eclectic shops and restaurants
• Don’t miss dining at Hot Suppa , a West End restaurant where I enjoyed the best breakfast of my life (and a spectacular maple latte)
• Traveling with kids? The Children’s Museum of Maine on Thompson’s Point is a total blast!

Portland hotel recommendation : Hotel Francis in the West End

Further resources for discovering Portland:  🍁 The Best Things to Do in Portland, Maine  🍁 Weekend in Portland Itinerary  🍁 7 Spots for the Best Breakfast in Portland Maine  🍁 14 Exceptional Airbnb Portland Maine Rentals 🍁 12 Best Hotels in Portland Maine

Days 16 & 17: Acadia National Park and Bar Harbor, Maine

Now we travel north to Bar Harbor. Admittedly, it looks like a far drive on the map. In reality, from Portland to Bar Harbor is just over a 3-hour drive. And trust me, visiting Mt. Desert Island is SO worth it.

Bar Harbor is the seaside town that will be your base for exploring Acadia National Park . You will be in awe over this beautiful part of Maine. Here is where rocky cliffs tumble into the sea, with iconic lighthouses at the top.

There’s abundant wildlife on land and in the sea, and countless opportunities for terrific hiking.

But the region is not just about the outdoors. Bar Harbor has lovely shops, restaurants, and extremely cozy inns . Truly, the region is ideal for travelers of all kinds. You’ll also find great camping, cabins , and vacation rentals in and near Acadia, too.

My top recommendations in Acadia National Park and Bar Harbor:

• Tackle the exhilarating Beehive Hike, that involves a bit of climbing and rewards you with unparalleled views
• Order popovers at the Jordan Pond House (delicious!)
• Take a whale watch or other wildlife tour from Bar Harbor
• Drive up Cadillac Mountain before dawn to catch the sunrise from the first place light touches in the Continental US
• Marvel at the natural wonder of Thunder Hole
• Bike the Carriage Roads in Acadia National Park

Bar Harbor hotel recommendation: The Bar Harbor Inn

More on Acadia: Check out my 3 Day Bar Harbor and Acadia National Park Itinerary for an awesome trip!

Read Next :  10 Coastal Towns in Maine That are Hidden Gems

Day 18: Portsmouth, New Hampshire

Your New England driving tour itinerary is nearing its end, but you’ve got a few more stops to make—-stops you won’t want to miss.

Portsmouth is first. We’re back in New Hampshire now! Between Maine and Massachusetts, New Hampshire is home to a very small strip of coastline. The hub of the Seacoast is Portsmouth, a small yet lively city with a great deal of history. You can see colonial architecture all over this beautiful city.

Taking a New England winter road trip? Portsmouth should definitely be on your list, as they do a month of celebrations and events with Vintage Christmas, one of the most magical New England Christmas celebrations !

Best things to do in Portsmouth:

• Strawbery Banke Museum: an outdoor living history museum.
• Dine at one of the many awesome restaurants: Portsmouth has become a major foodie destination in recent years
• Go shopping at the numerous boutiques around town. Some standouts: Gus & Ruby Letterpress , Pickwick’s Mercantile , and G. Williker’s Toy Shop
• Be surrounded by books and grab a tasty beverage at Book & Bar
• Wander the lovely Prescott Park
• Attend some award-winning theatre at Seacoast Repertory Theatre

Hotel suggestion in Portsmouth: The Hotel Portsmouth

Further Portsmouth NH travel resources for your trip : 🍁 The Best Things to Do in Portsmouth, NH 🍁 Top 10 Bars in Portsmouth NH

READ NEXT   18 Magical New England Christmas Towns that are Straight Out of a Hallmark Movie (Updated 2023)

Day 19: Salem, Massachusetts

Your final stop is the historically infamous Salem, Massachusetts. And though you’ll definitely want to spend time exploring its history with the Salem Witch Trials, there’s plenty to do in the area that isn’t witchy, too.

You can hit the highlights of Salem in one day, or extend for another 2-3.

If possible, you don’t necessarily want to plan your trip to Salem to coincide with Halloween. Although the town has a distinct, fun vibe this time of year, October is also its busiest and most crowded month.

No matter when you go, however, there are definitely some things not to be missed:

• Go to The Witch House, an atmospheric home you’ve definitely seen on Instagram, and a building that is one of the only Salem locations with direct ties to the witch trials. (One of the judges lived here).
• Get witchy in the magickal shops. Whether you want something more fun and touristy, or you’re after the real deal, Salem has a wide range of shops selling all kinds of goods.
• Tour the House of the Seven Gables
• Walk the neighborhoods around Federal Street and admire the stately historic homes
• Find the Hocus Pocus film locations! (Use my guide to take a DIY Hocus Pocus tour )
• Get spooked on a nighttime ghost tour ( top recommendations here !)
• Grab a photo with Samantha at the Bewitched Statue

Hotel recommendation for Salem : The Hawthorne Hotel or Hotel Salem (they have a great rooftop bar)

More on Salem: Check out its great restaurants , scope out some of its haunted history , and maybe even stay overnight in one of Salem’s classic New England inns or Airbnbs ! Nearby towns of Rockport, Gloucester , and Marblehead are worth visiting too if you’d like to explore more of this area of coastal New England.

READ NEXT   12 Fun and FREE Things to Do in Salem MA

Day 20 / End: – Boston, Massachusetts

You did it! You’ve completed an epic New England road trip! Congratulations! You’ve seen some of the prettiest places in the country, and you did it all by car!

Days 21+: Optional Add-Ons: Cape Cod/Nantucket/Martha’s Vineyard

You may be wondering why I didn’t include some of New England’s coastal gems on this New England road trip itinerary? I did this because destinations such as Cape Cod , Nantucket, and Martha’s Vineyard are harder to get to and don’t fit in well with the traditional road trip format. After all, Nantucket and Martha’s Vineyard are islands, so they are not an easy destination to access without in-depth planning.

Not only are they more complicated to travel to, these Massachusetts coastal destinations are terrific and truly worthy of their own vacations . I highly recommend devoting a trip specifically to exploring New England’s amazing coast.

If you wish to add to your road trip, by all means, hop in the car and continue the drive to Cape Cod. From there you can easily take a day trip to Martha’s Vineyard or Nantucket. And I hope these resources will help you as you plan:

More travel ideas here:

• 25 Things to Do on Cape Cod (Besides the Beach!)
• 13 Best Hotels on Cape Cod: Where to Stay on the Cape
• 10 Best Hotels on Nantucket: Where to Stay for a Nantucket Getaway
• 25+ Fun Things to Do in Martha’s Vineyard

The Ultimate New England Road Trip Map (2-3 weeks)

The map below includes all of the destinations I’ve outlined above.

In need of some extra New England road trip ideas? If you’re limited on time, check out my Northern and Southern New England road trip itineraries. These are ideal for 5 day, 7 day, or 10 day New England road trips. Your own personal planning maps are below!

Northern New England Road Trip 7-10 Day Itinerary

• Woodstock, VT
• Waitsfield, VT
• Lincoln, NH
• Portland, ME

Here’s a great New England road trip route if you just don’t have time to go everywhere, but you want to see the highlights of northern New England. In any trip you’ll have to make some choices about what to see and what to miss, sadly, but with this road trip itinerary, you’ll definitely have a broad experience of Northern New England.

This one week New England itinerary contains many of the same stops you’ll find on the ultimate version (that covers all six states). But this one also has the addition of Woodstock, Vermont, which is a classic New England spot, really a ‘Currier and Ives town.’

Southern New England Road Trip 7-10 Day Itinerary

• Provincetown, MA
• Newport, RI
• Providence, RI
• Stonington, CT
• Litchfield Hills, CT
• Gloucester, MA

The Southern New England road trip route is ideal for those who really seek a coastal trip, or who aren’t quite as interested in exploring the mountains. This trip adds a whole bunch of extra stops so you can really dive into coastal New England.

It gives you a feel for the more outdoorsy areas of these southern New England states, too, as the itinerary brings you through the Berkshires, and through charming parts of Connecticut. Definitely an option for a lovely New England summer road trip itinerary.

Shorter Scenic Drives in New England

Are you just looking for a short scenic route that allows you to see dramatic coastal cliffs, mountainscapes, scenic countryside, and more of New England’s charm?

Whether you’re looking for fall scenic drives in New England, beautiful routes along the coast, or just a short yet pretty New England drive, you might just find what you’re looking for on this list of short, scenic drives in New England.

Scenic Drives in New Hampshire

The Coastal Byway (Route 1A)

Location: Portsmouth to Seabrook 

Distance: 18.5 miles 

Where to Stop:  

• Hampton Beach
• Surf Portsmouth , Portsmouth 
• Strawbery Banke Museum , Portsmouth

Robert Frost Scenic Byway

Location: Southern New Hampshire

Distance: 43 miles (The Old Stagecoach Byway and the Robert Frost Byway combined) 

Where to Stop: 

• Robert Frost Farm State Park , Derry 
• Civil War Memorial, Chester
• Matthew Thornton House, Derry 
• Town Beach, Hampstead

New Hampshire Route 112 (Kancamagus Highway)

Location: Conway to Bath

Distance: 56.39 miles 

• Sabbaday Falls 
• Albany Covered Bridge 
• Swift River Lower Falls  
• Russell-Colbath House 
• Sugar Hill Scenic Overlook

The Lake Winnipesaukee Loop

Location: The Lakes Region 

Distance: 97 miles

• George’s Diner , Meredith 
• Mt. Major Trail, Alton 
• Dewey’s Ice Cream Parlor and Cafe , Center Harbor 
• Cotton Valley Rail Trail , Wolfeboro 
• Abenakee Tower , Tuftonboro

Scenic Drives in Maine

• Moosehead Lake

Location: Kennebec and Moose River Valley

Distance: 59 miles

Where to Stop:

• Lily Bay State Park
• B52 Crash Site
• Mount Kineo
• Stress Free Moose Pub & Cafe

U.S. Coastal Route 1 

Location: Kennebunkport to Bar Harbor

Distance: 200 miles

• Goose Rocks Beach , Kennebunkport
• Portland Head Light , Cape Elizabeth
• Old Orchard Beach Boardwalk, Old Orchard Beach
• The Holy Donut, Portland
• Farnsworth Art Museum, Rockland
• Jordan’s Restaurant , Bar Harbor

Acadia All American Road from Trenton to Acadia

Location: Trenton to Bar Harbor

Distance: 40 miles

• Thunder Hole
• Bar Harbor Inn & Spa

Scenic Drives in Vermont

Location: Wilmington to Jay 

Distance: 184 miles

• Molly Stark State Park, Wilmington
• Dot’s Restaurant , Wilmington
• The Vermont Country Store ,  Weston
• Green Mountain Sugar House ,  Ludlow
• Moss Glen Falls, Granville
• Ben & Jerry’s Factory , Waterbury
• Cold Hollow Cider Mill ,  Waterbury Center
• Trapp Family Lodge ,  Stowe

Route 9 – The Molly Stark Byway

Location: Brattleboro to Bennington 

Distance: 40.1 miles

• Vermont Country Deli , Brattleboro
• Creamery Bridge, Brattleboro
• Southern Vermont Natural History Museum, West Marlboro
• Hogback Mountain Scenic Lookout, Wilmington
• Bennington Battle Monument, Bennington
• The Apple Barn and Country Bakeshop – Bennington

Location: Bennington to Burlington 

Distance: 122 miles

• The Bennington Battle Monument, Bennington
• The Robert Frost Stone House Museum , Shaftsbury
• Cider donuts at the Equinox Valley Nursery , Manchester
• Downtown Murals, Rutland
• Woodchuck Cider , Middlebury
• The Burlington Waterfront – Burlington
• Church Street/Downtown – Burlington

Rhode Island Scenic Drives

Ocean drive.

Location: Fort Adams Park to Bellevue Ave

Distance: 10 Miles

• Castle Hill Lighthouse
• Brenton Point State Park
• Fort Adams Park
• The Breakers
• Marble House
• Rough Point
• The Red Parrot Restaurant

Scenic Drives in Connecticut

Connecticut state route 169.

Location: Norwich to Woodstock

Distance: 36 miles

• Lisbon Meadows Park, Lisbon
• Prudence Crandall Museum , Waterbury
• New England Center of Contemporary Art, Brooklyn
• Roseland Cottage , Woodstock

Connecticut Shoreline Drive

Location: New Haven to Stonington Borough

Distance: about 80 miles (depending on which routes you take!)

• Eat in Little Italy, New Haven
• Hammonasset Beach State Park, Madison
• Harvey’s Beach, Old Saybrook
• Rocky Neck State Park, East Lyme
• Mystic Aquarium, Mystic

Scenic Drives in Massachusetts

The berkshires.

Location: Stockbridge to Williamstown

Distance: 35 miles

• Norman Rockwell Museum , Stockbridge
• Berkshire Botanical Garden,  Stockbridge
• The Mount, Edith Wharton House , Lenox
• Berkshire Museum, Pittsfield
• Hancock Shaker Village, Hancock
• Mount Greylock , North Adams
• Massachusetts Museum of Contemporary Art , North Adams
• Williams College – Williamstown

Essex Coastal Scenic Byway

Location: Gloucester to Newburyport 

Distance: 24 miles

• Hammond Castle Museum, Gloucester
• Crane Wildlife Refuge, Essex
• Eat at the Clam Box , Ipswich MA
• Plum Island Beach, Newburyport
• Maudslay State Park, Newburyport

Wrapping Up this Northeast Road Trip

I hope this New England travel guide has given you all the information you need to help you plan a trip to the region’s most exciting and gorgeous places. With multi-day options to choose from and choices that are great for every season, I have aimed to cover all of the top places to road trip throughout these six amazing states.

Even more resources for your New England adventures: 🍁 25 Fantastic New England Day Trips 🍁 Hidden Gems in New England: 15 Secret Places to Visit 🍁 Best Fall Foliage New England Tours Worth Your Money

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Home » North America » USA » New England

EPIC New England Road Trip Itineraries (2024)

Going on a New England road trip  has to be one of the best ways to experience the region! With your own vehicle, you’ll be able to go wherever you want, stay where you like, and see whatever you fancy.

New England has been charming visitors for a long time. Of all of the regions in the USA, New England has some the richest history (being the birthplace of the nation and all), some of the most exciting locals, and best seafood, period.

And the fall foliage in New England? What more can be said about this phenomenon that hasn’t be said by dozens of movies – it’s simply one of the most romantic sights in the USA.

New England is by no means cheap nor easy to travel without some guidance. In order to see the best of New England, and not drop a fortune while doing so, you’re going to need a little assistance.

Don’t worry – we have the insider information you need for an EPIC journey. So what are we waiting for?! Let’s get the ball rolling on your New England road trip itinerary!

Best Time of Year to Road Trip New England

Best new england road trip itineraries, places to visit in new england, off the beaten path new england road trip ideas, new england road trips costs, final thoughts about new england road trips.

With something always going on, a road trip to New England is possible at any time of the year! In New England, summers are for beach trips, fall is for the foliage, winter is for skiing, and spring is for festivals.

If you can stand the occasional poor weather – the blinding snow and sometimes uncomfortable humidity – then you’ll do just fine in New England.

The climate in New England isn’t always agreeable, a fact that many residents will remind you of when you’re there. Winters are long and can be bitter cold and summers feel unfairly humid and short.

The weather in New England has a habit of being bipolar as well, appearing beautiful one moment only to turn to shit in a moment.

This doesn’t stop New Englanders from having a good time though as they seem to have something to do 365 days of the year. They take the weather with a grain of salt, as they should, and simply say, “if the weather’s no good, just wait 15 minutes (and it’ll be better).”

Outside of the mountainous regions, which can have Arctic qualities, there are no huge climatic swings in New England. Overall, temperatures are relatively cool and precipitation is spread throughout the year.

What makes New England feel so cold is the Canadian winds that come down and wreak havoc. These winds penetrate to the bone and can really ruin your day.

A thermometer may read 30 Fahrenheit but with the wind chill, it could feel like 0. Be sure to bring lots of layers and a windbreaker in the winter.

Fall in New England means changing foliage, the astounding beauty of which attracts every Joe Schmoe and his family to visit. If you’re on a road trip during this time, expect much higher prices and much less availability. Having said that, it’s one of the best places in the world to visit in September and October, so it’s worth it!

Get 15% OFF when you book through our link — and support the site you love so dearly 😉

Booking.com is quickly becoming our go-to for accommodation. From cheap hostels to stylish homestays and nice hotels, they’ve got it all!

Below is a list of sample New England road trip routes, from East Coast budget adventures to more comprehensive trips that cost a bit more. Varying from 4 to 14 days in length, they cover many of the top destinations in New England. Each itinerary provides day-by-day highlights, which are meant to give you some good New England road trip ideas.

The USA is  blisteringly beautiful. It’s also blisteringly expensive! Visiting two national parks in day can run you $70+ in entry fees.

Orrrr… you kick those entry fees to the curb, buy an annual ‘America the Beautiful Pass’ for $79.99,  and get unlimited access to ALL 2000+ federally managed sites in the States totally FREE!

You do the math. 😉

4-Day New England Road Trip Itinerary: Boston and the Cape

4 Days: Boston and the Cape

Arrive in Boston via Logan International Airport or by other means. Once you’re checked into your lodge and settled in, get ready to see the town!

Our  Boston itinerary  includes a visit to downtown Boston to see:

• Fenway Park
• The Freedom Trail
• Acorn Street
• Trinity Church
• Boston Commons

After that, head to bed because the next day we start again!

Today you’ll be getting off the beaten path in Boston.

• Southend for an authentic Bostonian experience
• Cambridge for Harvard and MIT
• East Boston for good food and views
• Walden Pond for transcendental fans
• Bunker Hill for history

Today we’re officially starting the drive, so have your car organized for a road trip to Cape Cod. Start driving on Highway 6 and then transfer to Highway 3 prior to the Cape Cod Canal. Once you’ve arrived, find your Cape Cod lodge/campsite and get set up.

Next, we’ll explore the Cape. Activities include:

• Lighthouses
• Charming settlements
• Trinket shopping
• Historical landmarks
• Biking and hiking
• Cape Cod Rail Trail

This is the last day of your short road trip from Boston. You can opt for a few different choices today.

Either consider visiting Nantucket Island or Martha’s Vineyard via the ferry. If not though, you can continue exploring the island and seeing what’s around.

When all is said and done, pack your things for a late flight in the evening or a flight the next day.

7 Day New England Road Trip Itinerary: New England’s Best Fall Foliage

7 Days: New England’s Best Fall Foliage

• Arrive at Logan International and organize your car; skip this if you’re coming by road from elsewhere.
• Hit the road immediately and head west on the I-90 and I-84 for Hartford, CT.
• Pass Hartford and continue onto the Litchfield Hills in West Connecticut.
• Spend the night in Kent, Cromwell or elsewhere.
• Admire the foliage.
• Depart from your lodge and head north on I-7 through the Housatonic Valley; red and gold foliage in abundance.
• Arrive at the junction between I-7 and Highway 2 near Williamstown.
• Highway 2 is colloquially referred to the Mohawk Trail, which offers some of the best of New England as well as excellent fall colors.
• Stay nearby and drive along the 2 to your heart’s desire.
• Drive on the Mohawk Trail if you haven’t already.
• When ready, head for Green Mountain National Forest of Vermont via I-7 again.
• Drive through the Green Mountains until Burlington.
• Grab a beer and chill for the night.

Today is a long but rewarding day.

• Depart from Burlington and head for Cambridge, VT.
• Hit the 108 and Smuggler’s Notch for excellent mountain views and foliage.
• Make your way east towards Bath, New Hampshire.
• Turn onto Highway 112 before Bath, which is the beginning of the Kancamagus Highway.
• Continue onto Lincoln, admiring the scenery along the way.
• Stay in Lincoln, North Conway or elsewhere in the White Mountains.
• Finish the Kancamagus Highway (112), which terminates at Conway.
• Head north upon reaching Conway on Highway 16.
• Enjoy Mt Washington and White Mountain National Forest, which is particularly fantastic in fall.
• Turn onto I-2 and then again onto 113 to reach Evans Notch.
• Finish up and head south towards Portland for the night.
• Drive to Acadia National Park , which is one of the best places for fall foliage in New England.
• Make a tour around Mt Desert Island and get a full dose of autumn splendor and coastline.
• Spend the night around Acadia or back in Portland.
• Consider spending the night in Camden as there is excellent foliage here.
• Pack up and head back to Boston.
• Spend the day exploring the city.
• Get ready to depart that evening or the next day.

14-Day New England Road Trip Itinerary: Ultimate New England

14 Days: Ultimate New England Road Trip

Follow the first East Coast itinerary listed here  except  instead of returning to Boston at the end of day 4, relax and stay the night in Cape Cod. We’ll be moving on from there the next day…

• Depart from Cape Cod and hit I-6, which will take you all the way to Providence, Rhode Island.
• Explore the city and its architecture.
• Be sure to drop by one of the many breweries and brewpubs.
• Spend the night in or around Providence.
• Wake up and head directly for Newport via Highway 114.
• Spend the day exploring the opulent town.
• Be sure to visit the many mansions and estates as well as Fort Adams in the south.
• Depart when you’re ready.
• Drop by Narragansett for some beach time if you have time.
• Stop in Old Saybrook for the night or continue onto New Haven.
• Depart from your lodge and make your way north.
• Head to the state capital Hartford.
• Wadsworth Falls
• Buttermilk Falls
• Settle in Hartford for some culture and good partying or…
• Head to Litchfield Hills for a quieter night.
• Make your way up Knowledge Corridor or Housatonic Valley towards Vermont.
• Be sure to drop by the Mohawk Trail in Northwest Massachusetts for some scenery and history.
• Hit highway 7 and make the long drive to Burlington.
• Reward your hard work today with a beer.
• Spend the day exploring the Green Mountains of Vermont.
• Climbing the  Camel’s Hump .
• Hiking around  Mt Mansfield .
• Check out  Smuggler’s Notch .
• Rafting on the  Mad River .
• Spend the night in Burlington again.
• Depart from Burlington and head east towards Lincoln, New Hampshire via I-89.
• Arrive in the White Mountains and settle into whatever lodge/campground you have booked.
• Spend the remainder of the day in the mountains.
• Flume Gorge
• Mt Washington
• Franconia Notch
• Arethusa Falls
• Lonesome Lake
• If you arrived early enough, considering overnighting in a backcountry campsite.
• Wake up and knock off any remaining activities.
• Consider doing the full-day Presidential Traverse but, full-warning, it’s quite arduous.
• Lay your head down for the night, preferably around a campfire with a drink.
• Depart from the White Mountains and travel on Highway 302 to Portland, Maine.
• If you stay in Portland, visit the many maritime landmarks, trinket shops, and breweries.
• Spend the day exploring Acadia National Park.
• Taking a road trip around  Mt Desert Island .
• Climbing  Cadillac Mountain .
• Visiting  Jordan Pond .
• Relaxing on  Sand Beach .
• Walking around  Bar Harbor .
• Head to your lodge for the night.

Below is a list of the best road trip destinations in New England. Study them well and decide which ones you like the most.

Road Trip to Boston

Boston is the largest city in New England and, honestly, one of the coolest cities in the entire United States. With gorgeous architecture, some of America’s most important history, and hugely diverse demographics, there’s little chance you’ll run out of things to do in Boston .

Downtown Boston – the area with all the skyscrapers – is where you’ll find the majority of the city’s attractions. Notable points of interest in Boston Downtown include Fenway Park , the Trinity Church, Boston Commons, Acorn Hill , and the North End. You could easily hit all of these places in a few hours by walking.

North across the Charles River is Cambridge , home to the famously exclusive Harvard College and MIT . Both campuses are worth visiting – the former for traditional architecture and the latter for ultra-modern. The whole of Cambridge is pretty affluent, being inhabited by students and leaders in tech, but thankfully doesn’t suffer from too much snootiness.

South Boston is the home of the “southies” aka those people that sound like Matt Damon from Good Will Hunting . Aside from the impressive JFK Library, there isn’t a whole lot to do here besides people watch, which is, admittedly, awesome.

Finally, across the Boston Channel and next to Logan International is East Boston, which is where most of the immigrants live. These means this is one of the best places in Boston to grab food! The views ain’t bad either.

While you’re travelling around Boston , be sure to also get outside of the city of as well! The historical city of Concord , as well as the hallowed Walden Pond , are both worth a day trip.

Road Trip to Cape Cod and the Islands

Cape Cod is a large, prominent peninsula located south of Boston. It is an immensely popular getaway destination due in part to its extensive coastline and profuseness of quaint coastal towns.

Combined with the ever-enchanting Martha’s Vineyard and Nantucket Island , both located nearby, and you have an assembly of some of the best of New England.

Cape Cod is a very large region, surprisingly so, and is broken into several districts. Because of its size, history, and prosperity, Cape Codians are very proud of their home and consider it more than just a tourist destination. There are loads of great places to stay in Cape Cod , if you fancy extending your trip!

There are several charming towns on Cape Cod that are worth visiting. Hyannis is most notable for the Kennedy Compound , which served as the holiday home for JFK and his family, as well the enormous Beech Tree on Main Street .

Fans of Kurt Vonnegut may also be interested in nearby Barnstable as it was his home for several decades. Affluent Chatham has one of the best lighthouses and local baseball teams on the Cape (Cape Codians are crazy for the sport).

Finally, Provincetown is famous for its artsy and expressive LGBT community.

Most everyone comes to Cape Cod to play in the sea as the peninsula has some of the best beaches in New England. Make no mistake, there are a lot of them too.

Stunning stretches of sand can be found at Nauset Beach, Lighthouse Beach, Sandy Neck Beach, Mayflower Beach, and pretty anywhere else along the Cape Cod National Shoreline Park . You may get lucky and even see a migrating humpback whale!

No road trip to Cape Cod is complete without a trip to Nantucket Island or Martha’s Vineyard – both are among the most desirable places to visit in New England, during summer especially so.

Martha’s Vineyard is full of grand residences for the rich as well as picturesque beaches. Nantucket is similar to Martha’s Vineyard but smaller and quieter. You can catch a ferry to either at Hyannis.

Road Trip to Rhode Island

Rhode Island has a little bit of everything. The largest city, Providence , is often considered a good alternative to Boston, and the surrounding state offers quintessential scenery including rugged coastline, quaint townships, and, of course, the fall foliage New England is so beloved for.

Providence is the third largest city in New England. For a long time, Providence had a bad reputation for being sketchy, crime-ridden, and corrupt but, following massive economic pushes, is currently undergoing an urban renaissance. It’s now a very appealing city thanks to its history with a bustling college scene, solid nightlife, and heaps of stuff to do .

Providence is a small city so getting around on a foot is a very reasonable task. Walk around and take note of the diverse architecture. Be sure to see the State House, the eclectic Brown University, the restored Arcade, and the First Baptist Church , among others, for a lesson in American architectural history.

For a languid afternoon, try visiting one of the many museums and/or parks in Providence. Certain neighborhoods, like Federal Hill, College Hill, and Downcity all offer nice urban panoramas as well. End your day at one of the many breweries in the city.

Rhode Island’s other noteworthy city is Newport . An opulent town, full of mansions and elegant avenues, Newport is a prime example of New England decadence. Rosecliff estate served as a setting in the recent Great Gatsby film and its neighbors – The Beakers and Marble House – are equally grandiose.

There is a thriving art scene in Newport and jazz, in particular, is praised here. There is an awesome jazz festival at Fort Adams. Festival or not, Fort Adams is worth seeing because it is one of the most important historical structures in New England.

Newport has many beautiful city beaches including Bailey’s, Easton, and Gooseberry. To see some real contenders for “best beaches in New England,” head across the Jamestown Verrazano Bridge to Narragansett . If you’re ever wondering where to stay in Newport, you should definitely consider staying in one of the more historic bed and breakfasts in Rhode Island there.

Coastal Connecticut Road Trip

Connecticut is an eclectic state visited often by both New Englanders and New Yorkers, the latter of which only live a short train ride away. It is a popular getaway for city folk who need a break from the grind and some time in rural New England.

With a lovely coastline, romantic countryside, and a number of dynamic cities, Connecticut is a great stop along any New England road trip route USA.

Connecticut can be broken down roughly into three parts: the coast, the “Knowledge Corridor,” and the countryside. This section will cover coastal Connecticut , which is a part of Southern New England.

Driving west along Highway 95 from Rhode Island, you’ll pass by some of the most beautiful beach towns in New England. Stonington is a good place to learn about the maritime history of the state – particularly at the Old Lighthouse Museum .

Old Saybrook is one of the prettiest coastal towns in Connecticut and is also a stone’s throw away from Gillette Castle . On the way to New Haven is Hammonasset Beach , which is the longest and busiest beach in the state. Make sure to stay in one of the stunning cabins in Connecticut to make the most out of all this natural scenery.

New Haven marks the beginning of a long stretch of urban development that spans all the way to New York state.

New Haven is most famous for Yale University , which is arguably the top attraction in the city. Being a college town, New Haven has a great art scene and nightlife. The pizza is also particularly good in this town.

As we continue further west along 95, we’ll pass by many more beautiful New England towns. There’s quiet Milford , which has a great beach called Silver Sands .

Next, you’ll pass through industrial Bridgeport . After that is upscale Stamford , glorified dockyard for millionaires from New York (there are some good beaches as well).

Finally, you’ll end up in Greenwich , which is one of the most admired towns in New England, due in part to its beauty and close proximity to New York.

There are a ton of awesome B&Bs in Connecticut where you can stay in a historical building and enjoy that welcoming East Coast hospitality.

Wanna know how to pack like a pro? Well for a start you need the right gear….

These are packing cubes for the globetrotters and compression sacks for the  real adventurers – these babies are a traveller’s best kept secret. They organise yo’ packing and minimise volume too so you can pack MORE.

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Road Trip through Connecticut and Massachusetts

The interior of Connecticut is dominated by the Knowledge Corridor , which hosts one of the densest collections of higher learning institutions, not to mention one of the largest populations in New England.

Travel outside this packed area and you’ll find some of some of the best of New England pastoralism including traditional townships, rolling hills, and a distinctive tranquility. Visiting either on a New England road trip provides excellent insight into the region.

Let’s start with the quieter section – the western part of Connecticut referred to as the Litchfield Hills. This part of the state is very rural with few inhabitants and even fewer visitors.

There are a number of beautiful New England towns here, including Kent , Cornwall , and New Milford , as well some lovely natural attractions like Kent Falls, Burr Pond, Candlewood Lake, and Mohawk Mountain . These are also some of the best places to visit in New England in the fall.

Moving along to our main destination, we first make for Hartford , Connecticut’s state capital and the beginning of the Knowledge Corridor. Hartford is considered one of the great culture capitals of the region.

There are several libraries and art collections dedicated to various historical figures, including Mark Twain, spread throughout the city. Reportedly, West Hartford also has a fairly active nightlife.

Outside of Hartford are a number of parks worth visiting. Examples include Enders State Forest/Falls, Buttermilk Falls , and Wadsworth Falls .

We continue our New England road trip north on Highway 91 through the Connecticut River Valley. This is the heart of the Knowledge Corridor, a title that refers to the huge concentration of colleges and universities in the area. This corridor runs all the way into Massachusetts and terminates in Springfield.

Springfield is a great city full of Victorian architecture and some of the coolest museums in New England. Be sure to visit the NBA Hall of Fame , if you’re interested in sports, as well as the Dr. Seuss Sculpture Museum , if you had a childhood.

Vermont Road Trip

True to its nickname, Vermont aka The Green Mountain State is a wild wonderland and a favorite playground for New England outdoors people. With some awesome skiing and hiking in addition to several fall foliage drives, which are among the best in New England, Vermont is a great escape from the more developed CT, MA, and RI. Here is the best opportunity to stay in a cabin in Vermont for a truly off-the-grid experience.

Starting in the south of Vermont, you’ll first arrive at the mountains from which the state gets its name, the Green Mountains . A subrange of the Appalachia, the Green Mountains are home to the state’s highest peaks as well as the best mountain activities.

Some of the best ski resorts in Vermont are Sugarbush, Stowe Mountain, Killington, Mount Snow , and Jay Peak. Though the slopes aren’t as epic as say those in Colorado or Oregon, they still get dumped on with snow and have decent runs.

If skiing isn’t your bag, why not try portions of the Green Mountain Long Trail ? This extension of the Appalachian Trail is noteworthy for hitting all the range’s highest peaks but is, for this reason, difficult at times.

Casual hikers and campers can also take advantage of the many free backcountry campsites and quaint bed and breakfasts in Vermont .

Other natural attractions worth visiting in Vermont are the Mad River, Quechee Gorge, Camel’s Hump , and the many gorgeous lakes – most notably Lake Willoughby and Lake Champlain.

Montpellier is the state capital of Vermont though Burlington is the largest and most exciting in the state.

Burlington is famous for being a hippy town as well as drop dead gorgeous because it lies on the banks of Lake Champlain. Burlington makes for an excellent base for exploring Vermont’s outdoor spaces with many quality bike paths for cycling enthusiasts.

Like any good liberal college town, Burlington has plenty of bars, and the breweries, in particular, are excellent. You ca check out Airbnbs in Vermont for cozy and comfortable stays.

Road Trip to New Hampshire

New Hampshire is very similar to Vermont in that it’s mostly visited for its epic settings and free-spirited culture. With the highest peak in all of New England, Mount Washington , as well as the beautiful White Mountains , New Hampshire is another great New England road trip destination for adventurous travelers.

If you’re on a summer New England road trip, then you’ll obviously want to hit the trails in New Hampshire. This state has some of the best hikes in New England in addition to some decent summits.

As previously mentioned, Mt Washington is the highest peak in New England and can be summitted in a day either by foot or by cog train (that’s cheating though). Be mindful of foul weather.

New Hampshire’s Mt Monadnock is argued to be the second most climbed peak in the world next to Mt Fuji, but many don’t count Monadnock because it has no glacier. (Mt Hood in Oregon is the second most climbed glaciated peak in the world.)

Another rewarding and arduous hike is the Presidential Traverse where you navigate across 11 of the state’s highest peaks. Also consider visiting Lake Winnipesaukee , Franconia Notch, Arethusa Falls, Lonesome Lake , and the Flume Gorge .

Those on a winter or spring New England road trip will be happy to hear the skiing is also quite good in New Hampshire. Popular ski resorts include Loon Mountain, Bretton Woods, Cannon Mountain , and Waterville Valley .

New Hampshire is pretty sparsely populated and there aren’t too many bustling urban centers here. There are a couple of little towns worth stopping in still.

Hanover is home to the famous Dartmouth University and is gorgeous in its own right. Jackson is a gorgeous place to stay in the White Mountains and makes for a great base. Finally, Portsmouth is one of the most historically significant towns in New England and, more importantly, has great breweries.

Road Trip on the Maine Coast

Maine will be a highlight for any New England Coast road trip! With epic seascapes and even more epic seafood, Maine has a lot to offer.

Many people have fallen in love with Maine’s coastline, too many perhaps. Coastal Maine isn’t exactly hidden these days and so anyone on a summer road trip in New England will have to deal with large crowds.

You can definitely get off the beaten path in Maine but that is a topic that we will be discussing in the next section .

Driving from Portsmouth, NH, you’ll head north on the 95 to Portland , Maine, catching glimpses of the shoreline along the way. You’ll pass by several of Maine’s best beaches and towns including York, Ogunquit, Cape Elizabeth , and Goose Rocks . Upon arriving in Portland, you may think that it’s a small coastal town but is, in fact, the largest “city” in the state.

Portland is one of the best places in New England, ridiculously charming and full of quaint little attractions. You’ll learn a lot about its maritime history at the Old Port and also be afforded the opportunity to shop for artisanal souvenirs. The seafood is obviously excellent in Portland and the beer is especially delicious if not abundant.

Moving on from Portland, we continue our New England coast road trip deeper into the state. Driving on the 1 you’ll have lots of opportunities to visit the coast. Boothbay is an elegant destination, Camden is gorgeous, and Popham Beach is arguably one of the best beaches in New England.

Our ultimate destination is Acadia National Park , the only national park in New England. It is a superlative place with some astounding scenery, not to mention some of the best hikes in New England.

Spend the night in the charming seaside town of Bar Harbour , where you’ll get to try Maine’s famous cold lobster roll. You’ll find some epic Maine B&Bs here run by friendly locals.

Then go for a drive around Mt Desert Island , the island on which Acadia is located, and then explore local sites like Jordan Pond and Sand Beach . Note that you’ll have to pay an entry fee for Acadia.

Below is an overview of the Great North Woods of New England, arguably the wildest place in the Northeast. Those with the will and proper transport will be rewarded with virgin woods, pristine rivers, and an abundance of local wildlife.

Great North Woods

The Great North Woods is one of the quietest, most underdeveloped, and most beautiful places in New England. It refers to the extremely wild and untouched woodlands of northern New Hampshire, Vermont, and Maine that separate New England from Canada.

With little, if any tourist infrastructure, the Great North Woods should be an awesome adventure for anyone looking for a proper USA backcountry experience on their New England road trip.

There are a fair bit of activities in the New Hampshire part of the Great North Woods. Many of New England’s best waterfalls are in this region including the spectacular Beaver Brook Falls . There’s a very complex and thorough network of trails here as well that penetrates deep into the woods.

You can drive to Great North Woods in Maine from New Hampshire via Highway 16 and pass some excellent scenery along the way. This area is one of the best places to visit in New England in the fall because of the spectacular foliage. Be careful of moose though! These giants will run into the road sometimes and seriously ruin your car.

Maine’s North Woods is expansive and is probably the most remote part of New England. It is, in fact, so out-there that certain counties like Aroostook are not even officially incorporated into the state and so have no “official populations.”

Stories of the wood’s frightful and fantastic inhabitants still circulate to this day as well, like that of the vengeful wendigo or of the murderous ding-balls.

Interior locations like Baxter State Park and Mt Katahdin are the most “accessible” places in Maine’s North Woods. Surrounding these is 100 Mile Wilderness , which is often visited by ACT hikers. If you want to travel further than these locations you may need a 4×4 as paved roads are no longer guaranteed.

If you can make it, the Allagash Wilderness is one of the great river adventures in America. Navigable only by canoe or raft, there is nothing out here besides moose, fish, and untouched landscapes.

A road trip through New England ain’t going to be cheap, folks. With the high costs of living and high demand, New England has some of the steepest hotel rates and dining prices in the USA.

That’s no reason not to visit New England in the first place though! You have us, after all. 🙂

We at The Broke Backpacker are constantly looking for new ways to save on travel and have a whole repertoire of useful tips to share with y’all. Even if we are unable to travel for $10/day like in our favorite countries (let’s be real here), we can at least help you minimize expenses to the utmost degree.

The average daily budget for a New England road trip is between $200-$250 – this includes gas, a rental car, lodging, food, drink, and entry fees.

On any road trip, New England or otherwise, the largest cost will be gas . This expense will always sneak up on you because it can be difficult to properly gauge how much you will actually use.

Lodging is also expensive in New England. Try and camp out as much as possible to lower your daily budget significantly. Take advantage of the cheaper public campsites and occasional backcountry site, which are sometimes free. Stay in hostels as well – they’re not so bad in New England.

Food costs are something you can control as you will have the option of cooking cheaply at home or the campsite. Dining is expensive in New England so be picky about how many lobsters you eat and clam bakes you attend.

Below is a breakdown of the average costs of a road trip in New England.

Average Costs of a New England Road Trip

Rental car : $50-$150

RV rental :  $100-$300

Gallon of gas:  $2.74

Private AirBnB home:  $140

Hotel room:  $150

Hostel:  $25-$35

Campground:  $10-30 (sometimes free!)

Sandwich:  $6-$9

Beer at a bar:  $5-$8

Coffee:  $3-$4

Bottle of Whiskey from the market:  $25

Dinner for two:  $35-$60

Best Places to Stay in New England on a Budget

Camping in new england.

Camping in New England is either done on public land, private land or in the backcountry . Each type offers different sorts of amenities and at different prices.

Private campgrounds usually have more amenities and can accommodate more types of campers. RV parks, hookup sites, and other sorts of demanding camping (we hesitate to use the word “glamping”) are usually found at private camps.

Private camps usually have lots of communal facilities like a kitchen and showers. Because of their greater comfort, private campgrounds are usually more expensive.

Camping on public land, run either by the state or the feds, is usually more basic. Electricity is possible as is the occasional shower but don’t expect the resort-like services that private campgrounds have. Fortunately, prices are far more reasonable at public campgrounds.

Both public and private campsites fill up quickly in the fall. Many take reservations though and we suggest you do this if you’re going on a fall foliage road trip in New England.

Backcountry campsites, being located on either private or public land, are harder to access but have the benefit of being extremely cheap if not totally free . These campgrounds usually require a hike or maybe a water taxi to reach, which makes them difficult and unattractive for the average camper.

The backcountry campgrounds are also very primitive, often with no restrooms and maybe running water. For the intrepid, these campgrounds can be very ideal as they’re super quiet, wild, and, as previously mentioned, usually free!

Backcountry campsites are usually found in the mountains, around the lakes, and on the remote islands of New England. Use this search engine for a compendium of free camping in New England .

Always have of plenty of powerful bug spray and mosquito repellent on you. Mosquitoes are a plague in the summer. Be sure to also wear long clothing to protect yourself from ticks when hiking in the backcountry. Local ticks often carry Lyme Disease, which is an autoimmune disorder with no cure.

Drink water from ANYWHERE. The Grayl Geopress is the worlds leading filtered water bottle protecting you from all manner of waterborne nasties.

Single-use plastic bottles are a MASSIVE threat to marine life. Be a part of the solution and travel with a filter water bottle. Save money and the environment!

We’ve tested the Geopress  rigorously  from the icy heights of Pakistan to the tropical jungles of Bali, and can confirm: it’s the best water bottle you’ll ever buy!

Renting a Car or Campervan in New England

Renting a car is the most popular way of getting around New England. There are a myriad of car rental agencies here that offer varying deals and varying models.

To find the best rental car deal in the USA, use search engines that compare the prices from individual companies. We personally like using rentalcars.com as they’ve never failed to give us a great price.

You can also rent and travel in a campervan , which means you don’t have to worry about packing camping gear. You will have to empty and refill the various wascampete and water tanks though, which will require a visit to the proper facilities. RVs also cost more to rent, use more gas, and demand higher prices at campgrounds. We suggest booking a campervan with Outdoorsy as they usually have a good selection and good prices.

Make sure you also purchase a RentalCover.com policy to cover your vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.

The roads in the Northeast are generally very good and a sedan or economy car should deliver you to most of New England’s top destinations. Only in the most remote portions of the Great North Woods, will the roads be so bad that you need 4×4 or at least high clearance.

If you’re on a road trip in New England during the winter and want to go to the mountains, you will definitely need all-wheel or 4-wheel drive.

Getting Insured for a Road Trip through New England

Concerned about staying safe in the USA? Well don’t be! Just make sure you’re insured, and you drive carefully.

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

New England is no doubt one of the most idyllic regions of the US. Quaint coastal towns and some of the best foliage in the country are but two reasons to take a road trip here–but there are so many more.

Hopefully, you now feel more prepared on where to go and what to do on YOUR New England road trip.

But rest assured that regardless of which spots you’re bound to find beauty, history and a whole lot of delicious seafood.

So what are you waiting for? The open, rural roads of New England awaits!

Updated February 2023 by Samantha Shea

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

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Wow! great article and suggestions.

thank you for all of the advinces it helps, can t wait to visit New England Vermont Maine, xxx

Lake placid in the Adirondack Mountains also a try while stop. There are several private and New York State campgrounds nearby.

Thank you for mapping this all out. I live in New England and would love to visit many of these places.

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Expert at cramming as much travel as possible into the little time available

One week new england roadtrip.

This post (likely) contains affiliate links, including Amazon Associates links, and I may receive a small commission if you click one. This is at no extra cost to you.

It is possible to have an incredible time in New England, even if you have limited time to spend there. This post covers how to have an epic one week New England Roadtrip and maximise the amount of time you have to spend there. Going on a roadtrip is one of the best ways to experience this part of the USA. It gives you the freedom and flexibility to get to some of the more off the beaten track locations and well as throwing in a few unplanned stops. Plus means you get to see some pretty epic views!

One Week New England Roadtrip Itinerary at a glance

Day 1 – Arrival / Boston

Day  2 – Brattleboro / Rockingham / Newfane

Day 3 – Quechee / Woodstock

Day 4 – Waterbury / Stowe

Day 5 – burlington / stowe, day 6 – kennebunkport, day 7 – rockport, day 8 – salem / depart.

Arriving into New England

The easiest and most convenient airport for New England is Boston Logan International Airport. This is one of the USA hubs, so there are plenty of flights daily from multiple locations all over the world.

From the airport terminal you take a bus to the car hire centre, which is open 24 hours. This is really handy if your flights arrives later in the evening.

One Week New England Roadtrip in detail!

Day. 1 – arrival / boston.

How you spend this day really depends on what time of day you arrive in to New England. If you have an earlier flight, it would be a great opportunity to head into Boston for a spot of sight seeing. However, if the flight lands later in the evening, then the best thing to do once you have collected the hire car is to head slightly out of the city.

Driving even half an hour or so North means the next day you are best placed to head straight out of Massachusetts into Vermont, and don’t get caught up in any city traffic. By leaving the city in the evening you avoid any Boston traffic jams that might occur during the day. The hotel prices are also a little cheaper than in central Boston.

Take a look at South Burlington, MA for a good distance out of Boston. If you are looking for something very functional, as simply a place to crash for the night, try Sonesta Suites Boston. Click HERE .

The hotel isn’t amazing, but it is in a good location.

Day 2 – Brattleboro / Rockingham / Newfane

Leave Massachusetts first thing and drive through New Hampshire into Vermont.

Start the day by heading to Brattleboro . The drive should take just under 2 hours. This town is located literally just over the border from New Hampshire into Vermont – cross a bridge and you are in Vermont. This is a nice town to stop and have a quick wander around, but perhaps not worth staying overnight in. When you arrive in Brattleboro head to Duo for some brunch. They have a great selection on their menu, including cider pork benedict or pancakes for your first taste of Vermont maple syrup!

Upon leaving Bratteboro there a number of places to head to continue with the New England Roadtrip!

Start by heading to Grafton Village Cheese to sample some local cheese, slurp on a maple creemee and take a look at the cute little farm buildings.

From there go via the town of Rockingham for a wander around. After this stop at Vermont Country Stores to spend all your dollars on things you didn’t even know you needed, but you absolutely did. It is also so traditional inside, selling all sorts of local goods. So worth a look even if you don’t want to splurge.

Following this head to your overnight stop in the town of Newfane.  This little town is incredibly picturesque, but there isn’t a huge amount to do as it isn’t very large. Therefore the best time to arrive would be late afternoon, early evening. This way you can check in, relax and have a wander of the town before going out to enjoy dinner.

Total driving time: 3 hours ( or 2 hours if you choose not to visit Rockingham)

Where to stay:   Four Columns

Where to eat: Fat Crow

Day 3 – Quechee / Woodstock

Set off from Newfane in the morning and make your way towards Woodstock, your overnight destination. There are, of course, a couple of places to check out on the way!

Firstly Sugar Bush Maple farm where you can try the local cheese made here, as well as seeing how maple is tapped.

After leaving the farm head towards Quechee . This isn’t a huge place, however there are a couple of places to check out when you are there. Upon arrival head to the Quechee Gorge bridge for outstanding views down the valley from quite the height. Then take the hike down to the bottom to see the river and look back at the bridge.

After you have visited the gorge Quechee Gorge Village is worth a stop, as it has lots of little shops to check out. Including the most enormous antiques shop you might ever possibly see in your life. If you are hungry there is also a diner housed in an old rail carriage, which is interesting!

Just after lunch head towards Woodstock , it is such a pretty town therefore you are going to want to make sure you have time to explore. Check out the traditional shops including FH Gillinghams and Sons. Plus, there is a Vermont covered bridge to be found here!

Total Driving time: 1 hour 45 minutes

Where to stay: The Shire, Woodstock

Where to eat: Worthy Kitchen

Today set off from Woodstock in the general direction of Stowe. Stowe itself is a lovely little town, so this one week New England roadtrip itinerary actually has a two night stop in the town. However, before you arrive there are a couple of places to check out on the way!

The location of these are in  Waterbury . First, how can any trip to New England or Vermont be complete without visiting the iconic Ben & Jerry’s factory? Vermont is the birth place of this brand and you can take a tour of the factory along with a sample of one of the flavours.

After filling up on ice cream, head to potentially one of the best stops in Vermont –  Cold Hollow Mill  ! Here you can munch on fresh doughnuts as well as taste delicious cider straight from the mill. There is also the most amazingly fresh apple juice to try. Plus a great gift shop!

Afterwards head towards Stowe to have a wander and get to know the town.

Total driving time: 1 hour 30 minutes 

Where to stay: Little River Inn

Where to eat: Doc Ponds

Having stayed overnight in Stowe you are in an excellent place to head out to see the city of Burlington in the morning. This city isn’t the capital of Vermont, but is the most populated city of the state.

It still isn’t a large city, but Church Street is worth taking a look at. Full of independent shops and cafes, its great to wander down and get a feel for the place. Also check out the famous Lake Champlain. The chocolates named after this famous lake are also worth sampling!

In the afternoon head back to Stowe, as you will want to take some time to get to know this town a little better. Take the walk from behind the church towards the upper part of the town, for some beautiful views across the town. Stowe also has a ski resort to explore, so if you have time head to the other area of this town. As well as taking a ride on the gondola! Make sure you check out a covered bridge or two! Emily’s bridge, which she apparently haunts, or the red covered bridge at Cole Hill Road.

For even more covered bridge inspiration:  Covered bridges in Vermont you need to see!

Today is the day to leave Vermont and head into Maine! This will be the longest day driving, but worth it for the coastal scenes. The quickest and most direct way to get to Kennebunkport is on the I89 and then the I95. However, instead of taking the I95 take the coastal highway – U.S Route 1 for some amazing views. You also drive through some very pretty villages, so you might be tempted to take some stops to have a look around and stretch the legs.

Leaving Stowe early morning is recommended as this means you can arrive in Kennebunkport in time for lunch. And there is only one place you need to head to – the Clam Shack  for the famous lobster roll. Even recommended by George W. Bush.

Afterwards just take a wander around the town, browse the shops – definitely check out Minka, eat the delicious tiny doughnuts at Satellite Doughnuts , try the local gin and watch the tide come in under the bridge.

Total Driving time: 3 hours 30 minutes (4 if you want to drive through White Mountain National Forest).

For more information on what to see in Kennebunkport, take a look at this post:

14 things to do in Kennebunkport, Maine

Where to stay:   King’s Port Inn

Where to eat: Baston River – for food and for the local gin!

Before leaving Kennebunkport head to Gooch’s Beach to dip your toes in the ocean! It’s a long stretch of beach; amazing when the sun is out. Finally take a quick drive by President Bush’s house – obviously can’t get close!

After leaving Maine on the final full day in New England head towards Boston and return to Massachusetts! Bearskin Neck and Rockport is the absolute gem of a place to spend your final night. A beautiful town; so easy to wander around. For rom com fans – it is where The Proposal, featuring Ryan Reynolds and Sandra Bullock, was filmed.

Home to the famous Motif #1; a fishing shack located on Bradley Wharf.  Said to be the most painted building in the world; surrounded by lobster cages, it does have a traditional feel.

To note-  if you come out of season, a lot of the shops have closed for winter. However in summer through to the end of September most are open.

Worth mentioning that it is hard to buy alcohol. Not all the restaurants have licences and only one shop sells it. This is due to to Hannah Jumper whose ‘Hatchet gang’ raided Rockport establishments that sold alcohol, back in 1856. As a result of this Rockport became a dry town until 2005 when residents voted that alcohol can be sold in restaurants if having a meal. It wasn’t until 2019 that alcohol was allowed to be sold in shops, hence the lack of options! The one store that does sell it is the Crackerjacks Whistletop market in Whistlestop mall. Definitely worth buying a bottle and drinking it while watching the sunset – especially if your accommodation has a deck!

Total driving time: 1 hour 40 minutes

Where to stay:  Bearskin Neck Motor Lodge

Where to eat: Blue Lobster 

For your final day on your one week New England Roadtrip, options depend on the time of your flight. If you have an evening flight, this is the perfect day to check out Salem . Famous for the witch trails back in 1692. However, Salem has a much richer history than just these trails.

An excellent way to discover more, is to take a trip on the Salem Trolley Tours. To find out more about this take a look at this blog post on the Salem Trolley tours !

If you still have some time before your flight, this is the moment to head to Target to pick up all the incredible bargains and homeware items to your hearts content!

Total driving time: 1 hour 15 minutes

Final thoughts on this One Week New England Roadtrip itinerary

When visiting New England you have to make some choices about which areas you want to focus your time and attention on, particularly if you are restricted on time. It is such a large area, it would be near enough impossible to cover everything in a one week New England itinerary. The danger with this would be to spend too much time driving to try and cover large distances and then not have enough time to actually get to know the places you are visiting.

This one week New England itinerary focuses on Vermont but gives a little taste of Maine and Massachusetts as well. Striking the right balance between distance and time.

Have you been to New England? What were your highlights? I’d love to know for where to go next time! 

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The Glenfinnan Viaduct Viewpoint and the Train

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I love this region. Almost exactly 22 years ago, still in my 20’s, I took my then 15-yr old sister on a 10-day adventure. It was the first major trip I planned and scheduled all on my own. It was amazing and definitely anchored a love for travel for us both. We stayed in Lynn, suburb of Boston for a few days. Day tripped to Boston and Salem. Then drove to Mystic, CT for a few nights and day-tripped from there. Then stayed on the Cape for the remainder of the trip and saw as much of the island as we could. We whale-watched in Salem and Portsmouth, took haunted tours in Salem, saw the Amistad replica in Mystic and ate our weight in lobster rolls.

I’ve often thought about replicating that trip with all 3 of my sisters. Your post is fueling that fire! A wonderful piece.

Wow. I bet that was an amazing trip. And also giving me inspo for my next one! I will definitely be returning to this part of the world soon. I hope you make it back ASAP and I’m so pleased this post has inspired!

Great post.

Ahhhh Charlie I have been waiting to have proper time to get the lap top out and read this. I wanted to see the pics in full glory! I really want to visit this area of the US, and your trip sounds amazing. The photos alone have got me wanting to hop on the plane! Fab post and a great trip xx

Oh Kerry!!! Thank you so much. This post did feel like a labour of love, and the trip was one of my favs in for ever. So this really means a lot! Xx

Great post. The photos are epic. Cheers!!

Oh that’s so lovely! Thank you!

Omggg, this looks like such a cozy road trip! Definitely hope to do this someday. I still have so much to see in the north east! The clam shack just sounds so good too!

It was amazing!! Just felt so happy to be there!

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Unforgettable New England road trip

• Post last modified: March 18, 2024

Planning a road trip through New England ? Get to the heart of the United States ‘ most idyllic corner with this ultimate itinerary, where soothing nature, delightful towns and proud tradition abound. Buckle up — here are all the gems you don’t want to miss.

Disclosure: All listings are independently selected. If you buy something through our links, we may earn an affiliate commission. Learn more ›

New England route

• Start: Boston
• North Conway
• North Adams
• Stockbridge
• Finish: Boston

Begin with a salty trip up along New England’s coast, where Portland, Camden and Acadia NP are highlights. While Interstate 95 is usually quicker, consider sticking to the parallel, more scenic Route 1.

Then, the character of the itinerary changes dramatically. Head west to see the White Mountains, Green Mountains and Berkshires, with the lofty scenery peaking along the iconic Kancamagus Highway.

Back on the coast, explore Mystic, Newport and Cape Cod. Home to Cape Cod National Seashore, Cape Cod provides some of America’s best beaches, making for the perfect finish to your epic drive.

Isn’t Boston the optimal starting point for you? Feel free to start the loop at the location that suits you best.

• Total distance: 1,213 mi / 1,952 km
• Total driving time: 25 h

1. Boston, MA

Massachusetts ‘ largest city, Boston is certainly a convenient place to begin a Northeast road trip. There’s the well-connected Logan Airport and an array of rental car companies to choose from.

But — most of all — Boston is a fun city to explore before you get deeper into the New England itinerary.

If one thing to do in Boston is mandatory, it’s the Freedom Trail . Walking the 2.5-mile (4 km) path, which presents top historic sites in the heart of Boston, is a one-of-a-kind activity.

After touring Boston, you don’t have to like baseball to enjoy a visit to Fenway Park. In all honesty, many visitors don’t even know the baseball rules when they enter Fenway Park for the first time.

However, baseball is an American tradition, and the Red Sox is the team in Boston. Catching a game and feeling the atmosphere at Fenway Park is a memorable experience before heading north — baseball fan or not.

More info: Where to stay in Boston

2. Portland, ME

• Driving distance:  112 mi / 180 km
• Driving time:  2 h

On Maine’s southern coast, Portland offers a lot for anyone looking for a good time.

In particular, the historic Old Port — characterized by cobblestone streets, red-brick buildings, quaint wharves and fishing piers — is the crown jewel. While its facades remind you of past glory days, the district is a modern-day gold mine with eclectic boutiques, watering holes and restaurants.

Capturing at least one of the many lighthouses in the Portland area is also a must, and especially one stands out: Portland Head Light was completed in 1791, making it Maine’s oldest lighthouse.

3. Camden, ME

• Driving distance:  81 mi / 130 km
• Driving time:  1 h 45 min

Countless scenic towns hug Route 1. Camden may be the most picturesque of them all.

Picture a small town lacing an Atlantic cove (Penobscot Bay) with steep slopes (Camden Hills). If you’re short on time, stretch your legs while you browse the stores on the timeless Main Street or sit down in the Camden Amphitheater, a small oasis facing the harbor.

With more time, hike into the rising Camden Hills State Park. But if you don’t want to work for it, you can also drive up to the top of Mount Battie, brilliantly capturing the scenery.

4. Acadia NP, ME

• Driving distance:  77 mi / 124 km

Welcome to the only national park in New England, Acadia. Calling Mount Desert Island home, it encompasses some of the Atlantic’s most untamed coastline — this is one of the most beautiful places in the US .

Although you find awe-inspiring nature all over the island, the eastern half of Mount Desert Island holds most of the park’s big-ticket spots.

An unrivaled eastern highlight is Cadillac Mountain. The views of Acadia are just spectacular from Cadillac Mountain’s summit, both the tallest point of the park and the USA’s eastern seaboard.

Cadillac Mountain peaks at sunrise and sunset but is a beautiful experience throughout the day.

On Mount Desert Island’s quieter western half, another photogenic spot not to miss is Bass Harbor Head Lighthouse. Built in 1858 on the island’s southern tip, it’s not quite as old as Portland Head Light — but no less pretty.

More info: Where to stay near Acadia NP

5. North Conway, NH (White Mountains)

• Driving distance:  212 mi / 341 km
• Driving time:  4 h 15 min

New Hampshire ‘s White Mountains region is filled with great things to do, boasting both stunning natural beauty and cozy towns to relax in.

A shining example of the latter, North Conway is the perfect White Mountains gateway when you come from the east. From here, you effortlessly reach many highlights in the dense White Mountain National Forest.

Within a few miles, Diana’s Baths Cascade — a series of waterfalls dropping 75 feet (23 m) — is a spellbinding place. Another nearby stop is Cathedral Ledge Lookout, offering White Mountains vistas destined for Instagram fame.

When traveling further west, you unlock even more of the White Mountain National Forest.

Driving the famous Kancamagus Highway — one of New England’s most scenic drives — is a jaw-dropping experience. As it runs from Conway to Lincoln, it also takes you right to your next base on the itinerary.

6. Lincoln, NH (White Mountains)

• Driving distance:  41 mi / 66 km
• Driving time:  1 h

Ready for more gorgeous terrain? At the end of the scenic Kancamagus Highway, Lincoln is a practical White Mountains gateway for highlights in the western part of White Mountain National Forest.

The Flume — a natural gorge offering a scenic pool, stunning waterfalls and, of course, mesmerizing White Mountain views — was discovered in 1808 by Jess Guernsey. She came upon it by accident while fishing in the Lincoln area.

After the finding, as the story goes, Jess first had trouble convincing her family about the discovery. It just sounded too magical to be true — but the rest is history.

Today, the Flume is a highlight in Franconia Notch State Park. You find a good variety of hiking trails in Franconia, letting you explore the White Mountains and its dense forests, stunning lakes and majestic peaks further.

7. Stowe, VT (Green Mountains)

• Driving distance:  85 mi / 137 km

A Vermont village with a postcard-worthy downtown area, Stowe sits at the foot of the Green Mountains.

Just strolling down Main Street in Stowe is an appreciated thing to do. It’s a small town, but thanks to its peaceful aura, a walk couldn’t be more rewarding.

When visiting Stove, you’re never far from fresh air and beautiful views. Stowe Recreation Path provides a convenient way to explore Stowe and the village’s lovely surroundings.

Walk, run or bike the paved trail — just be prepared that you will want to stop to take pictures.

Not in Stowe, but just a short drive away, you find the ice cream lover’s dream. Be careful so you don’t get a brain freeze at the original Ben & Jerry’s ice cream factory in Waterbury.

Extra stop: Consider stopping in Burlington, VT, a fun city on the shore of Lake Champlain. Because it’s just 36 miles (58 km) between Stowe and Burlington, you can easily include both on your New England itinerary.

8. North Adams, MA (The Berkshires)

• Driving distance:  159 mi / 256 km
• Driving time:  3 h 15 min

It’s the rolling hills and captivating culture that define The Berkshires region. Marking its northern end, where Vermont meets Massachusetts, North Adams is a great place to start exploring.

Be inspired by evocative galleries and performances at the Massachusetts Museum of Contemporary Art, set on the Hoosic River in downtown North Adams.

Or, simply cruise onwards, letting the peaceful landscape wash over you. North Adams sits along the Mohawk Trail, one of New England’s most scenic drives, finishing in nearby Williamstown.

9. Stockbridge, MA (The Berkshires)

• Driving distance:  35 mi / 56 km

America’s favorite illustrator, Norman Rockwell called Stockbridge home for 25 years. Here, with hundreds of original works, the Norman Rockwell Museum honors and showcases his legacy.

Before Rockwell, the writer Edith Wharton lived in the Berkshires, too. Visit her historic Lenox residence, the expansive Mount Home (maybe on your way from North Adams to Stockbridge), to learn and absorb the idyllic setting.

These are cultural treasures, but don’t forget that what makes the Berkshires outstanding is the mix of culture and nature.

For hiking, a beautiful spot is October Mountain State Forest . At roughly 16,500 acres, it’s Massachusetts’ largest state forest, offering both easy and strenuous trails.

More info: Where to stay in The Berkshires

10. Mystic, CT

• Driving distance:  127 mi / 204 km
• Driving time:  2 h 15 min

On the Connecticut coast, the village of Mystic peacefully sits. Get ready to discover its proud history as a waterside community and center for shipbuilding.

By the Mystic River, Mystic Seaport Museum is one of the USA’s leading maritime museums, preserving an array of seafaring artifacts. Enjoy an impressive collection covering 19 acres, with four National Historic Landmark vessels as the biggest draws.

Compact Historic Downtown Mystic has you covered for authentic shopping, diverse eateries and charming waterfront views. Especially pay attention to the Mystic River Bascule Bridge, a still-in-use drawbridge — nowadays a rare sight.

Extra stop: An alternative to Mystic or an additional stop on the itinerary is New Haven, CT, the home to the famous Yale University.

11. Newport, RI

• Driving distance:  48 mi / 77 km

The shore of Rhode Island is an essential ingredient on your New England road trip itinerary. On Aquidneck Island, Newport is an old colonial city with attractions covering a wide spectrum.

Walking the renowned Newport Cliff Walk, 3.5 miles (5.6 km) long, is a beautiful way to appreciate the Atlantic coast. Tracing Newport’s rocky coastline, it offers stunning natural scenery and fresh salty air.

As a bonus, eye-popping mansions frame the trail.

For the full experience, take a Newport Mansion tour to see how America’s wealthiest and most influential families used to live. The Breakers stands out for its extreme luxury, but the Elms and Marble House are also impressive.

More info: Accommodation in Newport, RI

12. Cape Cod, MA

• Driving distance:  120 mi / 193 km
• Driving time:  2 h 30 min

These 120 miles (193 km) take you all the way to the northern tip of Cape Cod , a peninsula separated from the mainland by the Cape Cod Canal since 1914. Be sure to make plenty of stops along the way.

Cape Cod Rail Trail, excellent for walking or biking, presents a healthy way to sightsee. Paved and extending for 25 miles (40 km) from South Yarmouth to Wellfleet, it follows the 19th-century rail lines that used to carry tourists to Cape Cod.

At the trail’s end, the landscape of Cape Cod National Seashore takes over. Hang out on the seemingly never-ending beach — seals thrive in the waters here — or hike around marshes and ponds.

The finish every peninsula should have, Race Point Beach, as far north as you get, is a phenomenal beach with huge sand dunes. On a sunny day, you might ask yourself: Is this Massachusetts or Florida?

More info: Best areas in Cape Cod

13. Boston, MA

• Driving distance:  116 mi / 187 km

It’s time to round off your unforgettable New England road trip. The last leg is the drive back to where the adventure started, Boston. From the isolated Provincetown, it’s 116 miles (187 miles) to Boston, but it’s shorter if you base yourself elsewhere on Cape Cod.

Where to stay when you road trip through New England

New England takes pride in its atmospheric, often historic inns. Consider making your road trip even better by booking one of our favorite places to stay on Cape Cod.

Appreciate the English Country style at the Old Harbor Inn , a luxurious bed and breakfast set in Chatham. Each of the twelve rooms is unique and the location spot-on for day trips across Cape Cod.

Or, stretch your budget by staying at the Breakwater Hotel , slightly outside Provincetown, at Cape Cod’s northern tip. Drive 5 minutes or walk 30 minutes to get to Provincetown’s heart.

New England itineraries with days

For the full New England road trip, we recommend allowing at least 3 weeks. If you have less time, it’s a good idea to break up the itinerary to focus on your favorite parts.

Ultimate itinerary (3 weeks)

• Day 1-3: Boston (2 nights)
• Day 3-5: Portland (2 nights)
• Day 5-8: Acadia NP (3 nights)
• Day 8-10: North Conway (2 nights)
• Day 10-12: Lincoln (2 nights)
• Day 12-14: Stowe (2 nights)
• Day 14-15: The Berkshires (1 night)
• Day 15-16: Mystic (1 night)
• Day 16-18: Newport (2 nights)
• Day 18-21: Cape Cod (3 nights)

2 week road trip (Atlantic coast)

• Day 1-2: Mystic (1 night)
• Day 2-4: Newport (2 nights)
• Day 4-7: Cape Cod (3 nights)
• Day 7-9: Boston (2 nights)
• Day 9-11: Portland (2 nights)
• Day 11-14: Acadia NP (3 nights)

7 day road trip (Mountain trip)

• Day 1-4: White Mountains (3 nights)
• Day 4-6: Green Mountains (2 nights)
• Day 6-7: The Berkshires (1 night)

New England road trip FAQ

This ultimate New England road trip is 1,213 miles (1,952 km) long, taking 25 hours excluding the time you need for the stops along the way.

The journey includes six states: Massachusetts, Maine, New Hampshire, Vermont, Connecticut and Rhode Island.

The main stops on the itinerary are Boston, Portland, Acadia NP, White Mountains, Green Mountains, The Berkshires, Mystic, Newport and Cape Cod.

For the full loop, we recommend allowing 3 weeks or more. But you can break the itinerary up and enjoy a shorter journey, too, for example, focusing on the coast or the mountains.

With 7 days, it’s as good idea to concentrate on a certain area. To see both a lively city and New England’s timeless coastal environment, a popular combo is Boston and Cape Cod.

More New England guides

• Cape Cod vacation guide
• Where to stay in Cape Cod
• Lodging near Acadia NP
• New England bucket list

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The Ultimate New England Road Trip Itinerary

Get acquainted with the birthplace of America on a New England road trip. Discover the quaint coastal towns, famous historical landmarks, and spectacular scenic drives the area has to offer. Our trip includes additional states, but the bulk of our itinerary is in six states: Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Vermont.

It’s for 60 days, starting and ending in Chicago and driving roughly 2,500 miles, but you can adjust it to your liking. Visit one national park, too-many-to-count lighthouses, a few state parks, picturesque small towns, and overindulging on copious amounts of seafood along the way.

If you are looking for more unforgettable adventures, check out these trips: Chicago to L.A. via Route 66 , hiking 500 miles on the Camino in Spain , and a cross country road trip to thirteen national parks.  

When to Visit New England

From our experience and research, there really is no bad time to visit New England. Each season brings something unique to the table.

Winter is cold and snowy but perfect for winter activities such as skiing and snowboarding. The thawing temperatures of spring bring wildflowers and maple syrup. Summer is known for its hot weather and sunny days filled with outdoor adventures. And last but not least, fall welcomes a blanket of blazing colored treetops and great hiking temperatures.

WAIT UNTIL YOU READ WHAT WE HAVE PLANNED! SCROLL DOWN FOR MORE INFO

One of the Top Spots for Fall Foliage in the U.S.

So why did we choose New England this trip? We have had an east coast road trip on our radar for quite some time and especially wanted to visit during the fall. It is touted as one of the best locations for fall foliage in the United States.

Donned in our heavy sweaters as autumn unfolds with rich colors of crimson and gold with the smell of fire and a hint of pumpkin spice floating in the air, I can’t imagine a better time.

Hopefully, from mid-September until the end of October, we will be leaf peeping fools.

Ultimate New England Road Trip Itinerary Summary

Keep Scrolling for our detailed New England Self Drive Itinerary.

Summary starting and Ending in Chicago, Illinois

• Put-in-Bay, Ohio (2 nights)
• Erie, Pennsylvania (1 night)
• Watkins Glen State Park, New York (3 nights)
• Litchfield, Connecticut (1 night)
• Hartford, Connecticut (2 nights)
• New Haven, Connecticut (1 night)
• Niantic, Connecticut (1 night)
• Mystic, Connecticut (2 nights)
• Block Island, Rhode Island (1 night)
• Portsmouth, Rhode Island (2 nights)
• Providence, Rhode Island (2 nights)
• Provincetown, Massachusetts (1 night)
• Falmouth, Massachusetts (1 night)
• Martha’s Vineyard, Massachusetts (3 nights)
• Plymouth, Massachusetts (1 night)
• Salem, Massachusetts (1 night)
• Hampton Falls, New Hampshire (1 night)
• Kennebunkport, Maine (1 night)
• Acadia National Park / Bar Harbor (8 nights)
• Bangor, Maine (2 nights)
• Baxter State Park, Maine (3 nights)
• Lily State Park, Maine (2 nights)
• White Mountains, New Hampshire (6 nights)
• Burlington, Vermont (2 nights)
• Stowe, Vermont (2 nights)
• West Dover, Vermont (7 nights)
• Buffalo, New York (1 night)
• Chicago, Illinois

Day 1: Chicago, Illinois to Put-In-Bay, Ohio

We leave Lake Michigan to head over to Lake Erie, the southernmost lake of the Great Lakes. It is also the shallowest which makes its water temps the warmest.

Our first stop is Put-In-Bay, a small village on South Bass Island. Known for its party-hearty culture, we are determined to not only imbibe a bit but also to discover the hidden gems on the island.

Driving Info: 279 miles, 5 hrs 20 minutes with a ferry ride

READ NEXT: TOP 10 THINGS TO DO IN PUT-IN-BAY

Day 2: Put-In-Bay, Ohio to Erie, Pennsylvania

We were beckoned to drive along the Lake Erie coast when we visited Cleveland a few years ago but didn’t include the ride on that trip. Up the waterline, we go, as we leave Put-In-Bay to explore the small towns and lighthouses along the way.

Who knew Pennsylvania has a sliver of land right on the lake? We stop for the night at Presque Isle State Park, a small park on a sandy peninsula that juts into Lake Erie. If you are interested in renting an RV and starting in Pennsylvania, check out RV Rental Philadelphia, the largest, most trusted RV Rental marketplace with a wide-ranging inventory.

Driving Info: 190 miles, 3 hrs 45 minutes with a ferry ride

RELATED: COOL STOPS ALONG OHIO’S LAKE ERIE COASTAL TRAIL

Days 4 – 6: Erie, Pennsylvania to the Finger Lakes, New York

The Finger Lakes region in New York is known for a series of pristine lakes and beautiful vineyards. The area is also home to a number of hiking trails, breweries, distilleries, and hard-cider producers.

Driving Info: 198 miles, 3 hrs 15 minutes

READ MORE: 3 DAY FINGER LAKES ITINERARY

Day 7: Finger Lakes to Litchfield Hills, Connecticut

Ever heard of the television show, Gilmore Girls ? Today, we reach our first New England state, Connecticut, where the fictional town of Stars Hollow was based on. We are touring the northwest hills in search of magical towns like Washington, New Milford, Bantam, and Litchfield which inspired the creators of the show.

Driving Info: 297 miles, 5 hrs

RELATED: A CONNECTICUT BUCKET LIST FOR YOUR NEXT TRIP

Days 8 & 9: Litchfield Hills to Hartford, Connecticut

And we are off to the state capital of Hartford, one of the oldest cities in the United States. Founded in 1635, we are bound to find some historical places to visit. A few on the list so far are Trinity College, Wadsworth Art Museum, and Bushnell Park.

The one I’m most excited about is the Mark Twain House where he wrote some of his most famous works and raised his family.

Driving Info: 32 miles, 50 minutes

Day 10: Hartford to New Haven, Connecticut

Let’s make our way to the water again, New Haven is situated along the Long Island Sound in southern Connecticut. It’s the first planned city in America and home to Yale, one of the oldest universities in America.

Oh and apparently, home to some of the best pizza in the country. This Chicago-born Midwesterner writes with a probably-not-side-grin. But hey, you never know!

Driving Info: 39 miles, 40 minutes

Day 11: New Haven to Niantic, Connecticut

On our way to Mystic, we plan to take a leisurely drive along the coast to dip in any beach towns with a view. At lunch, we will find our first lobster roll of the trip. The word on the street is that Connecticut’s rolls are not made with mayo, just butter and a squeeze of lemon so it’s a must-try.

Driving Info: 42 miles, 45 minutes

Days 12 & 13: Niantic to Mystic, Connecticut

Never did I imagine a New England road trip would have me hunting down pizza, but stopping at Mystic Pizza is a MUST in my eyes. My love for Julia Roberts isn’t the only reason we are stopping here, the seaside village is brimming with charm and boasts the nation’s largest maritime museum.

Driving Info: 18 miles, 25 minutes

Day 14: Mystic to Block Island, Rhode Island

With a declaration from the Nature Conservancy that Block Island is one of its “Last Great Places,” it was a given that we were going to zip our way over once we cross into Rhode Island. As if dramatic rugged bluffs weren’t enough to put us over the edge (literally and figurately), the 365 freshwater ponds and rolling green hills had us hooked.

Driving Info: 54 miles, 2 hrs 15 minutes with a ferry ride

Plan Your Trip Here: Amazing Things to Do on Block Island

Days 15 & 16: Block Island to Portsmouth, Rhode Island

Portsmouth is our base location for exploring the grandeur Newport Mansions of the social elite like the Vanderbilts and Astors. Ah, the Gilded Age, when the rich were rich and wanted everyone to know it.

After a few tours such as the Biltmore Estate and  Stan Hywet Hall and Gardens, we’ve become obsessed with these over-the-top homes. We can’t wait to stroll the Cliff Walk, a 3.5 mile National Recreation Trail that hugs the Newport shoreline offering gorgeous coastline and mansion views.

Driving Info: 46 miles, 2 hrs 11 minutes with a ferry ride

How to Choose the Best Newport Mansion Tour

Days 17 & 18: Portsmouth to Providence, Rhode Island

Cheers to hitting another state capital! Providence is the cultural hotspot of New England. With a vintage feel in a college town and the most coffee and doughnut shops per capita of any city in the country, I’m sure we’ll keep busy, or at least our mouths will.

Driving Info: 29 miles, 32 minutes

Day 19: Providence, Rhode Island to Provincetown, Massachusetts

Onward to the Cape! Cape Cod that is. And it is here where we will have one of the most anticipated experiences of the trip, a whale watching tour!

Situated at the tip of Cape Cod, Provincetown is a quirky artsy area that also happens to be a jumping point for whale watching tours.

Driving Info: 120 miles, 2 hrs 12 minutes

Day 20: Provincetown to Falmouth, Massachusetts

Today is a day for moseying around the island stopping at captivating waterfront villages and maybe a local food shack or brewery. Since we brought our bikes, we will roll onto the Shining Sea Bikeway, a 10.7-mile path that runs from the coast in Falmouth to Woods Hole and then past to North Falmouth. 

Overnight is at Falmouth so we can get an early ferry over to Martha’s Vineyard.

Driving Info: 68 miles, 1 hr 35 minutes

Days 21 – 23 Falmouth to Martha’s Vineyard, Massachusetts

Just south of Cape Cod and a short ferry ride away sits Martha’s Vineyard, a presidential getaway in my mind. I picture snazzy inns, upscale boutiques, and perfect stately homes; ritzy glamour degraded by the simplicity of the beach… where I will tell no one that our minivan turned campervan awaits us back on the mainland. Read here about all the fun things to do on Martha’s Vineyard Island. 

Driving Info: 19 miles, 1 hour 15 minutes with a ferry ride

Day 24: Martha’s Vineyard to Plymouth, Massachusetts

Advancing north, stop for an overnight at the first Pilgrim settlement, Plymouth, where I’m sure you will have mixed emotions about the small rock that marks the spot.

But the iconic landmark is not what keeps visitors coming back for more.

Driving Info: 55 miles, 2 hrs

Day 25: Plymouth to Salem, Massachusetts

If you haven’t heard of the Salem witch trials then you may be living under a rock. Plymouth rock, perhaps.

Salem is not shy about its history where the word “witch” is displayed all over town. It shouldn’t come as a surprise that a witch museum, cemetery and a house with a supernatural past are on our itinerary.

Driving Info: 64 miles, 1 hr 17 minutes

Day 26: Salem, Massachusetts to Hampton Falls, New Hampshire

Clutching the coast, swing past Manchester-by-the-Sea, Gloucester, Rockport, and Newburyport before crossing over to the next state of New Hampshire.

Make sure to detour to the Hammond Castle Museum, an exotic castle built in the early 1900s by an inventor.

Driving Info: 32 miles, 45 minutes

Day 27: Hampton Falls, New Hampshire to Kennebunkport, Maine

At 18 miles long, New Hampshire’s coastline is short-lived so progress to the state of Maine. It’s hard to believe you’ve hit five of the six New England states already!

Kennebunkport is going to be all about seafood, boats, and shopping.

Driving Info: 43 miles, 50 minutes

Days 28 – 35: Kennebunkport to Acadia National Park, Maine

It’s time for some hiking and biking! Park it in Acadia National Park for at least four days (more if you can swing it) because you’ll be in awe of the beauty around you.

Cadillac Mountain, Sand Beach, Bar Harbor, and Park Loop Road are just a few things on the list of things to see. 

Read about one of the most thrilling hikes in the Northeast that you’ll find within the park. 

Driving Info: 201 miles, 3 hrs 30 minutes

Days 36 & 37: Acadia National Park to Bangor, Maine

The main reason for our weekend in Bangor is to visit with friends, but items like a Stephen King’s house and the world’s largest Paul Bunyan statue might have you putting it on your itinerary as well.

Driving Info: 50 miles, 1 hr 15 minutes

Days 38 – 40: Bangor to Baxter State Park, Maine

Baxter State Park is home to Mount Katahdin and the end of the 2,168-mile Appalachian Trail. Take a few days to explore and hike to the peak of the highest mountain in Maine at 5,270 feet.

Driving Info: 88 miles, 1 hr 35 minutes

RELATED: SEE OUR FAVORITE FREE CAMPING APPS

Days 41 & 42: Baxter State Park to Lily Bay State Park, Maine

At Lily Bay State Park, you’ll find what’s often referred to as Maine’s crown jewel, Moosehead Lake, the largest lake in New England.

It is also known to sprout some bright fall colors and is a great area to spot moose.

Driving Info: 51 miles, 1 hr 35 minutes

Days 43 – 48: Lily Bay State Park, Maine to White Mountains, New Hampshire

The Kancamagus Highway, a 34-mile road through the heart of the White Mountains, is one of the best drives for fall foliage in the United States.

No stores, no houses – just forest; the scenic byway stretches from Lincoln to Conway.

Driving Info: 205 miles, 4 hrs 25 minutes

Days 49 & 50: White Mountains to Burlington, Vermont

Along the shores of Lake Champlain sits a vibrant city with a thriving arts scene and welcoming atmosphere. Vermont’s largest city, Burlington, has a little bit of everything.

Driving Info: 2 hrs 20 minutes

Days 51 & 52: Burlington to Stowe, Vermont

The birthplace of the infamous Heady Topper Beer from The Alchemist Brewery and a stone’s throw away from Ben & Jerry’s factory, I think I’m going to start calling Stowe, the adult playground of Vermont. 

Driving Info: 36 miles, 46 minutes

Days 53 – 59: Stowe to West Dover, Vermont

From Stowe, take the well-known Highway 100, another popular fall foliage route in New England, down along the Green Mountains.

Hopefully, those green mountains will be lit up with scarlet reds, glistening golds, and tangerine orange.

Driving Info: 147 miles, 2 hrs 41 minutes

Day 60: West Dover, Vermont to Chicago, Illinois

At this point in the trip, you could take an extra night to stop at the one and only Niagara Falls in New York. Otherwise, that’s a wrap folk!

60 days and a whole lotta unforgettable memories!

TIP: For those of you that would like to close the loop, head further south to the Berkshires of Western Massachusetts. A popular destination for fall foliage, cultural attractions, and outdoor fun. 

Driving Info: 13 miles, 13 hrs 36 minutes

See Below for a Map of the New England Road Trip Itinerary.

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Do you have any additions to our New England road trip itinerary? Let us know in the comments below!

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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

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13 Responses

So, I’m a fan of this trip. You had me at Gilmore Girls, Mystic Pizza and then solidified how much we are connected with Salem and Bangor.

I have wanted to do a Fall Foliage trip like this forever. I think I might try to make this happen one year…soon. I can’t wait to see your photos on the IG.

Dang Travelers

It has been on our list of places to get to for awhile now so we are ecstatic to finally be making it happen. I’m cracking up because when I (Angela) was making the itinerary I totally watched a few Gilmore Girls episodes and the movie, Mystic Pizza to get pumped! Leaving the GG reference out to Save though. He didn’t know that’s why I planned that area until a few days ago! LOL We will get started on all your planning so all you have to do is find the time. Thanks for following Kristi!

You didn’t include Mt. Washington and the cog railway. You should try to hit they in!!! I think you’re gonna love Block Island, Burlington, Acadia. The coast of ME. Mystic is nice. Portsmouth, RI has a ride the rails along the waterfront. Check that out. Too bad you are missing Boston!

We will be hitting Mt Washington in the White Mountains but didn’t know about the cog railway! So excited to explore Rhode Island and Connecticut or shall I say #47 and #48 of my states list. Dave really wanted to go into Boston but figured we could do it on another trip when we fly in. Always expensive and difficult to worry about parking in big cities but othwrwise we would have loved to. Thanks for the tips Cheryl!

Your trip sounds awesome. I cannot wait for all the pictures and to hear all about it. I would make a detour in Maine and stop in Freeport, Maine and go to LL Bean store. It is an absolute must see. It is open 24 hours (at least it used to be) and there are 9 floors and each one is better/more exciting then the next. It isn’t just clothes either. My husband enjoyed it as well and he isn’t a shopper.

Top Things to Do on Block Island: A Travel Guide – Dang Travelers

[…] SEE OUR ENTIRE 60 DAY ITINERARY […]

Found your trip itinerary and will definitely be putting it to use! Not too often do you find trips starting in the Midwest! I just went through and copied and pasted all the trip info you suggested. Or is there a printable version of this that I completely missed somewhere? Thanks so much for sharing!

Hi Nicole! I do not have a downloadable itinerary as of right now. Sorry, hopefully copying worked just fine. You’ll love it out east!

Cheryl Archambault

For anyone wanting to specifically see the foliage start in farthest north of New Hampshire generally around the 3-4 week of September. Foliage is peak around Concord during Columbus Day Weekend; but cool or rainy weather can change that. Encourage you to take a jacket and go up the Cog Railway to the top of Mt. Washington. It could be covered in snow there! In Rhode Island Block Island is lovely. Ferries leave from Pt. Judith or Newport. Newport is lovely and don’t miss seeing Waterfire in Providence. Acadia National Park and Bar Harbor and Boothbay is wonderful. East to west Vermont in Fall is a dream. Rte2 is a very scenic ride.

Thanks so much Cheryl!

my husband & I want to do an abbreviated version of your trip. What time of year did you do this trip? I have heard Sept is the best time for lobster but Oct is the best time for foliage.

We started right after labor day in September but took about 3 months. That year the fall color was starting to come in late September and lasted through the third week of October. Inland and lower elevations started earlier with Acadia National Park at peak around the second week of October. Unfortunately, every year is different so it’s hard to get it just right when planning ahead of time!

Thank you for the itinerary. It is a great start for me. I don’t have quite as much time but I hope I can get to a lot of the highlights as I’m starting from Virginia.

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7 Day New England Road Trip Itinerary: The Perfect Fall Getaway

This post may contain affiliate links, meaning if you buy or book through one of these links, I may earn a small commission .

Have you been dreaming of witch trials sites, fiery maple trees, and scenic rural drives? For fall lovers, one week exploring the vibrant foliage of New England is the ultimate bucket list experience. An adorer of autumn myself, I wrote the perfect 7 day New England road trip itinerary to fulfill your leaf peeping dreams.

This itinerary is inspired by my own road trip through New England last year, which included New Hampshire, Vermont, and Massachusetts. Although my home state of Ohio has gorgeous falls too and I’d already seen Massachusetts at peak coziness, I yearned to more deeply explore the hilly forests and farmland of the Northeastern United States. Sneaking in a lobster roll or two while revisiting Massachusetts wouldn’t hurt either!

New England’s compactness makes it easy navigate, while offering charming small towns, rewarding hiking trails, and coastal views. As this road trip covers three states, I’ve carefully planned this itinerary for the most efficient New England sightseeing route. Are you ready to get witchy in Salem, MA and cozy in Woodstock, VT? Let’s get into it.

Ultimate 7 Day New England Road Trip Itinerary

I have mapped out the below itinerary to further ease your navigation between these amazing New England destinations.

Related: 61 Awesome Bucket List Ideas for Your Best Fall Ever

Day 1: Massachusetts – Arrive Into Boston

This 7 day New England road trip itinerary kicks off in Boston, whose urban streets transform under autumn’s spell, particularly in the Beacon Hill neighborhood. If you are flying, you’ll land at Boston Logan International Airport, so grab a 10-minute Uber/Lyft into the city. Arriving either in the morning or the night before allows you to have a full day of sightseeing what they call “Beantown” .

The best thing to do during one day in Boston is to follow the Freedom Trail past sites significant to Boston’s Revolutionary War history. Either join a guided tour or simply follow the red line on the pavement from Boston Common. This self-guided app also provides an informative tour at your own pace.

Afterwards, stroll the boutiques and cobblestone streets of Beacon Hill or consume seasonal treats on the Underground Donut Tour .

Finish by dining at one of many Italian restaurants in Boston’s North End before turning in for the night. Don’t forget to stop in for a cannoli at Modern Pastry or a Boston cream donut at Bova .

Craving a spooky experience, but tired of walking? Take this Boston Ghosts and Gravestones Trolley Tour .

Suggested Stay: Courtyard by Marriott Boston Downtown/North Station

Day 2: Massachusetts – Salem, MA

No single 7 day New England itinerary would be complete without a visit to the Witch City, or Salem, MA, where the infamous 1692 witch trials took place. To make the 45-minute drive from Boston, pick up your rental car the morning of day two (we rented ours at the airport).

Note: If visiting during the super busy month of October, get into Salem by 9am to ensure you find parking and avoid traffic jams. An alternative is to stay in Boston for one more night and take a 30-minute train or ferry into Salem . I recommend booking a room at Courtyard by Marriott Boston Downtown/North Station to be close to both the train and Freedom Trail.

Here is the best way to spend one day (also consider following my Salem day trip itinerary ):

• Visit the Salem Witch Museum (purchase a timed entry ticket online)
• Stop into the Salem Witch House
• Stroll past the wand shops, fortune tellers, and apothecaries of Essex Street
• Take a spooky witch trials walking tour

For a nice dinner with lots of ambiance, dine at Ledger Restaurant . For less fuss and laid-back vibes, get a lobster roll and beer at The Lobster Shanty ; they serve delicious clam chowder too!

Suggested Stay: In Salem at the Hampton Inn Salem Boston or in Boston at the Courtyard by Marriott Boston Downtown/North Station

Related: 13 Best Things To Do In Salem , MA In October

Day 3: New Hampshire – Artist Bluff Trail

It’s time to get out of the city and into the White Mountains of New Hampshire, which deliver sweeping views over fall’s colorful tree canopies. On the morning of day three, depart from Massachusetts and drive about two hours north to Lincoln, New Hampshire. While there are plenty of hotels in and around Lincoln, you may opt to stay in a cozy cabin instead.

Recommended Hotel: Holiday Inn Express & Suites Lincoln East – White Mountains

You can find cabins all around the area, so I recommend doing a search on Airbnb and seeing what’s available during your travel dates. My husband and I stayed in this adorable dog friendly cabin in Wentworth, New Hampshire last year, where the stargazing looked like a sheet of glitter over the sky.

After settling in, it’s time for your first hike of the trip: the 1.5-mile Artist Bluff Trail in Franconia State Park. This steep loop trail leads to panoramic views over the fiery-colored treetops framing Echo Lake. For less climbing, take the Cannon Mountain Aerial Tramway just one mile away, which lifts you 4,080 feet to the peak of Cannon Mountain.

If you still have time and energy, also consider hiking the gorgeous two-mile Flume Gorge loop trail , which follows along an 800-foot natural gorge at the base of Mount Liberty. Just remember this trail has an entry fee of $18 online ( book here ) and $21 at the trailhead.

After hiking, visit a local brewery, like Rek-Lis Brewing Company , for dinner and drinks. As we were staying closer to Plymouth, NH, we stopped into Sole Track Brewing to share a tasting paddle. For dinner, we grabbed burgers at The Last Chair , a ski-themed brewery that had tasty burgers and peanut butter porter.

Day 4: New Hampshire – Kancamagus Highway

The next day in New Hampshire, you will experience the state’s most iconic leaf peeping adventure: the Kancamagus Highway . This 34.5-mile stretch of roadway between the towns of Lincoln and Conway leads past beautiful mountainscapes and other gorgeous natural scenery.

Keep in mind there are no gas stations along this route, so fill up before heading out. Also, you must pay $5 per day to park in White Mountain National Forest . You can simply put the cash or check in an envelope to leave at a drop box at the first stop along the highway.

Don’t be afraid to pull over frequently along the Kancamagus Highway. Otherwise, this enchanting stretch only takes about one hour to complete without stops.

Here are the must-see sights along the Kancamagus Highway, in order heading east:

• Otter Rocks
• Hancock Overlook
• Panoramic Overlooks
• Pemigewasset Overlook
• CL Graham Wangan Overlook
• Sugar Hill Scenic Vista
• Sabbaday Falls: Most popular hike along the way, only .5 mile trail that leads to a waterfall
• Russell-Colbath House
• Campney Fall: 3.1 miles out and back, .6 miles additional miles to reach the summit of Mount Chocorua, which has gorgeous 360-degree views
• Rocky Gorge: lovely in fall and nice place to picnic
• Lower Falls: this super short hike to a waterfall is the most popular stop of the drive
• Albany Covered Bridge

Stay overnight near Lincoln, NH again. If you are staying in a cabin, consider having a cookout or bonfire to make s’mores!

Otherwise, dine out at Moat Mountain Smokehouse and Brewery in North Conway before turning back to drive the Kancamagus Highway in reverse. You could also visit Woodstock Inn Brewery in North Woodstock upon completion of the drive.

Day 5: Vermont – Woodstock

The next morning, it’s time for the last leg of your trip: the friendly small towns of Vermont where even the automated speed signs scold you politely.

The drive to charming Woodstock (the one in Vermont, not New Hampshire) will only take about and hour and a half from Lincoln, NH. You could stay in a hotel in Woodstock or simply book an Airbnb in the surrounding area (we loved this adorable hobby farm ).

Recommended Hotel: The Village Inn of Woodstock

This route around Woodstock will be the delight of any 7 day New England road trip itinerary:

• Quechee Gorge: Visible from an overpass along Route 4, this 165-feet gorge (Vermont’s deepest) was formed by glaciers 13,000 year ago. You can park in a lot off Route 4 to quickly view the gorge or hike the Quechee Gorge Trail at Quechee State Park .
• The Skinny Pancake : A great breakfast/brunch stop in Quechee. I loved my savory crepe with apple, brie cheese, and a locally sourced blueberry compote.
• Woodstock: Explore the antique shops, cafes, and lovely covered bridges of this charming small town. Don’t forget that all parking is paid – even along the street!
• Billings Farm and Museum : For $17 you can explore the grounds and stables of this working farm tucked among the rolling hills. I purchased a small apple cider to sip as I strolled past dairy calls being milked, goats perched on top of fences, and horses grazing. Check their calendar for daily events.
• Woodstock Farmers Market: The perfect stop for locally produced products, like cheese and maple syrup.
• President Calvin Coolidge Historic Site : The site of several preserved buildings from Calvin Coolidge’s childhood home at Plymouth Notch, including his family homestead. Also see where the 30th president of the United States attended church, his father’s store, the post office, and Coolidge’s summer white house office inside of a dance hall.

Make a reservation to dine in downtown Woodstock at The Prince & The Pauper Restaurant or Santé .

Travel Savvy Tip

With the rise of social media, certain farms around the Woodstock area have become popular photo spots for Instagrammers. Sadly, this has escalated into a problem for local residents, with visitors clogging roads and trespassing onto private property.

Local governments have begun taking action, closing roads leading to Jenne Farm and Sleepy Hollow Farm during the month of October. Please respect these rules – there are plenty of other gorgeous locations all around Vermont to photograph!

Day 6: Vermont – Grafton

To get a true small town Vermont experience, drive one hour south of Woodstock to the tidy little village of Grafton. Grafton is especially pleasing during peak foliage season, when bright shades of red, orange, and yellow frame tall white church steeples and local shops.

However, don’t confuse Grafton’s impressive collection of well-preserved historic buildings for an open-air museum. This is a functioning, tight-knit community that still holds Gilmore-Girls-style town meetings to this day.

Just be sure to download any maps before heading out, as I found the town’s cell service to be weak to nonexistent.

Here are the best points of interest to check out in Grafton’s quaint and walkable town center:

• Learn about making maple syrup at Plummer’s Sugar House before buying some to take home with you.
• Hike a trail at the Grafton Trails & Outdoor Center . Grafton also has a cute welcome sign a bit further south down Grafton Road.
• Journey to the past at the Grafton Historical Society.
• Sample local cheese varieties at the Grafton Village Cheese Company .
• Browse locally produced gifts and home goods at Mercantile and adjacent Dover House Antiques.
• Wander into the Turner Hill Interpretive Center to learn the story of Alec Turner, who settled in Grafton and to raise his family after escaping slavery.
• Check out the Nature Museum to learn about native New England flora and fauna and wander down various nature trails.
• Discover unique copper sculptures honoring Northeastern Native Americans at Jud Hartman Gallery .

If you get hungry, the Grafton Village Store has you covered for coffee, pastries, and simple meals. For a sit-down dinner, book a reservation at the rustic Phelps Barn Pub or the cozier 1801 Tavern at The Grafton Inn .

Day 7: Complete Your New England Road Trip Itinerary at Boston Logan Airport

Just as the leaves must eventually fall to the ground, this New England road trip itinerary must reach its end too. Hopefully you had the fall foliage experience you’ve been dreaming about and are already planning your return trip!

If you drove from your house, then it’s time to make the trek back home. Otherwise, the drive from Woodstock, Vermont to Boston Logon International Airport will take about two and a half hours. I recommend arriving two to three hours before your flight to have time to drop off your rental car, check any bags, and find your gate.

Is Your New England Road Trip Itinerary Longer Than 7 Days?

There are so many options for New England itinerary add-on’s:

• Consider spending one extra day in Boston.
• Stay in Salem, MA for two days and day trip to nearby Danvers (formerly Salem Village) to see even more witch trials sites!
• Explore additional charming towns along the Vermont and New Hampshire border, including White River Junction, Windsor, Hanover, and Battlebro.
• Add an extra day to New Hampshire to take advantage of countless more hiking trails.
• Add an additional state: Maine! Explore trendy Portland, eat lobster rolls in Bar Harbor, or go hiking at Acadia National Park .

There you have it – the recipe for a dreamy and memorable 7 day road trip itinerary through New England. It’s the best combination of the bustling Atlantic coast of Massachusetts, the mountains of New Hampshire, and the farms of Vermont. You’ll see exactly why New England is beloved by leaf peepers, maple syrup addicts, and outdoor lovers alike!

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10 day New England Road Trip Itinerary (Portland to Boston Drive)

Looking to spend some time on the east coast by taking a road trip through new england this road trip itinerary will take you through some of america’s oldest cities and towns..

Get ready to be blown away by idyllic small-town vibes, white steeples with brick-red facades, fresh lobster rolls, whale watching, and history upon history on this New England road trip!

This New England road trip will take you from Portland, Maine up to Acadia National Park, then back down through Portsmouth and into Boston, Massachusetts.

🚗 When booking your New England Road Trip car rental online, I recommend using Discover Cars . They provide the best deals for car rentals in New England!

Prepare for yourself for this New England road trip by making sure you have all the gear you need to make the best of your time in the car!

Let’s jump in!

Quick Overview of the New England Road Trip Itinerary

Boston to portland maine map.

A quick summary of stops on your 10 Day New England Road Trip Itinerary

• Days 1-3: Portland, Maine (3-hour drive time on day 3)
• Days 3-5: Acadia National Park, Bar Harbor (4-6 hour drive time on day 5)
• Days 5-10: Portsmouth, New Hampshire, and Boston, Massachusetts
• Airports: Portland International Jetport in Portland, Maine (PWM); Logan International in Boston, Massachusetts (BOS)
• Transit: Rent a car for pick up at PMW and drop off at BOS

New England Road Trip Itinerary

The new england road trip itinerary days 1-3: portland, maine.

• Land at Portland International Jetport early in the day if possible and pick up your rental car
• You’ll want to book your stay for 2 nights in Portland

Where to Stay in Portland, Maine

The best accommodation option would be to stay in or very close to Old Port. This is the historic downtown area of Portland with many cute boutiques for shopping and restaurants within walking distance.

If the prices in this area are out of your budget, I would recommend staying at an accommodation in either Portland’s East End or West End as they are both near the heart of Portland, Old Port.

• The Portland Harbor Hotel | cute boutique style
• The Press Hotel | sleek and upscale style
• The Courtyard by Marriott Downtown/Waterfront | cost-effective option near all the fun sites

Day 1: Landing in Portland, Head Light, and Old Port

• Today you’ll see some great highlights of Portland including the lighthouse and Old Port
• Portland city drive time: 15-30 minutes around town, including the airport to Old Port

Start your morning off with breakfast at Becky’s in the West End. The blueberry pancakes are DELISH, however, the omelets are also great for a high-protein meal.

• Becky’s Diner | Address: 390 Commercial St, Portland, ME 04101

After breakfast, head over to Portland Head Light State Park for a short hike! This is one of the most popular sites in Maine and offers incredible views out over Casco Bay.

You can even do a lunch picnic here! Wear walking shoes (or sandals if you’d like to hike down to the water) and do some rock climbing to get some beautiful pictures of the Portland Headlight.

Spend as much time as you want here–it’s so beautiful! (We came here twice!)

Pro-tip: Tie up your hair and bring a jacket as it’s pretty breezy and a little chilly here!

• Portland Head Light State Park | Address: 1000 Shore Rd, Cape Elizabeth, ME 04107

In the afternoon, take an hour-long tour of the Wadsworth-Longfellow House which was Maine’s first house museum that opened up to the public. Longfellow was a national literary man of his time and most furnishings in his house are original or belonged to his family.

• Wadsworth-Longfellow Museum | Address: 489 Congress St, Portland, ME 04101

After getting your history fix, you can take a walk and explore Old Port. This area has many cute boutiques and fun restaurants to try out!

Stop by The Holy Donut for a delicious snack (even multiple times over a 2-day trip) with interesting flavors such as the Maine blueberry cake donuts or chocolate sea salt flavor.

• The Holy Donut | Address: 177 Commercial St, Portland, ME 04101

There are also so many restaurants lined up here that you can grab a quick lunch before doing all your shopping. Some recommendations include Duckfat (amazing Belgian-style fries with sauces) and The Honey Paw (ramen noodles and Asian infusion).

Or head over to the Maine Lobster Shack for a delicious lobster roll–nothing is better than this fresh-caught lobster. You can’t go wrong with the Maine Lobster Roll or the Brown Butter Lobster Roll, and try the Maine Root Soda while you’re here.

• Maine Lobster Shack | Address: 425 Fore St, Portland, ME 04101

Day 2: More of Historical Portland and Peak’s Island

• Today you’ll get some more historical experiences of Portland and explore Peak’s Island by ferry
• Portland city drive time: 10-15 minutes around town

The next morning, grab some breakfast at the Bayside American Cafe. With their delicious menu, you can’t go wrong – everything from Maine blueberry pancakes to Bayside eggs benedict!

• Bayside American Cafe | Address: 98 Portland St Portland ME 04101

After breakfast, check out another museum for the history buff: reserve a ticket to spend about an hour touring Victoria Mansion, a historical landmark that is one of the oldest in the country and known for its architecture and original interior design.

• Victoria Mansion | Address : 109 Danforth St, Portland, ME 04101

After touring the mansion, grab lunch at Hot Suppa! This Southern diner (and what I would consider hipster) has delicious offerings such as the Mother Clucker.

• Hot Suppa | Address: 703 Congress St, Portland, ME 04012

After getting a good bite in, take a 17-minute ferry to Peaks Island for some more exploring; we spent half a day here and had so much fun!

As you get off the ferry, rent a little golf cart From Mike’s Carts to get around the area. You can grab Lisa’s famous cinnamon bun at Peak’s Café as you start your cart tour.

Use this map to help you navigate your way around Peak’s Island. Head north first so that you can end your drive on Seashore Avenue, which provides endless views of the ocean.

Partway through your drive on Seashore Avenue, you can park your cart along the road and take a short hike to Battery Steele, which used to be a military fortification now graffiti-covered.

If you have time, you can also drive around the neighborhood and check out some of the cutest coastal homes–make it a game to find the best-named house!

You can also check out the Fifth Main Museum on the island as well to learn more about the history of the Civil war and other exhibits.

Keep track of the ferry schedule so you don’t miss the last one! Before you go, grab an ice cream cone from Down Front, a small convenience store.

• Ferry to Peak’s Island | Address : 56 Commercial Street, Portland, Maine 04101

Day 3: Close Out Your Portland Itinerary and Drive 3 Hours Toward Acadia

• Today you can choose your morning experience and then prepare for your drive to Bar Harbor
• Portland to Bar Harbor drive time: 3 hours

You can pack everything the night before and check out as you leave in the morning. Start off the day by heading back to Old Port to grab some snacks and breakfast in preparation to drive out.

Since you’ll be savoring your last moments in Portland, Maine, you can choose what you’d like to do:

• last-minute souvenir shopping in Old Port
• taking some last looks at Portland Headlight
• check out the Portland Museum of Art

You will want to leave Portland by 1 PM.

• Portland Museum of Art | Address: 7 Congress Sq, Portland, ME 04101

That’s everything for your 3 day Portland itinerary ! It’s about a 3-hour drive west to your next stop so you’ll want to have all your favorites (snacks, music, and conversation topics) ready to go!

The New England Road Trip Itinerary Days 3-4: Acadia National Park and Bar Harbor

• When you arrive in Bar Harbor, check into your hotel and get some dinner in town
• You’ll want to book a 2-night stay in Bar Harbor

Where to Stay in Bar Harbor

For accommodations, stay directly in Bar Harbor at a cute inn to get the best of your time. Keep in mind that cell service around these parts is spotty at best, so don’t be afraid to stop and ask for directions!

• The Inn on Mount Desert | affordable stay in Bar Harbor
• The Elmhurst Inn | old-fashion boutique style in Bar Harbor
• Acadia Hotel – Downtown | upscale stay in Bar Harbor

Day 3 Continued: Getting to Bar Harbor and Settling In

• Spend your time strolling through this charming small town
• Portland to Bar Harbor drive time: 3 – 3.5 hours

Continue your New England road trip itinerary and head west towards Bar Harbor, where Acadia National Park Pond is located. You should arrive in the afternoon and get lots of views of lakes and beautiful nature scenes.

Since you’ll be here later in the afternoon, head into Bar Harbor which offers a small-town feel and is a fantastic place to enjoy some delicious food.

We got ice cream cones every time we went (which was only twice!). While you’re at it, make sure to buy some snacks, maybe even a sandwich lunch to enjoy while in Acadia National Park Pond the next day.

This would be the time to grab souvenirs or do some window shopping in Bar Harbor. There are so many cute boutique shops to just browse through!

For lunner (lunch + dinner), Galyn’s is a cozy little seafood restaurant in a Victorian-era house that has options for outdoor seating.

Opt to sit out on the patio and enjoy the fresh air and views while you eat your clam chowder soup. If that’s not for you, they also have small plates, fettuccine, sandwiches, and many more options to choose from. It was wonderful!

• Galyn’s | Address : 17 Main St, Bar Harbor, ME

Day 4: Explore Acadia National Park Pond

• Get an early start at Acadia National Park and do all the exploring on the hiking trails and beaches
• Bar Harbor to Acadia drive time: 15 – 30 minutes going through the park

Continue your New England road trip and get an early start to Acadia National Park Pond, which is known as the “Crown Jewel of the Atlantic Seaboard” and it’s easy to see why.

Take your time in Acadia and explore all that it has to offer, you won’t be disappointed! The mountain views are incredible, the road is scenic and well-maintained.

The weather in Acadia is usually pretty nice, but it can get chilly in the evenings. Make sure to pack layers so you’re prepared for everything! I had a light jacket with me, but by midday, I was getting pretty warm from the sunshine and hiking.

One of my favorite hikes here is the Beehive Loop , which is a great way to get acquainted with the difficult trails.

If you are looking for an adventurous hike, this 450-foot cliff trail will get your heart pumping! As one of Acadia’s most popular hikes, expect steep granite staircases that challenge even experienced backpackers (think ladders and iron rungs), as well as exposed cliffs. The trail is about 1.4 miles roundtrip and can take anywhere from 1-3 hours.

Another more moderate hike is the Bubble Trail which branches into North and South.

Both trails are reasonable, but if you’re looking for a shorter trail, take the Bubble Rock trail to see “the bubble,” which is a huge rock shaped like a bubble sitting precariously on the cliff of the mountains.

If mountains aren’t your thing and you’re more of a beach lover, Sand Beach and Echo Lake Beach are great for swimming and hanging out. You’ll most likely come across Sand Beach first if you’re coming from the entrance at Bar Harbor, which will also bring you to the trailhead of the Beehive Loop.

At the beach, you can unpack your lunch and enjoy a nice view out into the ocean with the sun keeping you warm.

However, if you are hungry after your hiking expedition, enjoy lunch at Jordan Pond House where you can dine on traditional meals of New England that include lobster rolls, chowder, and more.

A popular fare here is popovers and tea and if you are like me who had no idea what a popover is… it’s a light roll made of egg batter and can be eaten with whipped cream or jam and tea. Delish!

• Jordan Pond House | Address : 2928 Park Loop Rd, Seal Harbor, ME 04675

For more adventuring in Acadia, make the drive to Cadillac Mountain or Thunder Hole. Cadillac Mountain is the tallest mountain on the East Coast at just over 1,500 feet with unparalleled views over Frenchman Bay and beyond.

Finally, no road trip to Acadia National Park is complete without a stop at the famous Thunder Hole! Don’t forget your raincoat because it looks like thunder when waves crash into rocks down below, causing an amazing sound experience for visitors nearby.

After a long day exploring Acadia National Park head back towards Bar Harbor at night to enjoy dinner in town. Grab a seat at one of my favorite restaurants, the family-owned Side Street Cafe.

The staff is so welcoming and the restaurant really fosters an atmosphere of community. Everything here is amazing–from appetizers to sandwiches and burgers.

• Side Street Cafe | Address: 49 Rodick St, Bar Harbor, ME 04609

After all the energy spent at Acadia, get some much-needed rest before the long 5.5-hour drive to Boston!

The New England Road Trip Itinerary Days 5-10: Boston, Massachusetts (with a stop in Portsmouth)

Where to stay in boston.

Driving around Boston can get congested during peak traffic hours, which will make your trip take longer than expected if you don’t plan accordingly.

Because of that, we decided to stay outside of Boston proper. Our Airbnb was about a 30-minute drive to Boston, which was actually more cost-effective for us since we weren’t always going to be in Boston proper.

If you would prefer to stay in Boston, you may be able to save on driving time on congested roads.

• Hampton Inn Boston Logan Airport | 16-minute drive to Boston, typical hotel stay
• The Newbury Boston | 3-minute walk to Boston proper, upscale stay

Day 5: Make the 5.5-hour drive South to Boston, with a short stop in Portsmouth, NH

• Check out of your rooms and prepare for a long drive south to Boston
• You’ll want to book your rooms in Boston for 5 nights
• Bar Harbor to Bass Harbor Light Station Drive time: 30 minutes
• Bar Harbor to Portsmouth Drive time: 3 hours, 55 minutes
• You’ll make a lunch stop in Portsmouth and get the chance to explore for a short while
• Portsmouth to Boston drive time: 1 hour

As you continue your New England road trip itinerary and start your drive down to Boston, you can make a stop at Bass Harbor Light Station. This historic lighthouse is off the beaten path but definitely worth checking out if you would like to add another lighthouse to your list!

After taking some pictures of the lighthouse, continue on your New England road trip and make a stop in Portsmouth, New Hampshire.

With a population of approximately 21,000 people, Portsmouth is the 13th largest city in all of New England! It’s also home to the Strawberry Banke Museum which consists of 11 historic homes and buildings dating back as early as 1695.

You can grab lunch in Portsmouth from places like the Clipper Tavern, The Wilder, or The Franklin.

If you’re game for ice cream (which is always on my list), check out Annabelle’s Natural Ice Cream, made with only the best ingredients! Then take a walk down the main street and explore the town on foot.

• Annabelle’s Natural Ice Cream | Address: 49 Ceres Street, Portsmouth

You’ll see an iconic New England church and steeple right in the town center. Right along this street are some cool shops like the River Run Bookstore, a fun game store called Diversions and Games, and a cute international boutique shop, Ten Thousand Villages.

After walking through some shops and exploring a little in Portsmouth, hop back in the car and finish out your New England road trip in Boston!

Next up on your New England road trip: Boston!

Day 6: Walk the Freedom Trail

• You’ll explore the freedom trail on foot and really get to see all the history in Boston proper – prepare yourself, it’s a long day of walking!
• Boston city drive time: 15-30 minutes depending on your stay

Take the rest of the days and go at your own pace. In this section of the New England road trip, you will not be driving across state lines or going long distances anymore.

There is SO much to see that you’ll need to make your itinerary work for you! Consider your top historic sites and your level of energy for all the walking you might do in the city. With that said, let’s jump into exploring Boston!

Boston is home to so much history! On the top of your list to do in Boston, the Freedom Trail .

This trail is a must-see for anyone who visits the city! The Freedom Trail is a self-guided historic walking trail that leads you to 16 of Boston’s most iconic landmarks. It is 3 miles long and will take you a whole day to complete as you make stops along the way.

You’ll want to get started on the Freedom Trail in the Boston Commons (1) . From here, you can visit the information center to get yourself a map and ask any questions. You’ll know you’re on the trail by following the marked trail embedded in the sidewalk.

As you get started, you’ll see the Massachusetts State House (2) located on a hill, and following that will be Park Street Church (3) , which was one of the first landmarks travelers would see coming into Boston.

Next, you’ll come upon the Granary Burial Ground (4) , which has some of the most influential historic persons like Benjamin Franklin’s parents, Paul Revere, and John Hancock. After this you’ll come upon a small square where you can visit King’s Chapel & King’s Chapel Burying Ground (5) , which is America’s oldest running pulpit – the bell still rings to call worshippers into the church.

You’ll also see Benjamin Franklin’s statue (6), the Old Corner Bookstore (7), and the Old South Meeting House (8) where the Boston Tea Party began!

At this point, you are right in the middle of a commercial hub to grab lunch – we got the familiar and ordered a burrito at Chipotle. However, there are so many restaurants to choose from.

Continue your trek on the Freedom Trail after lunch to the Old State House (9) , which is Boston’s oldest standing public building.

The trail will then take you to the site of the Boston Massacre (10) of 1770 where the Redcoats and Boston civilians broke out in gunfire. You’ll see the site marked with a marker.

Next up is Faneuil Hall (11), the “home of free speech” and “cradle of liberty,” you’ll see the popular golden cricket weather vane. It is now a cool marketplace and is one of Boston’s most popular attractions!

There is something for everyone with its many shops, restaurants, and music venues all in an old-fashioned market atmosphere. Right outside the marketplace, you might spot jugglers and dancers giving a great show!

After a little shopping, you’ll continue walking towards Paul Revere’s home (12) where you can take a tour inside. Continue your trek on the Freedom Trail to the Old North Church (13) , where you’ll see a statue of Paul Revere – this was the site of his midnight run.

You can also grab a snack in this area at Mike’s Pastries as he has some of the most delicious cannolis (address mentioned below)!

After the Old North Church, you’ll come to Copp’s Hill Burying Ground (14) , which is the final resting place for many artisans and craftsmen in the North End of Boston.

You’ll then take a 20-minute walk towards the USS Constitution (15) , which is the oldest commissioned warship afloat that fought during the war of 1812. Today, it is managed by the US Navy. You can purchase tickets and actually walk on the ship and even go underdeck to see the cannons and rooms.

Finally, head towards the last site of the Freedom Trail, Bunker Hill Monument (16) , which is a 221-foot granite obelisk.

At this point, it is likely that you’re well into the afternoon so I would recommend booking an Uber to drive you back to the Boston Commons, which is most likely where your car is parked.

If you would rather continue walking, you could walk the 3 miles back toward the commons.

From here, you can choose a place to grab dinner and call it a night! You’ll be exhausted from all the walking and sightseeing you’ve just completed.

Day 7: Whale watching, Boston Harbor, and the North End

• After all the walking yesterday, take it easy and go whale watching
• Explore the Italian district of the North End

Boston is the perfect place for whale watching ! There are several tour companies along the water where you can book a trip to see the whales.

The best time to see the whales in Boston is during the months of May – October when the whales migrate during the warmer temperatures.

Book your Boston whale-watching tour!

Boston Harbor Cruises has experienced marine biologists and tour guides to give you information while you are on the cruise. They are also experts in knowing the best spots where whales like to hang out.

You’ll head to Long Wharf, which is near the New England Aquarium to get in line for the tour. On our whale-watching expedition, we went to Stellwagen Bank National Marine Sanctuary.

It took a few minutes of watching, but we did spot some whales!

A whale-watching tour can take anywhere from 3-4 hours. Wear a jacket as it will get cold when you’re in the middle of the ocean.

• New England Aquarium | Address: 1 Central Wharf, Boston, MA 02110

After your tour, you’ll be right in the Boston Harbor. From here, you can walk along the waterfront and explore some sites. You can relax at the Charles River Esplanade which is a walking path along the waterfront with plenty of benches.

If you would like some more Boston history, check out some of the museums such as the Museum of Science, the Boston’s Children Museum, or the Boston Tea Party Ships and Museum.

For dinner, head to the Italian quarter in the North End which is the oldest neighborhood in Boston and has some of the most delicious food.

If you’re not into Italian food then there is still plenty of great places to try out including sushi, burgers, or lobster rolls that are sure to please everyone in your road trip group!

For dessert, try out the cannolis at Mike’s Pastry as they have been making these delicious pastries since 1926. The lines can look intimidating as they go out the door, but it goes quickly and the staff is very aware of your status in line.

• Mike’s Pastry | Address: 300 Hanover St, Boston, MA 02113

Day 8: Harvard University and Candle Pin Bowling

• Explore the college town of Harvard University
• Have fun candlepin bowling
• Boston to Cambridge drive time: 30 minutes – 1 hour depending on your stay

Boston is also home to many amazing colleges and universities. On this day of the New England road trip, we chose to take a visit to Harvard.

Start off by grabbing brunch at Le’s Vietnamese restaurant then check out the historic Harvard Bookstore.

After this, we wanted to take a walk around the Harvard Campus. Do note that visitors aren’t allowed within the buildings without a guest pass.

We just walked around the campus and noted the buildings as well as the plaques that were displayed. It was pretty cool to say that we went to Harvard!

If you’d like to experience Harvard University more deeply, you can book a 70-minute student-led tour to see everything the university has to offer. Either way, you’ll want to make sure that you don’t miss out on visiting Harvard Yard.

There are also three art museums and the Harvard Museum of Natural History to explore.

Book your Harvard Walking Tour

For a more relaxed New England activity, go candlepin bowling at Sacco’s bowling alley in Sommerville, which is about a 10-minute drive from Harvard University.

This type of bowling is a little different than what you might be used to. Candlepin bowling is played with smaller balls and the pins are thinner as well; it tends to result in more strikes which means more points!

Sacco’s does offer food for purchase so we ordered flatbreads off their menu for dinner.

• Sacco’s Bowling Haven | Address: 45 Day St, Somerville, MA 02144

Day 9: Fenway Park, New England Holocaust Memorial, Boston Public Market, Cheers, and a Ghost Tour

• Revisit Boston proper: there is so much more to see that might have been missed on the Freedom Trail – take your last day to visit all those last sites
• Boston city drive time: 15-30 minutes depending on where you stay

I’m not much of a sports fan, but I really enjoyed a walk around Fenway Park where the Red Sox play.

It was built back in 1912 and has been around ever since, also displaying members of the team around the stadium. With a guided tour, you’ll be able to visit the stadium’s collections of photographs, artifacts, and more!

Boston also has a memorial for the persecuted Jews during the Nazi regime where you can visit the New England Holocaust Memorial.

After walking through the memorial, you’ll end up near the Boston Public Market, which is filled with produce and gourmet food. This is the perfect spot to grab lunch!

• New England Holocaust Memorial | Address: 98 Union St, Boston, MA 02129
• Boston Public Market | Address: 100 Hanover St, Boston, MA 02108

If you’re a huge literary fan, you can visit the Edgar Allan Poe statue, which is so descriptive and very well-made. You can see one of his most notable works: The Tell-Tale Heart. The statue stands right across the street from the Boston Commons south of Boyleston Street.

Another iconic stop in Boston is to visit the Cheers restaurant filled with memorabilia from the show! It’s located on the other side of the Boston Commons where Edgar stands. You can grab dinner here and reminisce about the show.

• Cheers restaurant | Address: 84 Beacon St., Boston, MA 02108

For the brave, book a trolley ghost tour to hear bout Boston’s most haunted locations! The tour guides are historians, so you can be sure that the stories they tell will be accurate and interesting-we learned so much about the cemeteries and ghost sightings!

Fun fact: there’s a little girl who is regularly spotted right next to these gravestones!

Side Note: You can also spend one night in a historic hotel or B&B. Some of these places date back to the 1800s! Most hotels even offer their own ghost tours if you’re feeling brave enough to stay overnight at one of their historical spots.

As you hang out later in Boston, you can see the Massachusetts State House beautifully lit up in the night sky! You can grab dinner to go and have a picnic in the Boston Commons, which is a huge park area.

Day 10: Check out and return home

• Boston to Logan Airport drive time: 15-30 minutes depending on your stay

After exploring all you can in Boston, it’ll be time to head back home. Return your car to Logan International Airport and from there fly out to your home airport.

Summary of the 10 Day New England Road Trip Itinerary

• Breakfast at Becky’s Diner | Address: 390 Commercial St, Portland, ME 04101
• Explore Portland Headlight | Address: 1000 Shore Rd, Cape Elizabeth, ME 04107
• Get your history in at Wadsworth Longfellow’s place | Address: 489 Congress St, Portland, ME 04101
• Shop in Old Port and get a snack at the Holy Donut | Address: 177 Commercial St, Portland, ME 04101
• Grab food at the Maine Lobster Shack | Address: 425 Fore St, Portland, ME 04101
• Breakfast at Bayside American Cafe | Address: 98 Portland St Portland ME 04101
• Check out more history at the Victoria Mansion | Address : 109 Danforth St, Portland, ME 04101
• Grab a Mother Clucker at Hot Suppa | Address: 703 Congress St, Portland, ME 04012
• Take the Ferry to Peak’s Island | Address : 56 Commercial Street, Portland, Maine 04101
• Spend your morning experiencing the last of Portland: revisit Old Port, Portland Headlight, or explore the Portland Museum of Art
• Prepare snacks and drive 3 hours to Bar Harbor, where Acadia National Park is located
• Arrive and check into your accommodation in Bar Harbor
• Grab lunner at Galyn’s | Address : 17 Main St, Bar Harbor, ME
• Do some shopping and strolling in Bar Harbor – get some snacks for Acadia
• Get some rest!
• Start early – do a difficult hike on the Beehive Loop Trail or a moderate one on the Bubble Trail
• Eat snacks or your packed lunch at Sand Beach or Echo Beach
• Grab lunch or some popovers and tea at Jordan Pond House | Address : 2928 Park Loop Rd, Seal Harbor, ME 04675
• Drive to Cadillac Mountain and enjoy the views and Thunder Hole to check out the cliffs
• Finish your day in Bar Harbor at the Side Street Cafe | Address: 49 Rodick St, Bar Harbor, ME 04609
• Stop at the Bass Harbor lighthouse then make your 4-hour drive to Portsmouth, NH
• Grab lunch and ice cream – do some walking and shopping in Portsmouth
• Continue your New England road trip to Boston – check into your hotel
• Grab dinner – we got take-out pizza at a corner store and rested from our long drive
• Explore the Freedom Trail by walking to each site (3 miles long, but will take all day)
• Go whale watching at the Stellwagen Bank National Marine Sanctuary
• Explore the Boston Harbor: Charles River Esplanade, Museum of Science, Boston Children’s Museum, or Boston Tea Party Ships and Museum
• Check out the Italian Quarter in the North End
• Grab dessert at Mike’s Pastry | Address: 300 Hanover St, Boston, MA 02113
• Explore the college town of Harvard in Cambridge: Harvard Yard, Harvard Bookstore, Art Museums, Harvard Natural History Museum
• Experience New England candlepin bowling at Sacco’s Bowling Haven | Address: 45 Day St, Somerville, MA 02144
• Check out the iconic Fenway Park where the Red Sox play
• Walkthrough the New England Holocaust Memorial | Address: 98 Union St, Boston, MA 02129
• Grab lunch at the Boston Public Market | Address: 100 Hanover St, Boston, MA 02108
• Revisit Boston Proper – Edgar Allen Poe , and walking ghost tour , picnic in Boston Commons , do more shopping at Faneuil Hall Marketplace
• Grab dinner at the Cheers Restaurant | Address: 84 Beacon St., Boston, MA 02108
• Check out and return home

Map of the 10 Day New England Road Trip Itinerary

Options to Extend Your New England Road Trip Itinerary

If you have more time to spend on a New England road trip, here are a few other historic cities to stop: Concord, Massachusetts, New London, Connecticut, or Providence, Rhode Island.

• Concord, Massachusetts is also full of culture, museums, galleries, and shops. This was also the home to writers such as Emily Dickenson and Henry David Thoreau.
• Providence, Rhode Island is a small city with a lot of history and very friendly people. Be sure to check out the historic downtown area and the amazing restaurants.
• New London, Connecticut where you can visit the U.S Coast Guard Academy, Fort Trumbull State Park, and many more historical landmarks.

What to pack for your 10 Day New England Road Trip

Keep in mind that you’ll be in the car for a few hours, so also pack some comfortable clothes for a long New England road trip.

Boston can also be rainy, so you’ll want to make sure to have a rain jacket and/or water-resistant shoes for all the walking you’ll do.

Here is my recommended list:

• 4-5 tops or shirts
• 1 pair of leggings
• 1 pair of jeans
• 1 jacket (or rain jacket as it does get wet!)
• 1 pair of hiking boots or walking shoes
• 1 pair of sandals
• Sunscreen for Acadia

New England road trip itinerary

When is the best time to go on a 10 day new england road trip.

The best time for a road trip to New England is late spring through early fall. This region of the United States has a temperate climate with moderate temperatures, meaning you can usually avoid extreme heat or cold during these months.

In addition, this time of year offers more daylight hours and plenty of outdoor activities that are perfect for exploring!

You can also plan your road trip to New England during the autumn months, especially in late September to see the foliage change from green to beautiful oranges and reds. Take a drive through the White Mountains in New Hampshire for spectacular views of nature at its finest!

FAQs: 10 Day New England Road Trip Itinerary

Is boston worth visiting.

Absolutely! Boston is full of history and culture. From the Freedom Trail to Fenway Park, there are plenty of places to explore. The food in Boston is also fantastic with a variety of cuisines from Italian in the North End to seafood dishes on the waterfront.

How much money should I budget for a 10 day New England road trip?

It really depends on your budget and what activities you plan to do. For a mid-range budget, a good rule of thumb is to budget around $150-$200 USD per day for food and activities.

Accommodations tend to run between $100-$150 for stays that are close to the areas mentioned in this itinerary. Car rentals range between $80-$90 a day.

If you plan to travel with friends, you can save money by splitting the cost of the car rental and hotels. You can then set your own budget for food and fun activities.

Are there any special precautions I should take when driving in New England?

Yes, some roads can be narrow and winding so it’s important to be aware of the speed limit, road signs, and other drivers. It’s also a good idea to plan your route ahead of time so you know where you’re going.

You might find fog in the northern part of New England as well in the early morning. Be sure to know how to use your fog lights and take it slow.

When in Boston, be prepared for congested traffic, weird roundabouts, and confusing streets (from my own personal experience).

Final Thoughts: 10 Day New England Road Trip Itinerary

That’s a wrap on the ultimate 10 day New England road trip itinerary. New England is a beautiful destination with many historical landmarks, incredible coastal views, and delicious food!

Are you ready to explore New England? Check out these posts!

• 10 Day New England Road Trip (Portland to Boston)
• 3 Day Portland Itinerary
• Best Walking Tours in Portland
• One Day in Camden, Maine
• Boston to Wells Road Trip
• Day Trips from Boston by Train (MBTA Weekend Pass)

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My favorite travel tips + resources.

Here is a quick glance at all my go-to travel tips and resources that I use to plan every trip! For more information, check out my travel resources page .

• Booking flights: I use Google Flights to check all routes and find the best flights. Then I compare Skyscanner (for the lowest prices) before I book.
• For hotels, I go through Booking.com or book directly with Marriott (for points + rewards).
• When I travel internationally, I’ll book through Hostelworld for very budget-friendly stays.
• For vacation rentals, use Vrbo or Marriott Homes & Villas .
• Expedia also has some great bundles for hotels, flights, and car rentals altogether.
• Car Rentals: I love renting cars through Discover Cars . They have been consistent and provide the best customer service.
• Trains in Asia: Trip.com has the best options!
• Trains in Europe: Trainline or Omio .
• Visa Application: For a hassle-free process, apply for your visa from iVisa .
• Travel Credit Card: I book all my travel (flights, hotels, car rentals) through Chase Sapphire .
• Vaccines and Medications: Check the CDC website for updates on necessary vaccines to enter a country, including updates on Covid-19 and recommended places to visit. I recommend getting all the vaccines you need before you go!
• Tours + Experiences: I absolutely love my tours! Everything from eerie walking ghost tours to food tours, I’ll usually book something every trip either through Viator or GetYourGuide .
• Entertainment: Looking for entertainment like sporting events, theater shows, or concerts? Book with Ticket Squeeze !
• Tech : Keep your internet browsing safe, secure, and fast with ExpressVPN
• Language Learning: The best place to learn a new language is through Babbel as you travel to countries you don’t know the language.
• What to Pack: I almost always travel by backpack . For products I like, check out my packing guide page for all the things I take with me on different trips.

Pafoua is the author and creator of Her Wanderful World. Pafoua writes from her numerous excursions about all things travel, from fun itineraries to creating memorable experiences on the road. When she’s not traveling, Pafoua loves a fun board game night with her friends or is snuggled up reading a good book. You can find her on Instagram @herwanderfulworld.

The Best One Week Fall Foliage Itinerary for New England (Plus More Options!)

Here’s my guide to the best one week fall foliage itinerary in New England. New England is a classic American destination, the perfect place for a road trip.

As a born/bred/educated New England girl myself, I think New England is arguably one of the world’s most beautiful places in the fall.

Country roads wind through dense forests, stone walls, covered bridges, and idyllic farm properties.

Orange, red, and gold colors explode, rippling across the mountains. It’s the stuff of dreams.

If you want to escape the crowds and fall back into nature, I recommend adding a New England road trip to your USA bucket list .

Here’s my sample one week fall foliage itinerary, taking in the best fall colors in New England. I also give you plenty of options for extending your New England road trip if you have more vacation time.

In this 7 day New England itinerary, I spill the beans on the must see scenic spots in New England to experience the festival of colors, where to stay and eat, the top hikes, and photography inspiration.

You’ll start in the historic New England city of Boston and then head to the Berkshires, Vermont, and New Hampshire. I think New Hampshire and Vermont are the best place to see fall foliage, though I may be a tad biased.

If you have more than one week for your New England fall road trip, I give you some other options in Connecticut and Rhode Island to extend your time in this rural playground.

You can easily turn a 7 day fall foliage road trip into a 10-14 day itinerary for New England and stay longer in each place.

Overview Of One Week Fall Foliage Itinerary In New England

• Day 1 : Boston MA
• Day 2 : Berkshires MA
• Day 3 : Dixville Notch State Park NH
• Day 4 : Stowe Vermont
• Day 5 : Smugglers Notch NH
• Day 6 : White Moutains NH
• Day 7 : White Mountains NH
• Extra Time? Add Burlington Vermont, Connecticut, and Rhode Island

One Week Fall Foliage Itinerary For New England

Let’s begin the leaf peeping! Here’s where to go for fall foliage with one week in New England.

Day 1: Boston, Massachusetts

Begin your 7 day fall foliage road trip by flying (or driving) into Boston . Beautiful Boston Massachusetts is one of my favorite city in the United States. And fall is the perfect time to visit.

The country’s oldest city, Boston is steeped in American history. Boston played a pivotal role in the Revolutionary War.

Boston’s sometimes called the “hub of the world” or the “cradle of liberty.” The city was the source and inspiration for key ideas that shaped America.

READ : 3 Day Itinerary for Boston

Boston has a great foodie scene, wide open green spaces, quaint neighborhoods, and first rate museums. The prettiest neighborhoods, lit in colors in the fall, is Beacon Hill .

And Boston’s got loads of gorgeous fall foliage. To see the colors, head to Boston Public Garden, Boston Common, the Boston Esplanade along the Charles River, Beacon Hill, and Back Bay.

You can book a historic walking tour . The hop on hop off trolley bus takes you to Boston’s top attractions. You can also see check out the colors on a fall foliage lunch cruise .

After touring the city, pick up your rental car. Now, it’s time for some classic new England fall foliage. If you want to skip the big city altogether on this fall foliage trip, just add in one of my bonus destinations instead.

Where To Stay In Boston:

If you opt for downtown, I like the small  XV Beacon  or the  Klimpton Nine Zero Hotel. You could also splurge at the  Ritz Carlton  or the  Four Seasons .

The  Inn at St. Botolph , the  Lenox Hotel , and the  Hilton  in Back Bay are also nice options and central too.

If you can’t resist historic Beacon Hill, check out  The Boxer ,  Liberty , or the elegant  Whitney Hotel .

Where To Eat In Boston:

Barcelona Wine Bar, SVR, Yvonne’s, Beehive, Giacomo’s, Sarma, and o ya

Day 2: The Berkshires, Massachusetts

The Berkshires are a beautiful rural region of western Massachusetts that’s made up of 30 bucolic villages with some top tier leaf peeping, museums, and restaurants.

It’s a place of fall foliage glory In New England. The Berkshires are full of winding roads with rolling meadows and trees ablaze.

For some of the best fall foliage scenery in the Berkshires, take Route 7 and 8 from Great Barrington to North Adams (1:10 hours without stops).

You’ll go past storybook farms, wooden barns, and stone walls. And through the cute towns of Stockbridge, Lee, Lennox, and Pittsfield.

Stockbridge and Lenox are the two prettiest towns in the Berkshires, and make a great base for exploring. Stockbridge is home to the Norman Rockwell Museum and some of the Berkshires’ beautiful Gilded Age castle-cottages.

Lenox is home to The Mount , Edith Wharton’s home, more iconic properties, and fantastic restaurants.

The quaint town of North Adams is an arty town with an eye catching row of multi-colored Victorians called The Porches. If you’re in the mood for a museum after some leaf peeping, there are couple really good ones.

Try the Susan B. Anthony Birthplace Museum (in nearby Adams) or the spectacular Massachusetts Museum of Contemporary Art .

The Notch Road leads to Mt. Greylock State Reservation . You can drive up to the summit for Massachusetts’ highest viewing point.

There are plenty of marked hiking trails that start from the parking lot. Click here for the online trail map.

Then descend back down, exit the park, and take Route 7. This will take you to the small town of Lanesborough, where you’ll see pastures and horse farms. You can pick your own apples at Lakeview Orchard .

Near Route 7, you can also visit the home of Edith Wharton in Stockbridge. On your way back to North Adams, you can stop in Cheshire at the Whitney’s Farm Market.

Here’s my complete guide to the Berkshires .

Where To Stay In The Berkshires :

In Lenox, you can check out the intimate Wheatleigh resort fashioned as a Florentine palazzo. The Seven Hills Inn is a historic property on beautifully landscapes grounds with cottages.

In Stockbridge, you can stay at the historic Red Lion Inn or the Inn at Stockbridge , a charming B&B.

Where To Eat in the Berkshires:

Gramercy Bistro, Nuedel, Grazie, Mezze, Bistro Zinc, or The Portico at the Wheatleigh

Day 3: Dixville Notch State Park, New Hampshire

On day 3 of your 7 day fall foliage itinerary, get up early and drive 4.5 hours north to Dixville Notch State Park to venture into New Hampshire. Dixville Notch is a very small area. But what it lacks in size, it more than makes up for in unadulterated beauty.

The main road through Dixville features rolling hills and stunning scenery, including beautiful Lake Gloriette. Once there, hike the famed Table Rock Trail. You’ll need to pull off the shoulder and park on Route 26.

Table Rock Trail is a 1.5 mile out and back trail, with a relatively steep 700 feet climb. You’ll be rewarded with panoramic views over gorgeous Dixville Notch from above. If you’ve timed it right, you can even enjoy the sunset from your perch.

Another trail leaves from the parking lot of the Whittemore Family Cemetery on Google Maps. The trail winds its way through a vibrant forest, leading to a cute little bridge and stream. When you’re done hiking, head back to the nearby town of Colebrook for dinner and shut eye.

Where to stay : La Maison Bleue du Lac, Mohawk Cottages

Where to eat : Black Bear Tavern, Parsons Street, Wilderness

Day 4: Stowe, Vermont

Wake up early, grab some breakfast at Mostly Muffins in Colebrook. Then drive 2 hours west towards Stowe Vermont.

Along the way, you’ll pass scads of beautiful fall foliage and adorable rural towns, like the memorable Island Pond in Brighton.

Spend the day exploring the charming town. Where mountainous Stowe really shines is its hiking trails, with a range of options to suit every level of experience. Some take you to towering peaks, others end in waterfalls.

For beautiful fall views of Vermont’s Green Mountains, you can ride the ferry across Lake Champlain.

Another option is taking the Gondola Sky Ride at the Stowe Mountain Resort, for more beautiful aerial mountain views.

When you’re done hiking, snack on some apple cider donuts. Stowe also has a romantic and picture perfect downtown.

Its white steepled church is the focal point. Tiny Main Street is filled with boutiques, crafts stores, and antique shops. There are libraries, museums, theaters, and cultural organizations to keep your entertained.

Where To Stay In Stowe:

Stowe has some very nice hotels. The best option is the Topnotch Resort , with pools, a spa, and saunas. The Lodge at Spruce Peak is another good option. It’s at the base of Stowe Mountain and has awe inspiring views of the area’s lakes and peaks.

You can also check out the Trapp Family Lodge , with old world Austrian charm.

Where To Eat In Stowe :

Plate, Cliff House, Bistro at Ten Acres, Green Goddess Cafe

>> Click here to book a brewery tour in Stowe

Day 5: Smuggler’s Notch, Vermont

Day 5 of your one week New England fall foliage itinerary will be a busy one.

Wake up early and head 20+ minutes to the famed Smuggler’s Notch, detouring off Route 100 to Route 108. This magnificent area has a road that goes through a gap between two mountains (termed a “notch”).

Smuggler’s Notch is similar to Dixville Notch. But it’s even more stunning. The mountains on either side are massive.

There are many beautiful twists, hairpin turns, and massive boulders in the road. Unfortunately, there aren’t many places to stop and take photos. But there are two parking lots, at the Welcome Center and upper end of the notch.

From Smuggler’s Notch, drive south to Pomfret, Vermont. Take Cloudland Road south from Pomfret to Woodstock. You’ll drive along cute dirt roads lined with fall colors, rolling hills, and quaint farms.

If you’re hungry, stop in Woodstock for lunch at Mangalitsa or the Prince and the Pauper Restaurant.

Stop for a photography break at Sleepy Hollow Farm in Woodstock Vermont. It’s a great little stop that captures one of New England’s most photogenic farm properties now Instagram famous.

Sugarbush Farm is another local farm property that you can visit. Their maple syrup is famous.

Now, it’s time to head back to New Hampshire. At the base of the White Mountains, the town of Lincoln makes a good base for touring this area.

Then you don’t have to move every night. Lincoln is a creative foodie town, so plan on some fine dining there after your days of hiking and leaf peeping.

Where To Stay Near Lincoln: Omni Mt. Washington , Sugar Hill Inn , Riverwalk Resort at Loon Mountain , Red Sleigh Inn B&B

Where to eat : The Common Man, Gypsy Cafe, La Vista Italian Cuisine

Day 6: White Mountains, New Hamsphire

On day 6 of your one weeks fall foliage tour of New England, you’ll drive the sinuous Kancamagus Highway in the White Mountains.

It’s one of the most beautiful fall foliage drives in New Hampshire . You can drive the road with this self guided audio tour .

Be prepared to pump the brakes frequently. You’ll be dazzled by the incredibly epic roadside views on this 34 mile stretch of highway.

There a few places to pull over, providing great photo opportunities. Continue east until you hit the Rocky Gorge Parking Lot. Here, you can take a walk along the Swift River and get views of the beautiful Falls Pond.

From Rocky Gorge, backtrack a short distance to drive up Bear Notch Road. Bear Notch features a scenic drive along a mountainside and more roadside pullouts for gorgeous photo opportunities.

At the end of Bear Notch Road, drive north to Crawford Notch State Park .

Here, you can explore the backroads and revel in the beautiful fall colors. If you’d like to do some hiking, there are 35 hiking trails of varying difficulty.

The best hike in this area is the Mount Willard Trail . It’s a relatively steep, but short, 3.2 mile out and back hike to a clifftop vista overlooking Crawford Notch. The views are surreal.

Next, continue driving north where you can detour to the Mt Washington Cog Railway . Here, you can ride a historic train to the summit of Mt. Washington.

The mountain is the tallest one in the northeastern United States at 6,289 feet. At night, head back to your base in Lincoln.

Day 7: White Mountains | Franconia Notch State Park, New Hampshire

On day 7 of your New England fall foliage itinerary, you’ll head to Franconia Notch State Park. The park is a lovely spot nestled in the White Mountains, just 7 minutes from Lincoln.

Start your day with a sunrise hike up to Artist’s Bluff . This is a short 1.4 mile long loop trail up to a hilltop overlooking Echo Lake. The fall foliage here is simply breathtaking.

Continue on to Flume Gorge . This is one of the best stops on a New England road trip. The natural chasm stretches 800 feet along the base of Mt. Liberty.

A boardwalk provides a relatively easy 2 mile loop hike. Waterfalls, streams, and covered bridges keep the eyes riveted the entire way.

You can also be whisked away on the 80 person Canon Mountain Aerial Tramway , which takes you to the top of majestic Cannon Mountain for an “oh wow” view. Cannon Cliff is the northeast’s largest vertical rock face. Trails meander on the mountain.

You can also hike the Falling Waters Trail to beautiful waterfalls. Or bike or hike the 8.7 mile Franconia Notch Recreation Path.

The paved trail offer spectacular views of the White Mountains and access to Echo Lake. More adventurous travelers should pull in at Loon Mountain and zipline 700 feet across the Pemigewasset River.

Where to eat : Polly’s Pancake Parlor, Lovette’s Inn & Restaurant

Extra Time On Your One Week New England Road Trip?

It may be time to head back to Boston or home after your one week New England fall foliage road trip.

But if you have extra time on your hands, there are several places you can easily add to create a longer New England fall foliage itinerary.

1. Burlington Vermont

While you’re in Vermont, after Stowe, add a day in the lovely town of Burlington. As the largest town in a state of small hamlets, Burlington has developed a wonderful art scene.

To some, Burlington is akin to a mini Seattle — a politically and socially progressive enclave of college students, regional power brokers, and creative minds.

The city’s popular waterfront bike path includes miles of paths, many along Lake Champlain. Stop at Ethan Allen Park, with a 40 foot tower providing mountain views.

If you’re a foodie, Burlington will suit. It outshines much of the US with a bounty of locally grown food. Farm to table eating is a well established tradition. There’s even excellent street food at Farmers and Foragers Food Truck.

Where to stay : Willard Street Inn, Made INN Vermont

Where to eat : Bleu Northeast Seafood, Hen of the Wood, Juniper

2. Connecticut

If you want to venture south of Boston, Rhode Island and Connecticut also offer excellent fall foliage drives, with rolling foothills ablaze in color.

The best fall drive in Connecticut is the tree-lined State Route 169. This two lane scenic road connects picture perfect towns in a still rural corner of the state, often called New England’s “Last Green Valley.”

Along this relaxing and uncrowded drive, you’ll pass classic churches, orchards, stone walls, and 19th century homes. The pink neo-Gothic  Roseland Cottage operates as a museum.

It’s open for tours June through mid-October. For a break, stop at Mrs. Bridge’s Pantry for some tea and scones.

Another popular fall drive in Connecticut is from Milford to Litchfield. Along the way, you can stop at Hunt Hill Farm, with a gallery, shop, and cafe.

Continue to New Preston, where can you do some antique shopping at Dawn Hill Antiques . Then take the 8 mile drive around Lake Waramaug. In fall, it’s encircled with red maples, rusty oaks, and yellow birches.

Where to stay : Winvian, Grace Mayflower Inn & Spa, Inn at Stonington

Where to eat : Arethusa Farm, Schoolhouse at Cannondale

3. Rhode Island

The state of Rhode Island is the home of the red maple, which turns a glorious gold, purple, and scarlet come fall.

Start your tour of tiny Rhode Island in the amazing town of Providence. Providence combines big city sophistication with small town charm, vibrant culture with hot restaurants. Here’s may one day itinerary for Providence .

For leaf peeping in Providence, the tree lined vista from Prospect Terrace is stunning. There are beautiful trees along the downtown River Walk and on historic Benefit Street.

Drive north from Providence to the Diamond Hill Vineyards, which specializes in pinot noir. Then drive west to the village of Chepachet, where you’ll find Victorian homes and antique shops. A classic stop is at Brown & Hopkins Country Store .

Then hit the road and drive another 40 miles to Exeter. It’s lined with pristine hardwood forests with an abundance of red maple, white oak, elm, and poplar trees.

If time allows, you can continue on to the Colonial seaport town of Wickford, opening to Narragansett Bay.

Where to stay : Renaissance Providence , Graduate Providence

Where to eat : Gracie’s, Al Forno, Bacaro, Birch, Chez Pascal

When Is The Best Time To Take Fall Foliage Road Trip In New England?

The best time to see New England fall foliage is typically from mid September to late October. Even until early November in some places.

But it varies somewhat by state, fall coming earlier the further north you go. Some states have foliage trackers you can check to determine when peak fall foliage occurs: New Hampshire , Vermont , Massachusetts , and Connecticut .

I hope you’ve enjoyed my one week fall foliage itinerary in New England. You may enjoy these other United States travel guides and resources:

• 25 Prettiest Towns in New England
• Must See Places in the Berkshires MA
• 1 Week Road Trip for Vermont
• 10 Day Road Trip in Coastal Maine
• Flexible 10-14 Day Itinerary for Southwest US
• 10 Day Southern California Itinerary
• 21 Less Touristy Towns on the East Coast
• Best Art Towns on the East Coast
• Best Art Towns in California
• Famous Landmarks in Boston

If you’d like to take a fall foliage road trip in New England, pin it for later.

15 thoughts on “The Best One Week Fall Foliage Itinerary for New England (Plus More Options!)”

I like the sound and feel of your one week foliage road trip. When would you recommend doing that trip in the fall?

Thanks Eddie! Generally, mid September to late October is the best time.

Hi Leslie, do you do custom trip itineraries? We would like to fly into Maine and make a triangle Fall tour of Maine, NH and Vermont.

Thanks for your reply!

Hi Steve, I just don’t have time at the moment. I’m about to leave the country for travel again. But there is nothing better than fall in New England!

Thank you so much for this wonderful itinerary. It’s my first trip to the New England states. I am mapping things out now. Question: if I am driving to my final destination of Toronto, Canada, should I drive in the reverse order and go from Boston to the White Mountains to Stowe to Dixvill Notch, etc….?

Yes, that makes sense to me. Enjoy your trip!

Hi. Thanks for your lovely articles and suggestions. We are going on a NE Cruise in September and have available 5 extra days after the cruise in the NE area, we will be driving from Boston. We do not want to move around every night, and after reading your article I am thinking of just going to the Berkshires (maybe Lenox) and Stowe, then touring around those areas in the time we have. My question is where would you spend more time, Berkshires or Stowe? We will do 2 nights at one, and 3 nights at the other.

Definitely the Berkshires. I have a whole article on what to do in the Berkshires, if you use the search bar. I think Stowe is a one day visit unless you’re skiing.

This is awesome information. Thanks for putting this all together. Where would you suggest to stay on Day 6 & 7 ? There are no suggested places to stay in the article. Thanks so much !

There are lots of places to stay in the White Mountains. I should probably update the article. The nicest place is the Omni Mount Washington. You can also check out the Mountain View Grand resort and the White Mountain Hotel and Resort. Or opt for booking an Air Bnb.

This was exactly what I needed! Flying into La Guardia from Texas next week. We are renting a a car and doing a 6-day tour of New England. We were planning to end in Boston so we can go from there back to the airport. Can you give me an idea of where to start with having only 5 nights? Thanks so much for sharing this great information with us newbies!

You could just reverse the order and start in the White Mountains, staying only 1 night there instead. Or you could skip the white mountains and start in Smuggler’s Notch, spending an extra day in the Berkshires. I have a Boston itinerary, if you want one: https://www.thegeographicalcure.com/post/the-perfect-3-day-itinerary-for-boston-massachusetts

Hi Leslie! We’re planning to take your New England car tour and will be driving from southwest OH. We may stay at the American side of Niagara Falls on our way to Boston. Can you offer any tips on lodging or restaurants at Niagara Falls? Thanks much!!

Sorry, no, I haven’t been there in decades. Enjoy your trip Don!

We will be able to complete 5 full of the days of your itinerary, starting and ending in Boston. (Landing in Boston Sunday night, touring Monday – Friday, flying out of Boston Saturday late afternoon).

Which 5 days would you most highly recommend we hit? We do like hiking, if that helps.

Thanks for your great post!

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Last Updated on July 4, 2023 by Leslie Livingston

New England Wanderlust

Connecticut , Fall , Maine , Massachusetts , New Hampshire , Rhode Island , Vermont  ·  June 7, 2023

The PERFECT New England Fall Road Trip Itinerary: 3, 5, 7, 10 & 12 Day Options! (2024)

There’s a reason why New England is world-famous for fall foliage, and if you’re looking to plan the most amazing New England fall road trip, you’ve come to the right place! I’ve been traveling throughout this region for over 15 years, and have done so many fall foliage road trips. It took me a while, but I’ve finally put together the perfect itinerary for you based on real experience!

This post details where the best places are, the best times to plan your road trip, and also, which places may not be worth your time. So, you can rest assured that you’re truly seeing the best of the best with my itinerary.

This itinerary is also geared toward first-timers and those looking to find the best foliage spots . If you’ve experienced New England in the fall season before, many of these locations and tips may already be familiar. However, I’ve also sprinkled in some insider tips, so it’s still definitely worth reading 😉

During this trip, prepare to see idyllic countryside landscapes, blazing fall color, beautiful covered bridges, charming towns, general stores, epic overlooks and hiking trails, and so much more. Basically, you’ll get your fill of New England charm right from the start, and it won’t stop until the trip is over. Sound good? Then let’s get started!

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

Tips For Planning A Trip To New England In The Fall

There are some important things to know before you begin to plan your perfect New England fall road trip, so let’s get that out of the way first 😉

The first thing you need to know is that foliage will peak in the northern areas first, then peak in the southern areas later . For that reason, I recommend that you start in the north if you can, especially for a longer trip, but it’s not always necessary for shorter trips.

If you’re planning a bucket list 2-week adventure, starting in the north is a good call because peak foliage can begin to diminish quickly, depending on the season and climate patterns. However, if you’re traveling for closer to a week, this won’t be as important.

I go into peak foliage times in each region in a bit, so definitely be sure to read that through, too!

Another important thing to know is that you should anticipate all kinds of weather. I’ve done many fall road trips through this region, and have had warm, sunny days, and trips where it rained almost every single day. I’ll go more into what to pack for this trip at the end of the post to help you prepare, but this is a good thing to be aware of.

Also, book in advance . I can’t stress this enough. Hotels and accommodations book out well in advance for fall foliage season in prime areas, and these prime areas are where you’ll be heading! If possible, begin to book your hotels at least 6 months in advance, but even 8 months is better. For reference, while I began to plan my Vermont fall road trip for the 2023 season, my favorite place to stay in Stowe, VT was fully booked during peak foliage weeks – in FEBRUARY. Yep, February.

Offline Google Maps! I can’t tell you how important this is! Even as recent as a fall 2022 road trip, I barely had service through much of New Hampshire and Vermont. I spent a lot of time just driving around hoping my service would come back, or asking people for directions the old-fashioned way. I usually offline maps, but totally forgot that trip, and it was a harsh reminder that this is a must-do.

Lastly, prepare to pay . Yes, the sad truth is that peak foliage season in New England is expensive, and it won’t be your most budget-friendly trip ever. There are ways to keep costs down, and I’ll go more into that later in the post as well, but generally speaking, this is an expensive time to visit New England – at least, where the foliage is the best 😉

What Is The Best Time To Visit New England For Fall Color?

In a nutshell, the last week of September, or the first week of October. However, it does vary depending on where you’re heading.

As mentioned before, the colors will begin to change in the northern regions first, and then the southern regions will follow later. Most people will choose to visit Maine, New Hampshire and Vermont during their New England fall road trip (and spoiler alert: this is also where I’ll be suggesting you go!), so this timeframe works very well for these areas.

The central part of Vermont will often peak right around Indigenous People’s weekend in October, and for a getaway to popular towns like Stowe and Woodstock, this is the perfect weekend to plan your trip.

Massachusetts often peaks right around Indigenous People’s weekend as well, with southern MA peaking a week or so later.

The greater Boston area, and Connecticut will peak mid-late October, depending on the year.

How Many Days Do You Need In New England In The Fall?

The great thing about New England in the fall is that you can easily do a weekend getaway and still pack a lot in, or you can plan an epic 12 day road trip for the ultimate adventure. And either way, it’s going to be incredibly memorable.

If you’re coming in from a distance, especially if you’re flying in, I would say 10 days is a great option, 12 days is even better, and 7 days is also wonderful. Of course, with 12 days, you’ll be able to see so much or plan extra time in some places. But even with 7 days, you’ll get to see quite a bit.

If you’re local to New England, and don’t have 10 days, 7 days is again a nice sweet spot. 5 days will also work in this case. And, as mentioned, even a weekend away will allow you to experience some of the best this region has to offer in the fall season.

The great thing about the best places for fall foliage are located in some of the smallest states, so you can cover a lot of ground in a short amount of time.

Best Places To See On A New England Fall Road Trip

While every New England state has something special to offer during fall foliage season, for the purpose of seeing the absolute best spots, I recommend sticking to Maine , Massachusetts , New Hampshire and Vermont . And flying into Boston.

Because these areas offer the most spectacular displays of foliage, most picturesque scenery, tons of things to do, and they’re all reasonable close to one another, allowing you to maximize your time.

Here’s why I don’t necessarily recommend states like Connecticut or Rhode Island if you have less than 10 days – they’re further away from the best places to see in the fall.

I truly love every single New England state, and I do really enjoy Connecticut in the fall. However, it’s so far west that you’ll spend more time driving to get there, and possibly forgoing some really spectacular places in Maine, New Hampshire, Massachusetts, and Vermont.

If you have 10 days or more for a New England fall road trip, then I would highly suggest you consider adding in the Litchfield Hills regions of Connecticut , which you’ll see I included in my itinerary. It’s also very close to The Berkshires region, so you can combine it with that part of the trip, depending on how much time you have. However, with less than 10 days, I personally don’t feel like it’s worth it. Especially for first-timers.

If you’ve already seen some of the places I’m recommending in this post, then definitely try to swing over to Connecticut and experience a new area during the fall!

If you have less than 10 days, you may even want to focus all your time on Vermont and New Hampshire. The reason for this is because some of the best places for fall foliage in Maine are further north. I think places like Acadia National Park are very worth seeing (and you’ll see I’ve incorporated it into some of my itineraries!). However, if you prefer a slower pace and less driving, Vermont and New Hampshire are the absolute best places to see .

Some Things To Know About My Itineraries

They all begin in Boston , assuming that’s where most people will fly into if visiting from a distance. If you fly into a different airport, or are driving in, you can easily adjust your plans as needed.

They’re done in true road trip style , meaning there’s a lot of driving, and mostly 1-night stays. There are some places I recommend 2 nights in, but you can adjust this based on your preferences. If you want to stay longer in one place, definitely go for it!

I give you options! Of course, I stand by all my suggestions ☺️ However, I know everyone has different travel styles and speeds, so I encourage you to to tailor this to what you think you’ll enjoy the most. I’ve given you suggestions on how to adjust the itinerary based on your preferences.

10 Day New England Fall Road Trip Itinerary From Boston

Okay, let’s get into my perfect New England fall road trip itinerary options! We’re beginning with my suggestions for an incredible 10 day adventure.

10 Day Road Trip Overview

Day 1 : Arrival In Boston Day 2 : Explore Boston Or Take A Day Trip To Salem Day 3-4 : Bar Harbor/Acadia National Park + An Optional Stop In Salem Day 5 : Jackson, NH Day 6 : Franconia, NH (Driving The Famous Kancamagus Highway To Get There!) Days 7-8 : Stowe & Woodstock, VT Day 9 : The Berkshires and/or Litchfield, CT Day 10 : Back To Boston + A Stop In Sturbridge, MA or Litchfield, CT

Breakdown Of The 10 Day Itinerary Option

Day 1: Arrival In Boston Take this time to arrive, get settled, and maybe take in a few sites around the city! Have some time on your first night here? Jump down to Day 2 for some suggestions on what to do!

Where To Stay In Boston:

• Luxury : The Langham
• Splurge : Boston Harbor Hotel
• Moderate : Revere Boston Common

Pro Tip On Fall Foliage In Boston : Foliage peaks later than the rest of the places listed in this itinerary – usually mid-late October. So while you probably won’t see peak foliage in Boston if you plan your trip for peak foliage in Vermont, New Hampshire and Maine, it may catch a glimpse of it on your back if you’re planning a longer trip! Or, you can leave the airport to immediately begin your drive to Maine, and plan to stay a night or two in Boston before you have to fly out.

Day 2: Explore Boston

Boston during the fall season has so much to see and do, but here are some highlights to consider if it’s your first visit:

• Public Gardens (very scenic garden area with a beautiful pond and pedestrian bridge (also makes for lovely photos!). This is a good spot for fall foliage in the city, too.
• Newbury Street for shopping
• The North End for history and food
• Beacon Hill for charming cobblestoned streets at the famous Acorn Street
• Take a food tour if it works with your schedule. There’s incredible food to be had in Boston, and taking a tour with a local expert is a great way to sample lots of delicious things in a short amount of time!

Click here to check out my post on the best Boston food tours!

Day 2: Optional Day Trip To Salem

If you would prefer to take a day trip to Salem, rather than stopping on your way to Acadia National Park, this is a great option! And really, there’s no right or wrong choice here – it just comes down to which you prefer.

Salem is an easy day trip from Boston without a car because of this convenient ferry! Click here to check out the Boston → Salem Ferry!

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

Day 3: Drive To Bar Harbor & Acadia National Park

Acadia National Park is one of the best things to do in New England year-round, so this is definitely a must if you’ve never been. It also offers some really wonderful foliage, and fall is my personal favorite season to visit for this reason.

This drive from Boston to Bar Harbor takes about 5 hours without stops, which is why I usually suggest you make a pitstop to break up your journey. I actually have some posts on stops you can make along the drive, so be sure to check those out below.

But since Salem is really the ultimate fall destination in Massachusetts, I suggest you pick that as a stop on the drive 🙂

Bar Harbor is the town adjacent to Acadia National Park , and where most people will choose to stay when visiting. Once you arrive, take some time to get settled, and then head out into downtown Bar Harbor to explore this charming seaside town, visit the shops, and grab a great dinner!

Where To Stay In Bar Harbor:

• Bayview Hotel . An oceanfront boutique hotel with awesome views. Perfect for a splurge on your trip!
• Bar Harbor Villager Motel . Clean, updated and spacious. Also, walkable to everything in town.
• Little Fig Hotel . A cute, modern boutique hotel walkable to town.

Here are some posts that will help you further plan this portion of your trip:

• Best Stops To Make Driving Boston To Portland, Maine
• Best Stops To Make Driving Portland to Acadia National Park
• The Perfect Acadia National Park Itinerary (read this one for more information on Bar Harbor and things to do!)

Day 4: Explore Acadia National Park

Even in just 1 day, you can visit some of the best places in the park, and also some really wonderful fall foliage spots. Here how I suggest you plan your day:

If you’re up for it , starting your day with sunrise at the top of Cadillac Mountain is always incredible! This will be great for fall foliage, too. You can also choose to do this the following morning before leaving.

Next, head to the Jesup Path scenic walk , which is especially beautiful in the fall season.

Then, park at the Sand Beach parking lot , and walk the Ocean Path for incredible views . This is 1-mile each way, but offers some of the most iconic views in the park, including the Otter Cliffs and Thunder Hole. It’s also flat and easy, making it very relaxing. Have your camera ready for this one!

For a more advanced hike with awesome foliage views, you can do the Beehive Trail from Sand Beach lot, too.

Continue on Park Loop Road to Jordan Pond House for lunch , and enjoy the views of the pond and mountains. You can also choose to walk around the pond if you have time after lunch.

For more foliage views, hike the Bubble Rock Trail after lunch.

Day 5: Drive To Jackson, NH + Spend The Night

Without stops, this drive takes about 4 hours and 15 minutes.

One stop I suggest making on the way if you enjoy local craft beer is the Oxbow Beer Garden in Oxford , ME . It’s got a very cool outdoor setting, and they have fantastic craft beer.

I recommend spending the night in Jackson because it’s a longer drive from Bar Harbor, and there are some fun things to do in the area. Also, there’s a very scenic drive called The Kancamagus Highway that’s stunning in the fall season with foliage, and I want to make sure you have time to drive it. But more on that in Day 6 🙂

Here are some fun fall things to check out in Jackson:

• The Cog : This mountain railroad takes you to the summit of Mount Washington, the tallest peak in New England! It’s about 45 minutes from Jackson, but you’ll drive through Crawford Notch State Park , which is very scenic, and The Cog is simply incredible in the fall season. If you leave Bar Harbor early enough and have time to do this, I highly recommend it!
• Honeymoon Covered Bridge & Flossie’s General Store
• Glen Ellis Falls
• The cute town of North Conway

Where To Stay In Jackson:

• Christmas Farm Inn (this place is super cozy!)
• The Inn At Thorn Hill & Spa

Option To Stay In North Conway : North Conway is only about 12-15 minutes from Jackson, so you can really stay in either. I think Jackson has better hotel options, and it’s a bit closer to The Cog, which is why I suggested you stay there. But either town works for your New England fall road trip!

Here are some fun things to check out in North Conway if you choose to visit:

• Cathedral Ledge Distillery
• Ledge Brewing Company (between North Conway and Jackson, technically)
• The cute downtown area and Zeb’s General Store (one of my all-time favorite general stores!)
• North Conway Scenic Railroad

Day 6 – Drive The Kancamagus Highway To Franconia, NH

The Kancamagus Highway (Route 112) is a scenic drive that’s regarded as one of the best drives for fall foliage, so this is something you’ll definitely want to do on your New England fall road trip. It connects the towns of Woodstock and Conway, so you can easily start this drive just a few minutes from Jackson or North Conway.

For this day, I suggest you get up early to make sure you have time to explore Franconia Notch State Park after driving The Kanc.

Tips For Driving The Kanc:

• Remember earlier in the post when I said you’ll lose cell service in much of New Hampshire and Vermont? Well, this is one of those drives where there’s no service, so offline your maps before starting!
• There are no bathrooms or gas stations on the drive, so plan accordingly.
• The Kanc takes about 45 minutes one-way without stops, but you’ll want to budget about 2 hours to make some stops at the overlooks.
• During the fall season, especially on weekends, it’s possible traffic could slow down as people try to pull in and out of the parking areas. Plan for some slower traffic.

Pro Tip : Before hopping onto The Kanc, there’s a great little place called Cheese Louise just before the entrance to The Kanc, and this is an awesome place to grab some food before the drive! Especially on a chilly, fall day, a grilled cheese sandwich totally hits the spot, right? 😍

Stops To Make On The Kanc (in order from Conway to Woodstock):

• Albany Covered Bridge
• Rocky Gorge Scenic Area (parking can be found at 44.0016667175862, -71.27716637107925)
• Sabbaday Falls
• Sugar Hill Scenic Overlook
• CL Graham Wangan Overlook
• Hancock Overlook (this one is right at the famous hairpin turn – can’t miss it!)
• Lincoln Woods Trailhead – Scenic suspension bridge over the river that’s not far from the parking lot.

🍁 Before hopping on The Kanc, consider downloading this great audio tour to enhance your drive – Click here to check out this audio tour!

There are also tons of hiking trails along The Kanc , so if you’re looking to squeeze in a hike on the drive, this is something to consider. But if you don’t have extra time, I would suggest moving on to Franconia Notch State Park, and only doing hikes along The Kanc if you’re able to add an extra day in.

After The Kanc, your next stop is Franconia Notch State Park . And this is where most of the top things to do are , especially in the fall season .

Flume Gorge is one thing I recommend you do if you can only pick one attraction. Flume Gorge is a very fun 2-mile loop trail that takes you over 2 covered bridges, and through the granite gorge. Along the trail, you’ll have some really gorgeous spots to admire the fall foliage, too.

Not sure if this is right for your itinerary? Click here to check out my detailed post in if Flume Gorge is worth visiting , and everything you need to know to plan the perfect visit.

Pro Tip: Buy your Flume Gorge ticket online in advance to save a few bucks! On weekends in the fall season, it’s also possible that certain time slots will sell out. This is another reason to book in advance.

If you have time to explore more of Franconia Notch State Park, I also recommend these activities:

• Cannon Mountain Aerial Tramway
• Artist Bluff Trail (famous spot that ends overlooking Echo Lake – amazing during foliage season!)
• The views at Echo Lake Beach

Where To Stay Near Franconia:

• Sugar Hill Inn – 15 mins from Franconia Notch Park, and is rated as the best B&B in New Hampshire!
• Riverwalk Resort – 5-7 mins from the top attractions in Franconia.
• Woodstock Inn & Brewery – Cozy inn with a brewery.

Here are some posts to help you plan this portion of your trip:

• Fun Things To Do In Franconia, NH
• Fun Things To Do In Littleton, NH
• Fun Things To Do In Lincoln, NH
• Where To Stay In New Hampshire In The Fall
• Where To Stay In The White Mountains: Guide To The Towns

Day 7 – Drive To Stowe Or Woodstock, VT

Begin your day in New Hampshire with a country breakfast at Polly’s Pancake Parlor! This place is famous in New England, and truly has some of the most amazing pancakes I’ve ever had. It does get busy in the fall season, but man, it’s so worth it.

Then, on to Vermont you go! For the next 2 nights, you’ll want to choose between Stowe and Woodstock, VT as your home base. These towns are the absolute best to visit in Vermont during a New England fall road trip because of foliage views and small-town charm. They’re only 1 hour and 15 minutes from each other, so, you can choose where you want to stay, and then visit the other as a day trip.

The drive to both Stowe and Woodstock is 1 hour and 30 minutes from Franconia , and since this is a shorter drive, you can make some stops along the way, or drive straight there. Stowe and Woodstock both have a lot to do, even though they’re small towns, so it’s beneficial to drive straight there and make sure you have plenty of time to explore.

If you choose to stay in Woodstock, I suggest stopping at the King Arthur Baking Company campus on your way because it’s pretty much on the direct route. It’s a really fun place with fresh baked goods and breads, a café, and a fun shop where you can stock up on pantry staples and baking mixes.

Do I recommend you stay in Stowe or Woodstock? I honestly love both equally! There’s no wrong choice here.

The biggest difference between the two is that Woodstock feels a bit more upscale, and Stowe definitely has a very casual feel to it. But the difference is minor. Both have charming covered bridges, great shops, amazing restaurants, a quaint town feel, and plenty of things to do.

Where To Stay In Stowe :

• The Green Mountain Inn . It’s located right on Main Street, so you can walk to a lot of places.
• Spruce Peak Resort . Perfect for those wanting a resort feel, and it’s right off the scenic Smugglers Notch drive. There are rooms with gorgeous mountain views here, too.

Where To Stay In Woodstock :

• The Woodstock Inn & Resort . It’s referred to as Vermont’s most beautiful address, and it’s in the heart of Woodstock’s village. This is a luxury hotel that’s worth it!
• 506 Inn On The River . Located just outside of the village, this is a modern and cozy inn, well … right on the river 😉

Here are some posts that will help you plan your time in Stowe and Woodstock:

• Best Things To Do In Stowe
• Best Things To Do In Woodstock

Day 8 – Explore Stowe & Woodstock, VT

Depending on where you stay, you’ll want to take a day trip to the other town this day. Below are breakdowns of the can’t miss things to do in each town .

Best Things To Do In Stowe :

• Explore the cute shops along Main Street (don’t skip the Stowe Mercantile!)
• Drive Smugglers Notch for amazing foliage.
• Ride the gondola to the top of Mount Mansfield, the highest peak in Vermont (this is epic during the fall season!). This is located at the midway point along the Smugglers Notch drive.
• Visit Emily’s Covered Bridge, and learn about it’s spooky history.
• Sample the hard cider at Stowe Cider.
• Sip on craft brews at Alchemist Brewing (one of my favorites in New England).

Best Things To Do In Woodstock:

• Stroll through the charming downtown shops and eateries.
• Pop into Mon Vert Café for a warm drink.
• Snap a photo with Middle Covered Bridge in town.
• Drive over Taftsville Covered Bridge to visit Sugarbush Farms. You’ll be able to sample homemade cheese and fresh maple syrup here, and also take in amazing foliage views.
• Visit Billings Farm & Museum.
• Drive over to Sleepy Hollow Farm to see the famous farm landscape spot.

Day 9 – Drive To The Berkshires Or Litchfield, CT

Next up – The Berkshires or Connecticut! This choice is yours entirely. Let’s start with the option to drive to The Berkshires.

The Berkshires is an iconic region in Massachusetts that’s a really great one to visit for fall foliage. Here, you’ll find cute towns, loads of fall color, lots of scenic hikes and walks, and awesome dining options.

Depending on which town in Vermont you’re coming from, the northern region of The Berkshires area will be just over 2 hours from Woodstock, or just over 3 hours from Stowe .

The drive from either town to The Berkshires will pass through Rockingham, VT, and you’ll definitely want to stop here to visit the Vermont Country Store! There’s also the very cute Kissing Covered Bridge here that makes for a fun photo.

Once you arrive in The Berkshires, I suggest you start in Williamstown, and drive the scenic Route 7 down to Sheffield. This drive without stops takes about 1 hour and 15 minutes, but I would budget at least a few hours to make stops and enjoy some other fun activities. This route packs a lot into a perfect fall day, without a lot of driving.

During this drive, these are the best stops to make:

• The Mount Greylock Auto Road to the highest peak in Massachusetts (absolutely amazing in the fall season!).
• Make a detour off Route 7 to Bartlett’s Orchard in Richmond for the perfect fall farm experience.
• Continue with your short detour to Hilltop Orchards, which is 5 minutes from Bartlett’s, and where you can sip on artisanal craft ciders!
• Walk through the charming town of Lenox.
• Stroll through quaint Stockbridge, too!
• Snap photos with the covered bridge in Sheffield.

Where To Stay In The Berkshires:

• The Red Lion Inn . A historic and famous inn in the heart of Stockbridge.
• The Dewey . A cozy, traditional New England B&B in Lenox.

The other option is to drive to Litchfield, CT , which is south of The Berkshires. It’s a longer drive from Vermont, but you could also turn this into a fun road trip day by driving the same Route 7 itinerary as mentioned above through The Berkshires, and then continue on to the Litchfield Hills. I would probably only choose this option if you wanted to take your time exploring the awesome stops along Route 7 in The Berkshires, arrive in CT in the evening, and then explore this region of CT the next morning before your drive back to Boston.

How To Spend Your Time In Litchfield Hill, CT:

Since you’re likely coming down through the western border of Massachusetts, I would start in Kent, and work your way east. You probably won’t have time to do everything on this list, but pick and choose based on your preferences and schedule.

• Explore the cute town of Kent, and then visit Kent Falls State Park if you have time.
• Continue to follow Route 7 to New Milford. The drive is very scenic!
• Stop in New Milford to enjoy the quaint town, and then visit Lover’s Leap Bridge.
• Head over to Washington, and then continue on to Mount Tom State Park for awesome foliage.
• End in the charming town of Litchfield.

Where To Stay In The Litchfield Hills : Litchfield Inn . Refined and still very cozy, and one of the best in the area!

Should I do The Berkshires or Litchfield, CT? Personally, I would stay stick to The Berkshires since this will allow you a more relaxed itinerary. There’s so much to do, and plenty of foliage scenery to take in. If you do the Route 7 drive quicker than you were anticipating, you could always shoot down to the Litchfield Hills for an impromptu adventure 🙂

I would choose to add on the Litchfield Hills if you’re feeling adventurous, and really want to see as much of New England as possible.

Day 10 – Drive Back To Boston, Stopping In Sturbridge or Litchfield On The Way

If you have time to explore another cute town on your drive back to Boston, I would suggest either tacking on a quick drive through the Litchfield Hills, CT if you didn’t already, or a stop in Sturbridge, MA. Sturbridge is more on the way to Boston, and offers beautiful foliage.

How to spend your time in Sturbridge, MA :

• Visit Old Sturbridge Village for all the cozy fall New England vibes (this is a must if you have time!).
• Pop into Saw Dust Coffee & Dessert Bar for lunch and treats.
• Sip on craft beer at Altruist Brewing Company.

And of course, as mentioned in the previous day’s itinerary, the Litchfield Hills region has plenty to offer for foliage views, small towns, and beautiful scenery.

But, if you have a flight to catch, then don’t risk it, and head straight to the airport! 🙂

Optional Adjustments For The 10 Day Itinerary:

• You can easily cut out Acadia National Park, and head straight to New Hampshire, and choose to spend more time there. Acadia is out of the way, and further north, so I know it doesn’t suit everyone’s plans. This would allow you time to definitely ride The Cog, and have a more relaxed schedule.
• If you would rather have more time in Vermont, you can skip The Berkshires/CT. This is personal preference! Both areas are amazing for fall foliage, but nothing is quite like Vermont in the fall. This would allow you time to move at a slower pace. If you decide to skip The Berkshires/CT and stay in Vermont for a third night, see my 12 day itinerary, option 3 for suggestions on what to do!

12 Day Road Trip Itinerary Option

If you have 12 days (or more!), this is truly awesome. I would follow my 10 day itinerary, and then take one of these suggestions:

Option 1 : Add in 1 day to see Litchfield, CT after The Berkshires . Since you have the extra time, you can definitely see the Litchfield Hills region of Connecticut with this itinerary! I would recommend this option for those who really want to see as much of New England as possible, and make all the rounds.

Option 2 : Add an extra day to Littleton/Franconia. This region has so many great hikes and places to spot fall foliage. It’s well worth adding a day to this part of the trip if you have the extra time. This would allow you a half day to ride The Cog, and takes more scenic walks and hikes to enjoy the fall foliage.

Option 3 : Add an extra day to Vermont. On your extra day, you can take a day trip to Burlington and Shelburne, or spend the day driving the back roads .

Burlington & Shelburne, Vermont things to check out :

• First, the drive from both Stowe and Woodstock to Burlington on I-89 is beautiful in the fall. You’ll see lots of mountains ablaze with fall color.
• In Burlington, check out the waterfront area, and walk along Lake Champlain.
• Burlington also has an awesome craft brewery scene, and Foam Brewers is especially great.
• The American Flatbread restaurant in Burlington is a cozy place to stop for lunch.
• Church Street Marketplace in Burlington is a must!
• In Shelburne, you’ll want to spend most of your time walking around Shelburne Farms. This is a historic farm once owned by the Vanderbilt family, and has beautiful hiking trails, and you can also sample their homemade cheeses. Definitely do the Farm Trail, which takes you to an epic view of Lake Champlain.

Vermont back roads driving itinerary near Stowe :

This drive is easier to do from Stowe, but it’s also doable from Woodstock if you’re okay with a longer day. This itinerary is is order based on departing from Stowe, but you can also adjust based on which town you’re coming from 🙂

• The covered bridges in Montgomery, including Montgomery covered bridge (which is actually in Waterville), and Longley Covered Bridge.
• Barn Owl Bistro is a hidden gem nearby that’s a great little pitstop.
• The town of Cabot and the nearby AM Foster Covered Bridge are really beautiful areas to visit full of rustic Vermont charm.
• Peacham is a very small town with iconic landscapes and scenery.
• Bogie Farm in East Ryegate is a landscape that worthy of a postcard, and is especially beautiful in the fall.
• The drive between all these destinations will also be lovely and scenic, and packed with fall color.

1 Week (7 Day) New England Fall Road Trip Itinerary

If you have 7 days, welcome to your itinerary! This option is the same as the 10 day option, but eliminates Acadia National Park to save time.

7 Day Road Trip Overview

Day 1 : Arrival In Boston Day 2 : Drive To Jackson, NH + A Stop In Salem, MA Day 3 : Drive To Franconia Along The Kancamagus Highway Days 4-5 : Drive To Stowe or Woodstock, VT + Stay 2 Nights Day 6 : The Berkshires Day 7 : Return To Boston

For this itinerary, you can also eliminate The Berkshires, and stay an extra night in Jackson or Franconia.

5 Day New England Fall Road Trip Itinerary

With 5 days, you can go in a few different directions, and below, I break down my suggested options, and the benefits of each. This way, you can tailor it to your preferences.

Option 1 : Spend two nights in Boston with a day trip to Salem, then spend 3 nights in Stowe/Woodstock, VT.

Option 1 is perfect if you prefer staying in one place longer. This itinerary will allow you to stay in the same hotel in Boston for 2 nights, and take an easy day trip to Salem for the perfect fall day of Halloween fun and history! Then you can pick up your rental car (if you haven’t already), and drive to Stowe or Woodstock, VT for 3 days to explore both towns.

With 3 days in Vermont, you can easily see both Stowe and Woodstock, and maybe even plan a day of driving around the back roads. See the 12-day itinerary option for my suggestions on driving the back roads around Vermont during foliage season .

Option 2 : Spend 1 night in Boston, stop in Salem on your way to Franconia and spend 2 nights in Franconia. Then spend 2 nights in Stowe/Woodstock, VT, and then drive back to Boston.

Option 2 is perfect for those who still want to see as much as possible in 5 days. You’ll get to see a bit of New Hampshire and Vermont, while making a stop in Salem.

Note: For this itinerary, I would drive from Salem to Conway, and the drive The Kancamagus Highway on your way to Franconia so you get to experience the fall foliage along this route. But this itinerary option eliminates the stay in Jackson, as there are more fall things to do in Franconia.

Option 3 : Spend 1 night in Boston, 1 night in Salem, 3 nights in Stowe/Woodstock, VT, and then back to Boston.

Option 3 is perfect for those who really want to spend some time in Salem. This itinerary allows you to spend a whole night in Salem to really enjoy all the Halloween festivities and tours, and then you can spend 3 beautiful days in Vermont.

I excluded New Hampshire from this option because I felt like it would be too much to cram in when adding 1 night in Salem. But if you were feeling adventurous (I’ve been there, I get it! 😂), you can drive to Franconia, NH for 1 night after Salem, and then do 2 nights in Vermont instead of 3.

3 Day New England Fall Road Trip Itinerary

3 days in New England is the perfect long weekend getaway!

With 3 days, I suggest you stay in one location , and add day trips . If you’re flying into Boston, you can stay 1 night in Boston if needed, and then drive to Vermont or New Hampshire for 2 nights. If you’re not flying in, you can spend all 3 nights in Vermont or New Hampshire.

Stowe is very close to New Hampshire, and it’s only about 1.5 hours from Franconia. You can easily do a day trip from Stowe to New Hampshire, or vice versa, for this type of itinerary.

It would also be easy to work in a stop in Salem, MA, either on your way in or out of Boston.

Weekend New England Fall Road Trip Itinerary

For a weekend getaway in New England (essentially, 2 days), I would also recommend you stay in one place and take a day trip. For this itinerary, I almost always suggest Stowe or Woodstock. You can stay in either town, and spend 1 day exploring that town, and then the next day, exploring the other as a day trip.

Vermont Fall Road Trip Itinerary

Looking to just see Vermont? Excellent choice. It’s my personal favorite fall destination in New England (even though it’s a very close call 😉)

For a Vermont fall road trip , you can really do it in anywhere from 5-7 days. Of course, more is better to really see everything, but generally speaking, you can actually make it happen in a week or less. A popular route to take in Vermont is Route 100 , which runs the entire length of state, right through the middle. This allows you opportunities to veer off and see some other places as well.

For the purpose of this itinerary, I’m going to provide a week-long (7 day) itinerary, and you can adjust it to your own plans.

Day 1 : Bennington & Manchester Day 2 : Drive to Woodstock, stopping in Grafton and Weston on the way Day 3 : Spend the day in Woodstock Day 4 : Drive to Stowe, stopping in Montpelier if you’d like Day 5 : Spend the day in Stowe Day 6 : Staying in Stowe, take a day trip to Burlington & Shelburne Day 7 : Drive back

Day 1 Suggestions : Bennington and Manchester are pretty close to each other, so you can easily do both in one afternoon. There are some wonderful covered bridges in the area to see, and here are some more things to check out:

• The Bennington Battle Monument for fall foliage scenery.
• Downtown Bennington for shopping on Main Street (small, but cute!).
• Apple Barn is a few minutes from Main Street for a fun country store and bakery.
• Zoe’s in Manchester for lunch (great sandwiches!)
• Downtown Manchester for shopping in a cute town (don’t skip Northshire!)

Day 2 Suggestions : Grafton is a very small town, but it’s quintessential Vermont. It has a cute little cheese shop, and a nice little market/cafe called MKT Grafton, which is perfect for a quick bite. Also, swing by Weston to visit the Vermont Country Store.

For the rest of the itinerary, refer to the 10 day option for details 🙂

Click here to check out my post on a Vermont covered bridges road trip!

New Hampshire Fall Road Trip Itinerary

My second favorite fall foliage destination! Here’s my suggested itinerary for a New Hampshire-only fall road trip.

To just see New Hampshire , you can also spend anywhere from 4-7 days.

With 4 days, you can easily just stick to the White Mountains region, but I’m here to give you all my tips on even more awesome places to see in the fall season in New Hampshire ☺️ So, this itinerary will be 7 full days , but adjust as you need to!

Day 1 : Portsmouth Day 2 : Lake Winnipesaukee Days 3-4 : Littleton/Franconia Days 5-6 : North Conway/Jackson Day 7 : Drive back

Connecticut Fall Road Trip Itinerary Option

If you’ve seen all the “hot spots” around Vermont, New Hampshire, Massachusetts, and Maine, and you’re looking to explore a new part of New England in the fall, Connecticut should be next on your list!

As mentioned, my favorite place in Connecticut for fall foliage is the Litchfield Hills region. I always like to share that this region was what inspired Amy Sherman-Palladino’s creation of Stars Hollow, so Gilmore Girls fans will especially love this area.

The Litchfield Hills is very compact, and you can easily do a lot in a weekend here. However, 3-4 nights will allow you a nice, leisurely pace to explore all the amazing things this region has to offer in the fall.

The best towns to stay in in the Litchfield Hills region are:

• New Milford
• Washington/Washington Depot

Of all these towns, Litchfield probably has the most options when it comes to shopping and dining, however, they’re all very quaint and charming. I would pick whichever one has the best hotel for your plans.

If you have extra time for your Connecticut fall road trip, you can tack on places like Canaan to the north of the Litchfield Hills region, drive to Glastonbury, and then through the River Valley region, which includes the adorable towns of Chester and Essex. You can also choose to end your road trip in Mystic.

What To Pack For A New England Fall Road Trip

I always start every New England packing guide with the same thing, and this post is no different: begin to check the weather reports 5 days out from your trip to get an idea of what the weather will be like . And keep checking it until the day before you leave .

This is because weather in New England can change quickly, especially in the fall season. It’s not quite as dramatic as say … Iceland 😉 But, it can change and vary a bit. Generally speaking, fall will be chilly and a bit rainy. However, you could also have warm and sunny days. For longer trips, you’ll want to pack for both scenarios.

Here are some things I recommend you consider when packing for a fall road trip through New England:

Waterproof hiking boots . If you plan to do any hiking, or even nature walks, you’ll want a pair of sturdy boots that are waterproof. Even some attractions like Flume Gorge and other waterfalls in New Hampshire are pretty wet, so this is a good idea to stay dry and comfortable. I really like the Eddie Bauer K-6 Hiking boots. Find the women’s version here and the men’s version here . They’re a much less expensive version of the famous Danner hiking boots featured in the movie Wild !

Good hiking socks to keep your feet dry . An awesome brand to support is Tarn Tough Socks , which is a Vermont-based company. They’re an investment, but they’re also the best, and come with a lifetime guarantee!

Waterproof rain jacket to stay dry if it rains . You won’t want to let the rain slow you down, especially if there’s a lot in the forecast! So definitely pack one that’s completely water proof ( not water-resistant).

Layers . The best way to dress in the fall season is with layers. Under your rain gear, flannels, sweaters, and lightweight t-shirts (both short-sleeved or long-sleeved) work great.

Jeans . These work really well for most days. Fall in New England is pretty casual.

Hiking clothing . For any hikes you want to do, pack whatever clothes you typically wear and feel comfortable in 🙂

Comfortable sneakers or boots . When it’s not raining, a good pair of comfortable sneakers or cute boots work perfectly, depending on your plans. Since I drive from New York, I don’t usually have to worry too much about weight limits on a suitcase, so I’ll throw a pair of sneakers, flat boots/booties, and my hiking boots into the car. This is usually all I ever need.

Dinner outfits . New England is home to incredible places for farm-to-table dining, some of which are a bit more fancy. If you plan to go out for a nice dinner or two, you’ll want to pack accordingly. New England isn’t super fancy, so women can do a casual dress/jeans and a nice top with booties in the fall, and men can easily do dark-wash jeans and a button down top.

Reusable water bottle . You’ll need to stay hydrated while out exploring!

Day pack . If you plan to do any hiking, you’ll want to bring a day pack with you to carry your essentials. If you don’t plan to do any hikes, you can probably skip this, as you can keep most everything you need in your car or room.

Does It Snow In New England In The Fall?

Here’s the thing – it might if you’re up in the mountains. However, it doesn’t usually snow during peak foliage times. Usually, New England gets its first snow of the year later in October or early November. So, I wouldn’t worry about packing any snow gear or winter boots for your fall road trip.

How Do To A New England Fall Trip On A Budget

So, first thing’s first, you’ll unfortunately have to rethink what “budget” means in New England, especially during peak season in the fall. It’s generally more expensive than other areas of the country regardless of the reason, so during prime foliage times, prices will go up significantly.

Especially in the past, I never had the money to spend on several nights at hotels during this time of the year, so I have learned to do it on more of a budget. Not necessarily cheap, but not as tough on the wallet 😉 Here are my tips:

• Stay in motels. I love a good hotel splurge, and do it more now than I did in my 20s and early 30s. But for most of my road trips when the focus in exploring outdoors, I stay in motels with efficiency kitchens . You can find some really nice ones, and while they’re likely to be outdated, they’re usually clean and cozy.
• Efficiency kitchens allow you to make some meals at home. For a road trip style trip, this may be more challenging, as it’s hard to bring perishable items with you to store in a fridge. But I usually try to make my own breakfasts to save money, and pack snacks to have for lunch.
• Stay outside of town. If you’re really on a tight budget, you can stay outside of the towns you’re visiting. Places like Franconia, Stowe, and Woodstock charge premium rates for peak season, so you’re likely to find deals a town or two away.
• Go camping! If you’re really adventurous, you can go camping! There are camp sites all over New England, and this will definitely be more affordable. One thing to keep in mind is the colder weather, and for this reason, some camp sites may close down after Indigenous People’s weekend in October. But many remain open, and offer Yurt-style camping, too.

Is Fall In New England Worth It?

A resounding yes! I truly believe this is such a magical time to visit – if not the most magical time. Despite the crowds and the cost, it’s more than worth it. Many of the landscapes you’ll see are actual stock photos and postcards, and since so many people equate the fall season to all things cozy, there’s really no cozier place to be than in New England during foliage season.

More posts you may enjoy:

• Fall In New England: The Best Things To See & Do
• Vermont In The Fall: Festive Things To Do!
• Fall In New Hampshire: The Best Things To Do
• Fall In Massachusetts Ultimate Guide: All The Best Things To Do & Foliage Spots!
• The Best 7 Day New England Road Trip Itinerary For Any Season
• Best Stops To Make On A Boston To Stowe, VT Road Trip
• Vermont vs. New Hampshire In The Fall
• Maine In October: Best Towns For Foliage & Things To Do!
• Best Vermont Pumpkin Patches & Farm Stands To Visit In The Fall
• Awesome Corn Mazes In Vermont
• Best Time To Visit New England
• Best Time To Visit Vermont

That’s A Wrap On The Best New England Fall Road Trip Itinerary

And there you have it! All my tips and expert advice on planning the most epic New England fall road trip during foliage season! This truly is such a wonderful, once-in-a-lifetime experience that everyone should do at least once, and hopefully, you’re now well on your way to planning your own foliage adventure through New England!

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Adventures in New England

A local's guide to savoring the history, culture, food and nature of the Northeast USA

A Local’s Guide to New England: Traveling New England, USA

Table of Contents

Why Visit New England?

When I first moved to Rhode Island in New England from the West Coast , some of my California friends were very confused about New England. New England is a geographic area comprising the states of Connecticut, Rhode Island, Massachusetts, Maine, New Hampshire, and Vermont. It is in the northeastern United States and has bustling seaside towns, complete with gorgeous lighthouses on its rocky coastline or islands, and quaint ski or artist towns in forested mountains.

Native Americans originally occupied New England until colonists settled here around 1600. Colonial history still abounds in places such as Salem, Massachusetts, Plimoth Plantation, and Newport, Rhode Island. New England was a staging ground in the abolition movement, religious freedom in the burgeoning United States, and the Industrial Revolution.

Its geography is some of the most diverse in the United States. New England has coastal grasslands, many islands, and a gorgeous mountainous coastline. And in just a week or two, you can explore it on a New England road trip.

One of the highlights of New England, and the reason many people know it, is its astounding, vibrant, and multicolored fall foliage, which can be found throughout the region.

Plan a Trip to Visit New England

Due to the distances you must cover and the relatively rural nature of our northeastern states, really experiencing New England requires a car. Alternatively, you could take a train throughout the area but would have difficulty leaving the cities.

Where to Begin Your New England Road Trip

The largest New England airport is in Boston. You can also fly into any of New York City’s airports and drive about an hour into Connecticut to start your journey.

The New England States

Clicking on any state name will bring you to a list of all my articles about that state.

Connecticut

Connecticut has many shades, from the affluent suburbs of NYC to the rural treed areas of the Eastern state; Connecticut is the inspiration of the Gilmore Girls’ Star’s Hallow.

Connecticut Highlights

• Fairfield County – Affluent suburbs of New York City.
• Litchfield County – Rural farmland with cute little villages.
• Hartford – Connecticut’s capital with a hip waterfront and great hiking nearby at Talcott Mountain. Be sure to visit the Mark Twain House.
• West Hartford – One of my favorite restaurants anywhere, Restaurant Bricco , is in this shopper and diner’s paradise.
• Mystic is a Colonial town with an excellent aquarium, a cute downtown, a working drawbridge,  and a Colonial Seaport.
• Connecticut’s coastline is perfect for kayaking among its grassy marshland, although they are not the best New England Beaches.
• The Connecticut River winds through most of the state. Take a boat ride down it or explore a few towns nestled along its shoreline, like Essex.
• Wethersfield-  Wander along the streets of the oldest town in Connecticut, then enjoy a walk by its riverfront.

Rhode Island

This state is one of my favorites, maybe because it is where I live, but also because even though it is small- just 37 by 48 miles- it has 384 miles of serpentine, rocky coastline. Here are a few of my favorite places to visit. Check out 47 Fabulous Things to Do in Rhode Island.

• Newport –  a historic summer retreat for America’s elite. This coastal town is my favorite, and most of my time is spent exploring this town!
• Providence – Spend an evening dining in our version of Little Italy, Federal Hill, or catching a spectacular public art exhibit, Waterfire, on our capital city’s canals.
• Block Island – a quickly accessible New England island perfect for beaches, biking, and boating.
• Westerly- This town has the opulent Ocean House, the casual beaches of Misquamicut, and the stunning natural beauty of the Napa Tree Conservation area, one of the best spots to see the sunset in Rhode Island .
• Narragansett has the best flat, white-sand beaches in the state.

Massachusetts

Most people center their time in Massachusetts in its capital city, Boston, a small, bustling city full of US history. But I recommend you head out into its beautiful mountain areas, such as the Berkshires.

• While in Massachusetts, you must visit its capital, Boston , a city of immigrants steeped in colonial history but with a vibrant art, music, and food scene.
• Salem was the site of the witchcraft trials of the 1600s and the home of Nathaniel Hawthorne, and it is one of the most unique New England towns.
• The Berkshires in Western Massachusetts is perfect for camping or attending an outdoor concert at Tanglewood.
• While in the Berkshires, see the Bridge of Flowers in Shelburne.
• Northampton is one of my favorite Massachusetts towns and is an arty hippy haven.
• Springfield is the home of the Basketball Hall of Fame, Yankee Candle, a butterfly museum, and The Eric Carle Museum.
• Visit Massachusetts’s famous islands, such as Nantucket and Martha’s Vineyard .
• Cape Cod is a peninsula with great bike rides and hikes, fabulous beaches, and seafood.

New Hampshire

New Hampshire has the chillest New England vibe. It has excellent foliage with its Presidential white mountain range and many laid-back, family-friendly ski towns.

• The White Mountains are part of the Appalachian range and are full of waterfalls, lakes, and ski mountains. They are a perfect place to escape for families or couples. The White Mountains are among the best places to experience a good New England autumn. Here is a list of my favorite New Hampshire hikes.
• If you don’t have much time for your road trip, consider this 4-Day New Hampshire fall road trip.
• Lincoln, one of our yearly haunts, is surrounded by great hiking, skiing, and many family activities.
• North Conway – Full of shopping, North Conway is a perfect family town oozing New England charm and near Santa’s Village and Storyland amusement parks.
• Skiing! Although you can ski in Maine, Vermont and New Hampshire are where most New Englanders head to ski. We love to ski; even Rhode Island has a tiny ski hill.

One of my favorites, Vermont highlights its artists and locally grown food and is a ski destination. It is the most upscale of the mountainous New England states.

• Vermont is an outdoor lover’s paradise. We often go to tennis camp at Sugarbush, where there is also skiing.
• Ben and Jerry’s Factory – Ice cream is one of my favorite foods, and it is so worth a visit to this factory tour, which includes tastings at the end.
• Visit the ridiculously charming mountain town of Woodstock , where you can shop, eat, and do any outdoor activities.
• Learn all about the local arts scene in Quechee . Read about a weekend in Woodstock and Quechee .
• Read more about exploring Vermont in A Family Road Trip from Boston to Montreal .

Maine is an outdoor lover’s paradise, and Mainers are a rugged breed. Although the coast is relatively populated, there is plenty of untouched wilderness in this state, which covers half of the landmass of New England.

• Maine’s western mountains are a place of supreme peace, not overly populated, and full of glorious wilderness.
• Acadia National Park in Northern Maine is one of the US’ prettiest parks, with wooded forests along Maine’s long coastline. Although it is a long drive to get to, it is a must-see! Please read  about my visit to Acadia National Park.
• The coastal town of Portland is close to Boston and has an incredible food scene, lighthouses, and plenty of coastal outdoor activities. Read 47 Fabulous Things to Do in Portland.
• While you are in Portland you can take a day trip to Peak Island and bike around the island.

When to Visit New England?

There are good reasons to explore New England in its distinct seasons.

Summer in New England

If you love the outdoors, summer will allow you to take advantage of all the beaches, lakes, and waterfalls New England offers. Of course, with such perfection can come crowds. If you want to visit our islands, this is an ideal time to visit.

Fall in New England

Although the waters will be too cold to enjoy, there is nowhere in the world with better autumn colors than New England, especially in the northern states. It is the main reason people know about New England and visit. The farther north you travel, the more vibrant the colors are generally. It is tricky to know when the leaves will change, so you may have to change your itinerary to chase the leaves when you come, as they are only in peak for about a week, and the time varies by year.

Spring in New England

This shoulder season has the fewest crowds and the joy of spring flowers and bright green leaves. You won’t be able to lay on the beach, but you can usually still take a bike ride or hike. We may still get snow in spring, and some places won’t be open until after Memorial Day.

Winter in New England

New England epitomizes Christmas, so it is an ideal place to feel winter. Our winters are mild enough that although there is enough snow in our mountains, it is generally warm enough to enjoy skiing or any winter sport. And, of course, enjoy a hot chocolate by the fire in our cute mountain bed and breakfasts.

This area of the US is one of the best. I hope this article inspires you to plan a trip here. Let me know in the comments if you have any questions or ideas of places that you think I missed.

Continue your planning with my New England Bucket List.

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3 thoughts on “A Local’s Guide to New England: Traveling New England, USA”

We were lucky enough to visit this area and see all the beautiful foliage a few years ago. I enjoyed reading your road trip guide and seeing all your lovely photos. Such an incredible area!!

New England is such a stunning part of the country, especially in the fall. It’s hard to find the words to adequately describe its beauty or condense the views into photos. How lucky you are to live here!

Thanks a ton for sharing these awesome safety tips! Your post is like a travel buddy, guiding us through the must-knows for a safe adventure. I love how you make things simple, highlighting the prep and being aware of our surroundings – things we might forget in the excitement!

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New England Fall Road Trip Itinerary: 10 Stunning Stops

By: Author Mark and Kristen Morgan

Posted on Published: August 23, 2021  - Last updated: December 8, 2023

Categories North America Travel Blog

There are many places in the world you can see leaves turn in Autumn, but they pale in comparison to one famed and celebrated region in the US northeast where science, nature and climate combine to put on an extraordinary light show each year. We are of course talking about fabled New England and we’re going to show you 10 places you can’t miss when planning your New England fall foliage road trip, with 5 day itinerary, 7 day itinerary and 10 day itinerary examples included to help you nail down the best possible route for your trip.

We will use our first hand experiences from road tripping New England in fall to bring you tips, advice and unmissable stops to take on your visit. This is one of those true bucket list USA road trip experiences in which it pays to be organized, plan effectively and make the most of every day.

So, let’s get stuck into those 10 unmissable stops and planning your perfect New England fall foliage road trip itinerary!

The Science Behind Fall Colors

What do we know about the changing of colors to give ourselves the best chance of being in the right place at the right time?

Well, we know that fall colors peak furthest north and work southward through the latitudes. So for example, the Blue Ridge Parkway in Virginia and North Carolina is gorgeous in fall, but the colors won’t change there until much later in the season.

Also, we know elevation plays an important role in when peak colors will be on display. Colors will change first in mountainous regions of Maine, New Hampshire and Vermont before they do at lower elevations.

But the most important aspects are weather conditions leading into Autumn, and amount of daylight. It all starts way back in Spring! A late Spring or intense Summer drought can potentially delay peak fall colors by a week or two.

Conditions Affecting Predictions For Peak Fall Colors

In addition to elevation, latitude and weather conditions before fall, there are more specific conditions that can affect peak fall once we actually reach Autumn:

• Soil moisture levels
• Amount of sunlight during the day
• Length of night
• Day and night temperature (important)

So what would constitute as perfect conditions for the best chance at ‘peak’ fall colors being their most radiant and predictable?

• Wet and warm Spring conditions
• Summer without drought or unusually high / low temperatures
• Warm Autumn days and cool but not freezing nights

And what causes the colors to change once conditions are right?

Sunlight pumps leaves full of chlorophyll during Spring and Summer. Once daylight wanes in Autumn, so does the amount of chlorophyll.

That leaves room for other pigments in the leaves, such as anthocyanin and carotenoids to shine.

Why Focus On VT, NH, ME and Even NY

The region of New England technically contains 6 states; Connecticut, Rhode Island, Massachusetts, Maine, New Hampshire and Vermont. In fall, this entire region transforms into an adventure playground for leaf-peeping lovers and passionate photographers.

However, there are three New England states among the six that we feel just have to be prioritized for the very best scenery and most radiant colors; New Hampshire, Maine and in particular Vermont.

But we’re also going to throw a curve ball by including a region not technically part of New England (gasp!) … New York’s Adirondack Mountains are a stone’s throw from the border with Vermont and the colors are just as special.

We want you to see the best places in New England when you take your fall road trip, but we would prefer you to see the best colors. That means skipping the likes of Boston, Portland and Providence on this particular visit to the northeast.

They’re all awesome places and we visited them all on our New England road trip in fall. But they don’t have the colors of rural Vermont and New Hampshire, plus we had days to spare.

Here’s why you should focus on the northern parts of New England for a fall foliage road trip:

Vermont’s rolling hills are overflowing with charming rural towns, barns and covered bridges. But the state is 80% covered in forest and that can only mean one thing; spectacular fall foliage everywhere you look.

Further Reading: The best places to visit in Vermont

New Hampshire

New Hampshire mixes excellent hiking options in stunning mountainous areas with staggeringly beautiful fall foliage colors.

It also has one of the best mini road trip routes in New England during fall – the Kancamagus Highway.

Maine is huge. It is much bigger than the other New England states and that means it’s hard to fit most of the northern parts in to your road trip. Unless you have more than 2 weeks of course.

However, Acadia National Park is one of the very best places you can visit in all of New England in fall so if you have the spare time, it’s hard to skip.

New York’s Adirondack Mountains, including Winter olympic town Lake Placid and its surroundings are beautiful in Autumn. The popular mountainous region is incredibly popular thanks to a host of activities and of course glorious foliage colors.

When Should You Plan Your New England Road Trip For Peak Fall Colors?

It is impossible to plan the perfect ‘peak’ fall road trip itinerary in New England. You would need to be in many places at the same time for that to be possible. We’re not quite there, yet!

Historically, the last 2 weeks of September and the first 2 weeks of October are when the colors change. So that would put October 1st in the middle of that and therefore a ‘peak’ fall foliage target.

Science tells us that colors change in the North and at elevation first, eventually working South and to lower levels.

We’ll get into example itineraries below, but here are some rough dates to use for each itinerary time frame working North to South:

• 5 Day New England Fall Road Trip – We would suggest aiming for September 29 through October 3.
• 7 Day New England Fall Road Trip – Add a day either side, so September 28 through October 4.
• 10 Day New England Fall Road Trip – Add a day before and two after, so September 27 through October 6.
• 14 Day New England Fall Road Trip – Add a day before and three after, so September 26 through October 9.

Should You Book Your Trip In Advance?

Here are two scenarios:

• You don’t book in advance and keep an eye on live fall foliage updates to guarantee hitting peak fall. This also means you have flexibility on bad weather days. However, there are very limited hotels available and those that do have rooms will be more expensive.
• You plan and book your whole trip in advance, getting good value in hotels and can relax. But there’s a chance you won’t time it just right and you will have to deal with whatever weather comes your way.

We can’t offer a ‘better’ solution here because both have pros and cons.

Our trip was mainly booked in advance which meant we spent less but we had to put up with a lot of disappointing rain days, as you will see in the photos below!

Need a hand planning your New England fall road trip? Our popular 40+ page New England Fall Road Trip Guidebook includes the 10 best places to visit, 8 example itineraries ranging from 5-14 days and an extensive interactive map to help you plan a successful leaf-peeping vacation.

Top Tips For Planning Your New England Fall Road Trip Itinerary

Finally, before we jump into the 10 unmissable stops and the New England fall road trip itineraries, let’s have a quick look at some important tips to consider when planning your vacation:

• New England is insanely popular in fall.
• Booking accommodation in advance will save you a lot of money.
• Carefully plan where you want to spend each night based around hikes and photography.
• Start in the North and work South through New England.
• Expect frequent rain and clouds in fall and accept that there’s nothing you can do about it!
• Always carry loads of water and snacks in the car.
• Try to find elevated vantage points as often as possible.
• Some of the best and most unique fall photos are along rural country roads.
• You need multiple spare batteries for your camera!
• You can use a drone in many parts of New England for aerial photography.
• Don’t worry if you miss ‘peak’ colors.

Our popular road trip resources:

• Road trip packing list essentials
• How to plan the perfect road trip

10 Places You Can’t Miss On The Best New England Fall Road Trip

Let’s take a closer look at the 10 stops we think are unmissable on a first New England trip to see the fall colors.

1. Lake Placid, New York

Lake Placid of 1980 Winter Olympics ‘Miracle on Ice’ fame is located at the heart of New York’s revered Adirondack Mountains. It is the perfect base for adventure activities throughout all four seasons, from hiking in Summer to skiing in Winter.

The charming town of Lake Placid is an incredibly popular centralized location for leaf peeping in the Adirondacks. As a result, hotels here are in high demand and not cheap from the end of September until mid October. We know from experience when our bank balance took a mighty hit!

Walk around Mirror Lake in town for the easiest way to soak up gorgeous fall colors. If you have time and enjoy challenging hikes, you can’t miss Mount Marcy. It isn’t the prettiest trail but it is the tallest peak in New York.

Things To Do In Lake Placid, NY

• Take a relaxing walk around serene Mirror Lake.
• Visit the Olympic ski jumping complex.
• Photograph John Brown barn.
• Drive to the summit of Whiteface Mountain.
• Take the Cloud Splitter cable car to Little Whiteface.
• Walk through picturesque High Falls Gorge.
• Hike Mount Marcy, the tallest peak in New York.

Where To See Fall Foliage In Lake Placid, NY

• Mirror Lake in town is gorgeous, walk through residential areas surrounded by colorful trees.
• John Brown barn is a hidden gem for fall colors.
• The top of the ski jump provides sweeping views over the Adirondacks.
• Mount Marcy summit is the highest point in the entire region, providing the best views over rolling hills.
• Whiteface Mountain and Little Whiteface offer more stunning views of fall foliage.

Read our Lake Placid guides for more information:

• 10 best things to do in Lake Placid NY
• Mount Marcy complete hiking walkthrough
• 8 best hotels in Lake Placid NY

2. Burlington, Vermont

Burlington in Vermont might not be the first place you think of for a New England fall foliage road trip destination. However, it is one of the easiest places outside of Boston to fly into the region if you are visiting from further afield.

The small town also happens to be filled with beautiful and radiant foliage colors at every turn. From lakeside bike paths to park towers with stunning views, Burlington is the perfect stop off between Lake Placid and the more famous foliage destination of Stowe.

Hotels in downtown Burlington can be limited and expensive in Autumn, so if you are visiting New England on a budget, try looking for hotels in surrounding villages and towns.

Things To Do In Burlington, VT

• Eat, drink and soak up the atmosphere along Church Street.
• Walk through Waterfront Park alongside Lake Champlain.
• Cycle the Burlington bike path to Grand Isle.
• Explore Ethan Allen Homestead and Museum.
• Stand on top of Ethan Allen Tower for amazing views.
• Taste chocolate at Lake Champlain Chocolates flagship store.

Where To See Fall Foliage In Burlington, VT

• Anywhere along the Lake Champlain waterfront where there are trees.
• Ethan Allen Park and the top of the tower in particular have the best fall foliage views in Burlington.
• Ethan Allen homestead and museum are surrounded by beautifully colorful trees.

Read more about Burlington:

• 10 best things to do in Burlington VT
• 8 best hotels in Burlington VT

3. Stowe, Vermont

Stowe is one of the unmissable fall foliage classics on any New England road trip. The white church in town is one of the most photographed churches in the US and almost all of those photographs are taken in fall.

The town is quaint and attractive but be sure to spend the majority of your time up in Stowe Mountain Resort. This is where you will find hikes, Mt Mansfeld, waterfalls and Smugglers Notch.

Colors will change first up in the higher elevations. So, if you’re a little early, head up to the resort. On the other hand, if you’re a little late, stick to the lower elevations around Stowe town for the most vibrant colors.

Personally, we love to hike, we like flying our drone and we enjoy photographing waterfalls. Stowe was one of the best stops on our New England fall road trip circuit for allowing us to do all of those things.

Things To Do In Stowe, VT

• Photograph the famous white church in Stowe town.
• Drive or hike to the summit of Mount Mansfield.
• Drive through stunning Smugglers Notch pass.
• Ride a bike along Stowe Rec Path or Lamoille Valley.
• Take the SkyRide Gondola to Mt Mansfield.
• Hike a wide range of awesome trails.
• Visit both Bingham Falls and Moss Glen Falls.

Where To See Fall Foliage In Stowe, VT

• In Stowe town, the iconic white church backed by a hill of fall colors is unmissable on your New England road trip.
• But the best colors are in Stowe Mountain Resort. The drive up from town is gorgeous.
• No matter how you get to the top of Mt Mansfield, you can guarantee spectacular fall foliage views.
• Smugglers Notch is our top recommendation for Stowe. If you have a drone, this is the place to fly.

Read more about Stowe, Vermont:

• 15 best things to do in Stowe VT
• 12 best hotels in Stowe VT

4. Woodstock, Vermont

Woodstock in central Vermont is arguably the most picturesque and charming town you will visit on your New England fall road trip itinerary. It truly is like something out of a fairytale. We had no choice but to include Woodstock in our popular guide to the 50 best places to visit in the USA .

Remarkably pretty farms with golden leaves dancing in sunlight and reddish-brown leaves covering the ground create picture perfect scenes. Sleepy Hollow Farm and Jenne Road Farm are featured on many fall foliage calendars you will see in shops on your visit to New England.

Don’t miss the many stunning historic covered bridges around Woodstock. Middle covered bridge is right in town, Taftsville and Quechee are very close by and Cornish-Windsor is a 30 minute drive. The beautiful bridge in the photo below is a privately owned bridge near South Woodstock on the main road to Jenne Farm.

Woodstock is one of the more expensive places to visit on a road trip through Vermont, but it is worth taking a hit on the extra chunk of budget. Simply driving around the narrow country roads near Woodstock for a few hours would provide enough fall foliage colors to last a week of photography.

Things To Do In Woodstock, VT

• Walk around the charming town and admire diverse architectural styles.
• Photograph two postcard perfect farms – Jenne Road Farm and Sleep Hollow Farm.
• Visit a host of historic and stunning covered bridges.
• Explore Marsh Billings Rockefeller Park and hike to amazing viewpoint overlooking Woodstock.
• Visit nearby Quechee Gorge and village.
• See Jersey dairy cows at Billings Farm and Museum.

Where To See Fall Foliage In Woodstock, VT

• Woodstock is incredibly photogenic during fall throughout the town and immediate surroundings.
• The lookout over Woodstock from Mount Tom hike is iconic fall photography.
• The best two fall photographs in Woodstock are at Jenne Road Farm and Sleepy Hollow Farm. They are two truly unmissable stops on your New England fall road trip itinerary.
• Drive your car around the narrow rural roads near Woodstock for some of the most special colors.

Read more about Woodstock, Vermont:

• 15 best things to do in Woodstock VT
• 7 best hotels in Woodstock VT

5. Manchester, Vermont

Similarly to Stowe, Manchester is a four season resort with skiing in Winter and hikes during Spring or Summer. In fall, the town located in the heart of Green Mountain National Forest transitions into a colorful paradise for leaf-peepers.

Manchester can be split into the old historic district and the newer modern resort town. The newer part is livelier and closer to amenities but the historic district is quieter, prettier and more colorful.

Use Manchester as a base for one night to explore nearby elevated areas for some of the most expansive views of rolling hills on a New England fall road trip.

Equinox Mountain is the tallest peak in the area. You can hike it or drive it to open up far-reaching views over three US states. But our top tip is to simply stick to the narrow country roads again and you will find more unique fall foliage photographs.

Things To Do In Manchester, VT

• Drive the Skyline Auto Toll Road to Mount Equinox summit.
• Explore Hildene, the Lincoln Family Home.
• Walk around quaint Manchester Historic Village District.
• See the American Museum of Fly Fishing Museum exhibits.
• Buy a book in popular Northshire bookstore.
• Visit nearby covered bridges.
• See the Bennington Battle Monument.
• Visit Robert Frost stone house museum.

Where To See Fall Foliage In Manchester, VT

• Manchester is the heart of the Green Mountains, so the entire area surrounding the town is staggeringly attractive.
• Rolling hills for endless miles covered in glowing fall colors can be seen from any elevated vantage point.
• Equinox Mountain summit provides the best panoramic views over three states.
• Another place you jump in the car and find unique fall photography opportunities on rural roads.
• Manchester Historic Village District is leafy and the church is surrounded by golden yellow leaves.

Read more about Manchester, Vermont:

• 15 best things to do in Manchester VT
• 9 best hotels in Manchester VT

6. Franconia Notch State Park, New Hampshire

Franconia Notch is one of New Hampshire’s premier tourist regions for hiking, picturesque mountains, skiing and of course fall foliage. A two lane highway mountain pass dissects the Kinsman and Franconia mountain ranges, with a number of fantastic recreational stops along the way.

Artists Bluff is a very short but steep hike leading to a rocky ledge. Its summit overlooks Echo Lake and is most popular in fall when the colors change. As you can see, we hiked the trail on an incredibly cloudy and grey day, which doesn’t help with highlighting the beauty of this viewpoint. We have included Artists Bluff in our popular guide to the 50 best hikes in the US .

Franconia Notch State Park is where you will find the stunning Flume Gorge hike. A little over 2 miles of waterfalls, narrow gorges and forested paths welcome thousands of visitors each year. For us, the best part of Flume Gorge were the two ultra-photogenic covered bridges; Flume and Sentinel Pine.

Things To Do In Franconia Notch State Park, New Hampshire

• Hike the short but steep trail to Artists Bluff summit for stunning views.
• Walk through impressive and extremely popular Flume Gorge.
• Hike Cannon Mountain or take the Cannon Mountain Aerial Tramway.
• See a whole host of waterfalls or hike one of a dozen other mountain trails.
• Ski Cannon Mountain Resort in Winter.

Where To See Fall Foliage In Franconia Notch State Park, New Hampshire

• The single most well known fall foliage photograph in Franconia Notch NH is from the summit of Artists Bluff.
• However, don’t miss the chance to walk through the incredibly picturesque Flume Gorge in fall.
• Not only are the colors vibrant, but waterfalls are attractive and two special covered bridges are incredibly photogenic.
• Anywhere at elevation, which means every hike up a mountain side or the tramway with sweeping valley views.

Read more in our Franconia Notch guides:

• Artists Bluff Trail Fall Foliage Hike
• Flume Gorge Complete Hiking Walkthrough

7. Kancamagus Highway, New Hampshire

New Hampshire’s supremely scenic Kancamagus Highway is one of the very best parts of New England to road trip in fall foliage season. We would put it firmly in the category of ‘unmissable’.

The road between Lincoln and Conway NH is only 35 miles long, but it 35 miles of pure foliage bliss. You can either drive it in one go and simply soak up the colors roadside. Or you can stop at a multitude of overlooks, hiking trails, waterfalls, lakes and covered bridges.

If there’s one part of your New England road trip itinerary to time it right for peak foliage colors, you would do well to beat the Kancamagus Highway in its prime.

A note for photographers and videographers – You can use your drone in many parts of the Kancamagus Highway. We captured amazing photographs and videos of endless miles over rolling hills covered in radiant color.

Things To Do On Kancamagus Highway, New Hampshire

• Stop at various high elevation overlooks with spectacular views over White Mountain National Forest.
• Walk to Sabbaday Falls, Champney Falls and Lower Falls.
• Hike Lincoln Woods or Mount Chocorua.
• Walk out on Rocky Gorge boulders.
• Photograph Russell-Colbath House and the picture perfect Albany Covered Bridge.
• Explore ponds and lakes to your hearts content.

Where To See Fall Foliage On Kancamagus Highway, New Hampshire

• Views over rolling hills from every overlook are astonishing in fall.
• Once the Kancamagus Highway reaches its highest elevation, you will see an ocean of color in all directions.
• Walk through any forest trail or along any waterfall hike to immerse yourself into those foliage colors.
• Albany covered bridge is one of the most picturesque bridges you will find in New England.
• Rocky Gorge and nearby lake with reflecting fall colors are wonderful.
• Even on both ends of the road in Lincoln (Loon Mountain) and Conway the colors are vibrant.

Read more about the Kancamagus Highway:

• 13 best places to stop along the Kancamagus Highway in fall

8. Mount Washington, New Hampshire

At 6,288 ft tall, Mount Washington is the tallest peak in Northeastern United States. It is renowned for wild and unpredictable weather, including the recording of a world record wind speed over over 230 mph.

As our images indicate, Mount Washington can be very wet and cloudy in Autumn. But if you get slightly more luck on your road trip and time it on a sunny day, you will enjoy some of the most beautiful colors and scenery in the entire region.

Avid hikers can climb to the summit, otherwise you can take a historic cog rail train or drive up an auto toll road to reach the top. Views from almost 2,000 meters high over an ocean of bright colors are incredible.

Things To Do Around Mount Washington, New Hampshire

• Hike a very challenging but rewarding trail to the summit of Mount Washington.
• Consider a night hike, fall colors won’t matter in the dark but it is hugely popular for astro and sunrise photography.
• Alternatively, drive the Mt Washington Auto Road to the summit.
• Or, take the most scenic and historic route to the top – by Cog Railway.
• Conway scenic railroad nearby ventures deep into fall foliage forest.
• Endless miles of hiking, 100 waterfalls and a handful of covered bridges to discover.
• Crawford Notch State Park is close by and features more views, hikes and waterfalls.

Where To See Fall Foliage Around Mount Washington, New Hampshire

• Just gain elevation in the White Mountains and you’ll open up valley views with a sea of foliage colors.
• Mt Washington summit is the iconic NH vantage point for sweeping Autumnal vistas.
• For a unique experience, the Conway Scenic Railroad cuts through some of the best colors in NH.
• Crawford Notch State Park is stunning in fall, with fantastic valley views from hikes.

9. Lake Winnipesaukee, New Hampshire

Heading due South of Mt Washington you will find Lake Winnipesaukee encircled by gorgeous fall foliage colors. Unfortunately for us, the rain was back in full swing but you can still see how vibrant the colors are in this area.

You can drive an 81 mile loop road around the entirety of the lake, or take to the waters aboard M/S Mount Washington cruise boat.

Visit Castle in the Clouds for family entertainment and hiking, Weirs Beach for arcades or Wolfeboro for a more relaxing experience. The most popular trail in the area is Mount Major, which we highly recommend for hikers looking for excellent views over the lake.

Things To Do Around Around Lake Winnipesaukee, New Hampshire

• Take a cruise on the M/S Mount Washington.
• Or rent a boat of your own for the day.
• Ride the Lake Winnipesaukee scenic railroad.
• Try your hand at arcade games in Weirs Beach.
• Hike the popular half day trail to Mount Major summit for fantastic lake views.

Where To See Fall Foliage Around Lake Winnipesaukee, New Hampshire

• Elevation is your fall foliage friend around the lake if you want expansive views.
• Mt Major is the perfect moderate hike to include on your New England fall road trip itinerary.
• But nearby Belknap Mountain is also a popular choice for fall hikers.
• Gunstock Mountain Resort has zip lines and ski lifts for easy elevation gain.
• For easier and more close up Autumnal color vistas, simply hire a boat on the lake and explore.
• Or sit back, relax and soak up the views on Lake Winnipesaukee scenic railroad foliage tour.

10. Acadia National Park, Maine

Acadia finds itself in the list of top 10 most visited and best US National Parks each year. Millions of tourists descend on Bar Harbor annually to enjoy a diverse range of amazing things to do inside the awesome park.

Varied hikes suitable for all ages and abilities, including the famous adrenaline pumping climbs Beehive Trail and Precipice Trail , are a huge draw. But despite being a typical Summer destination in the north of America, Acadia is equally as popular in Autumn and that is purely down to its glowing fall foliage colors.

Sunrises from Cadillac Mountain or Schoodic Point can be extraordinarily beautiful if conditions are right, and sunset at Bass Harbor Head Light is a very highly regarded spectacle. You will need to bring your best hiking gear, spare camera batteries and a lot of energy to the wonderful National Park in Maine.

The only problem you will face with including Acadia on a New England fall foliage road trip is its location. You will have a long drive to and from Acadia from Vermont or New Hampshire. However, if you have the time, it is unquestionably worth the extra effort.

Things To Do In Acadia National Park, Maine

• Hike various amazing trails from easy to hard (to exhilarating!).
• Photograph stunning sunrises, landscapes and Bass Harbor Head Light.
• Drive to Cadillac Mountain summit, the tallest peak on the US east coast.
• Walk or cycle maze-like carriage roads through the park.
• Explore Jordan Pond and swim in Echo Lake.
• Eat and drink in glitzy Bar Harbor, Maine.

Where To See Fall Foliage In Acadia National Park, Maine

• Mountain summits from any hike opens up special views over rolling hills covered in fall colors.
• Carriage roads are the perfect way to explore forested trails which are surrounded by trees.
• Drive the national park loop road for easiest access to fall colors.
• Jordan Pond in particular is encircled by vibrant autumnal hues.
• Cadillac Mountain summit opens up 360 degree views over Maine and the ocean.

Read our Acadia National Park guides to learn more:

• 17 best things to do in Acadia National Park
• 10 hikes you can’t miss in Acadia National Park
• Where to stay in Bar Harbor and Acadia National Park
• 10 key things to know about visiting Acadia in the fall

Planning Your New England Fall Road Trip Itinerary

New England is an enormous region and choosing exactly where to visit can be challenging. Here are a few questions to ask yourself before you begin plotting a route:

• Which places are top of your list? Vermont? New Hampshire? Acadia?
• How many days can you spare on your trip?
• Do you want to book accommodation in advance or take it day by day?
• Are you in New England solely to see and photograph fall colors?
• Or are you focused primarily on hiking with colors as an added bonus?
• Do you want to use small and quaint towns as your main places to stay?
• Or are you more interested in being rural and remote each night?
• What is your budget? Can you afford to splurge on activities?

Once you have an idea about how you see your road trip panning out, use that idea as a guide to make the best decisions based on your travel style.

Next, we will go through a number of potential scenarios for 5 day, 7 day and 10 day road trip examples through New England in fall.

Use the examples as a reference but remember, they are generic and based on how we personally would plan our itineraries with hikes and photography in mind.

5 Day New England Fall Road Trip Itinerary

Only having 5 days isn’t as much of a negative as it might usually be. Yes, you are going to have to be selective and it is going to be none stop action. But one of the major benefits to a road trip in fall is that all of the best scenery is seen when driving.

Also, the smaller states of Vermont and New Hampshire don’t require a huge amount of drive time between their most scenic places for fall foliage. Include Lake Placid in the Adirondacks and you can easily tick off most of the places in our list in 5 days.

Another consideration is with just 5 days you don’t need to worry as much about ‘following’ peak fall colors. They won’t change too much in that time frame when compared to 10 days.

Example 1 – Lake Placid NY to Manchester VT

D1 – Lake Placid : Walk around Mirror Lake, drive up Whiteface Mountain and explore High Falls Gorge. Stay in Lake Placid.

D2 – Burlington and Stowe : Walk down Church Street, cycle Burlington bike path, explore Smugglers Notch and Stowe Mountain Resort, sunset at Stowe church. Stay in Stowe.

D3 – Franconia Notch and Kancamagus Highway : Hike artists bluff trail, walk around Flume Gorge, drive Kancamagus Highway and down to Wolfeboro. Stay in Wolfeboro on Lake Winnipesaukee.

D4 – Lake Winnipesaukee and Woodstock VT : Spend morning exploring the lake or hike Mt Major, then drive to Woodstock in Vermont via Cornish-Windsor covered bridge, Quechee Gorge and Taftsville covered bridge.

D5 – Woodstock and Manchester : Visit the farms near Woodstock, drive through Green Mountains to Manchester and end at the top of Equinox Mountain.

You could start and end in New York City if flying into Newark or JFK works from your origin and budget. Alternatively, Montreal would be a better place to start for Lake Placid, hire a car and drop it off in NYC or Boston after leaving Manchester, VT.

Example 2 – Lake Winnipesaukee NH to Manchester VT

D1 – Lake Winnipesaukee : Explore the lake, hike Mt Major, take a cruise and stay in Wolfeboro.

D2 – Kancamagus Highway and Franconia Notch : Drive Conway to Lincoln across Kancamagus Highway, hike Flume Gorge and Artists Bluff. Sleep in Franconia.

D3 – Stowe and Burlington : Stowe church, hike to waterfalls in Stowe Mountain Resort, drive Smugglers Notch and on to Burlington. Ride the bike path for sunset. Stay in Burlington.

D4 – Lake Placid : Whiteface Mountain, High Falls Gorge, Ski Jump and Mirror Lake. Or hike Mount Marcy instead but that is a full day commitment. Stay in Lake Placid.

D5 – Woodstock and Manchester : Visit the farms, covered bridges and drive through Green Mountain countryside to Manchester, finish with Equinox Mountain again.

This version would allow for a round trip loop from Boston, MA airport or Portland, ME airport.

The key to making the most of this shorter trip is to accept that you will be in the car driving a lot but that is where you will see most of the best scenery.

7 Day / One Week New England Fall Road Trip Itinerary

With a week, you can get more creative, include more places or take things slower. You have more flexibility but still not enough time to add a trip to Acadia, unless you really can’t miss it and don’t mind the driving.

Colors can change a noticeable amount in 7 days, so (if possible!) factor in starting your one week trip just before ‘peak’ begins.

Either of the 5 day examples above would work with 7 days by simply taking more time in certain spots. The alternative is to add in more places to visit. Let’s look at both:

Example 1 – Lake Winnipesaukee NH to Manchester VT

D2 – Kancamagus Highway : Take the awesome road trip slowly, stop at every attraction and stay in Loon Mountain or Lincoln.

D3 – Franconia Notch and Stowe : Hike Flume Gorge and Artists Bluff before driving to Stowe to photograph the church. Hike the waterfall trails and see Smugglers Notch. Stay in Stowe.

D4 – Burlington and Lake Placid : Church Street and Burlington bike path, then drive to Lake Placid, get stuck into the best bits of Lake Placid and spend the night there.

D5 – Lake Placid and Woodstock : Spend the morning in Lake Placid and drive to Woodstock later in the day. Hike to Mount Tom for amazing views over Woodstock. Stay in Woodstock.

D6 – Woodstock : Sunrise at Sleepy Hollow Farm, Jenne Road Farm, visit the nearby covered bridges and relax in town. Drive to Manchester later in the day to stay over.

D7 – Manchester : Hildene, Manchester old town and stunning Green Mountain country roads, finish at Equinox Mountain.

This variation could begin and end at either Boston, MA or Portland, ME as in the itinerary above. It just gives you more downtime and time to fully explore the places you will visit.

Example 2 – Manchester VT to Lake Winnipesaukee NH

D1 – Manchester : Drive from Boston airport to Manchester, spend the day at Hildene, Equinox Mountain and exploring the town. Stay in Manchester.

D2 – Woodstock : See the best of Woodstock and spend the night.

D3 – Stowe : Hit the top highlights in Stowe and stay there for the night.

D4 – Mount Washington : Take the cog train, drive to the summit or even take on the hike. Sleep in North Conway.

D5 – Kancamagus Highway : Spend a full day on The Kanc. Sleep in Loon Mountain or Lincoln.

D6 – Franconia Notch : Hike Flume Gorge and Artists Bluff but drive to Lake Winnipesaukee later to spend the night.

D7 – Lake Winnipesaukee : Spend the last day around the lake, cruising, hiking or relaxing.

This loop direction was reversed to give an idea about how you could make it work in a clockwise route. Again this would be starting and ending in Boston or Portland, with JFK or Newark as alternative options.

Instead of driving out to Lake Placid, you could stick to Vermont and New Hampshire, which is where the very best colors are found.

10 Day New England Fall Road Trip Itinerary

With a full 10 days to spend on your New England fall road trip, you can either max out your itinerary and see all of the best bits or choose to spend more time in fewer places.

Personally, we’re the max out itinerary type and we would definitely include Acadia National Park in our 10 days. It adds in some serious driving time but the journey there is picturesque, rural and most importantly colorful.

Here’s one way you can include each of the places mentioned in this list, including Acadia National Park (this is the way we drove but we spent 14 days doing this route with other non-fall foliage places included in our itinerary):

Example 1 – Lake Placid, NY to Manchester, VT via Acadia National Park, ME

D1 – Lake Placid : Spend the day hiking and surrounded by gorgeous colors. Sleep Lake Placid.

D2 – Burlington : Full day exploring town and cycle the entire bike path to Grand Isle. Stay in or near Burlington.

D3 – Stowe : Smugglers Notch, Mountain Resort, Mt Mansfield and church in town. Stay in Stowe.

D4 – Franconia and Kancamagus Highway : Hike Artists Bluff and Flume Gorge, drive The Kanc and sleep in North Conway.

D5 – Mt Washington and drive to Acadia : Drive to the summit or take the cog train before driving US-2 all the way to Acadia. Sleep in Bar Harbor.

D6 – Acadia : Sunrise Cadillac Mountain, Hike Acadia Mountain and Beech Mountain, sunset at Bass Harbor Head Lighthouse. Stay in Bar Harbor.

D7 – Acadia : Sunrise Schoodic Point, Hike Beehive Trail and Precipice Trail, Walk around Jordan Pond, Great Ocean Path and carriage roads by bike to see the best fall colors. Final night in Bar Harbor.

D8 – Lake Winnipesaukee : Final morning in Acadia, long drive to Wolfeboro and explore Lake Winnipesaukee.

D9 – Woodstock : Photograph Sleepy Hollow and Jenne Road, hike to Mt Tom, see covered bridges.

D10 – Manchester : Hildene, Mount Equinox, nearby Bennington battle monument and covered bridges.

Tips For The 10 Day Itinerary

The only concern with this itinerary is the inclusion of Acadia National Park. It’s a 4 hour drive from Mt Washington to Acadia and 4 hours 20 minutes back from Acadia to Wolfeboro.

However, if you do have more time you can include stops on the way to and from Acadia to break up the longer drives. US-1 and US-2 are picturesque but slow going. If you’re pushed for time, take the less scenic but faster I-95 instead.

Alternatively, if you’re not so bothered by Acadia, plan to spend even more time in each of the other 9 places in this list. That would give you wiggle room in case of bad weather and plenty of time to relax.

Notice how the route starts furthest north and loops around Acadia then comes back further south?

That’s because with 10 days you should try to ‘follow’ the peak colors as they transition southwards over the first two weeks of October.

New England Fall Road Trip Map

Red Markers – Locations of the 10 best places to visit on a New England fall road trip itinerary.

Click or touch the map to activate.

Zoom in and out, move around the map of New England to find locations for the best places to visit in the area.

More From New England

• Best things to do in Burlington Vermont
• Best things to do in Woodstock Vermont
• Driving the Kancamagus Highway in fall
• How to visit Flume Gorge in New Hampshire
• The best things to do in Lake Placid New York
• The best things to do in Stowe Vermont
• Top things to do in Manchester Vermont
• Unmissable things to do in Acadia National Park

We hope this New England fall foliage road trip guide with itinerary ideas helps you plan the perfect leaf-peeping vacation!

Please let us know if you have any questions about New England or need any help planning your visit in the comments below.

Happy Travels,

Mark and Kristen

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Mark and Kristen Morgan are travel, hiking and photography experts. Over the last 6 years traveling full time, they have explored more than 40 countries and 30 US states.

Where Are Those Morgans has been featured in USA Today, Gestalten, Get Your Guide, CityPASS and Condé Nast Traveler along with various other publications. Read more about us .

Share this article!

Monday 24th of July 2023

I really appreciate your compressive guide to New England for travel in the Fall. We have enjoyed most of the areas you mention in years past and loved it. My sister is visiting from Australia at perfect Fall Foliage time so we're planning to do your 10-day roadtrip this year. I was wondering if you have an App you prefer to use to plan each segment of the roadtrip. I used Roadtrippers earlier this year and found it good, but would welcome your suggestions for a roadtrip App. I plan to download your digital guide as well. Thank you and happy travels.

Saturday 5th of August 2023

@Mark and Kristen Morgan, I have accommodations booked from Lake Placid to Woodstock. Since we want to add a couple of nights in Boston to walk the Freedom Trail and visit the Boston Tea Party site, would you recommend skipping Manchester, Vermont and going directly to Boston from Woodstock. Or, would we be missing out if we skip Manchester. Appreciate your advice.

Friday 4th of August 2023

@Mark and Kristen Morgan, Thank you so very much for your advice. I downloaded the digital guide to use. So looking forward to this trip and having your guide to get organized makes this a lot less daunting. Keep up the great work and happy traveling.

Mark and Kristen Morgan

Tuesday 25th of July 2023

Hi Sharon, we're happy to hear you will be visiting New England again and this time with your sister. If you are looking for alternatives to Roadtrippers you could check out Wanderlog which is another useful resource. But to be honest we don't use any apps for our road trips except for the basic and free Google Maps app. We plot points for attractions, restaurants and hotels as we research before visiting a new place, and we plan ahead so we can really get organized. If you download our digital guide and go to the end, you will find a map we created that will open in your Google Maps app and it already contains the locations for top attractions, foliage photo spots, hikes, restaurants and hotels that we discuss throughout the guide. You can of course see more places but we have preloaded the map with the essential spots to visit around New England in fall. Have a fantastic trip!

Saturday 15th of July 2023

I would love a copy of the book as well, to use as we travel Thank you for a wealth of information!

Thursday 22nd of June 2023

Wow, amazing information, thank you. Have you written it in book form by any chance? I would love to drive with the book on hand for reference.

Sunday 9th of July 2023

@Mark and Kristen Morgan, I'm using this article to plan our New England fall leaves trip and would also be interested in a copy of your digital guidebook, please. The information you provide is outstanding -- thank you! ~ Carol

Friday 23rd of June 2023

Hi Helen, you have asked at just the right time. We are currently in the process of creating a digital guidebook filled with key information and itinerary ideas for the New England fall road trip. It will be ready within the next week or so and we will email you once it is live. You will be able to either keep it on your smartphone or print it if you prefer to have a paper copy.

Friday 17th of February 2023

Hello! What a wonderful site you have given us :). Question...do any of the New England fall road trips include the Berkshires? I would love to include a quick visit to The Mount/Edith Wharton's home. Thanks, Jo

Thank you, Jo! Yes absolutely, you could easily add The Mount / Edith Wharton's Home to the end of our 10 day New England fall road trip itinerary because it is just 1 hour 30 minutes drive to the south of Manchester VT (which is the last stop in our guide), before heading back to the Boston / NY airports. It wouldn't be much of a detour and if you are heading that way you might also want to consider including a short drive along scenic highway 2, also known as The Mohawk Trail. Have a fantastic trip later this year!

Tuesday 9th of August 2022

Hi There! We are flying into Portland, (Sept 23rd) Maine and flying out of Boston, Mass (October 2nd) We have about one full week for our Fall Foliage road trip. Knowing we arrive Portland and depart Boston, what would you map out for itinerary.

Part II question, I prefer staying at one hotel for a few days and taking day trips as opposed to staying one night in several places.

Would it be wise to stay 3 nights near Acadia Nat'l Park and then 3 nights in New Hampshire (near all of the Franconia State Park and Kancamagus Hwy ?

Thursday 11th of August 2022

Hi Erin, yes staying 3 nights in Bar Harbor and then 3 nights somewhere near Franconia Notch sounds like the best idea if you would prefer to stay in one hotel for each part of your trip. You can easily visit the most popular fall foliage areas in VT and NH from Franconia. Depending on how much driving you want to do, you could split your days into Vermont and New Hampshire. So one day you do Stowe, Woodstock and Manchester (the driving in between is just as picturesque as the towns), then another day you do Mt Washington, Kancamagus, Artists Bluff and Flume Gorge (which are all much closer together). Then stop at Lake Winnipesaukee on the way down to Boston. Hopefully the peak colors will be in north / central VT and NH early Oct for your trip - have a great time!

Try This 7 Day New England Road Trip Itinerary

This New England road trip itinerary might just be perfect to help you knock off 3 states from your list in just one week.

Are you interested in traveling to New England but unsure of the best things to do in Connecticut or what to do in Rhode Island?  

Are you looking for Massachusetts vacation ideas that don’t involve the extremely pricey Boston accommodations?  

This itinerary is full of 7 days of activities including travel between cities.  

You may want to consider adding an extra day at the beginning or end of the trip if you live far away and have a significant travel time to get to New England.  

Days 1-2: Start Your New England Road Trip in Connecticut

This trip starts out in Connecticut.  

Specifically in the southeast corner of the state at the Foxwoods Resort and Casino.  

If you enjoy casino vacations then you will be more than happy to start your trip at the second largest casino in the US, which is actually made up of 6 separate casinos with over 22 types of table games, over 250 tables, and the only $1 blackjack tables in Connecticut.  

Foxwoods also has 4,800 slot machines, bingo games, and more.

However, you don’t have to be a gambler or even of legal gambling age to enjoy your stay at Foxwoods.  

Here are some of the other activities you could enjoy:

• Spas – Romantic Connecticut getaways wouldn’t be complete without one of the many Foxwoods spa packages.  Whether you just want to get your hair or nails done to start off your vacation or you are looking for complete pampering and a massage, you can purchase individual services or build a spa package that fits your individual needs at Foxwoods.
• Golf – Foxwoods offers golf packages for the award winning Lake of Isles course.  Some of these packages combine 18 holes of golfing with hotel accommodations, food & beverage vouchers, casino match play credits, and even spa credits.
• Bowling & Arcade – Whether you are bringing kids on your vacation or you are just young at heart you’ll enjoy the High Rollers Luxury Lanes (Bowling) and Tree House Arcade.
• Shopping – Not only does Foxwoods have high end boutiques, but now there is also an 80 store Tanger Outlet shopping center at Foxwoods all under one roof.
• Walking Trails and Museum – If you are looking for a break from the bright lights of the casino and want to get some fresh air, there are miles of walking trails along with the Mashantucket Pequot Museum that you can explore. It’s no East Coast National Park , but it’s just as gorgeous.
• Shows and Nightlife – Just as you would expect of a casino in Las Vegas, Foxwoods has plenty of shows and nightlife to entertain guests of all ages.

You could spend two full days at the Foxwoods Resort and Casino and still not get to everything on your list.  

However, if you are at all interested in the history of nuclear powered submarines, US Navy nuclear powered ships, or the history behind nuclear power, then you really should pull yourself away from the casino for a couple of hours to go explore the Submarine Force Museum in Groton, CT, home of the USS NAUTILUS.

The USS NAUTILUS is the world’s first nuclear propelled submarine and is docked next to the museum.  

There is an audio self guided tour so that you can explore this historic submarine for yourself.  

The museum is the only one of it’s kind owned by the US Navy, and has a large collection of artifacts, documents, and pictures on display.

Days 3-4: Continue Up the Coast to Massachusetts

On day 3 you’ll want to get an early start to make the 3 hour drive out to Provincetown Massachusetts, which is the furthest town at the tip of Cape Cod.  

I’ll start by adding a quick disclaimer that Provincetown (or P-Town as it is affectionately referred to) is known for being a vacation destination for the LGBTQ community.  So if you’re gonna hate, then go somewhere else, or better yet just stay at home.

If you reject the food, ignore the customs, fear the religion and avoid the people, you might better stay home. – James Michener

Now that we got that out of the way I’ll say that my husband and I absolutely loved Provincetown.  

There were rainbow flags flown outside pretty much every store, people were incredibly friendly, the town was very walkable, there were lots of great restaurants, bars, and small shops.  I don’t recall seeing a single chain restaurant.  We look forward to making the trip back out to Provincetown at some point in our future.

While in Provincetown there are plenty of activities to pack your day with.  

On your first day I’d suggest getting a lobster roll for lunch from a local restaurant on Commercial Street (the main shopping district through the town) then walking to the Pilgrim Monument and Provincetown Museum.  

Once inside, you can climb to the top of the monument where you can get some really spectacular views of Cape Cod, so don’t forget your camera!  

On the way back into town stop in an ice cream shop (there are plenty of them!) and enjoy a couple scoops while you finish walking around town and out onto the pier.

Whale Watching and Race Point Beach

On Day 4 you should rent bikes from a local shop down on Commercial Street and ride out on the well maintained bike paths to Race Point Beach .  

Sit out on the beach for a while and see if you can spot any seals swimming near the shore or whales out closer to the horizon.  

My husband and I were lucky enough to see both before turning back and riding our bikes back into town.

Once you return your bikes, head back over to the pier and go for an afternoon or evening whale watching tour with Dolphin Fleet of Provincetown.  

You definitely won’t be disappointed!

Here are two of our better pictures.  

The first one is of a humpback whale eating with his mouth wide open, and the second is of his tail sticking out of the water as he makes a deep dive back down under our boat.

Days 5-6: Back to Rhode Island

On Day 5 you’ll have about a 2.5 hour drive to get to Newport, RI, so you’ll have a little bit of time in the morning to get breakfast and maybe take one last stroll through P-Town before you hit the road.  

Aim to get to Newport at least by early afternoon.

Newport is the perfect type of town for staying at a local B&B.  

Staying at a B&B can give you the feeling of staying with a family friend and is a cozy place to call home for a couple of nights.  

You’ll also have more opportunity to talk with the owners and other vacationers for recommendations on local restaurants and activities to make sure you enjoy your stay.

Once you get checked in to your lodging accommodations it’s time to go out and explore!  

Historically, Newport was the vacation home to many wealthy New Yorkers so keep your eyes open and see how many beautiful mansions you can find.

I’d recommend that you start by driving down Bellevue Avenue (where a ton of these historic mansions are located) and then that you follow signs for the scenic ocean drive down Ocean Avenue.

If you are ready to get out of the car and stretch your legs, there is a 3.5 mile public walkway named the Cliff Walk which is a beautiful way to take in the views of both the coast and many of the ocean front mansions.

To finish off your day you could walk around the Thames Street shopping area and grab dinner and a bowl of fresh New England clam chowder at the historic Red Parrot restaurant.

Visit 5 Newport Mansions

Yesterday you had the chance to admire the historic Newport mansions from a distance, but today you’re going inside!  

The Preservation Society of Newport County now owns eleven mansions representing the Colonial, Victorian, and Gilded Age.  

Your best option for purchasing Newport mansions discount tickets is to buy the “Newport Mansions Experience” tour ticket.  This ticket allows access to up to 5 properties and is a significant discount from purchasing each ticket individually.  

You can purchase this ticket at the first mansion you stop at.

By far, the most famous of these, and a real “must see” is the Breakers Newport mansion, which was the summer home to the Vanderbilt family.  

If you are interested in seeing how these mansions were maintained between all of the cooking, cleaning, and grounds maintenance, then you should consider adding the “Servant Life Tour” at the Elms so that you can see “behind the scenes” to the places in the house that were intentionally kept out of view from family house guests.  

The Servant Life Tour includes a tour through the servant bedrooms, the kitchen, the laundry room, the coal cellar, and the boiler room.

Day 7: Never Fun to Say Goodbye

All good things must come to an end unfortunately.

Head out for one last stroll along Easton’s Beach and grab any souvenirs you may have forgotten to pick up along the way.

It’s time to head home.

How Was Your Trip?

I certainly hope you’ve enjoyed your 7-day vacation and all of these New England travel ideas.  

Do you have any suggestions for travelers booking a New England vacation?  

Did you get any great photos of whales on your Massachusetts whale watching tour?  

Which was your favorite of the Newport mansions?  

Let me know in the comments below!

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The ultimate 10-day new england road trip itinerary.

New England, with its quaint villages, idyllic landscapes, rich history, and mouthwatering culinary experiences, is a treasure chest of delights waiting to be unlocked. From the rugged beauty of the Maine coastline to the vibrant, artistic vibe of Providence, this is a region that never fails to enchant.

If you’re up for the crisp smell of the ocean mingled with pine trees, the rustic charm of cobblestone streets lined with centuries-old houses, and the taste of the most succulent seafood freshly plucked from the sea, then you have to start planning your New England road trip!

» You might be interested in a shorter version with this Boston to Bar Harbor road trip itinerary.

» Looking for more travel inspiration in the United States ? See our U.S. Summer Vacation Ideas and 12 U.S. National Parks to Visit . Here are a few more fabulous U.S. Cities to visit .

The only real problem is deciding what to do and see and how to fit everything into ten days. Lucky for you, we’ve done this road trip multiple times and have passed through these states on a number of different trips, so we have the knowledge to help you plan an amazing time on one of the best road trips in the United States .

Table of Contents

Essential New England Road Trip Info

Comprising six states – Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont -there’s a lot of ground to cover during a New England driving tour. It’s not a small amount of driving, despite how close together many of these states are. So if you’re planning to embark on this road trip, keep this in mind.

You can either fly into a set starting point – we recommend Boston – or you can drive in from where ever you’re located in the United States. In any case, you’re going to need a car – either your own or a rental car . If you’re renting, we suggest going through Discover Cars to get the best deals from all the top car rental companies in one place.

How to Get to New England

If traveling from Europe or another destination outside the States, you’ll fly into Boston for this itinerary. Considering the region’s most popular international airport, Boston Logan International Airport (BOS) is where your trip will start and end.

If Boston doesn’t work for you, you can also fly into New York City , Philadelphia, or even Washington, DC. It will just take you a little longer to drive to the start point of this road trip, but there is plenty to see along the way.

When Should You Do on a New England Trip?

Unless you’re a winter die-hard, the best time to visit New England is undoubtedly during the fall, from September to December, or spring, from March to June. 

Fall is when the landscape takes on a magical element with changing colors in every shade of gold, orange, red, and brown imaginable. Aside from that, the crisp, clear fall air and the New England sun bursting through the morning mists are second to none, making it one of the best fall destinations in the USA .

If you can’t swing a fall road trip, the second best time is during spring. This is before the heat of the summer really sets in, so temperatures will be mild and enjoyable. I would definitely not go in summer, if at all possible, because it can get really hot and humid.

New England Road Trip Itinerary

Are you ready to buckle up and join me on a 10-day road trip across these six picturesque states? I’m thrilled to share this thoroughly curated itinerary that will ensure you make the most out of this journey, exploring the hidden gems as well as the must-see spots.

Whether you’re a history buff, a foodie, a nature enthusiast, or simply someone who enjoys the thrill of exploring new places, this 10-day New England road trip has something for everyone. So pack your bags, put on your favorite road trip playlist, and let’s hit the road.

Boston, Massachusetts (Day 1)

After arriving in Boston, Massachusetts , you can jump directly into the first day of your trip by visiting Boston. Drop off your bags at the hotel and explore Beantown (as it’s locally known). 

In a city defined by a rich history and vibrant sports culture, you’ll find a million historical things to see alongside plenty of sports bars to grab a beer in at the end of your day. While there’s no way to see the best of Boston in one day, we suggest you include these highlights on your first day:

• Walk the Freedom Trail past some of the most important sites that shaped the American Revolution
• Explore the Boston Tea Party Ships and Museums
• Head to the Italian cuisine-filled North End of Boston for either lunch or dinner
• Grab a few snapshots of America’s most photographed street, Acorn Street
• Visit the Boston Library and marvel at its exquisite architecture

Where to stay: The Newbury Boston

Salem, Massachusetts & Portland, Maine (Day 2)

Your second day of this New England vacation itinerary involves the first stretch of road to tackle. Heading out north via the Essex Coastal Scenic Byway (or Route 127), you’ll drive for about 40 minutes to reach Salem.

Infamously known for being the site of the Salem witch trials of 1962, the town is a global epicenter for everything occult. If you’re visiting during October, prepare for an overload of everything spooky. No matter when you’re in town, here are some spots you shouldn’t skip:

• The Salem Witch Museum
• Salem Witch Trials Memorial
• The House of the Seven Gables

When you’re done exploring spooky Salem, jump back on Route 127. After about an hour and forty minutes, you’ll reach Portland, Maine. 

Similar to its west coast counterpart in Oregon , Portland, Maine, is a city with a bustling passion for the arts, the outdoors, and local microbrews and distilleries. Arriving in the city, you can leave your bags at your hotel and set out for a taste of Portland.

Some of the top things to see and do while you’re in town include:

• Visit Fort Williams Park and the Portland Head Light
• Tackle a brewery tour of Portland to some local craft breweries
• Shop the local boutiques and specialty shops of Old Port
• Grab a sunset view along the Eastern Promenade
• Eat lobster rolls at Luke’s Lobster on the pier

Tours to look out for while you’re in Portland:

• Old Port Culinary Walking Tour
• Cusco Bay Sea Kayaking Tour
• A Walk Through Time Tour in Portland 

Where to stay: Portland Regency Hotel & Spa

Bar Harbor & Acadia National Park, Maine (Day 3)

Your third day along this New England trip requires an early start and a three-hour drive, but the rewards are totally worth it. Driving from Portland to Bar Harbor, the beach town gateway to Acadia National Park, prepare for some out-of-this-world scenery.

Along the route, you’ll pass through a few towns worth a stop. The first is Bristol, where you can spend a minute or two at the Pemaquid Point Lighthouse , then stop at the Camden Hills State Park in Camden to see the view from the top of Mt. Battie.

After dropping off your belongings at your overnight spot in Bar Harbor, it’s time to head into Acadia National Park. You need a U.S. Park Pass to get in. If you’re going to be visiting more than one park in the year, you should definitely consider getting the America the Beautiful annual pass, which is just $79.99 from REI.

On Maine’s largest island, Mount Desert Island, the 47,000-acre Acadia National Park has dramatic mountains, picturesque lakes, and endless miles of hiking trails. It’s one of the biggest draws to this part of the U.S.

The top three things to add to your Acadia itinerary include:

• Hiking to the summit of Cadillac Mountain (vehicle reservations are required for Cadillac Summit Road from May 25 through Oct 22). Book online.
• Kayaking on Swan Lake
• Biking or driving the Park Loop Road. The Park Loop Road can be very crowded. Have a backup plan if the area you wish to visit is full.

Where to stay: Bar Harbor Inn

White Mountain National Forest, New Hampshire (Day 4)

While you technically did venture into stunning New Hampshire earlier in your road trip, day four is all about heading to and roaming around one of the state’s top attractions. The drive to get there is another 3 hours 30 min drive, so get up early!

Topping most driving tours of New England, especially those focused on New Hampshire, White Mountain National Forest is a beautiful collection of natural landscapes. The best thing about the National Forest is that there are many unique activities to indulge in regardless of what time of year you’re visiting.

• In springtime, thanks to warmer weather and melting snow, the forest delivers the perfect setting for hiking and camping.
• During the summer, you can fill your day by hiking, fishing, or canoeing.
• When fall arrives, you should set out to drive New Hampshire’s scenic Kancamagus Highway.
• Wintertime brings with it a lot of snow-capped mountains fit for winter sports enthusiasts at numerous ski resorts.

Where to stay: The Inn at Thornhill & Spa

Stowe, Vermont (Day 5)

Once you’ve said farewell to New Hampshire, it’s time to head to NEK or the North-East Kingdom of Vermont. It’s a 1 hour 30 minute drive. Known for its spectacular green mountains, eye-catching lakes, and charming small farms, the state is a buzzworthy must-visit.

On the way to Stowe, you’ll stop in Waterbury for a genuine pilgrimage to the ice cream empire and the original store of Ben & Jerry’s.

Next up is a short 20-minute drive north to the ski resort town of Stowe. This world-famous ski destination showcases an authentic small-town charm, a lively main street, and some iconic steepled churches.

Be sure to check out some of Stowe’s one-of-a-kind local favorites, such as Laughing Moon Chocolates, Shaw’s General Store, and The Deep End (the hippest pizza place in the state). Other options here include:

• Skiing at the Trapp Family Lodge
• Hiking in Green Mountain National Forest
• Heading on a scenic drive on Mountain Road

Where to stay: The Lodge at Spruce Peak

Litchfield & Mystic, Connecticut (Day 6)

Another early start on day six, you’ll drive down the Route 100 Scenic Byway, Vermont’s longest highway, through Wilmington, across the border into Connecticut. First stop of the day? Litchfield; a charming New England town brimming with local history. It’s a 4-hour drive to get there.

Founded in 1719, today, the town is a popular tourist destination known for its antique shops, numerous art galleries, and historic homes.

Delving further into Connecticut, you’ll head east to the town of Mystic. This historic seaport sits snuggly on the Mystic River and is most famous for its maritime heritage and the setting of the 1988 film Mystic Pizza .

Here are some highlights in Mystic:

• Visit the Mystic Seaport Museum , one of the largest in the world
• Explore early colonial farm life at the Denison Homestead
• Dive into some aquatic adventures at the Mystic Aquarium
• Hike a trail or two in Bluff Point State Park

Where to stay: Hilton Mystic

Newport, Rhode Island (Day 7)

Continuing the coastal New England road trip, the next stop along your journey is in Rhode Island. Although it’s the smallest state in the US, it is home to some of the country’s most historic towns, most notably Newport. This is only an hour drive.

This seaside town, once a summer retreat for America’s most wealthy families, boasts breathtakingly stunning mansions built during the Gilded Age and is quite the sight to behold. Beyond that, you’ll find pristine beaches and some of the best seafood in the country here.

When you’re planning your day in Newport, be sure to include these must-do activities:

• Stroll along Cliff Walk, a coastal 3.5-mile pathway hugging the Atlantic Ocean
• Indulge in some retail therapy along Bellevue Avenue and Thames Street
• Head out wine tasting at Greenvale Vineyards
• Tour the famous Newport Mansions
• Explore Bowen’s Wharf or take a boat cruise from Long Wharf
• Relax on the sands of Easton Beach

Where to stay: Newport Marriott

Cape Cod (Day 8)

Next up, and after an entire week on the road, it’s time for some rest and relaxation on the flexed arm of Massachusetts, in Cape Cod, a 1-hour 30-minute drive. Sitting on a peninsula in the state’s southeastern region, Cape Cod has long been a summer destination for the rich and famous.

Now if you’ve ever wondered why New England beach vacations are so popular, the almost 560 miles of coastline that encircle Cape Cod provide a clear answer. Yes, there are many great towns here worthy of a stay, but for this road trip, you’ll spend the day and night in Sandwich.

The official oldest English settlement in Cape Cod, Sandwich, dates back to 1639 and stuns with calm beachfront, quaint eateries, and a vibrant historic district. Fill your day in Sandwich with some of these standouts:

• Breakfast at Cafe Riverview
• Stroll along East Sandwich Beach
• Visit Sandwich Boardwalk
• Explore the Sandwich Historic District
• Indulge in the best lobster in town at Mattakeese Wharf

Where to stay: Sandwich Lodge & Resort

Plymouth, Massachusetts (Day 9)

What would an itinerary for a New England road trip be without a stop in Plymouth? That’s why your second-to-last day in the area is all about exploring the town that dates back to 1620. It’s a 30-minute drive from Cape Cod.

Today this quintessential New England town is most known as the site where the very first Thanksgiving took place and is home to Plymouth Rock. Steeped in history, this is where the Pilgrims first landed way back when.

With all that history, here are a few top spots you should visit while in Plymouth:

• Explore Plimoth Patuxent , a living history museum with a replica of the Mayflower ship
• Grab a few snapshots at Plymouth Rock and delve into the Pilgrim Hall Museum
• Roam around Plymouth’s historic downtown harbor area, home to several notable buildings such as the Plymouth Courthouse
• Cap off your day with a stroll along Plymouth’s famously historic waterfront and catch the sunset over Cape Cod

Where to stay: Thomas Sea Suites at Harbourtown

Boston, Massachusetts (Day 10)

Finally ending your epic 10-day New England road trip, you’re back in Boston . Luckily the drive from Plymouth to Boston is only 45 minutes to an hour, so you can start the day a bit later and still be back in Beantown with some time to spare for any extra activities.

We’d recommend fitting anything you didn’t have time for on day one into your final day. If you’ve got a few extra hours, here are some other Boston highlights to add:

• For history lovers, pay a visit to the USS Constitution Museum or the Paul Revere House
• Art lovers should definitely head to the Isabella Stewart Gardner Museum and the Museum of Fine Arts
• Sports fanatics should take a one-hour tour of Fenway Park or catch a Boston Red Sox game ( check their calendar here )
• For food lovers, be sure to check out our foodie guide to Boston .

Where to stay: Hyatt Centric Faneuil Hall Boston

Wrapping Up Your Road Trip Through New England

There you have it – the best road trip through New England you could possibly do in ten days. Although numerous other attractions and standout activities can be included on any trip, this New England trip itinerary features the best of the best.

Of course, you can play around with other vacation ideas in New England or discover hidden travel tips heading off-the-beaten-path. Now all you have to do is decide when to go and prepare for some exciting road-tripping in New England.

Be Prepared For Travel Planning is the most important part of any successful trip. Do it the easy way:

🧳 Travel Packing List | ✔️ Why You Need Travel Insurance | ✈️ What to Do Before You Leave Home

• Find and book the best hotel (our favorite booking site is Expedia)
• Research flight options (our favorite tool is Skyscanner )
• Book a tour (we always use Viator to find the best tours)
• Rent a car through Discover Cars (they search the best deals for you!)

YOU MIGHT ALSO LIKE

8 Foodie Things to Do in Boston Massachusetts

17 Awesome Places to Visit in the United States

13 Best Cities to Visit in the United States

5 Top Historic Cities in the U.S.

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Laura Lynch, creator and writer of Savored Journeys, is an avid world traveler, certified wine expert, and international food specialist. She has written about travel and food for over 20 years and has visited over 75 countries. Her work has been published in numerous guidebooks, websites, and magazines.

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The Ultimate New England Road Trip Itinerary

New England has some of the most beautiful scenery in the United States. However, if you are planning on taking a New England road trip, you need to plan ahead. There is so much to see and do that it can be easy to burn through a 5-day New England road trip without having seen nearly all that you want to see.

Part of it is proper time management. You definitely cannot wing it when checking out New England vacation spots. There is so much to do on the New England coast alone that you will need to take more than a few trips to see it all.

A map of New England is just the starting point. Plan your New England coast road trip with a 7-day New England road trip itinerary. There are key points to hit the first time to see the essential things the first time around.

This post may contain affiliate links. Please read our  disclosure and privacy policy  for more information.

How to Prepare for a New England Road Trip

It helps to have an RV Generator when planning a New England road trip itinerary, especially taking a recreational vehicle. This way, you have fuel to cook with, and you can run minor electronics off of it for a little while at a time. It makes the road trip a little more like home while on the road.

You also have two options. You can get a New England map and do it like the old days. Or you can find a digital map of New England states online anywhere. Just make sure you scout ahead because New England weather can be finicky, and you can be taken by surprise by the conditions.

Make sure that you have an idea of New England tours available when you go, too. Tons of great tours show all the historical sites in the area, allowing you to get the most of the vast history that the area has to offer.

Finally, make sure you are familiar with New England law. Some things might take you by surprise if you are not adequately prepared. Even just a quick overview is enough to give you an idea about what to expect.

There are plenty of excellent road trip options, especially for those looking for ways to spend time with their families . Here are the best options when planning your itinerary.

5 New England Road Trip Itineraries

Are you looking for a good New England road trip itinerary? Everyone who has been to the area will no doubt have their suggestions. The key is to make sure that time is managed efficiently to be seen during the trip.

There are plenty of essentials to see, but which places do you have to go to in a shorter period? Here is the itinerary that will leave you feeling great about your trip and make you want to come back a few more times to see everything else.

1. Downtown Boston

If you are planning a Boston vacation of any kind, you know that you could easily spend the entire trip in Boston. It is one of the most historical and famous cities in the United States, and there is more to do than you could imagine.

Where is Boston, you may be asking? It is the heart of New England, one of the biggest cities on the east coast, located in Massachusetts. It is a destination for millions every year and one of the most popular cities there is.

You can start around the greater Boston area, hitting up some of the most famous things like the old Boston Garden. Catching a game at Fenway Park is another must as the Red Sox are a staple of Boston and America. Or you can just tour Fenway Park.

It is also one of the most historical places in the United States, dating back to the colonial period when America was just a collection of colonies owned by Britain. It is a great place to learn much about the beginnings of the United States.

Don’t Miss These In Boston

• Boston Ghosts & Gravestones Night-Time Trolley Tour
• Boston’s North End Secret Food Walking Tour w/ Private Tour Option
• Martha’s Vineyard Daytrip from Boston with Round-Trip Ferry & Island Tour Option

2. Maine National Parks

You have no doubt heard about Bar Harbor, Maine. But what is it? What to do in Bar Harbor, Maine, that makes it worth the visit? If you are looking for things to do in Bar Harbor, Maine, look no further than the largest national park in the country.

The national parks in Maine are worth the trip alone. It is the largest national park in the US, and the park loop road will keep you busy for far longer than you could have ever hoped. Whether you are someone who enjoys the outdoors or not, you will love these national parks. Wolfe’s Neck Woods State Park, in particular, is a favorite among locals and tourists alike.

Don’t Miss These In Maine

• 2-Hour Tall Ship Cruise from Bar Harbor
• Narrated Bus Tour of Bar Harbor and Acadia National Park

Whereas Boston is a great place to see historical sites, Maine is the place to go for those who love the outdoors. The beautiful national parks will keep you occupied for days and definitely will be something you want to see again.

3. Vermont Cities

Vermont tends to get lost in the shuffle when thinking about the destinations in New England. But cities in Vermont, particularly the small towns in Vermont, can wind up becoming significant destinations. The biggest cities in Vermont have that quaint feeling, though, which makes it feel like small-town life no matter where you are.

You can also partake in many outdoor activities. Ski-in ski-out Vermont, check out Crystal Lake Vermont for some stunning outdoor scenery, and Rocky Neck State Park is camping for a unique outdoor experience like no other.

Don’t Miss These In Don’t Miss These In Vermont

• Day Tour through Stowe,
• Vermont Snowmobile Tour ~ St Johnsbury Vermont’s

New Haven city hall is a historical destination as Vermont is also from the colonial era though it doesn’t get nearly as much love as Massachusetts. There is much and more to do in Vermont, even if they may not jump out immediately.

4. Cities in Connecticut

Like Vermont, Connecticut towns don’t get the love that they should. Connecticut National, Connecticut River Valley, and Connecticut beaches are beautiful and one of the hidden gems of the entire New England region.

The best beaches in Connecticut rival some of the best beaches in the country. Even better, they are not relatively as crowded as some of the popular ones in, say, Florida or California. That means being able to spend time quietly on the beach, enjoying the sun and the sand.

Much like Boston and Vermont, there are plenty of historical sites to see as well. There are more than a few trips worth of historical sites worth visiting in New England for those who consider themselves to be history buffs. Even if history isn’t your thing, there are more than a few sites that can get even the furthest thing from a history buff interested in the beginnings of the United States.

5. Cape Cod Town

Cape Cod weather is an attractive aspect in itself. The Cape Cod Canal is a destination for those in New England looking to take a trip but stay within the region. The National Seashore in Cape Cod is one of the most beautiful areas in the region and a must-see for locals and visitors alike.

Race Point offers some of the most beautiful, sandy beaches that you could hope to see as well. And because it is in New England, you can also get a little bit of a historical touch with the Race Point lighthouse. It is the perfect combination.

Cape Cod Town is home to some of the most beautiful natural scenery in New England. There is so much more than meets the eye, from the trails to the beach, the heritage museum, to the Pilgrim monument. It is an eye into the area’s history without being a little too “boring” like some historic areas.

Don’t Miss These In Cape Cod

• Cape Cod Sunset Private Charter
• Open-Air Pedicab Tour in Provincetown
• Whitney Plantation Audio Tour

There are plenty of things to do in Provincetown, too, from a great food scene and even the excellent Provincetown beaches. You can get the best of both worlds depending on where you go, with warm days to spend at the beach and crisp evenings to get the entire New England atmosphere.

Closing Thoughts

There is so much to see and do in New England that you can’t possibly hope to see it all in one trip. Still, with the proper itinerary, you can make the most of your 5- or 7-day New England road trip and get a ton fit into one trip.

When you have the proper itinerary, not only can you hit the essentials, but you can get an idea of what you may have missed. Besides, you will want to come back for more than a few trips to see all that New England has to offer.

Not only that, but you can also get a better idea of what weather may be like during that time of year, what to expect from road conditions, what you might spend on things like food, and more. You will become an expert on New England road trips in no time and better prepared when you inevitably go back in the future.

Looking for more posts to inspire you? Start here:

• Big Cedar Lodge in Missouri – The Bass Pro Shop Golf Resort
• Big Cypress Lodge – The Bass Pro Shop Resort – Memphis
• Diana’s Baths – New Hampshire’s Most Beautiful Waterfall
• Riding the Sand Dunes in Michigan
• Westgate River Ranch Resort and Rodeo

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Nikki Webster is a travel writer who covers how to travel while grinding a day job without breaking the bank. Nikki is always in search of off-the-beaten-track experiences and unique stays. She is particularly fond of Florida and writes extensively about the state. She flies around 60,000 miles annually and has visited 74 countries, 50 states, and six continents. You can read all about her travels at www.britonthemove.com or follow along on Facebook, Pinterest, and Instagram.

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New England Road Trip with Kids

This post may contain affiliate links for which I may earn a small commission if items are purchased via the link. As an Amazon Associate I earn from qualifying purchases at no additional cost to you.

Are you planning a New England road trip with kids and wondering what stops to make? The Northeast United States is one of the best family road trip destinations because the states are close together and you can cover a lot of ground in not a lot of time. Read on for the ultimate New England road trip itinerary with kids and plan your next trip to the Northeast. Here are the best places to visit in New England with kids.

Where should I start my New England road trip?

That’s totally up to you! We ended up flying into Manchester, NH and flew home from Providence, RI. There are many different possibilities and we chose based on cheapest airfare from our home airport as well as the cheapest car rental. Since one way car rentals are usually more expensive, we checked several cities to see which would be the best option.

We used hotel points and free night certificates for every single hotel we stayed in on this trip, making our accommodations completely free. If you aren’t playing the points and miles game, you are missing out on lots of free travel! This was peak travel time in this area, and many hotels were in the $300+ per night rate, which we would not be willing to pay. For hotels, we use the Marriott Bonvoy Boundless card from Chase, the World of Hyatt Chase card, and the IGH Rewards Club Premier from Chase. Our airfare was also free using points and companion pass on Southwest Airlines. We use the Southwest Airlines Chase card , which helps us earn lots of free flights. The only thing we paid for was the car rental. To rack up UR points, we use the Chase Freedom card.

How long does a New England road trip take?

Again, this is entirely up to you. You can spend a week or three weeks exploring the region. We had one full week and felt that was enough to see the places we wanted to see.

Best time to visit the New England region

While summer months are very popular since most kids are off from school and able to travel, the best time to visit New England is in the fall. The temperatures are cooler and fall foliage is in full swing, making it a great time for a New England road trip. It gets very cold in the New England states in the winter months and many places are open seasonally, so I personally wouldn’t recommend visiting in the winter.

We visited in July and the temperatures in Maine were in the low 70s. It was hotter in the other regions however nowhere near as hot as our Florida summer!

New England Road Trip Itinerary

• Day 1 : We flew into Manchester, NH (MHT) and drove to Scarborough, ME (1.5 hours). After lunch, we drove to Augusta, ME (1 hour) where we spent our first night.
• Day 2-3 : Drive from Augusta to Ellsworth, ME (1.5 hours). We had plans to visit Acadia National Park so our home base was Ellsworth for 2 nights.
• Day 4: Drive to Portsmouth, NH (30 minutes) for the next night.
• Day 5 : Drive to Cape Cod for one night. (2 hours, 15 mins)
• Day 6 : Drive to Rhode Island for one night. (1.5 hours)
• Day 7 : Drive to CT, day trip to Mystic. (1 hour)

Our first stop on our New England road trip was Scarborough, ME for some lunch. We went to a little seafood shack called Scarborough Lobster and had a lobster roll, some lobsters and mussels. The lobster roll wasn’t good at all to be honest, so I would skip that. We did like the lobsters and mussels though.

After, we drove a bit down the road to an awesome ice cream place called The Dairy Corner. Don’t miss this place, it’s some of the best ice cream we have ever had!

After we ate, we drove to Augusta, to get closer to our desired destination in ME, Acadia National Park. We spend our first night here before heading up North. We stayed at the Fairfield Inn and Suites Augusta , which was conveniently located right off the highway. It’s a great family friendly hotel in Augusta.

Our second stop was Ellsworth, ME which is close to Bar Harbor and Acadia National Park. We based ourselves here for Acadia and Bar Harbor.

What to do in Ellsworth with kids: Ellsworth is a cute town, with a small town feel. They have a cute downtown, a playground and great family friendly restaurants.

Where to stay in Ellsworth with kids: There are several family friendly hotels in Ellsworth, we chose to stay at the Hampton Inn Ellsworth . It’s about 25 minutes from Bar Harbor and Acadia National Park, making it one of the best family friendly hotels near Acadia National Park.

Where to eat with kids in Ellsworth: We love seafood, so of course we headed to a lobster shack yet again! The Union River Lobster Pot is a cute little restaurants, where you can sit outdoors on picnic tables and your kids can play while waiting for the meal. We opted to sit inside since we were tired from being out all day, but lots of families took advantage of the outdoor seating. They have great seafood here and be sure to try the blueberry pie!

Of course, no dinner is complete without dessert so we headed down the street to Mortons Moo ice cream for some really good homemade ice cream. The downtown Ellsworth area is super cute to explore as well. It’s only 2 blocks, but there are some really cute shops including a 3 level antique store that our daughter was fascinated with!

If your kids need to burn some energy in Ellsworth, one of the best playgrounds in Ellsworth is Knowlton Park, not too far from the downtown area. They have a splash pad as well, so if you are coming in the summer months, you might want to bring a change of clothes.

Our main reason for staying in Ellsworth was to visit Acadia National Park. I have an entire post on what to do in Acadia National Park with kids , so be sure to check it out! This was National Park number 27 for our 10 year old and definitely in the top 5!

On the same day as Acadia, we explored downtown Bar Harbor, which is one of the cutest little cities we visited on this trip. Bar Harbor is one of the best cities to visit with kids in Maine. There are lots of cute shops, restaurants and parks in the area. Be sure to try some Popovers at one of the bakeries!

After visiting the Bar Harbor area, we drove south to Portsmouth, NH. It’s a super cute little town and definitely worth a stop!

What to do with kids in Portsmouth: If the weather is rainy or cold, head to the Children’s Museum of NH. There is also an outdoor local history museum called the Strawbery Banke Museum. Your kids can see and learn all about what life was like hundreds of years ago. And the Seacoast Science Center is a short drive from downtown.

Our favorite thing to do in Portsmouth with kids was to walk around the downtown. There are so many cute, locally owned shops and restaurants. We love supporting small business and certainly did on this trip! We found an amazing board game store called Diversions Puzzles & Games (we have over 100 board games at home!) and you can even play the games downstairs in their game room. An independent book store, where Milana picked her next book and lots of other cute shops.

Where to stay in Portsmouth with kids: There are many family friendly hotels in Portsmouth. We chose to stay at the Sheraton Portsmouth Harborside Hotel , which was steps to the downtown area so you don’t even need to use your car once you are here. We had a club level room due to my status, with unlimited snacks and drinks in the lounge throughout the day. It was a great clean, hotel in a great location and one of the best hotels for families in Portsmouth.

Where to eat in Portsmouth with kids: There are lots of restaurants in downtown Portsmouth, so the possibilities are endless! We’ve had enough seafood at this point of our trip, so we went to a place called The Goat for some burgers and poutine. They were great and we would eat here again!

Our next stop on our New England road trip itinerary was Cape Cod. We wanted to stop in MA but not in a busy city like Boston so we decided to come to the Cape instead.

What to do with kids in Cape Cod: There is so much to do in this area! There are many cute towns with charming downtowns. Since we only had one night here, we visited downtown Chatham and Hyannis as well as the Chatham lighthouse and beach area.

Don’t forget to go to Kandy Korner where you can get a bag of penny candy. This is candy that most adults will remember buying when they were kids and your kids can now enjoy them! Spoiler alert: They are nowhere near a penny now! The bags will cost you $7.99, $12.99 or $17.99, depending on size.

Where to stay in Cape Cod with kids: Since we used points for our stay, we chose the Courtyard Marriott Hyannis . It was just 5 minutes to downtown and centrally located to both sides of the cape.

Where to eat in Cape Cod with kids: There are so many restaurants, it’s hard to recommend a place! It all depends on what you want to eat. We really didn’t want more seafood, so we went to Dragon Lite for Chinese food in downtown. We loved our dishes and it was a nice change from seafood.

For breakfast, head to The Daily Paper in downtown Hyannis. The food is great and it’s a very family friendly restaurant.

Don’t forget about dessert! There are several ice cream places in Hyannis but our favorite was Katie’s. They had many homemade flavors that they make on site, including quite a bit of soft serve flavors. It’s the best ice cream shop in Cape Cod!

Our New England road trip itinerary continues with a stop in Rhode Island. We first stopped in Providence for a few hours followed by Newport, which was a very last minute addition to our trip.

What to do in Providence with kids: One of the best things to do in Providence with kids is visit the children’s museum. It’s located in downtown, with a free parking lot. If you have reciprocal membership, this museum will be free.

In downtown Providence, there is also a playground inside Burnside Park, called Brandon’s Beach. This is a great playground for older kids, since a lot of the equipment involves climbing. I will have to be honest though, this is a super sketchy area and I would have never in a million years walked into this park had it been one of our mom-daughter trips. It’s such a shame that such an awesome playground exists in such a bad area. There’s a reason we were the only family here!

Another fun thing to do in Providence with kids is to visit the Roger Williams Park Zoo. It’s a fairly small zoo, so you won’t need too much time and can easily fit it on your trip.

Where to eat in Providence with kids: We were here during lunch, so we stopped into the Ocean State Sandwich Company in downtown to have lunch. Milana loves sandwiches and chose the BLTTA which had bacon, lettuce, tomatoes, turkey and avocado. The owner was shocked that a child ordered this and said most kids order plain bread and just meat or cheese. We were shocked to hear that, since Milana has been eating what we eat since she was a toddler and never stopped!

After an afternoon in Providence, we headed to Newport for the night. This is one of the cutest downtowns and cities on our New England road trip itinerary and a must visit! I wouldn’t come here for the beaches but the town was super cute and we enjoyed just wandering around.

What to do in Newport with kids: One of the best things to do in Newport with kids is to explore the downtown area. There are lots of shops and restaurants and the entire area is just super cute.

We went to Easton’s Beach in the evening but honestly I wouldn’t recommend it. The water wasn’t clean and there was this weird foam all over the sand, probably the reason it was deserted on a hot July evening! They have something called red algae and the water was bright red. While it’s technically safe to swim in, we would never get into that water. But like I mentioned, this was a super last minute addition for us so we weren’t expecting to hang out on the beach anyway (or even be in Newport) and we live in FL so beaches aren’t a draw for us when we travel.

I know locals will say there are better beaches, so if you want to hang out on the beach, maybe research which are best though personally I would head to a different destination if beaches are a must on your itinerary!

I will also note that many people recommended touring the different mansions in Newport, however that did not interest us in the least bit so we skipped this activity. But if you are into guided tours and walking around mansions, then for sure do it!

Where to stay in Newport with kids : The Wyndham Inn on the Harbor is one of the best hotels for families in Newport. It’s in a great location with large suites that are perfect for families.

Where to eat in Newport with kids: One of the best places to eat with kids in Newport is the Brick Alley Pub & Restaurant. It’s a very family friendly restaurant in Newport, with a ton of food options. They are known for their nachos, so of course we had to try them, and the beef brisket ones were really good!

After dinner, we headed across the street for some dessert at Sandcastles Sundaes & Shakes. If you like crazy shakes and sundaes, this is the place for you! Kids can also order their ice cream in a tiny beach bucket. We shared the strawberry twinkie sundae and it was really good!

Our final stop on our New England road trip itinerary with kids was Connecticut. We wanted to visit Mystic for the day so we found a hotel not too far from the city.

What to do in Mystic with kids: One of the best things to do in Mystic with kids is to walk around the downtown area. It’s only a couple of blocks but super cute!

Another fun place to visit with kids is the Olde Mistick Village. This is a cute outdoor village that looks like something from the past, with lots of shops and restaurants. It’s located near the Mystic Aquarium, so if you are doing that, it’s great to combine the two.

If you’re familiar with Mystic, you know they are famous for their 100 year old drawbridge. The Mystic River Bascule Bridge goes up every hour, at 40 minutes after, so be sure to time it right so your kids can watch it! Walk across to the park across the street, you will have a much better view from there.

Where to stay near Mystic with kids: Because we were using Hyatt points for a free night, we stayed at the Hyatt Place Mohegan Sun . It was 25 minutes from Mystic in a quite area near the Mohegan Sun casino.

Where to eat in Mystic with kids: One of the most popular places to eat in Mystic is Mystic Pizza, however we were not in the pizza mood. Our entire family loves salads, so we went to Mystic Salad Company to pick up some salads to go to eat at the park next door. Milana and I shared this awesome kale/romaine salad with lots of yummy toppings. Their salads are all create your own, so everyone can get what they want.

If you like ice cream, there are 3 ice cream shops within a block of each other. We chose the Mystic Drawbridge ice cream shop and it was amazing! I had the wild Maine blueberry ice cream and it was my favorite of the entire trip. Milana ordered an Italian soda (they have so many flavor combinations!) and it was great as well.

Have you done a New England road trip with kids? We would love to hear what your favorite stops were in the comments below! Want to save this to read later? Pin one of the images below.

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Planning a New York to Maine Road Trip Itinerary

Whether you are going for the beaches and the lobster rolls, or trying to hit peak fall foliage and everything pumpkin and apples, May through October is the perfect time to plan a New York to Maine road trip.

While it is tempting to rush through Southern New England on your way from New York to Maine, take some time to stop and see the sights along the way. This New York to Maine road trip itinerary was designed for a one-week trip, but can easily be extended to include more time at each destination or you can continue up the Maine Coast to see more of Vacationland.

This road trip is designed to go from New York City to Portland, Maine. However, if you want to include more stops between New York and Boston, you will also want to look at my New York to Boston itinerary for additional ideas.

Or, if you want to see more of Maine, you can continue north for a road trip through the Maine Highlands . This itinerary will take you from New York City to Maine, with stops in:

• Mystic, Connecticut
• Newport, Rhode Island
• Boston, Massachusetts
• Portland, Maine

New York to Maine Road Trip

If you are taking a New York to Maine road trip, the quickest route will be under six hours through Hartford, Connecticut. This makes the best return trip from Maine, but on your way, I’d recommend taking a slightly longer and a smidge more of a scenic route on your way to Maine.

From New York City, take Interstate 95 approximately 3.5 hours (traffic can vary) to the historic seaport town of Mystic, Connecticut. If you need a pitstop along the way, downtown Stamford and New Haven both offer great dining options, or grab some lobster rolls at Ford’s Lobster in Noank, Connecticut.

Stop #1: Mystic, Connecticut

Your first overnight stop should be in the charming seaside town of Mystic. I’m not sure if it is more famous for Mystic Pizza, the 1988 film starring Julia Roberts, or the historic Mystic Seaport, a must-see family attraction. You will probably want to stay here for two nights, as there is plenty to do in town and nearby.

Mystic Seaport is a recreated 19th Century seafaring village, complete with ships, shops, and workplaces staffed with costumed interpreters ready to tell you about their craft and day-to-day life in a 19th Century town. The cooperage, print shop, and general store are all popular stops with kids. Visitors can also step on board the Charles W. Morgan, the last wooden whaling ship in the world, or get out on the water on a Mystic River boat ride.

Downtown you can grab an ice cream and watch the drawbridge go up and down as ships pass by, browse the shops, or get something to eat at one of the many seafood restaurants. In addition to Mystic Pizza, I’m a huge fan of the Engine Room for lunch or dinner, or Kitchen Little for breakfast.

Kids will also love watching the beluga whales at the Mystic Aquarium or exploring the trails at the Denison Pequotsepos Nature Center. If you are visiting in the fall, it is worth waiting in line at B.F. Clyde’s Cider Mill for some hot, fresh apple cider donuts.

If you have time to spend a couple of days, nearby you can enjoy a ride on the Essex Steam Train, a visit to the Pequot Museum on the land of the Mashantucket Pequot Nation, a lighthouse tour from New London, a day at the beach in Misquamicut State Beach in Westerly, Rhode Island, or some wine tasting at Jonathan Edwards Winery near Stonington, CT.

Read more: things to do in Mystic with kids

Where to stay: Hyatt Place Mystic (includes free breakfast) and Mystic Marriott Hotel & Spa (not in downtown Mystic but a good full-service hotel option).

Stop #2: Newport, Rhode Island

From Mystic, it is about one hour drive to your next stop in Newport, Rhode Island. You can potentially just visit for the day and continue on to Providence or Boston, but staying overnight will give you more time on the Classic Coast.

Whether you are visiting in the spring, summer, fall, or winter , there is always something to do in the historic town of Newport, Rhode Island . Once a summer getaway for the wealthy New York industrialists, Newport still attracts the yachting crowd as the “sailing capital” and the classic coast. You can do Newport in a day, as it is only an hour from Mystic, but if you want to enjoy nearby beaches, farms, or take a day trip to Providence, Rhode Island , plan on staying one to two nights.

Two must-do things when you are in Newport are paying a visit to at least one of the famous Newport Mansions and getting out on the water for a sailing tour. The Newport Mansions are former homes of the business titans like the Vanderbilts, which were once used as “summer cottages” but more closely resemble palaces than a beach house. The largest and most famous is The Breakers, but I also enjoy visiting Marble House.

If you don’t want to tour the homes, take a drive down Bellevue Avenue to see them from the front and then walk along the three-mile Cliff Walk to get a glimpse of some of the backyards, along with gorgeous ocean views.

There are many sailing options in Newport, from sunset schooner sails to seal-watching eco-tours (in the winter). Leave time to enjoy shopping and strolling along Thames Street and Broadway in downtown Newport. You can also pop into the International Tennis Hall of Fame or one of two car museums around town. There are plenty of options for a great meal, including Bowen’s Wharf, the Black Pearl, Diego’s, and Midtown Oyster Bar.

In the evening, be sure to take a drive along Ocean Drive and try to catch a sunset from either Brenton Point, the Lawn at Castle Hill Inn, or Newport Island Harbor Resort on Goat Island. On your second day, either hit the beach (my favorites in Newport are Gooseberry Beach and Second Beach) or take a drive over to the neighboring island of Jamestown to visit my favorite spot in Rhode Island, Beavertail State Park. If you prefer an urban outing (or if you are visiting on a Waterfire night), head up to Providence for the day or afternoon/evening.

Where to stay: Newport Marriott has a great location and nautical decor, The Brenton Hotel is a hip hotel in central waterfront location, and The Vanderbilt is an upscale, historic property with a great rooftop bar.

Stop #3: Boston, Massachusetts

When it is time to bid adieu to Rhode Island, drive two hours north to Boston. Now if you have extra time, you will want to spend three days in Boston, especially if you want to take some day trips to Gloucester , Rockport, or Salem, or stop at Plymouth along the way.

Boston is rich in history and charm, and like any large city, it has its fair share of great museums too. If you are interested in history, taking a walk along the Freedom Trail is a must-do. Of course, you may get more out of it if you sign up for a tour with a costumed guide.

To better understand Boston’s pivotal role in the Revolutionary War and founding of the country, pay a visit to the Boston Tea Party Ships & Museum . Kids will especially love tossing the tea into the Boston Harbor or a snack at the tea shop.

Within a short walk of the Boston Tea Party Museum, you can also visit either the Boston Children’s Museum or the New England Aquarium. If you are visiting in the summer, I’d recommend booking a whale-watching cruise in advance for an afternoon on the water and a glimpse of some magnificent creatures. If you don’t have time for a whale watch, you can still enjoy some time on the water with a harbor cruise or a ferry around the Boston Harbor Islands.

Afterward, take a walk along the Rose Kennedy Greenway and either enjoy some of the food trucks congregated there, or walk over to the North End, Boston’s “Little Italy” and pick up some cannoli at Mike’s Pastry. And while it is touristy, the street performers around Fanueil Hall are always entertaining and there are plenty of places to grab a quick bite. For a more upscale food hall, drop into the Boston Public Market or head across town to Eataly Boston.

Sports fans should try to book a tour of the “Green Monster” and Fenway Park or try to catch a Boston Red Sox game in this classic stadium. If you appreciate art, visit the Museum of Fine Arts, or the intriguing Isabella Stewart Gardner Museum nearby (and learn about the famous heist that took place there.)

While you are in town, take a stroll through the Boston Common and Public Gardens, and take a ride on a Swan Boat before you visit the famous “Make Way for Ducklings” sculpture. You can also pop into Cheers on Beacon Hill and see if anyone knows your name. Movie and television fans would also enjoy a tour with On Location Tours of popular Boston filming sites from Good Will Hunting, Ted, The Departed, and others.

Read more: Things to do in Boston with teens

Where to stay : Boston is notoriously pricey, so for a family, you may want to consider one of the following options: Residence Inn Boston Downtown/Seaport Hotel has a convenient location to downtown, North End and harbor; Element Seaport is in newer seaport district with family size rooms; and Hyatt Place Boston/Seaport District has free breakfast and a good location in popular Seaport District.

Stop #4: Kennebunkport, Maine

On your way to Portland, head two hours north of Boston to the charming coastal town of Kennebunkport, Maine. As soon as you pass into Maine, get off the highway and hightail it to Bob’s Clam Hut for some of the best lobster rolls and fried clams in New England. Then meander up the coast, taking your time to stop into a few of the best towns in the Maine Beaches region.

If you need to stretch your legs, stop in York for a walk along the 1.5 mile Cliff Walk or stock up your kitchen pantry at the Stonewall Kitchen company store. Another must-stop destination on your road trip to Maine has to be in Cape Neddick at the Nubble Lighthouse. Located on an island just off the coast, this is one of the most photographed lighthouses in Maine. If you are hungry, you can get some fresh lobster at Fox’s Lobster House right next door or Dunne’s Ice Cream down the street.

Just a little further along you will arrive in Kennebunkport (you might want to drive past the Bush Family compound along the way.) In town, you can enjoy shopping and dining at the many restaurants such as Federal Jack’s, Allison’s, Mabel’s, or the famous Clam Shack.

We also like to head out of town to Cape Porpoise Chowder House, which is popular with locals and tourists alike. Just be warned that parking is hard to find so you may need to walk a bit. You can stay in Kennebunkport or drive another 40 minutes to Portland, Maine. Your final destination on this New York to Maine road trip.

Where to stay: The Boathouse is a waterfront hotel right in Dock Square is perfect for when you want to be in the center of the action. If you prefer a bed and breakfast, try the The Inn at English Meadows .

Stop #5: Portland, Maine

Portland , Maine is one of the best small cities on the East Coast . Plan to spend at least a couple of days exploring Portland and the surrounding area. The park and area around Portland Head Light in Cape Elizabeth is a perfect spot for a picnic and to clamber over the rocks and watch the boats go by. When you are there, be sure to pick up a lobster roll from the Bite into Maine food truck.

Back in Old Port, take an afternoon to explore the boutiques along the harbor and wharves. There are so many amazing restaurants in Portland to try including Luke’s Lobster, Duckfat, Eventide, and Fore Street. There are also many craft breweries in the Portland area and you can board the Brew Bus for a tour if you don’t want to risk driving.

On your second day, you can take a ferry around the Harbor Islands or try a lobster cruise where you learn all about lobster fishing and even get to keep and cook what you catch. Or, spend a day shopping up in Freeport, home of the flagship L.L. Bean store.

Read more: Things to do in Portland in winter

Where to stay: Press Hotel or the AC Hotel Portland

While this New York to Maine road trip itinerary only takes you into Southern Maine, it is easy to extend this to head up to the coast with a stop at either Boothbay Harbor or Rockland before reaching Bar Harbor and Acadia National Park .

This road trip gives you a great introduction to Southern New England and includes some of the region’s highlights. If you are looking for more road trip ideas and want to dig a little deeper into New England, I’d recommend:

• New England road trips to take in the fall
• Vermont road trip itinerary
• Off-the-beaten path Maine road trip

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Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of YourTimetoFly.com and the co-host of the Vacation Mavens travel podcast.

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Publish Date: March 23, 2024

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Naperville Sun Opinion | McGrath: Remembering back to that Easter week…

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Naperville sun opinion | mcgrath: remembering back to that easter week that could have changed lives if not for one heroic act.

Our bond was alphabetical: Miller, Messerich, McGrath.

As high school sophomores at St. Joseph’s Franciscan Seminary in Westmont, we lined up together in class, sat in the same church pew and at the same cafeteria table, and slept in the same row of dormitory bunks.

The lone exception was Frank Oberle, a Cleveland resident who, in spite of being further down the alphabet, shared our love of hockey, Simon and Garfunkel, and Lucky Strike cigarettes.

Fred Miller came from Neopit, Wisconsin, where he had been persuaded by his pastor to pursue the priesthood. Hulking and athletic, Fred was a full-blooded Menomonee with a lively wit.

Mike Messerich, from Minnesota, was thoughtful but not outspoken, offering his judgment only when asked. His was a family of hunters and anglers, and he had a crew cut and freckles.

I was flattered that they thought of me as a “greaser” and gangster because I was born in Chicago, my Sunday shoes pointy black leather with Cuban heels. I did nothing to persuade them otherwise since it seemed preferable to my real identity as the quasi-nerd middle child in a family of 10.

The week before Easter in our Tuesday night study hall, Oberle crossed the aisle with an open book so as not to arouse the attention of the friar on duty.

“It’s supposed to be 80 degrees tomorrow,” he said.

As we had conspired to swim in one of the campus lakes in violation of school rules, I asked Fred if he was up for it.

“Maybe,” Fred said. “Lessin’ there’s a trap, like a Franciscan hiding underwater, breathing through a cattail reed.”

“Ain’t that an Indian thing?” Frank asked.

“Nah. You watch too many John Wayne movies.”

“What about you, Mike?” I said.

Messerich didn’t immediately answer. He had a whetstone with which he had been sharpening a knife pilfered from the refectory. He raised it above his head and released it, letting it plunge into his desktop.

“When do we swim?” he responded.

St. Joe’s sat on several hundred acres of what used to be the Peabody estate in Oak Brook, stretching south from 31st Street to 35th Street and east from Midwest Road to Ogden Avenue.

The closed campus rule was meant to keep us isolated from the secular world. But we still had room to roam through multiple sports fields and the trail around two lakes. A third body of water, Mayslake, was where St. Paschal’s monastery housed the Franciscan brothers and was strictly out of bounds. We glimpsed it from afar, its beauty sparkling and inviting compared to the muddy ponds where we were allowed.

On Wednesday, we managed to hike to Mayslake unnoticed. The water was freezing so Frank and I plopped on the grassy bank and lit up a contraband Lucky.

“Chicken**** bastards,” said Fred, pronouncing it “bos-turds” with his up-north twang.

We watched him strip off his clothes and wade in. He was up to his chest by the time Mike caught up, the two of them splashing each other till Fred muscled him down into the water.

Mike surfaced and swam out. He went 20 yards before he turned, swimming back in a wide arc around Fred.

Fred shot us a glance before plunging under. He bobbed up and spun around like a trick bear, the back of his head and inky black hair all we could see.

On land, Mike was drying himself off with his shirt when he abruptly looked up. Fred was saying something, but not very loudly. We hushed to hear a barely audible “help.”

“He’s screwing with us,” I said, taking a drag off my Lucky.

But Mike Messerich charged back into the water. He dove in and with swift, smooth strokes was instantly there, their faces inches apart. He wrangled Fred into a headlock and commenced a kind of sidestroke to tow him to shore.

We watched, mesmerized, till they touched bottom, disentangled and got to their feet.

Frank asked Fred if he was OK.

He was now, he said. He had had a cramp all up his left side, and Mike saved his life.

Mike protested. Anybody would have done the same, he said, and it was lucky he had taken Red Cross training.

As they dressed, no one said a word.

Finally, Frank broke the silence. He offered that there’d be less chance of being caught if we cut across Pine Hill.

“Don’t be expecting the Indian scout to guide you through the woods,” Fred said.

Frank leapt from behind to steal his cap, and Fred stuck out a leg to send him sprawling.

By the end of senior year, we had all left the seminary. Mike, fittingly, became a first responder and the police chief of South St. Paul, Minnesota. Fred would go on to be elected tribal sheriff.

Sadly, Frank’s life was cut short in a motorcycle accident on a Nebraska highway.

On April 16, I hope to see Mike and Fred at St. Joe’s reunion at the Embassy Suites in Oakbrook Terrace.

We’ll reminisce, and I’ll say how they helped me learn about life, fraternity and responsibility.

I’ll ask if they remember Mayslake. I won’t, however, describe the nightmare our lives might have been had Mike not acted heroically.

But if I can manage to tell them I love them, I think they’ll understand.

David McGrath is an emeritus English professor at the College of DuPage and author of “Far Enough Away,” a collection of Chicagoland stories. He can be reached at [email protected].

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Road Trip: 5 Days In New England

I f you've got five days of freedom and the traveling itch, you might as well scratch it in New England, one of the most beautiful places in the States . Five days can make for a decent staycation, but when you're talking about seeing a chunk of the country that is made up of six states, it's really not much time at all. Sure, New England is made up of some of the smallest states, but size really doesn't matter – especially when it comes to how much beauty is packed into a state like Vermont.

However brief the time you have, you absolutely can and should see some pretty awesome things in New England in five days' time, and road-tripping is actually one of the best ways to see the historic and gorgeous area. We've developed a route that not only allows you to see all six of New England's gorgeous states but also takes you into some of the biggest and most popular cities in the region, where you can get a great idea of what the area has to offer.

Getting Started

Depending on where you reside, you'll want to consider where you'll be coming into New England and getting started on your adventure. With how massive the United States is, you're likely located a decent distance from the New England area. If this is the case, you'll want to fly into Portland, Maine and you can take the road trip exactly how we've designed it here. You may be wondering why we're telling you to fly into a road trip, but just bear with us here. Once you're at your starting point in New England carless and confused, you can rent a car for a one-way road trip. That's right, pick up your car in northern New England and drop it off states away — the perks of capitalism and corporate America!

Before heading out, you'll want to do your own research on the destinations mentioned in this guide, as we can't cover everything New England has to offer. As you'll come to see, it's quite a beautiful place, no matter what you value most while on vacation. While we may suggest a place to crash or a fun attraction, the great thing about road trips is they are fully customizable. Everything isn't for everyone, and adjusting the itinerary to fit what you'd like to get out of a trip is not only possible but encouraged for the ultimate fulfilling road trip . Cities in New England aren't too far from one another, so even larger deviations may not make a huge difference.

What To Bring

Your packing situation here will differ somewhat from most road trips, as you likely won't be packing for a car as much as a flight. Flying will limit what you take with you, but remember that you can always hit the store after renting a car to pick up all the necessities the TSA would have tackled you over – like a bottle of water. Depending on what time of year you set off for this journey, you will absolutely want to pack appropriate clothing and even some necessities for driving in the snow . Autumn is the perfect time to explore New England, and it's best to have light layers for adjustable temperatures.

Plan ahead and consider what kind of car you will be renting once you get off the plane, and make sure you're not over-packing the vehicle. For five days, you can likely get away with just bringing a carry-on, though this totally depends on your capabilities in packing light .

Bring plenty of money for tolls, and consider signing up for an EZ Pass for a quick and automatic way to pay tolls in the northeast. Some tolls can't be paid in cash and it's a lot easier just to roll right through the toll booths anyway -- this will help you avoid getting a bill in the mail for all the tolls in New England, especially around Massachusetts.

Day 1: Portland, Maine

Maine is the largest of New England's states, and all of it is utterly beautiful. Since we are short on time and Portland is not only the largest city in the state and the one with the most extensive airport, but also pretty convenient for visiting the other areas of New England, we'll be kicking off the road trip there. Once you arrive in Portland via jet plane and rent a one-way car, you'll be free to explore the city a little bit. Booking a flight that has you arriving in the city in the morning will give you a little more time here.

Although there's a city on the opposite side of the country that is more famous for beer, Portland, Maine is an established beer city, too. While here, you should check out its local breweries – though make sure you are perfect to drive before setting out again. No matter where you're coming from, chances are you've at least heard of Allagash Brewing Company. The brewery is local to Portland and less than 15 minutes from the airport – the perfect post-plane ride reward.

Staying the night in downtown Portland or the nearby Old Port neighborhood will give you a good view of the city and its nightlife. On your way out of the city in the morning, stop off at Holy Donut for a freshly made potato donut that, by all rights, should be on Maine's state flag.

Day 2: Portsmouth, New Hampshire

Portsmouth is less than an hour south of Portland and, if you hit the road early, you will have the majority of the day to explore the port city, which is great considering there is plenty to see. Staying at the Water Street Inn, even though it's technically in Maine, is just a 3-minute drive or 30-minute walk from the historic downtown Portsmouth, a destination you will want to explore while in the city.

You'll be cooped up in your car well enough during your five-day adventure, so taking the city by foot may be the way to go when considering just how to explore Portsmouth. Walking around downtown will not only help you immerse yourself in the city and really take your time to see the details in its culture and vibe, but walking around will also allow you to take in the historic buildings that make up the almost 400-year-old city.

The Envio is a great choice for a place to eat if you want to make the most out of your time in Portsmouth. Its rooftop bar and restaurant will give you an immaculate view of the city and not waste any of the precious, limited time you have in Portsmouth to take in not only the city itself but its surrounding waterway. Consider hitting up Prescott Park on your way back for an enchanting way to end the day.

Day 3: Scenic Drive Through Vermont

Practically any drive through Vermont is a scenic one, and you could spend a full road trip just discovering all the curvaceous, natural beauty of the state. Unfortunately, we're a little strapped for time, so a day trip through central New England will have to do. Over half of the completed drive time will take place on Day 3 – don't worry, though, it's all gorgeous and just over four hours on the road isn't all that much driving considering the overall road trip.

Taking Route 202 is the fastest way to get from Portsmouth to southern Vermont, and luckily, it's also a stunner of a highway. The view will change depending on what time of year you choose to embark, but whether your path is lined with blooming wildflowers or vibrant and fiery treetops, your time spent traversing the crisp Vermont landscape won't seem nearly long enough.

Day 3: Stop In Brattleboro

While there won't be enough time to stay the night in Brattleboro, the town is about halfway into the day's drive and offers a great pitstop to get out of the car and explore one of Vermont's cherished communities. The small city is more than just a convenient halfway point that allows for further exploration of Vermont -- it's actually a perfect low-key New England getaway destination in and of itself.

Brattleboro is a great place to engage with the locals and experience what it would be like to be a full-time New Englander. Grabbing lunch at a local favorite like Echo Restaurant and Lounge will give you the opportunity to do just that, while also placing you in a good area by the water and the nearby Main Street. The city is also big on art, and the Gallery Walk is a great way to see Brattleboro's artistic side.

If you plan your trip so your stop in Brattleboro lands on a Saturday, you'll be able to attend the Brattleboro Area Farmers' Market, which is one of the best in Vermont. No worries if not, though, because this leg of the trip still has plenty in store for you.

Day 3: Arrive In New Haven, Connecticut

After lunch and a little exploration in Brattleboro, it's time to get back on the road. The second half of today's scenic route will take you down Interstate 91 through the middle of Massachusetts and into Connecticut. You'll pass through the cities of Springfield, Massachusetts, and Hartford, Connecticut, both of which you can make a pitstop in.

Springfield, being the birthplace of Dr. Seuss, is home to a memorial garden with wacky sculptures honoring the children's book author and would be a perfect place to stop if you're road-tripping with the whole family. Hartford, which all the "Gilmore Girls" fans should recognize, is so full of history it'd take a good chunk of time to explore it all, so stopping at the Bushnell Park Carousel offers a fun yet brief break from the road.

The real goal, though, is making it to New Haven, where you'll have dinner and stay the night. You can accomplish both of these tasks at The Blake Hotel in addition to having a couple of drinks at their popular rooftop bar. Don't let the wining and dining of the stellar spot keep you up too late, as you should get an early start the next morning if you want to have some exploration time in New Haven.

Day 4: Spend The Morning In New Haven

Depending on what you value when visiting a new place, there are a couple of great options when it comes to having a fantastic morning in New Haven. If you've only got eyes for New England's natural beauty, grabbing a coffee and heading to one of the stunning parks is probably ideal. Being on the larger side of a city in the United States' northwest, New Haven has quite a lot of greenery and nature spots. One such spot is East Rock Park, which is an expansive protected park that not only includes a summit you can hike to but also a river and many recreational accommodations for park-goers.

On the other hand, if you are more into history, culture, and art, taking a look at Yale and one of its affiliated attractions could be just the thing to make your scholarly eyes shine. Yale itself is, of course, a sight to behold, but other comparable options are the university's Peabody Museum of Natural History as well as Yale's Art Museum, which is home to thousands of pieces and is the oldest university art museum in the country.

New Haven is a Mecca for scholars, whether it be those who learn from nature or institutions. No matter which you are, your morning in the city will be ripe with learning.

Day 4: Head To Providence, Rhode Island

After you've spent the morning having your fill of Connecticut, it's time to head over to Rhode Island. It's just under a two-hour drive from New Haven to Providence and you will have the rest of the afternoon and evening to see what the capital city is all about.

Staying in the downtown area will give you a good feel of the city, which is both urban and refreshing as it's on the water and has ample vegetation throughout the city. Hotel Providence offers prime accommodations at a reasonable price.

Walking throughout the downtown area around the hotel is a great way to get to know Providence. Here, you'll find ample shops to explore and art galleries to see. Craft Land doubles as both, and you can find a keepsake from your trip here, as well as something unique to bring back to your loved ones. The gift shop carries products from various local artists, allowing you to take a piece of New England home with you.

Day 5: Arrive In Boston, Massachusetts

Your road trip ends in Boston, home to the largest airport in New England, ideally, a place that allows you to make it back home with very little trouble. Boston is only about an hour's drive north of Providence so if you have scheduled your flight later in the day, you should have some time to explore a bit. We'd recommend keeping it somewhere that is easily accessible to the airport, as traffic in Boston can be unpredictable and you'll need to return your car at some point -- though the airport shuttle and the local subway can be a useful resource for getting around.

You may opt to stay in Boston for the night and head out in the morning to give yourself more time, as Boston is by far the largest city in New England. Even if you do buy yourself more time in the city, you likely will be unable to see some of the nearby attractions like Salem. Within the city are spots like Fenway Park and the Freedom Trail, both important and historical landmarks that hold value in different ways. No matter what you decide to do with your time in Boston, you'll likely only get a small taste of what the large city has to offer. That's okay, though, as you'll have plenty of reasons to come back another time.

Tips For Staying Safe

As is life, you can never truly plan for everything that could be thrown your way while traveling. You can, however, prepare, take precautions, and hope for the best. One of the best and most simple ways to increase your safety exponentially is to not travel alone. While you can certainly enjoy yourself by solo-tripping a drive through one of the most peaceful areas in the United States, taking someone whose company you enjoy can add so much to a trip, both in terms of making memories and keeping yourself safe.

Whether you decide to travel alone or bring some friends along with you, it's important to stay in contact with people back home. There are so many ways a trip can get off track; staying in contact with your loved ones and communicating your plans throughout the trip could be lifesaving. Taking that a step further, sharing your real-time location with people back home using an app on your phone is a great way to put minds at ease and ensure the people who care about you will be able to tell if your movements aren't matching up with your itinerary.

Variations Of A New England Road Trip

Our New England road trip itinerary may be the perfect one for you and the time you have available to explore the area, but our feelings aren't going to be hurt if you want to change it up a bit – promise! The destinations mentioned here are really only a scratch on the surface of the northeast's luscious landscapes and coasts, and there are so many potential routes and modifications you could make here to craft the perfect New England getaway.

For example, cutting out Vermont will shorten the road trip exponentially to allow longer stays and deeper explorations of the trip. Alternatively, if you are driving up from the south, you can rearrange the same destinations to New Haven, Providence, and Boston, then hit Brattleboro before heading to Portsmouth and Portland for a more straight shot. Of course, turning a one-way road trip into a there-and-back adventure will extend the drive time and shorten the time spent at various destinations.

Travelers who opt to cut out Maine may wish to fly into Boston and do a loop back to the city. If that's the case, Dorchester is a great neighborhood to stay in and will put you just south of Boston so you don't need to worry about getting out of downtown in the morning. Waking up early and grabbing some breakfast and a coffee at McKenna's Cafe is a great way to start out the first stretch of the road on your journey.

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