new england day trip ideas

The 37 Best New England Day Trips by Season (2024)

New England may be small compared to other regions in the U.S., but there are endless places to visit. I’ve lived here for almost five years and still feel like I’ve only scratched the surface of all there is to see and do.

The six states that make up this region — Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont — offer a beautiful blend of coastal landscapes, picturesque countryside, and vibrant urban centers.

After traveling extensively in this stunning corner of the country, I’ve compiled this list of the 37 best day trips in New England.

⏰ Short on time? Here are my top four New England day trip recommendations:

☀️ summer top pick: ogunquit, maine, best things to do in ogunquit:.

• Soak up the sun on Ogunquit Beach
• Browse the shops at Perkins Cove
• Hike Marginal Way
• Walk along Main Street
• Eat seafood at Ogunquit Beach Lobster House

Best Hotels if You Want to Extend Your Stay: 

📍 Ogunquit River Inn & Suites 📍 The Grand Hotel

🍁 Fall Top Pick: Acadia National Park, Maine

Best things to do in acadia:.

• Drive or hike to the summit of Cadillac Mountain
• Hike the Ocean Path Trail and relax on Sand Beach
• Hike around Jordan’s Pond and order popovers at Jordan’s Pond House Restaurant
• Drive the scenic Park Loop Road
• Visit the nearby town of Bar Harbor

Best Hotels if You Want to Extend Your Stay:

📍 The Inn on Mount Desert 📍 Bar Harbor Grand Hotel

❄️ Winter Top Pick: Stowe, Vermont

Best things to do in stowe:.

• Ski at Stowe Mountain Resort or Smugglers’ Notch Resort
• Explore the shops and galleries in downtown Stowe
• Hike or snowshoe along the Stowe Recreation Path

📍 Trapp Family Lodge 📍 Stowe Village Inn

🌸 Spring Top Pick: Boston, Massachusetts

Best things to do in boston:.

• Tour the Freedom Trail  
• Visit the Boston Tea Party Ships & Museum
• Go on a Duck Boat Tour
• Explore the Public Garden and Boston Common
• Stroll along Newbury Street and the Charles River Esplanade
• Take a walk down Charles Street in Beacon Hill

📍 Hyatt Regency Boston Harbor 📍 Omni Parker House

Best Day Trips in New England in the Summer

New England summers are fantastic. Since most of the states have their own coastline, it’s no surprise that many of the top places to visit in the summer are near the water. But I’ve included a couple of amazing inland destinations as well!

Here are my favorite summer day trip destinations in New England:

1. Ogunquit, Maine

Best as a day trip from Boston, MA; Portland, ME; Manchester, NH

I had never heard of Ogunquit until my husband surprised me with a birthday trip there one year, and this coastal town quickly became one of my favorite places in New England.

Start your day with some fun in the sun at Ogunquit Beach , the largest and most popular beach in town. The beach sits on a small strip of land separated from the mainland by a small saltwater river. People often sit on the riverside to enjoy the calm water (especially great if you have small kiddos!).

Stop for seafood at the Ogunquit Beach Lobster House before walking to Main Street to browse the many shops and cafes lined on either side.

Be sure to also visit Perkins Cove, a cluster of quaint shops and restaurants nestled along Ogunquit Harbor. From there, you’ll find the entrance to Marginal Way , a 1.25-mile trail that stretches along the coast and provides stunning views of the ocean the entire way.

2. Portland, Maine

Best as a day trip from Boston, MA; Bangor, ME; Portsmouth, NH

Pay a visit to Maine’s largest city, Portland . Also located on the Atlantic Ocean, Portland is an eclectic city with both a rich New England heritage and artsy, hipster vibes.

Here you will find one of New England’s smallest lighthouses, Bug Light , which is only 26 feet tall. From there, walk along the beautiful Eastern Promenade for incredible views of Casco Bay.

Experience what it was like to ride a train in the 1800s and early 1900s by purchasing tickets for the historic Maine Narrow Gauge Railroad . Then fill up on fresh seafood from the Portland Farmer’s Market (open Wednesdays and Saturdays) or Harbor Fish Market .

You also can’t miss making the quick drive over to Cape Elizabeth to see Portland Head Light , America’s most photographed lighthouse. This is one of the most breathtaking places I have seen in all of New England.

3. Portsmouth, New Hampshire

Situated along the Piscataqua River and just a couple miles from the Atlantic Ocean, Portsmouth is another historic city with a rich maritime heritage. 

Wander the cobblestone streets and browse through the numerous boutiques, art galleries, and cafes of Market Square .

Stop for brunch at the original The Friendly Toast restaurant, known for its eclectic and colorful interior and expansive menu. I love their Eggs Benedict and French Toast! 

The Flatbread Company is another local favorite where you can enjoy delicious flatbread pizza made with locally sourced ingredients.

Take a walk along the Portsmouth Harbor Trail and admire the views at Prescott Park , located right on the water.

When in Portsmouth, it’s also worth a quick drive down the coast to Rye Beach and Jenness Beach if you’re craving some fun in the sand and sun.

4. Gloucester, Massachusetts

Best as a day trip from Boston, MA; Worcester, MA; Portland, ME; Portsmouth, NH

When I first moved to Boston, locals recommended I check out Gloucester for the perfect beach day. They weren’t wrong! This lively town on Cape Ann exudes traditional New England coastal vibes and is one of the best places to spend a warm summer day.

Two of the most popular beaches in Gloucester are Good Harbor Beach and Wingaersheek Beach . I loved Good Harbor Beach for its soft sand and rocky coastline views. There’s also an island not far from the coast called Little Salt Island that you can walk to during low tide!

Another exciting option for your day in Gloucester is going on a whale-watching tour. Take a four-hour cruise to the Stellwagen Bank National Marine Sanctuary to see a variety of whales and dolphins.

🐳 Book Your Gloucester Whale-Watching Tour

While in town, grab a scoop or two (why not three?) from Holy Cow Ice Cream Cafe . If you’re craving a meal, stop for fish and chips from Turner’s Seafood — a local favorite.

Cap off your day by touring a medieval-inspired castle, Hammond Castle , the former home of inventor John Hays Hammond, Jr. You’ll be wowed by both the castle’s interior and the stunning ocean scenery from its grounds.

5. Rockport, Massachusetts

Rockport is a sister town to Gloucester, also located on Cape Ann. While there is enough to do in both Gloucester and Rockport for a day, you could plan to see both places in a single trip. Rockport is another historic seaside town that will have you feeling like you stepped into a painting.

Speaking of painting, Motif #1 is a replica of a former fishing shack in Bradley Wharf, and it has been the subject of artists’ paintings and photography for years. If you want a quintessential New England nautical scene, this is your place.

Motif #1 is nestled near Bearskin Neck , a collection of small boutiques and art galleries lined along the harbor. You could spend hours exploring the whimsical variety of items in these shops.

If you’re craving a walk in nature, check out Halibut Point State Park with its many trails that loop along the ocean.

Catch a show at Rockport’s famous Shalin Liu Performance Center , which features an array of musical and dance performances throughout the year. The building is positioned right on the ocean so you can admire the stunning scenery throughout the performance.

And of course, Rockport has its own share of beautiful beaches. Long Beach and Front Beach are two excellent places to sunbathe and swim.

6. York, Maine

Best as a day trip from Ogunquit, ME; Portland, ME; Portsmouth, NH; Boston, MA

The coastal towns continue! York exudes New England charm and boasts a rich history dating back to the early 17th century. Nestled along the southern coast of Maine, York offers a blend of stunning beaches, quaint neighborhoods, and historical landmarks. 

A highlight destination in York is Nubble Lighthouse , perched on a rocky island just off the shore. The lighthouse is a short drive from the popular Long Sands and Short Sands beaches.

Grab some ice cream from the parlor at the historic Goldenrod Restaurant and explore the various souvenir shops nearby. Just up the road is the popular York’s Wild Kingdom , part zoo and part amusement park. The park has been providing fun for all ages since 1951!

York is also home to what might be the world’s shortest suspension bridge, Wiggly Bridge . The bridge, which — true to its name — wiggles and jiggles as you walk across, spans York Harbor and leads to peaceful trails in the Steedman Woods.

7. Newport, Rhode Island

Best as a day trip from New Haven, CT; Providence, RI; Boston, MA; Worcester, MA

Newport is one of those places I could visit over and over again and never get tired of it. This historic Rhode Island town is a perfect blend of fascinating architectural sites and stunning natural beauty.

One of the most popular things to do in Newport is walk the scenic Cliff Walk , a 3.5-mile oceanside trail with panoramic views of the Atlantic Ocean almost the entire way. 

While in this part of town, you can also tour one of the famous Gilded Age mansions. The most famous mansion is The Breakers , one of the former summer “cottages” of the prominent Vanderbilt family.

🚋 Take a Newport Mansion Trolley Tour

Downtown Newport is filled with interesting shops and restaurants. One of my favorite restaurants is Red Parrot , which has amazing fish and chips. You could also visit the oldest operating restaurant in the U.S., White Horse Tavern .

🍽 Reserve Your Newport Walking Food and History Tour

Stop by Kilwins for ice cream and sit on a bench in Queen Anne Square to look over the beautiful Newport Harbor . Then hop on the Newport Harbor Shuttle at the harbor and take it to Fort Adams State Park . There is a walking path around the entire fort that provides amazing water views the entire way.

8. Block Island, Rhode Island

Best as a day trip from Newport, RI; Mystic, CT; Providence, RI; New London, CT

Block Island is a summer paradise located off the coast of Rhode Island. You can get there by hopping on the one-hour-long Block Island Ferry from Newport or Point Judith, RI, or New London, CT.

Explore the island’s beauty by hiking, biking, or renting a moped .

For breathtaking views of the ocean, visit Southeast Light , a historic lighthouse perched on the Mohegan Bluffs . 

The great thing about being on an island is you can find amazing beaches anywhere you turn. Some of the best ones to check out include Crescent Beach , Mansion Beach , and Ballard’s Beach .

There’s also a large natural harbor on the west side of the island called Great Salt Pond , where you can enjoy boating, kayaking, or paddleboarding.

You also can’t miss exploring Block Island’s quaint downtown area, known as Old Harbor . Here you’ll find a charming blend of boutiques, art galleries, and restaurants serving fresh seafood. 

For a unique ecological landscape, check out Rodman’s Hollow on the southern part of the island. Part of Block Island National Wildlife Refuge , this large glacial bowl provides awe-inspiring views and is home to a variety of plants and wildlife.

9. Griswold, Connecticut

Best as a day trip from: Mystic, CT; Providence, RI; Newport, RI; Boston, MA

Griswold is a quaint area in southeastern Connecticut with scenic hills and picturesque farmlands. It’s a great day trip option if you want to experience rural New England. 

One of my favorite places in this area is Buttonwood Farm , where you can find one of the largest sunflower fields in New England. The sunflowers reach their peak in July and August. Buttonwood also has an ice cream stand with a delicious assortment of flavors — all made fresh on their eco-friendly farm!

For a peaceful walk in nature, visit Pachaug State Forest, the largest state forest in Connecticut, consisting of more than 26,000 acres with 15 trails to explore.

Bonus activity if you visit in the spring instead of summer: Drive from Griswold to nearby Preston to visit the largest “pick your own” tulip farm in New England, Wicked Tulips Flower Farm . The farm is open to flower-pickers in the spring, where you can find over 100 tulip varieties and more than 1.5 million blooms!

10. Watch Hill, Rhode Island

Best as a day trip from Newport, RI; Providence, RI; Boston, MA

Situated on the southwestern tip of Rhode Island, Watch Hill is known for its stunning ocean views and elegant, historic architecture.

Napatree Point Conservation Area i s a thin, sandy peninsula stretching out from Watch Hill that’s a preserve for bird nesting and migration. It’s a beautiful area to walk and take in the scenic views on all sides, or sit and relax on one of the pristine beaches.

Watch Hill Lighthouse dates back to 1745 and can be found at the southernmost point of Watch Hill. The lighthouse with its surrounding ocean panoramas is an unforgettable sight to see.

Not far from there, you’ll come to Watch Hill Beach , the perfect place to relax in the sand and sun.

While in Watch Hill, take a ride on the oldest carousel in the U.S., the Watch Hill Merry-Go-Round , known for its “flying horses.”

While this post is focused on day trips, I would be remiss if I didn’t mention the historic Ocean House of Watch Hill, a luxurious seaside resort and the first and only AAA Five Diamond and Forbes Five-Star hotel in Rhode Island. Want to consider extending your visit? 😉

11. Narragansett, Rhode Island

Best as a day trip from Newport, RI; Providence, RI; New Haven, CT; Hartford, CT; Boston, MA

If you’re looking for a pretty Rhode Island beach town without the crowds of places like Newport, try Narragansett, only about a 20-minute drive away. Narragansett is home to beautiful beaches and seaside pathways where you can spend a perfect day in the salty ocean air. 

One of my favorite places to visit in Narragansett is Point Judith , a small cape with a historic lighthouse and breathtaking views of the ocean from all sides. If you’re planning a visit to Block Island, there is a ferry that departs from Point Judith, too.

A unique aspect of Narragansett is The Towers , a castle-like structure that crosses Ocean Road and is an iconic venue for public and private events throughout the year. Even if you don’t go inside, the exterior of the building makes for a great photo op. 

Near The Towers is a highly-rated seafood restaurant with ocean views called Coast Guard House Restaurant . You’ll also be right by Narragansett Town Beach , a mile-long stretch of sand that is one of the most popular places in Rhode Island for summer beachgoers. 

Salty Brine State Beach is another fantastic beach option in Narragansett that’s especially nice for young kids as it’s situated along the seawall and has no waves. Kids will enjoy watching the boats and ferries go by here. Just note that the beach is small and you’ll need to reserve a parking pass ahead of time.

12. Bristol, Maine

Best as a day trip from Portsmouth, NH; Portland, ME; Augusta, ME

With its picturesque harbor and rocky coastline, Bristol captures the essence of Maine’s seaside charm. Come here to enjoy fresh lobster from local fisheries and immerse yourself in the town’s rich maritime heritage through its museums and historic landmarks. 

A must-see place in Bristol is Pemaquid Point Lighthouse , where you can climb to the top of the light tower, tour the museum, and climb the rocks along the shore below. The scenery around the lighthouse will take your breath away.

If you’re craving a beach day, Pemaquid Beach Park is known for its gentle waves and smooth, sparkling sand. For a more local, rustic swimming experience, you can also visit The Swimming Hole at Bristol Dam.

La Verna Preserve is a 120-acre nature preserve in Bristol, where you can walk the entire rocky coastline at all tides and enjoy panoramic views of outer Muscongus Bay and its islands. 

Not far from Bristol are the Coastal Maine Botanical Gardens , one of Maine’s top attractions. They have a variety of gardens and natural areas, including a butterfly house, bee exhibit, dahlia garden, children’s garden, fairy house village, and much more.

13. Nantucket, Massachusetts

Best as a day trip from various parts of Cape Cod, MA

Nantucket is a timeless, quintessential New England location known for its rich history and maritime culture. This island, located 30 miles off the coast of Cape Cod, offers a picture-perfect combination of pristine beaches, a charming downtown, and iconic grey-shingled houses.

In downtown Nantucket , you’ll find plenty of boutiques and galleries to explore. If you’re a history buff, you might also enjoy the Whaling Museum , which tells the story of Nantucket over four centuries.

Not far from downtown is Brant Point Lighthouse where you can take in beautiful harbor and ocean views.

One of the most remote and breathtakingly beautiful parts of Nantucket is the Costkata-Coatue Wildlife Refuge . At the very end of the seven-mile barrier beach that protrudes from the tip of Nantucket is the historic Great Point Lighthouse . This area of the island is one of the best places to see grey seals!

💡Note that if you plan to drive to Great Point, you will need to purchase a permit from the Trustees . But you can also bike in! Taking a self-guided bike tour is one of the most popular activities in Nantucket. You can either bring your own bike onto the island or rent from one of the shops downtown.

Of course, since Nantucket is an island, there are beautiful beaches virtually anywhere you go. Some popular beaches include Madaket Beach , Surfside Beach , and Jetties Beach (the most family-friendly option, not far from town).

If you want to see both traditional Nantucket architecture and stunning ocean vistas, try the Sconset Bluff Walk . The path begins near town and winds through residential neighborhoods before opening to a scenic trail along the coast.

14. Litchfield Hills, Connecticut

Best as a day trip from New Haven, CT; Hartford, CT; Worcester, MA

Litchfield Hills is a picturesque region in northwestern Connecticut filled with rolling hills and charming small towns. Here you can escape the traffic and crowds of more urban parts of New England and take in the scenic beauty of the Connecticut countryside.

Visit the Railroad Museum of New England in Thomaston to learn about the rich railroad heritage of Litchfield Hills. See more than 100 years of carousel history at the unique Carousel Museum in Bristol.

Near the town of Kent, hike the 0.25-mile trail at Kent Falls State Park to admire the series of waterfalls. In the small town of Cornwall, snap a photo of a traditional covered bridge, Cornwall Bridge .

Another prime summer activity in New England is fruit picking! March Farm in Bethlehem lets visitors pick their own cherries, blueberries, and peaches. Mmm.

Best Day Trips in New England in the Fall

It’s no secret that New England is one of the most beautiful parts of the U.S. to see fall foliage and enjoy all the cozy vibes of autumn. Here is my list of favorite New England day trips in the fall!

15. Acadia National Park, Maine

Best as a day trip from Augusta, ME, or Bangor, ME

Acadia National Park is one of the most beautiful and popular U.S. national parks and one of the best day trip options in New England (though you will likely want to visit for longer!). The park is comprised of more than 47,000 acres of mountains and forests with dramatic ocean vistas that will take your breath away.

One of the best things to do at Acadia is hike or drive to the summit of the largest mountain, Cadillac Mountain (note the Cadillac Mountain Summit Road is only open to vehicles from April to October). If you plan to drive up, you will need to reserve a timed entry slot on Recreation.gov.

Don’t want to drive?  🚌 Reserve a guided bus tour of Acadia National Park from Bar Harbor

Another must-see trail is the scenic Ocean Path Trail with its jaw-dropping ocean panoramas. The trail will lead you down to Sand Beach , one of Maine’s only sandy beaches (hence the name, perhaps?). 

Be sure to stop at Jordan’s Pond House Restaurant for their well-known tea and popovers before hiking around Jordan’s Pond and seeing the iconic Bubbles — twin mountain peaks with rounded shapes.

Most of the key attractions at Acadia can be found by driving the scenic Park Loop Road . For a different vantage point, bring your bicycle and ride along the historic carriage roads that wind throughout the park.

Want more ideas of things to do at Acadia National Park? Check out this post !

16. Bar Harbor, Maine

Best as a day trip from: Bangor, ME; Augusta, ME

Bar Harbor is a picturesque coastal town on Mount Desert Island, right next to Acadia National Park. If you’re planning a trip to the park, it’s worth spending a day here as well.

For fresh Maine blueberry pancakes, start with breakfast at Jordan’s Restaurant . Then walk over to Agamont Park at the end of West Street, where you’ll have scenic views of the Bar Harbor pier and Frenchman Bay.

Try one-of-a-kind flavors at Mount Desert Island Ice Cream , including options like Bay of Figs, Lemon Poppy Berry Jam Swirl, and Salt Wildflower Honey. 

You can enjoy your ice cream on a park bench in the Village Green across the street. There’s a community piano in the park’s gazebo that’s open for anyone to play — feel free to stop and plunk out a tune!

Main Street is filled with lots of shops and boutiques to explore, including Maine’s oldest bookstore, Sherman’s Bookstore .

After you’ve finished exploring downtown, you might also enjoy a stroll through Bar Harbor’s neighborhoods with their beautiful homes and gardens.

17. Burlington, Vermont

Best as a day trip from Stowe, VT; Middlebury, VT; Killington, VT

Burlington is a vibrant city on the shores of Lake Champlain, offering a mix of urban life and outdoor adventures. Because it’s home to the University of Vermont, Burlington has a youthful energy that complements its historic charm.

A highlight attraction in Burlington is Waterfront Park , a clean and spacious public park right on Lake Champlain , where you can see the Adirondack Mountains in the distance. 

From the park, hop on the Burlington Greenway , an eight-mile scenic bike path that stretches from Queen City Park Road to the Winooski River. If you’re not up for a bike ride, you can also walk part of the trail and stop at the lookout points and beaches along the way. 

Church Street Marketplace is another popular part of town. This pedestrian-only street is lined with shops, restaurants, and cafes on either side, where you can easily spend a few hours exploring.

Burlington is where Ben & Jerry’s ice cream was founded, so you definitely should stop for a scoop or two from the Church Street shop.

To experience more of Lake Champlain, book tickets for a Spirit of Ethan Allen cruise. You can enjoy a day tour or reserve a dinner cruise for something a little fancier.

If you’re traveling with kids, it’s also worth going to the ECHO, Leahy Center of Lake Champlain , an interactive science and nature museum on the waterfront.

18. Kancamagus Highway, New Hampshire

Best as a day trip from Manchester, NH; Montpelier, VT; Bethel, ME

If you google the best places to see fall foliage in New England, the Kancamagus Highway of New Hampshire will likely appear at the top of the list. This 34.5-mile scenic drive begins in the town of Lincoln to the west and ends at North Conway to the east.

Check out these stops along the highway for some of the best leaf-peeping viewpoints:

• Lincoln Woods Trail: Walk the suspension bridge over the Pemigewasset River and hike the leisurely out-and-back trail along the river with towering trees overhead.
• CL Graham Wangan Overlook: Here you’ll see one of the prettiest views of the Swift River Watershed and White Mountain peaks in the distance.
• Sabbaday Falls: A short hike will lead you to this beautiful waterfall, which has a guardrail on one side for you to stand and see the falls up close.
• Sugar Hill Overlook: This popular stop features sweeping views of the Swift River Valley and surrounding mountains.
• Rocky Gorge: Walk across the small footbridge over the gorge for scenic views of the Swift River.
• Albany Covered Bridge: Snap a photo of one of New England’s traditional covered bridges.

19. Northampton, Massachusetts

Best as a day trip from Worcester, MA; Hartford, CT; New Haven, CT; Boston, MA

Northampton is a vibrant and eclectic city nestled in the scenic Pioneer Valley of Massachusetts. The city boasts an array of independent boutiques, art galleries, and live music venues, making it a haven for artists and creatives. 

If you love coffee, you could spend a lot of time hopping from one coffee shop to the next in Northampton. There are many options to choose from — one of my favorites is The Roost . 

While exploring the shops downtown, take time to admire the street art . There are large murals on the sides of buildings everywhere. It’s one of the features that make Northampton so unique.

Fall is the perfect time for apple picking ! Park Hill Orchard and Outlook Farm are both close to Northampton and have pick-your-own areas where you can hunt for your own fruit.

About 15 minutes outside of Northampton is Look Park , filled with a variety of fun and relaxing activities for all ages, including a steamer train, water spray park, mini golf, pedal boats, playgrounds, tennis courts, walking trails, and more.

20. Stockbridge, Massachusetts

Best as a day trip from Worcester, MA; Hartford, CT; New Haven, CT; Albany, NY

Stockbridge is located in the heart of the Berkshire Mountains and offers a mixture of historic architecture and stunning natural landscapes. This town has been an inspiration to writers and artists for generations, including Norman Rockwell, who captured the essence of Stockbridge with his iconic paintings. 

Visit the Norman Rockwell Museum to learn more about Rockwell’s life and see some of his original artwork.

Wander along Main Street to explore the antique shops, art galleries, and cozy cafes. Inside the old Stockbridge General Store is Main Street Cafe , which still maintains a lot of the original interior.

Stop by the historic Red Lion Inn (or book a night for the full experience), which has been a landmark of hospitality in the Berkshires for over 250 years. The hotel also owns two local boutiques, Township Four and Shop Around the Corner.

Tour a Gilded Age mansion, Naumkeag , which consists of 44 rooms and eight acres of gardens, including the famous Blue Steps. The property also features a seasonal outdoor Rose Garden Cafe, serving high tea in the gardens on select weekends.

People travel from near and far to visit Tanglewood , the famous summer home of the Boston Symphony Orchestra and a beloved music hall for many prominent musicians. Visit the Tanglewood website for the current line-up of performances.

21. Bennington, Vermont

Best as a day trip from Albany, NY; Stockbridge, MA; Manchester, NH

Surrounded by the stunning natural beauty of the Taconic Mountains, Bennington is a peaceful town filled with tree-lined streets, historic buildings, and a vibrant arts community.

Explore the Bennington Battle Monument , a symbol of Vermont’s role in the American Revolution, and learn more about the city’s history at the Bennington Museum .

See one of New England’s iconic white-steepled churches and Vermont’s oldest Protestant church (dating back to 1805), Old First Congregational Church .

Learn more about the history of Bennington by taking a self-guided Old Bennington Walking Tour ( download the brochure from the Bennington website ). 

Enjoy carefully curated dollhouse exhibits at the Dollhouse and Toy Museum of Vermont . The museum itself is located in a quaint 1850s Victorian home. Bennington is also home to several antique shops , where you can find hidden treasures from days gone by.

If you’re on a hunt to find the most covered bridges in New England, Bennington is home to three of them: the Burt Henry, Paper Mill, and Silk Road bridges . 

And for poetry lovers, the Robert Frost Stone House Museum is not far from Bennington, in the town of Shaftsbury.

22. Mystic, Connecticut

Best as a day trip from New Haven, CT; Hartford, CT; Providence, RI; Newport, RI

Mystic is a 19th-century coastal village that enchants visitors with its scenic waterfront and traditional New England atmosphere. Located on the Mystic River, the town has a timeless charm that points back to its seafaring past. 

Step back in time by touring the Mystic Seaport Museum , one of the largest maritime museums in the U.S., and see the nation’s oldest merchant vessel, the Charles W. Morgan whaleship.

⚓️ Take a guided tour of the Mystic Seaport Museum

Mystic’s Main Street has several character-filled boutiques and restaurants to explore. I really enjoyed the seafood at The Mariner .

Not far from downtown Mystic is Olde Mistick Village , a quaint outlet mall with dozens of shops selling handcrafted gifts, jewelry, accessories, and Mystic-made souvenirs.

Another top attraction in Mystic is the Mystic Aquarium , where you can see thousands of species of marine mammals, fish, invertebrates, and reptiles.

23. Marblehead, Massachusetts

Best as a day trip from Boston, MA; Portsmouth, NH; Ogunquit, ME

Marblehead is on the North Shore of Massachusetts and is renowned for its picturesque harbor, rocky shoreline, and beautifully preserved colonial architecture. It’s one of the oldest towns in the United States, with a rich history dating back to 1629.

One of my favorite things to do in Marblehead is browse the cute boutiques , especially along Atlantic Avenue and Washington Street. Sweetwater Trading Company, Chic Streets, and MacRae’s Sustainable Goods are some excellent places to check out.

Shubie’s Marketplace is a great place to stop for lunch. They have a deli counter where you can order delicious, fresh sandwiches, as well as coffee, cannolis, and other treats. If the weather is still nice, they have an outdoor seating area to enjoy, too.

A hidden gem in Marblehead is Castle Rock Park , one of my favorite places in all of New England. It’s located in the middle of a neighborhood, and if you blink, you’ll almost miss the entrance. Once you walk down the short path from the street, you’ll be greeted with the most stunning ocean views. There’s a giant rock formation you can climb to have an even better lookout point.

As weird as it sounds, one of the most picturesque graveyards in New England can also be found in Marblehead, called Old Burial Hill .

Not far from there is the historic Fort Sewall , an old fortification located on Gale’s Head, on the northeastern point of the Marblehead peninsula.

Like many New England towns, it’s also fun to simply walk the residential streets of Marblehead and admire the historic homes , which are kept up well and full of character and charm.

24. Salem, Massachusetts

Best as a day trip from Boston, MA; Portsmouth, NH; Portland, ME

Another North Shore gem is Salem , a town filled with cobblestone streets, colonial architecture, and a host of historic landmarks. It’s best known as the location of the Salem Witch Trials in 1692. 

Traveling to Salem from Boston? 🚢 Book a high-speed ferry from Boston’s Long Wharf!

If you are curious about Salem’s dark past, visit the Salem Witch Museum , Salem Witch Trials Memorial , and Old Burying Point Cemetery . Because of Salem’s spooky history, the town is especially popular to visit around Halloween.

Salem is also famous for The House of Seven Gables , a historic home featured in Nathaniel Hawthorne’s 1861 novel of the same name. You can purchase tickets to tour the house and grounds.

Another key attraction in Salem is the Peabody Essex Museum , featuring over 1.8 million pieces of art, architecture, and cultural artifacts. What started as a collection of objects by Salem sea captains in 1799 has turned into one of the most famous museums in Massachusetts.

If you’re craving something sweet, stop by Harbor Sweets for some locally-made chocolate and other sugary goodness. Their sailboat-shaped Sweet Sloops, made of almond buttercrunch, white and dark chocolate, and pecans, are one of their most popular items. (I’ve tried them and can attest that they’re delicious!)

25. East Haddam, Connecticut

Best as a day trip from Hartford, CT; New Haven, CT; Providence, RI

Nestled along the Connecticut River, East Haddam offers a picturesque setting with rolling hills, peaceful rivers, and dense forests.

One of the top attractions in East Haddam (and all of Connecticut actually) is the quirky Gillette Castle , the former home of actor William Gillette. Pay to tour inside the fascinating residence or simply walk the grounds, which provide scenic views of the Connecticut River.

Devil’s Hopyard State Park has hundreds of acres of beautiful hiking trails. One of the most popular stops in the park is Chapman Falls, whose staircase-like shape represents what some people say to be the “devil’s footpath.” 

Just outside of Devil’s Hopyard, stop by Boho Farm , a small family-owned farm near town with a gift shop selling handmade and locally sourced items.

Walk around East Haddam’s quaint Main Street to explore its boutiques and grab some ice cream. See a show at the iconic Goodspeed Opera House in town, which has been hosting performances since the 19th century.

Best Day Trips in New England in the Winter

Winter is a beautiful time to visit New England. Escape the crowds of summer and fall while still taking in the natural beauty and historic sites of the region. And of course, if you’re into winter sports like skiing or ice skating, then this is the prime time to go!

Here are my top picks for New England day trips in the winter:

26. Stowe, Vermont

Best as a day trip from Burlington, VT; Killington, VT; North Conway, NH

Located in northern Vermont, Stowe is known as the birthplace of alpine skiing in the state. Its first lift-operated ski trail started in 1937 on Mount Mansfield (the tallest point in Vermont at 4,939 feet).

The Stowe Mountain Resort is the place to be if you want to ski in Stowe. With 116 trails and 12 lifts, it has been an internationally acclaimed ski resort since the 1940s. Not far from Stowe is another popular skiing location, Smugglers’ Notch Resort .

If you’d prefer ice skating over skiing, there is a complimentary ice rink at the Spruce Peak Village Center, part of Stowe Mountain Resort. You can bring your own skates or rent them on-site.

Downtown Stowe is filled with quaint shops, galleries, and restaurants to explore — a great way to escape the winter cold. Be sure to snap a photo of the iconic white-steepled Stowe Community Church .

Another popular activity is the Stowe Recreation Path , which stretches from Stowe Village to Top Notch Resort on Mountain Road. In the winter, this 5.3-mile trail is open to walkers, runners, bikers, cross-country skiers, and snowshoers. There’s also a free shuttle that provides transportation along Mountain Road if you want to make it a one-way trip!

27. North Conway, New Hampshire

Best as a day trip from Manchester, NH; Portland, ME; Augusta, ME

North Conway is a scenic town in the heart of the White Mountains, in Mt. Washington Valley, and the perfect place to spend a snowy winter day.

In the town of North Conway itself, spend time browsing more than 100 shops, galleries, and factory outlets in North Conway Village .

If you’re interested in skiing, North Conway is within easy driving distance from three popular resorts: Cranmore Mountain Resort (5 minutes), Attitash Mountain Resort (15 minutes), and King Pine Ski Area (25 minutes).

While people flock to the Kancamagus Highway in the fall as one of the prime areas to see colorful foliage, this scenic road is equally beautiful in the winter with the snow-covered mountain peaks and fir trees. Just check the weather before you go as the highway sometimes closes when it snows.

North Conway isn’t far from Mount Washington , the tallest peak in the northeastern United States, towering at 6,288 feet.

The Mount Washington Auto Road is closed to private vehicles in the winter, but you can book a ride on a SnowCoach that takes you up two-thirds of the way, where you’ll have amazing views of the Presidential Range.

Hop on a traditional steam locomotive at the Conway Scenic Railroad . While train times are more limited in the winter, the company still offers picturesque trips through the snowy White Mountains. Check the website for available tours and to book tickets in advance.

If you don’t mind driving an hour to the other end of the Kancamagus Highway, experience the Ice Castles of New Hampshire in North Woodstock. This icy paradise includes ice slides, caves, and crawl tunnels, as well as an illuminated walking path, a snow tubing run, a Winter Fairy Forest, and more.

28. Killington, Vermont

Best as a day trip from Burlington, VT; Stowe, VT; Manchester, NH

On the Green Mountains side of New England lies the town of Killington, one of the most beloved skiing areas in the eastern United States.

Killington Resort is referred to as “The Beast,” with 1,509 skiable acres, 155 trails, and 21 lifts. Its tallest trail has an impressive 3,050-foot vertical drop.

Pico Mountain Ski Resort and Okemo Mountain Resorts are two other popular resorts not far from Killington.

If you fancy snowshoeing over skiing, try one of the trails in Gifford Woods State Park . This park is a common pass-through area for hikers on the Appalachian Trail from Georgia to Maine.

For an easy winter hike, the two-mile out-and-back Deer Leap Overlook Trail leads to a rock outcrop with beautiful views of the Coolidge Mountain Range and Sherburne Pass.

After a long day in the snow, warm up with a hearty dinner in downtown Killington . A couple of highly-rated restaurants include Casey’s Caboose and The Garlic.

29. Washington, Connecticut

Best as a day trip from New Haven, CT; Hartford, CT; Albany, NY

Washington is a picturesque town in the Litchfield Hills of western Connecticut. Known for its charming New England ambiance, it offers a peaceful retreat away from the hustle and bustle of city life.

See the beautiful, white-steepled First Congregational Church before strolling through Washington’s quiet neighborhoods with their historic and well-landscaped homes.

Stop for lunch at Po Cafe , located in the old post office building. They have a delicious selection of food and drinks with both indoor seating and heated outdoor seating. (Note they are closed on Sunday and Monday and are only open until 2 p.m. on the other days.)

For a luxurious winter day trip experience, book a special spa treatment at the renowned Mayflower Inn & Spa . (If you’re a Gilmore Girls fan, this place inspired the creation of the Independence Inn on the show.)

Washington is also home to three scenic nature preserves, the Hidden Valley, Macricostas, and Steep Rock preserves . Each of these preserves allows cross-country skiers and snowshoers on their hiking trails during the winter months. Enjoy snow-covered landscapes as you glide along the various loop trails.

30. Concord, Massachusetts

Best as a day trip from Boston, MA; Worcester, MA; Hartford, CT; Manchester, NH

Concord is a picturesque town just a short drive from Boston, with an interesting blend of colonial architecture, historic sites, and literary landscapes. 

Concord looks like a postcard in the winter, especially during the Christmas season when its quaint Main Street is beautifully decorated with wreaths and lights.

One of my favorite shops in downtown Concord is Nesting , an eclectic boutique with unique gifts and home goods. You can find lots of Christmas ornaments and other winter decor there this time of year.

Another highlight attraction near Concord that’s open year-round is Minute Man National Historic Park , which preserves the sites involved in the first armed conflict of the American Revolution on April 19, 1775. A key place to visit in the park is Old North Bridge , where the famous “shot heard round the world” was fired.

Walden Pond State Reservation is the place that inspired Henry Wadsworth Longfellow’s novel Walden . Take a peaceful winter hike around the pond and you’ll come across the former site of his log cabin where he wrote the book.

For another historic, literary experience, take a tour of the Louisa May Alcott Orchard House , the home where the famous author wrote and set her novel Little Women in 1868.

31. Bethel, Maine

Best as a day trip from Portland, ME; Augusta, ME; North Conway, NH

Bethel is a popular ski town in Maine and is referred to as “Maine’s most beautiful mountain village.”

Sunday River Resort is one of Maine’s largest ski resorts with 19 lifts and 139 different trails and glades. It’s also home to the fastest eight-person chairlift in North America. 

Not far from Sunday River Resort is the Sunday River Covered Bridge , built in 1872 and part of the U.S. National Register of Historic Places.

Mt. Abram Ski Area is a smaller ski resort near Bethel that is a popular choice for families and first-time skiers, or those looking for a quieter, more local skiing experience.

Another “gem” in Bethel is the Maine Mineral and Gem Museum , where you can see meteorites from Mars, the moon, and the Asteroid Belt. There’s also a Rock Garden showcasing 26 geological specimens from around the state.

If you’re up for a good winter hike, try the Old Speck Trail in Grafton Notch State Park , a 7.6-mile round-trip trail that ascends Maine’s third-highest mountain at 4,180 feet. There are also places in the park to cross-country ski or snowshoe.

Best Day Trips in New England in the Spring

New England gets a lot of press in the fall with its beautiful foliage colors, but I absolutely love it here in the spring. New England often has very harsh winters, so there’s nothing quite like seeing those first blooms after the snow has melted away. The weather starts to warm up, but you don’t have to worry about the crowds and traffic of summer.

Here are my top recommendations for New England day trips in the spring:

32. Boston, Massachusetts

Best as a day trip from Worcester, MA; Providence, RI; Hartford, CT; Manchester, NH; Ogunquit, ME

Boston makes for a great day trip in New England at any time of the year, but I especially love the city in the spring. After a long, harsh winter, it’s so pretty to see all the trees come into bloom, and the streets come alive with people once again.

To understand Boston’s important role in the American Revolution, take a guided or self-guided tour of the Freedom Trail , a 2.5-mile path that leads you to 16 different historic sites throughout the city. You can also experience a reenactment of the Boston Tea Party at the Boston Tea Party Ships & Museum .

🇺🇸 Book a guided Freedom Trail tour

Learn more about Boston’s history on a one-of-a-kind Duck Boat Tour, an amphibious vehicle that takes you past sights on both land and water.

🦆 Book your Duck Boat Tour (They sell out fast!)

Taste authentic Italian food in North End , also known as Boston’s Little Italy. Mike’s Pastry and Modern Pastry are rivals for the best cannoli. (Most locals seem to point to Modern Pastry, though I think both of them are good — but hey, I’m no cannoli connoisseur.)

Experience Boston’s Chinatown , a center of Asian-American life in New England. There are many amazing Asian restaurants to choose from, and I love to go here for bubble tea!

Walk over to Copley Square and tour the Boston Public Library , especially the historic section of the library that includes the stunning Bates Hall.

Spend some time browsing the shops along Newbury Street with its iconic brownstone buildings before heading to the Charles River Esplanade for scenic water and city views.

A visit to Boston wouldn’t be complete without walking through the Public Garden and Boston Common , two of America’s oldest and best public parks. 

End your day with a walk down Charles Street in the charming Beacon Hill neighborhood (one of my favorite places in Boston!). If you have time, sneak up to Acorn Street to see one of the last original cobblestone streets in Boston. It’s one of the most photographed streets in America.

Related read: 24-Hour Boston Itinerary: Best Things to Do in 2023

33. Martha’s Vineyard, Massachusetts

Best as a day trip from Provincetown, MA; Hyannis, MA; Providence, RI; Boston, MA

Martha’s Vineyard is a prime island getaway in New England, just off the coast of Cape Cod, Massachusetts. The high season for the island is in the summer, so I recommend visiting in May if you want to beat the crowds. (But if you want to see the stunning hydrangeas, those typically don’t start blooming until July.)

The only way to get to Martha’s Vineyard is by ferry or plane. There are several places to catch the ferry, including the Falmouth and Hyannis harbors on Cape Cod. There are also tour options from Boston!

🚢 Book a Martha’s Vineyard Day Trip from Boston

Once you get to the island, spend some time exploring the various shops and boutiques downtown, including the beloved Vineyard Vines store that was founded on the island.

Visit the Oak Bluffs area of the island to see the iconic gingerbread cottages . In this neighborhood, you will also find the Flying Horses Carousel , the oldest operating platform carousel in America. The carousel was first located in New York City but was moved to Martha’s Vineyard in the 1880s.

For stunning cliff and ocean views, stop by the Aquinnah Cliffs Overlook on the western side of the island. (This is an awesome place to watch the sunset, too!)

One of the best beaches on Martha’s Vineyard is South Beach , located on the southeast side of the island. But you really can’t go wrong — you’ll find stunning beaches all over Martha’s Vineyard.

34. Provincetown, Massachusetts

Best as a day trip from Boston, MA; Hyannis, MA; Plymouth, MA

On the tip of Cape Cod is the charming town of Provincetown. It’s the oldest continuous art colony in the United States, with numerous galleries, studios, and theaters showcasing the work of local artists. And with Provincetown stretching 60 miles into the ocean, it’s also filled with natural beauty and seaside fun.

Note that you can drive to Provincetown if you want to see the entire Cape, or take a ferry directly there from Boston’s Long Wharf.

Commercial Street is the center of activity in Provincetown, where you’ll find numerous shops and restaurants to explore.

Provincetown is also a prime location to catch a whale-watching tour . Boats depart from the Provincetown Harbor and last for 3-4 hours, giving you ample opportunity to see a variety of whales and dolphins in their natural habitat.

Check out the 252-foot-tall Pilgrim Monument , which is the actual place where the pilgrims first landed in the New World before sailing on to Plymouth.

The monument is part of the Provincetown Museum , where you can learn more about the Mayflower pilgrims’ arrival and the rich maritime and theater history of Provincetown.

Two of the best beaches in Provincetown include Race Point Beach and Herring Cove Beach . You may not want to swim yet in the spring, but it’s still worth walking along the shore or relaxing on the sand. 

The Race Point Lighthouse is also worth seeing when you’re in Provincetown, but note that contrary to the name, the lighthouse is about a two-mile hike (or 11-minute drive) from Race Point Beach.

Province Lands Bike Trail , one of three bike trails at Cape Cod National Seashore, is a 5.45-mile trail winding through pine forests, sandy dunes, and cranberry bogs. The trail includes easy exit points to Race Point Beach and Herring Cove Beach.

35. New Haven, Connecticut

Best as a day trip from Hartford, CT; Mystic, CT; Providence, RI; New York, NY

New Haven is on the southwestern side of Connecticut, about an hour and a half from New York City. It’s a dynamic and diverse city with a vibrant academic atmosphere, rich history, and plenty of natural beauty to explore.

New Haven is most famous as the home of Yale University , one of America’s oldest and most prestigious colleges, founded in 1701. Book a walking tour to learn more about the university’s history and take in the stunning architecture.

Not far from Yale’s campus is the historic New Haven Green that has been around since 1638. Walk through this nine-acre green space, enjoy the canopy of elm trees above you, and stop to see three of New Haven’s historic churches: Trinity Church, United Church, and Center Church.

From the Green, walk a short distance to Louis’ Lunch , one of the tiniest restaurants you’ll ever see. This little hamburger joint has been around since 1900, and they still serve their burgers on toast.

If you’re craving time in nature, visit Lighthouse Point Park for scenic views of New Haven and Long Island Sound. 

Another popular option is East Rock State Park , a unique trap rock formation in the middle of the city. Hike to the top of the “rock” for a birds-eye view of New Haven and Long Island Sound beyond.

In the neighboring town of Hamden, hike the trail around the peaceful Lake Wintergreen . 

Bonus: About 20 minutes outside of New Haven, in Milford, is Silver Sands State Park , one of my favorite places in Connecticut. This unique seaside park includes a sandy beach, boardwalk, and — the most unique feature — a “tombolo” (sandbar) that you can walk across to Charles Island only during low tide. (Be sure to come back before the tide rises or you’ll be stuck on the island with the nesting birds!)

36. Beverly, Massachusetts

Best as a day trip from Boston, MA; Worcester, MA; Portsmouth, NH; Ogunquit, ME

Beverly is a hidden gem on the Massachusetts North Shore. Most people mention towns like Gloucester and Rockport when they talk about escaping the city for a day by the shore, but there are several attractions that make Beverly worth a visit, too.

Start your day in Beverly with a delicious cup of coffee and fresh scone from the tiniest little cafe you may ever see: Beantrust Coffeebar. There isn’t much space inside to sit and relax, but it’s worth grabbing your items to-go and strolling through the pretty neighborhoods nearby.

Lynch Park is known as the Crown Jewel of Beverly with its beautiful rose garden, beaches, amphitheater, playground, and splash pad. It’s the perfect place to spend an afternoon near the water. (Note that parking is $15 on weekdays and $25 on weekends during high season from the end of May through Labor Day.)

Dane Street Beach is one of the most popular beaches in Beverly, and one of the few beaches on the North Shore where you can find free street parking. You may not want to swim in the water in the spring, but it’s still a beautiful beach for a walk or to sit and watch the waves roll in.

See a show at the North Shore Music Theatre , the largest operating theatre in New England, attracting more than 250,000 people each year. It’s also one of the few remaining “theatre-in-the-round” stages left in the U.S.

Enjoy the lovely gardens and walking trails at Long Hill , the former summer home of the Sedgwick family from 1916 to 1979.

37. Hartford, Connecticut

Best as a day trip from New Haven, CT; Boston, MA; Worcester, MA; Providence, RI

Located in central Connecticut, the state’s capital city of Hartford offers an interesting mix of historic sights, public parks, and high-quality museums to explore.

The Connecticut State Capitol is one of the most beautiful capitol buildings I’ve ever seen, with its gold dome and Victorian Gothic architecture. Surrounding the capitol is the scenic Bushnell Park , featuring a historic carousel and several monuments. 

Another beautiful park to check out is the Elizabeth Park Conservancy . Its focal point is the Helen S. Kaman Rose Garden with its many arches of roses that come into full bloom by mid-June.

Tour the 25-room mansion where the iconic author Samuel Langhorne Clemens (Mark Twain) and his family lived from 1874 to 1891. The Mark Twain House & Museum has been designated a National Historic Landmark.

If you’re interested in art history, visit the Wadsworth Atheneum Museum of Art , which is home to nearly 50,000 works of art spanning 5,000 years.

The Connecticut Science Center and The Children’s Museum are two other fun places to visit in Hartford if you have kids. Both museums are full of interactive exhibits where kids can try their hand at STEM activities and see scientific wonders.

Best New England Day Trips for Families

New England is a wonderful place to visit with the whole family! So many locations have attractions geared toward kids, and there are plenty of activities that can entertain all ages.

These are some of my top recommendations for family day trips in New England:

• Hartford, Connecticut: Kid-focused museums and parks
• Mystic, Connecticut: Fun maritime activities, including a historic ship and large aquarium
• Acadia National Park, Maine: Endless hiking trails and areas to explore
• Ogunquit, Maine: Shoreside fun, with beaches, trails, kayaking, and more
• York, Maine: Home to one of New England’s largest zoos and awesome beaches
• Boston, Massachusetts: Playgrounds, parks, and museums galore!
• Gloucester, Massachusetts: Family-friendly beaches and a hidden castle
• North Conway, New Hampshire: Snowy paradise with ice castles, ski resorts, and more
• Burlington, Vermont: Lakeside parks, hiking trails, and a one-of-a-kind science museum

Related read: 13 Awesome Family Day Trips in Massachusetts by Season

Best New England Day Trips for Couples

If you’re planning a romantic trip for two, here are my favorite options:

• Litchfield Hills, Connecticut: Small towns and scenic landscapes to explore
• Bar Harbor, Maine: Relaxing restaurant and cafe scene at the doorstep of Acadia National Park
• Portland, Maine: Foodie paradise along with plenty of outdoor activities
• Martha’s Vineyard, Massachusetts: Quaint island getaway with lots of history and charm
• Nantucket, Massachusetts: Similar to Martha’s Vineyard, but even more remote
• Portsmouth, New Hampshire: Walkable downtown and close proximity to beaches
• Stowe, Vermont: Cozy mountain escape

Best Places to Stay in New England

If you’re taking multiple day trips in New England and need a “base camp” where you can crash for the night, here are some excellent options throughout the region:

The Goodwin , Hartford, Connecticut

Nearby day trips recommended in this post:

• Hartford, CT
• New Haven, CT
• Washington, CT
• East Haddam, CT
• Griswold, CT
• Stockbridge, MA
• Northampton, MA

🛌 Check room availability and book!

Ogunquit River Inn & Suites , Ogunquit, Maine

• Ogunquit, ME
• Portland, ME
• Portsmouth, NH

Bar Harbor Grand Hotel , Bar Harbor, Maine

• Acadia National Park, ME
• Bar Harbor, ME

Omni Parker House , Boston, Massachusetts

• Marblehead, MA
• Martha’s Vineyard, MA
• Provincetown, MA
• Concord, MA

Wentworth by the Sea , Newcastle, New Hampshire

• Gloucester, MA
• Rockport, MA
• Beverly, MA

Newport Marriott Hotel & Spa , Newport, Rhode Island

• Newport, RI
• Narragansett, RI
• Watch Hill, RI

Trapp Family Lodge , Stowe, Vermont

• Burlington, VT
• Killington, VT

Here are answers to other common questions about New England!

What month is best in New England?

New England is lovely any time of year, so it all depends on what activities you want to do! I especially like the months of June through September here.

I love New England summers when all the coastal towns come alive and you can enjoy many days at the beach. The water is warmest in August and September but don’t expect the water to ever be “warm” since it is the North Atlantic Ocean. 🙂

Spring and fall have milder but still pleasant temperatures. These are my favorite seasons to explore New England because you don’t have the traffic of the summer crowds or the unpredictable weather of the winter. In the fall, you have the stunning foliage and in the spring, the beautiful blossoming trees.

In the winter, it’s not uncommon for snow storms to make travel difficult and cause certain places to shut down. But New England is a prime skiing and snowshoeing destination, so if you come prepared, December through March are great months to visit.

How many days do you need in New England?

If you want to get a taste of all six New England states, I recommend spending at least one week here. I provide a sample seven-day New England itinerary in this post .

If you have time to spare, two weeks would allow you to explore some of the more remote parts of New England, like Acadia National Park or Martha’s Vineyard.

That being said, if all you have is one or two days in New England, you can still cover a lot of ground. Any of the day trips in this post are great options to choose from, and below are some other posts I have written on day or weekend trips in New England:

• Weekend in Burlington, VT: The Perfect 2 or 3-Day Itinerary
• A Weekend in Newport, Rhode Island: 7 Best Things to Do
• 13 Awesome Family Day Trips in Massachusetts by Season
• Day Trip to Salem from Boston: All You Need to Know

How should you spend five days in New England?

There are many excellent itineraries for five days in New England. To get a perfect blend of coastal views, hilly rural areas, and mountain landscapes, here is one sample itinerary I would recommend:

• Day 1: Litchfield Hills, Connecticut (if traveling by plane, fly into Hartford)
• Day 2: Newport, Rhode Island
• Day 3: Boston, Massachusetts
• Day 4: Portland, Maine
• Day 5: North Conway, New Hampshire (fly out of Portland)

But feel free to mix and match any of the day trips in this post for other itinerary options!

What are the best day trips in each New England state?

These are my top day trip options in each New England state:

• Connecticut: Mystic, Litchfield Hills, Griswold
• Maine: Acadia National Park, Portland, Ogunquit
• Massachusetts: Boston, Marblehead, Gloucester
• New Hampshire: Portsmouth, Kancamagus Highway, North Conway
• Rhode Island: Newport, Narragansett, Watch Hill
• Vermont: Burlington, Stowe, Bennington

Conclusion: Best Day Trips in New England

There you have it: my list of the 37 best day trips in New England! Whether you’re interested in some “vitamin sea,” a long hike in the mountains, a food tour, or visiting museums and historic sites, there are plenty of options to choose from. 

I hope this list has given you lots of inspiration as you plan your New England day trip. Have an amazing time, wherever you go!

PLANNING A TRIP? These are the resources I recommend: ✈️ Flights:   Skyscanner 🛌 Hotels:  Booking.com ​ 🚗 Rental cars:   DiscoverCars 🎟 Tours: Viator  or  GetYourGuide

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• Destinations

25 Best New England Day Trips

Last Updated By VI on April 14, 2024 in Weekend Getaway from Boston & Day Trips

Block Island, RI

Freeport crossing.

• See the Complete List

Other attractions include the International Tennis Hall of Fame, the beautiful Easton's Beach, the historic Fort Adams State Park and great restaurants . More ideas: Where to Stay in Newport and Romantic Weekend Getaways in Rhode Island

When you're ready to have lunch or do a bit of shopping, head to Olde Mystick Village to admire the colonial style buildings, browse the gift shops, and enjoy some fresh seafood . Browse best Mystic Beaches

The water surrounding the island provides plenty of recreational opportunities as well, and some of the most popular activities include swimming, surfing, kayaking, and charter fishing. Browse best Block Island beaches

200 Lower Main St, Freeport, Maine 04032, Phone: 617-232-8900 , Map

Green Mountain Byway

The byway also passes through the towns of Waterbury and Stowe, where you can stop to have lunch or do a bit of shopping. More weekend getaways in Vermont

Hammonasset Beach State Park

Hammonasset Beach State Park , 1288 Boston Post Rd, Madison , CT 06443, Phone: 203-245-2785

Horseneck Beach State Reservation, New England

Horseneck Beach State Reservation , 5 John Reed Rd, Westport, MA 02790, Phone: 508-636-8816

Housatonic Valley National Heritage Area

If you're more interested in the area's natural sights, you can stop at the Cathedral Pines to admire the old growth forest, check out the 43 varieties of fern in Bartholomew’s Cobble, or snap some photos at the picturesque Beckley Bog.

Cape Cod, New England

Spend a few hours browsing the art galleries in Provincetown, enjoy a fresh seafood lunch at one of the local restaurants , or rent a bike and cycle along part of the beautiful Cape Cod Rail Trail.

Lexington, MA

After that, you can take a Liberty Ride trolley tour, stop by the historic Buckman Tavern, or visit some of the historic sites along the Battle Road Trail. More day trips from Boston

Mashantucket Pequot Museum and Research Center

Mashantucket Pequot Museum and Research Center , 110 Pequot Trail, Ledyard, CT 06338, Phone: 800-411-9671

Mohawk Trail, New England

Highlights include the Massachusetts Museum of Contemporary Art, the Mount Greylock lookout point, and the Natural Bridge State Park, and if you're visiting in the spring, summer, or fall, the spectacular Bridge of Flowers is a great stop as well.

Bar Harbor, ME

Kayaking and whale watching are two favorite activities, and much of the island is protected by Acadia National Park , which invites visitors to stroll along the rocky coast, photograph the spectacular scenery, and climb Cadillac Mountain, the tallest peak on the East Coast.

Old Orchard Beach

If you bring your kids, you can also spend some time at Palace Playland, an exciting amusement park with a Ferris wheel, a carousel, and plenty of other exhilarating rides. Old Orchard Beach Map

Old Sturbridge Village, MA

Old Sturbridge Village, MA , 1 Old Sturbridge Village Rd, Sturbridge, MA 01566, Phone: 800-733-1830

Plymouth, MA

When you've learned enough about history for the day, you can take a scenic ride on the Edaville Railroad, go for a walk in the beautiful Brewster Gardens, or rent a kayak and paddle around on the Billington Sea. Best Beaches in Plymouth

Rangeley Lakes Scenic Byway, New England

The byway makes for an excellent road trip year-round, but it's particularly spectacular in the fall, when the foliage turns vibrant shades of red, yellow, and orange.

Reid State Park

Reid State Park , 375 Seguinland Rd, Georgetown, ME 04548, Phone: 207-371-2303

More ideas: kid-friendly things to do in Massachusetts

Sherwood Island State Park

Sherwood Island State Park , Sherwood Island Connector, Westport, CT 06880, Phone: 203-226-6983

Silver Sands State Park

Silver Sands State Park , 1 Silver Sands Pkwy, Milford , CT 06460, Phone: 203-735-4311

Wethersfield

If you'd like to learn even more, you can visit the Webb-Deane-Stevens Museum or the Buttolph-Williams House. When you're ready to do some shopping, you can browse the antique stores in the historic district or head to the Comstock Ferre & Co seed store.

Woodstock, VT

Driving around the back roads is a great way to get a feel for the countryside, but if you want to see more, live farming demonstrations are regularly held at the Billings Farm and Museum, a beautiful property that was formerly owned by businessman Laurance Rockefeller.

Most of these homes can only be seen from the outside, but the 1721 Ladd-Gilman House has been transformed into the American Independence Museum, and seven of the rooms are open for tours. More day trips in New Hampshire

Guilford, CT

If it's the right season, you can also visit one of the orchards on the outskirts of town to wind through a corn maze or pick some fruit to take home. Guilford, CT Map

• 2. Mystic, CT
• 3. Block Island, RI
• 4. Freeport Crossing
• 5. Green Mountain Byway
• 6. Hammonasset Beach State Park
• 7. Horseneck Beach State Reservation, New England
• 8. Housatonic Valley National Heritage Area
• 9. Cape Cod, New England
• 10. Lexington, MA
• 11. Mashantucket Pequot Museum and Research Center
• 12. Mohawk Trail, New England
• 13. Bar Harbor, ME
• 14. Old Orchard Beach
• 15. Old Sturbridge Village, MA
• 16. Plymouth, MA
• 17. Rangeley Lakes Scenic Byway, New England
• 18. Reid State Park
• 19. Salem, MA
• 20. Sherwood Island State Park
• 21. Silver Sands State Park
• 22. Wethersfield
• 23. Woodstock, VT
• 24. Exeter, NH
• 25. Guilford, CT

Filled with quaint towns, spectacular scenery, and rich history, New England is an incredible place to go on a trip. There's something for everyone--history lovers, outdoor enthusiasts and beach goers. If you're more interested in the journey than the destination, the Green Mountain Byway, the Rangeley Lakes Scenic Byway, and the Mohawk Trail are wonderful driving routes that draw visitors from all over New England.

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The Best Day Trips in New England

From hiking in the lush Green Mountains of Vermont to whale watching off the coast of Massachusetts, these are the best day trips in New England.

New England, covering the north east corner of the United States, is packed with natural, cultural and culinary treasures. Venture out of the main cities which include Boston, Portland and Burlington, and you’ll find green rolling hills, wild national and state parks, quaint historic towns and beautiful beaches along the coast.

Road trips in New England are sure to provide you with plenty of surprises, whether it’s sampling a delicious lobster roll on the rugged coast of Maine, or marvelling at the autumn leaves in Vermont and Massachusetts.

As the first destination for many of the earliest settlers from Europe, New England is steeped in American history. A great way to learn about the region’s fascinating past is at one of its renowned living history museums. However, the real delight of going on a day trip in New England is found in the remarkable scenery – plunging gorges, lush forests and tall mountains await, so make sure you have your camera ready.

The best way to get to know the region? Hop in the car and go for a drive. New England road trips are pretty special (especially in the autumn) and being mobile will allow you to discover the wilder side of this enchanting corner of the United States.

The Best Day Trips In New England

Explore acadia national park.

One of Maine’s finest natural treasures, Acadia National Park is a must if you’re looking for active day trips in New England. From hiking, mountain biking, skiing and fishing, there’s something to do here in every season. Plus, here you’ll be able to enjoy some of the most breathtaking views on the Eastern Seaboard. Climb to the top of Cadillac Mountain (the tallest peak on the Atlantic Coast), or marvel at the spectacular show at Thunder Hole, where the pounding sea meets the dark rocks.

Acadia National Park is also a wonderful place for cycling, with hundreds of miles of trails winding through forests, hills and along the dramatic coastline. This wild, rugged part of Maine can be difficult to access, so we’d recommend choosing it as a day trip if you’re staying in Portland or other parts of Maine.

Head To A Food Festival

If you’re a foodie like me then you’ll probably want to go on a day trip in New England that involves some delicious grub! From the coast to the mountains, New England is known for its local produce, and there’s no better way to spend a day in Maine, Rhode Island or Massachusetts than by heading for a regional food festival. Whatever time of year you visit, you’ll have plenty to choose from.

In August, the Maine Lobster Festival draws huge crowds, eager to sample the iconic lobster rolls and watch the oyster shuckers compete to see who can work the fastest! A handy shuttle bus runs from major cities in Maine and the rest of New England, so this is an excellent choice for a day trip if you’re visiting Boston or other parts of the region.

Drive inland from Bar Harbor and you’ll find a sea of wild blueberries, also celebrated in August as part of the Wild Blueberry Festival. In May and June, Vermont hosts a Garlic and Herb Festival, followed by the Chocolate and Cheese Festival in the summer. Finally, beer lovers shouldn’t miss the New England Beerfest, a one-of-a-kind celebration of the region’s craft beer.

Go Whale Watching from Gloucester, MA

If you’re looking for unforgettable day trips in New England, then whale watching should be at the top of your list. The teeming waters of the Atlantic play host to all kinds of migrating whales between May and October, and one of the best places to see them is just off the coast of Gloucester, Massachusetts.

There are plenty of companies running day trips, and you can expect to see many different whale species, including blue whales, sperm whales, minke whales, and fin whales. You might also have the chance to spot dolphins, porpoises and several kinds of marine birds.

Visit A Living History Museum

For a unique day trip in New England, pay a visit to Old Sturbridge Village . It’s the perfect place to step back in time and immerse yourself in the history of Massachusetts. This world-class living history museum, boasts a complete reconstruction of a rural 1830s New England town. Just a stone’s throw from Worcester in south Massachusetts, Sturbridge Village includes 40 antique 19 th -century buildings, all set in beautiful grounds. You’ll get a taste of New England life in the 1830s, as well as having the chance to cook and sample an authentic 19 th -century New England community dinner.

If you’re a history nerd, don’t miss the chance to check out other innovative New England living history museums, such as the Plimouth Plantation , which recreates the earliest colony established by the pilgrims who arrived in Cape Cod from England in the 17 th century. This fantastic complex of open-air museums also include the Wampanoag Homesite, which provides the perfect introduction to the culture of the Native Nations of the New England coast. When it comes to interesting day trips in New England, any one of these museums would be an excellent choice.

Ride The Kancamagus Highway

Visitors often plan road trips in New England in autumn to see the dazzling array of fall colours. This hype is completely justified – in September and October the forests explode in a kaleidoscope of golds, yellows and reds. One of the best ways to experience this annual spectacle is by taking a New England road trip along the Kancamagus Highway, a 35-mile scenic drive through the White Mountain National Forest.

Regardless of the time you visit you can expect stellar views of the White Mountains, the Swift River and Sabbaday Falls, as well as a beautiful vista from Kancamagus Pass, the highest point on the highway. However, in autumn, the scenery along the ‘Kanc’ reaches another level. You’ll definitely want to bring your camera for this epic drive!

Tour The Town Of Salem

One of the best day trips in New England, especially if you’re staying in Boston, is to ride out to the historic town of Salem, site of the infamous 1692 Salem witch trials. Salem is a 30-minute train journey from Boston (costs around $10) and there’s plenty to see and do in a day.

Don’t miss the Salem Witch Museum , its impressive Gothic exterior and fascinating exhibits. Art lovers will enjoy spending a few hours in the Peabody Essex Museum . Plus, while you’re in Salem, be sure to stroll around town on the Salem Heritage Trail and pick up some spooky souvenirs on Essex Street, the downtown shopping hub. Time your visit for Halloween fo ran extra spooky experience.

Where To Stay In New England

The old inn on the green, new marlborough.

This beautiful 18 th -century coaching inn is set in idyllic rolling green hills. The Old Inn on the Green is one of the most romantic places to stay in New England. It’s perfectly located in the heart of the Berkshires in western Massachusetts, making it the ideal destination for those wanting to see the fall leaves or couples seeking a romantic getaway.

There’s an excellent restaurant lit only by candlelight, which serves up delicious meals made from locally-sourced produce. With bags of character, period décor, and stunning views over the hills, this lovely inn is one of the top places to stay in New England.

Check availability and latest prices here

The Chesterfield Inn, West Chesterfield

Looking for a cosy retreat in New Hampshire? Look no further than the Chesterfield Inn, located in West Chesterfield in the Connecticut River Valley. If you stay here you’ll be in the perfect location for exploring New Hampshire and Vermont, with easy access to Chesterfield Gorge and Spofford Lake.

The rooms are sumptuously decorated, many with wooden beams and open fires, making it a wonderful spot for autumn or winter weekend getaways. The service is friendly and the food is excellent, but the real draw here is the scenery, which you can admire from a lounger in the lush garden.

Hidden Pond Resort, Kennebunkport

The Hidden Pond Resort, tucked away in a dense forest on Maine’s southern coast, is one of the most unique and beautiful places to stay in New England. Spread over 60 acres and surrounded by tall birch trees, the resort boasts small cottages and bungalows, decorated in a rustic style with all the modern comforts you’ll need for a blissful retreat into nature.

Wondering about food? Here the produce comes directly from the on-site farm. Plus, while on holiday you can enjoy luxury treatments in the treetop spa. With an outdoor pool, bar, and hammocks swinging peacefully from the trees, this is the kind of hotel you won’t want to leave!

Wherever you choose to stay, there are so many amazing great day trips in New England! Hopefully this has given you lots of inspiration to plan your adventure. Looking for some other great places to visit? Don’t miss my guide to visiting Vermont in winter.

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Chloe Gunning

With a passion for food, fun and adventure, Chloe is the content creator behind one of the UK's top travel blogs Wanderlust Chloe. From volcano boarding in Nicaragua, to sailing around Sicily and eating her way around Japan, her travels have taken her to some of the coolest spots on the planet. Named Travel Influencer of the Year in 2022, Chloe regularly works with a number of tourism boards, producing inspirational travel content across multiple platforms. Find out more about Chloe here.

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35+ Amazing Day Trips From Boston Massachusetts

Wondering where to go on a day trip from Boston? Boston has always been my most frequent city of travel. I’ve lived there too. Based on my own experience exploring the region, here’s my list of 35 great day trips from Boston.

Boston is perfectly situated in the northeastern region of the United States . This area of New England boasts gorgeous beaches, charming Colonial towns, seaside ports, and destinations steeped in history.

These destinations are all less than 2 hours away from Boston. Any more than 2 hours is just too far afield for a proper day trip.

Because of its central location, Boston makes a great launchpad for day tripping in New England. Boston is well-connected to other towns and cities. Boston’s main arteries (I-90, I-93 and I-95) give you easy access to Maine, New Hampshire, Connecticut, Rhode Island, Western Massachusetts, and even Vermont.

Boston’s main arteries (I-90, I-93 and I-95) give you easy access to Maine, New Hampshire, Connecticut, Rhode Island, Western Massachusetts, and even Vermont.

On a day trip from Boston, you can escape the city’s adoring (and sometimes maddeningly intense) crowds.

Best Day Trips From Boston

Here are my picks for the best day trips from Boston. I’ve given you a whopping 36 options, along with expected drive times. I’ve listed them in alphabetical order for ease of reference.

The options for Boston day trips are endless and incredibly varied. There’s something of interest for everyone, from culture vultures to history buffs to nature lovers.

You can pick what suits you most, whether you want to relax on the beach or explore a cozy New England town.

If pressed to choose, I’d have to say my top three picks for Boston day trips are Portland Maine (cool foodie city), Stockbridge Massachusetts (quintessential New England town), and Portsmouth New Hampshire (adorable arty village).

1. Bristol Rhode Island (1:10 Drive)

Bristol is a beautiful New England town that’s full of history and charm. With a red-white-and-blue painted stripe down Hope Street, it exudes Americana. 

Bristol has everything you need for a relaxing break from Boston — fine dining, bike trails, art galleries, and ocean views. A highlight of Bristol is its well preserved historic architecture. In Bristol, you’ll find Colonial, Federal, and Gilded Age buildings. 

Linden Place Museum features a stunning spiral staircase and movie memorabilia. Blithewold Mansion has immaculately curated gardens, hosts concerts in the summer, and offers dramatic harbor views.

If you like to hike or bike, the East Bay Bike Path will suit. It’s a 14.5 mile paved path connecting Providence and Bristol, which gives you panoramic views of Narragansett Bay.

2. Cambridge Massachusetts (5 minute drive)

The easiest day trip from Boston is to its next door neighbor, Cambridge. Historic Cambridge is a lively university enclave, with the Charles River as its playground and backyard.

Cambridge is home to the renowned Harvard University (where you’ll be wrapped in red brick) and the Massachusetts Institute of Technology (where you can admire eclectic modern architecture). You can book a walking tour of Harvard here and a tour of MIT here .

And it’s not just the universities that dazzle. In Cambridge, visitors can enjoy outstanding museums, a vibrant performing arts scene, and delicious haute cuisine restaurants.

The  Harvard Art Museums  are the best art spot, with a range of works from antiquity to present, including a prized Van Gogh .

Be sure to hang out in Harvard Square, the iconic center of Cambridge. It’s a triangular plaza located at the intersection of Battle Street, John F. Kennedy Street, and Massachusetts Avenue.

You’ll find all manner of humanity — students, tourists, political activists, buskers, chess players, and other street creatures.

You can also visit  Longfellow House . It’s located on Brattle Street, the historic road connecting old Cambridge and Watertown.

The house museum is famous as the one time home of Henry Wadsworth Longfellow. He was a novelist and poet who wrote stirring tales that thrilled 19th century America, including the  Midnight Ride of Paul Revere .

3. Cape Elizabeth Maine (2 Hour Drive)

Cape Elizabeth is gorgeous little town just south of the city of Portland. The town faces out into Casco Bay.

People have lived in Cape Elizabeth for thousands of years. In 1765, Cape Elizabeth officially became a town. For a glimpse of those early days, stop by the  Spurwink Meeting House . The austere white clapboard church was built in 1802.

The town’s stretch of coastline is stunning, dotted with lighthouses. The cliff walk is a lovely must do experience in Maine.

The 19th century Fort Williams Park in Cape Elizabeth guards the entrance to Portland. It’s home to the Portland Head Light. You can walk the park’s Arboretum trails, enjoy a picnic, or explore the fort’s old batteries.

3. Charlestown Massachusetts (5 minute drive)

Charlestown is Boston’s oldest neighborhood. It’s just across the river from the North End.

If you’ve walked the Freedom Trail in Boston, you’ve already been to Charlestown. The town is home to the Bunker Hill Monument and the USS Constitution, which are must visit landmarks in Boston .

In 1775, Charlestown was the site of one of the most important battles of the Revolutionary War. American patriots defeated the British in the Battle of Bunker Hill. Nearly the entire town was destroyed during the battle and it wasn’t rebuilt until after the war ended.

Nowadays, Charlestown is a pretty place that’s well worth a stroll. A sense of Colonial charm permeates the streets and parks of Charlestown. The town has a classic main street, town square, and pretty clapboard homes.

4. Chatham Massachusetts

A visit to Cape Cod is a no-brainer day trip from Boston. But where to stake your claim?

Try the inimitable charms of Chatham, a tony New England town. In Chatham, the homes induce jaw drops, the historic center is walkable, and the seafood is hauled in just offshore.

Chatham’s curving Main Street conjures up low key elegance and old world charm. Chatham is the only Cape Code town bounded on three sides by water. It’s consistently ranked as one of the US’ best beach towns.

Chatham Lighthouse Beach is considered the most scenic public beach. It’s set beneath Chatham’s iconic lighthouse. This wild stretch of the Atlantic is the place for long walks and sunbathing (the surf is rough).

If you need a dose of culture with your beach retreat, head to the Orpheum. It’s a restored vintage theater showing first run movies and classics.

Or, take in a play or musical at the Monomoy Theater, after browsing the casual to high end shops.

5. Concord Massachusetts (35 Minute Drive)

Just 15 miles north of Boston is the small town of Concord. It’s the perfect Boston day trip for literary buffs. Concord is a steeple-studded town home to pretty  Walden Pond . Walden Pond is a nature preserve that’s home to countless local flora and fauna.

Walden Pond is forever linked to novelist Henry David Thoreau. From 1845 to 1847, he lived in a one room cabin , the property of his friend and mentor Ralph Waldo Emerson. A replica of the original cabin is about half a mile from Concord.

There, he wrote one of America’s most famous novels,  Walden  or  Life in the Woods.   Walden  explored simplistic living, solitude, and harmony with nature.

In Concord, you can also visit Emerson’s House and Louisa May Alcott’s Orchard House . The novelist based  Little Women  on her experiences growing up in this house with her sisters.

Today, the historic home is a museum. It has 80% of its original period furniture.

You can tour the kitchen, dining room, parlor, art studio, and the bedrooms. Louisa’s bedroom has the small white desk where she penned  Little Women  and other books.

If you want to learn about Concord’s Revolutionary War and literary legacy, visit the Concord Museum . On display, you’ll find Native American artifacts, Thoreau’s snowshoes and furniture, Ralph Waldo Emerson’s study, Paul Revere’s original signaling lantern, and period collections of decorative arts and furniture.

If you want to pay homage to Concord’s famous authors, visit Sleepy Hollow Cemetery. You’ll find the final resting places of Thoreau, Emerson, Alcott, and William Ellery Channing.

6. Concord New Hampshire (1:10 Drive)

Concord is the capital of New Hampshire. It’s a sleepy New England town that I used to spend parts of the summer in. Founded in 1734, Concord embodies the American spirit. There are a fair number of things to do in Concord.

You can visit the New Hampshire State House, built in 1819. It sports a gleaming eagle topped gold dome, reminiscent of Boston’s own state house. The New Hampshire legislature still uses the original chambers.

Just steps from the capitol is the New Hampshire Historical Society. It boasts a sculpture by the famous Daniel Chester French.

You can also visit Pierce Manse, the former home of President Franklin Pierce. Via a guided tour, you can see period artifacts. Franklin’s grave is also in town.

7. Essex Connecticut (2 Hour Drive)

Essex just exudes small town charm. It has a bucolic setting on the banks of the Connecticut River. The town is consistently rated as one of America’s best small towns.

Essex seems halted in time, looking much as it did during the height of its ship building prosperity. Essex has a picture perfect harbor. It’s scattered with charming inns and historic architecture.

On Main Street, whitewashed houses jostle side by side, in early Colonial and Federal styles. Pop into the Griswold Inn, especially for its vaunted Sunday breakfast. The cute shop Good and Curiosities sells gifts with a historical theme.

Essex is famed for its riverboat tour, the Essex Steam Train & Riverboat. On a 2.5 hour tour, you can travel by train and boat through the countryside. By boat, you’ll glide by farms, inlets, coves.

8. Exeter New Hampshire (1 Hour Drive)

Exeter was founded in 1638 by Reverend John Wheelwright. This pretty new England town brims with charm at every turn. The beauty of Exeter will appeal to everyone from art lovers to history buffs to recreational seekers.

You can take a leisurely stroll in the quaint and historic downtown. You’ll find elegant buildings with shops, restaurants, art galleries, and more.

Or, walk down tree-lined streets to discover historic homes, including the Ladd-Gilman House that’s now the  American Independence Museum .

If you want to experience the great outdoors, Essex has hiking, biking, and water sports. During New England’s fall foliage season , the colors are truly breathtaking.

9. Hanover New Hampshire (2 Hour Drive)

As a graduate of Dartmouth College, Hanover is a sentimental favorite of mine. And it clocks in at 2 hours, my limit for day trips from Boston.

Forbes named Hanover one of America’s Prettiest Towns. For a remote rural town, Hanover packs a surprising cultural punch.

The best place to get your art fix is the wonderful Hood Museum of Art . It’s one of the oldest teaching museums in the country. It has a large collection of artifacts and art dating back to Assyrian culture in 900 BC.

But it’s not all ancient. The museum has a surprisingly good collection of contemporary art, with works by Rothko and Ed Ruscha. It also showcases contemporary African and Native American art.

You should also pop into Baker Library. You’ll find eye catching murals by Jose Clemente Orozco in the reading room.

Hanover is also home to the Hopkins Center for Performing Arts (the “HOP”). There, you’ll find a wide variety of performing arts — plays, shows, concerts, special events, movies, etc.

Here’s my itinerary for spending  one day in Hanover . In addition to just driving to Hanover, you can take the Dartmouth Coach from Logan Airport.

10. Hartford Connecticut (1:35 Drive)

Hartford is one of the oldest cities in the United States. It makes a great day trip from Boston if you want to visit another city. The capital of Connecticut is home to historic sites, art museums, and beautiful parks.

It’s also the birthplace of Mark Twain, a culinary powerhouse, and home to one of the best “little downtowns” in New England.

The Mark Twain House & Museum is a national historic landmark. The museum has it all: inspiring architecture, gorgeous interior design, lovely grounds, and fascinating stories about its owners. It offers visitors an opportunity to learn about the novelist Mark Twain, his family, and his legacy.

Another good reason to visit Hartford on a day trip from Boston is to visit the magnificent Wadsworth Atheneum Museum of Art . The castle-like museum is one of the best museums in New England .

The Wadsworth first opened its doors in 1844. It’s since grown to a collection of over 50,000 works of art from over 5,000 years. There are significant works of modern and contemporary art.

You’ll find works by Frans Hals,  Caravaggio , Orazio Gentileschi, and Bernardo Strozzi. There’s a beautiful painting by pre-Raphaelite artist William Holman Hunt called  The Lady of Shallot . There’s also an American art collection, with works by John Singleton Copley and Charles Wilson Peal.

11. Keene New Hampshire

Keene is a beautiful hidden gem in New England’s Monadnock Region. A lively college town, Keene combines culture and the great outdoors.

Keene offers stunning brick streets, charming maple farms, and quaint specialty shops. Keene even has a white clapboard church with a soaring steeple, the United Church of Christ.

Keene is also home to one of the loveliest and widest main streets in New Hampshire. The historic downtown area is centered on Central Square. It’s an eclectic mix of old time shops, bookstores, and funky craft stores.

Keene is also home to covered bridges and museums. The Horatio Colony House and Nature Preserve is housed in a 1806 Federal style building. The museum houses historical artifacts for the history buff. The nature preserve offers miles of hiking trails for the nature lover.

12. Kennebunkport Maine (1.5 Hour Drive)

Kennebunkport is a classic beauty, one of the most beautiful towns in New England . It’s effectively the Hamptons of the Pine Tree State, known for its dramatic mansions. To see them, take a drive between Kennebunkport and its sister town Kennebunk.

Kennebunkport has a lively downtown, the epicenter of which is called Dock Square. It’s chock full of restaurants, boutiques, and art galleries.

There are plenty of patio cafes for people watching perches. The Clam Shack serves up fried claims and lobster rolls.

For a walking tour of Kennebunkport’s historic buildings, start at the Brick Store Museum on Main Street. Head south and you’ll see several extraordinary structures from the 18th and 19th centuries, including Lexington Elms, Horace Porter House, and Benjamin Brown House.

Summer Street is also an architectural showcase, with an array of Federal and Colonial buildings. To get the complete scoop, you can take a guided 90 minute tour of Kennebunkport’s National Historic District. Buy tickets at the Brick Store Museum.

If you want to hit the beach, try Gooch’s Beach along the Victorian-lined Beach Avenue. Or drive 10 minutes north to the beautiful 3 mile long Goose Rocks Beach.

If you’d like to take a day tour from Boston, this excellent tour combines history and lobster. If you’d just like a guided walking tour once you’ve arrived in Kennebunkport, click here for a 2 hour historic tour.

13. Kittery Maine (1 Hour Drive)

The small town of Kittery is just a short drive from Boston. It’s located on the border between Maine and New Hampshire and is linked by bridges across the Piscataqua River.

Kittery was once known for its shipbuilding. Nowadays, people day trip to Kittery from Boston mostly for its shopping. Kittery has both outlet malls and boutique craft shops. You’ll find stores like Crate and Barrel, Le Creuset, Lululemon, Under Armour, and Nike.

If the weather is warm, head to the beach for a swim. Seapoint Beach is a picturesque shoreline perfect for a dip or a stroll.

You can also visit Fort McClary State Park . It’s a unique historic site that was formerly a defensive military fortification. It has stood for over 275 years protecting the mouth of the Piscataqua River at the entrance to Kittery.

14. Lenox Massachusetts (2 Hour Drive)

Lenox is the perfect day trip from Boston for art lovers. It’s a pretty town of art galleries and upscale boutiques housed in historic buildings.

You’ll find iconic properties like Blantyre, Wheatleigh, Canyon Ranch, and The Mount. At one point, there were so many lavish summer homes that Lenox was known as “the inland Newport.”

In 1902, Edith Wharton, the first woman to win the Pulitzer Prize in Literature, built  The Mount . It was a stately country retreat for the literary lioness and her then-husband. The Mount was modeled after European mansions, but lacked without their ostentatious excesses.

The Mount is home to a summer lecture series, weekly bird walks, concerts, theater performances, and outdoor sculpture exhibits. Edith Wharton’s library has been returned to the house, with 22 first editions of her work.

Lenox is also home to  Tanglewood , the summer home of the Boston Symphony Orchestra. Tanglewood is a must do for music lovers. You can hear symphony orchestras, solo performances, and world class musicians.

15. Lexington (30 Minute Drive)

If you’re a student of U.S. History, Lexington should ring a bell. In 1775, the American Revolutionary War started in Lexington and nearby Concord. Lexungtin is the best day trip from Boston to immerse yourself in Revolutionary war history.

Lexington has more than 10 historic battle sites, cemeteries, and memorials that you can tour. You can see the site of the first battle of the Revolutionary War.

A renowned statue by sculptor Henry Hudson Kitson marks  Battle Green , where the Colonial Minutemen clashed with British troops. In Minuteman National Historical Park, you can see a multimedia exhibit on the Road to Revolution .

While waiting for the British, the Minutemen and their commander, Captain Parker, gathered in the  Buckman Tavern . The interior is preserved exactly as it appeared in the 18th century, complete with the original seven foot wide open fireplace. The old front door still contains British musket-ball holes.

Wrap up your tour of Lexington by seeing the Lexington Depot historic train.

16. Madison Connecticut (2 Hour Drive)

Madison is a shoreline town only East Coasters know about. This beautiful New England day trip from Boston proves the adage that good things come in small packages.

With a population of only 18,000+ residents, Madison delivers a major dose of quintessential New England charm. During his time at Yale, Bill Clinton was so taken with Madison that he mentioned it in his memoir,  My Life , calling it “especially old and beautiful.”

One of the main draws of Madison is Hammonasset Beach State Park . There you’ll find two miles of beaches, wetlands, woodlands, and a nice boardwalk.

The town itself is charming and pedestrianized, full of shops and cafes. A popular haunt is RJ Julis Booksellers, one of the nation’s finest independent shops for book nerds looking for the perfect read.

Madison is also a culture-filled hamlet. A fun outdoor activity is walking the Sculpture Mile . Created by the Hollycroft Foundation, it offers a unique museum-like exhibition that features art work by some of the nation’s most significant sculptors.

17. Manchester New Hampshire (1 Hour Drive)

You might think New Hampshire is all mountains and lakes. But it also boasts a rich cultural history. In particular, Manchester has some fine art offerings that merit a day trip from Boston.

Manchester is home to the state’s only fine art college, the New Hampshire Institute of Art. It also has an internationally acclaimed museum, the  Currier Museum   of Art .

The museum’s permanent collection includes works by Picasso, Monet, Rothko, Wyeth, and O’Keefe. It hosts touring exhibitions. The museum also manages Zimmerman House, designed by architected  Frank Lloyd Wright . It’s the only Wright house open to the public in New England.

Manchester also has a premiere contemporary arts gallery, the Gallery of the New Hampshire Art Institute. It’s multi-functional, serving as an art center, lecture hall, and performance theater. On display you’ll find a diverse mix of traditional and modern art forms, from photography to installation art.

18. Mystic Connecticut (2 Hour Drive)

Mystic is calm and exquisite, a charming waterfront town set on the shores of the Mystic River. It’s quaint downtown is filled with boutiques, galleries, and eateries.

On Main Street, you’ll find Mystic Pizza , made famous by a kitschy 1980s movie. Mystic’s main landmark is Bascule Bridge, the most photographed bridge in Connecticut and a perfect spot for river views.

Mystic Seaport is Connecticut’s #1 attraction, an example of “living history.” It covers 19 acres along the Mystic River.

There are indoor and outdoor exhibits, including four vessels that are National Historic Landmarks. You can climb aboard or peruse the recreated village.

19. Newburyport Massachusetts (1 Hour Drive)

First settled in 1635, Newburyport is an immaculate seaside town. It has a classic New England feel — with red brick streets, lobster shacks, and cobbled lanes. Plus, “the Port” is only 35 miles from Boston, making it the perfect day trip or weekend getaway.

State Street is the heart of Newburyport. You’ll find an eclectic treasure trove of shops — clothing boutiques, bookstores, cafes, and vintage shops. The Firehouse Center for the Arts is Newburyport’s cultural hotspot, offering concerts, musicals, and plays.

When you tire of shopping, surf and sand lovers can hit the beach. Plum Island is only a 20 minute drive from Newburyport.

Plum Island has beautiful and beloved sandy beaches and dunes. And it’s home to the Parker River National Wildlife Refuge, a hidden gem sanctuary with prime bird watching opportunities.

20. Newport Rhode Island (1.5 Hour Drive)

Just two hours south of Boston lies the tony coastal town of Newport. Founded in 1639, Newport is a treasure trove of historic European-style mansions set against ocean views.

Think the Gilded Age’s Astors, Vanderbilts, and Kennedys — families who built the first palatial mansions in the US. Newport is a fancy place.

Most of the mansions are on Bellevue Avenue and a few are on the waterfront. Built by Cornelius Vanderbilt, Breakers Mansion is Rhode Island’s #1 attraction. It’s located on the scenic 3.5 mile Newport Cliff Walk .

If you’d like to tour the magnificent mansions of Newport, this is an excellent day tour from Boston .

The Newport Art Museum is the core of the creative community. The Artists’ Open Space serves up local and regional shows year round.

There’s a dozen commercial galleries in town as well. Island Art is the best, noted for its contemporary pieces.

On the performance arts side, Newport really excels. It offers up everything from Shakespeare plays in Queen Ann Square to musical festivals dedicated to jazz, classical, and folk music in July and August. There’s also the Newport Fine Arts Festival in September.

21. Old Sturbridge Village Massachusetts (1 Hour Drive)

Old Sturbridge Village is a living history museum located in Sturbridge Massachusetts. The museum recreates life in rural New England as it was during the 1790s through 1830s. 

There’s a working farm with heritage breed animals, historic buildings, and horse drawn sleighs. Costumed historians are very engaging and will regale you with historic tales.

You can walk the village and meet the skilled craftsmen who still practice their trade. You can also take a wagon ride. The Village offers several events throughout the year — Winter Photo Walk, Sunday Brunch, and Dinner in a Country Village.

22. Ogunquit Maine (1:30 Hour Drive)

Feeling like a beach day? Nestled along the coast, tiny Ogunquit has been a resort village since the 19th century.

The word Ogunquit translates to “beautiful place by the sea.” You can see why immediately. Ogunquit is like a mini Provincetown. 

The town is a popular summer beach destination in New England, and I came here often as a child. Ogunquit has two beautiful long beaches, Ogunquit Beach and Footbridge Beach. Footbridge is the quieter of the two beaches.

Ogunquit is most renowned for its coastal path, the Marginal Way . It’s a paved 3 mile seaside stroll, starting at Ogunquit Beach and meandering to Perkins Cove.

Perkins Cove is a tiny artisans village, filled with sea-weathered buildings, where you’ll find some art galleries and seafood eateries.

23. Northampton (2 Hour Drive)

Just under 2 hours from Boston, the rural town of Northampton is a cultural nerve center in New England. It’s a pretty town, ringed by 5 colleges and college museums.

Grand mansions line tree-shaded streets. The beautiful Main Street is filled with with shops, art galleries, bookshops, etc.

In downtown Northampton, there are more than a dozen visual arts venues. The Northampton Center for the Arts offers poetry readings, film screenings, and concerts. The Calvin Theater is the premiere concert venue, hosing major touring music and comedy acts.

Four of the five colleges near Northampton offer theater and visual arts. Smack in the middle of Northampton is Smith College. Its beautiful  Smith College Museum of Art  just received a $35 million makeover. The museum offers a year round series of art lectures, contemporary art exhibitions, and films.

Just down the road is  Mount Holyoke College Art Museum . It offers contemporary and traditional exhibitions year round.

You can also admire contemporary work at Amherst’s Mead Art Museum or check out national and international exhibits at Amherst’s University Gallery.

Northampton has a good foodie scene too, with both great pizzerias and haute cuisine. There are two dairies nearby, so the town’s cheese and ice cream options are among the best in New England.

24. Peterborough New Hampshire (1:30 Hour Drive)

Peterborough is a charming New Hampshire hamlet set along the Contoocook River. Peterborough is rich in art and culture, with a charming downtown centered on Depot Square. Thornton Wilder’s Pulitzer Prize winning play,  Our Town , was based on Peterborough.

Peterborough has two theater groups and a renowned artist colony, The MacDowell Colony. The colony is the oldest artist’s retreat in the US, hosting many exhibitions. 

In 1997, it was awarded the National Medal of Arts. Peterborough is also known for its antique shops and galleries.

Nature lovers can head to Miller State Park , which has several trails (and a road) leading to the summit of Mount Monadnock. Edward MacDowell Lake has trails as well, in addition to a beach and boat ramp.

25. Plymouth (45 minutes)

Situated at the mouth of Cape Cod Bay, Plymouth is a historical haven for Boston day trippers. The town was the very first permanent settlement by Europeans north of Virginia. Today, it’s a thriving small town with a lovely historic district, perfect for history buffs.

After parking, first head to the  Mayflower II . It’s is a full scale replica of the original 17th century Mayflower.

The Mayflower is famous as the ship that brought pilgrims to the US in 1620. You can even take a tour of the ship itself, which is docked in Plymouth Harbor

Also, to learn the pilgrims’ tale, stop in the state’s oldest museum,  Pilgrim Hall . There, you’ll find an unmatched collection of ancient artifacts and possessions of the pilgrims. Afterwards, you’ll get to wander around historic  Howland House  and visit the 18th century Court House.

If you want to really step back in time, head to  Plimoth Plantation . It’s a living museum that aims to explore the daily lives of the Colonial Americans. The village has been carefully recreated, with thatched roofs and giant open fireplaces.

The actors in the museum are in period costume and never step out of character. You can watch them performing 17th century tasks including building, gardening, and military exercises.

26. Portland Maine (1:45 Hour Drive)

 Located on a peninsula jutting into Casco Bay, Portland is a rare metropolis in a state filled with small hamlets. It’s a hip and laid back place that almost seems too cool for one of  New England’s most beautiful towns . Portland is a great day trip from Boston for foodies.

Portland has myriad cultural offerings and is a bastion of historical preservation. The restored Old Port is a warren of cobbled streets with a movie set feel. This area is filled with vibrant Victorian buildings and buzzing farm to table eateries.

Start on Commericial Street, the main drag, and work your way inward. The Old Port is known for its cobblestone streets, 19th century brick buildings, and fishing piers. It’s also a hive of activity.

In downtown Portland, there’s a thriving art school, infusing the city streets with creative types. And there are 24 commercial art galleries.

Opened in 1983, Portland’s crown jewel and premiere art destination is the  Portland Museum of Art , an architectural masterpiece designed by I.M. Pei of  Louvre  fame. Its innovative architecture allowed curators to redefine the art viewing experience.

Restaurants and coffee bars are filled with visual art. In June, the revived downtown hosts the Old Port Festival, described as “part freak show, part art festival, part fashion parade.”

Portland is also a hot spot for restaurants, coffee shops, and entertainment. Did I mention breweries? Beer lovers will be happy to know that Portland has 18 breweries all its own. It’s the Craft Bew Capital of America.

If you want to delve more deeply into Portland’s foodie culture, there are some awesome tours.

This tour takes you on a culinary walking tour of the Old Port and this tour lets you feast on seafood in the Old Port. If you’re a fan of craft beer, this tour gives you a taste of Portland’s amazing brew pubs.

27. Portsmouth New Hampshire (1 Hour + Drive)

The New Hampshire town of Portsmouth has also made an appearance on Forbe’s list of America’s Prettiest Towns. Portsmouth is a small town in southern New Hampshire along the Piscataqua River. 

Portsmouth is a great Boston day trip destination for art lovers and foodies. It’s known for its upscale farm to table eateries and art galleries.

Portsmouth’s funky downtown is adorable, with activity centered on Market Square. You’ll find classic white steepled churches, rustic brick shops, and sidewalk cafes. Portsmouth Book & Bar combines books, coffee, and live events.

History lovers should check out the Strawbery Banke Museum . It’s a 10 acre outdoor museum featuring period gardens, preserved historic buildings and detailing the story of how the Portsmouth settlement was founded. 

There are 39 historic buildings dating from 1695 to 1820. The Goodwin Mansion is the most impressive.

Prescott Park is a waterfront park near Strawberry Banke, which is great place to picnic. Enjoy the gardens and the Prescott Park Arts Festival, featuring concerts and foodie events.

in 2017, Travel & Leisure called Portsmouth the “Christmas Capital of North America.” It’s a wonderful New England Christmas destination. “Vintage Christmas” is a month long celebration kicking off December 1. A trolley does a loop of the downtown and a candlelight stroll is held on weekends.

Here’s my guide to the best things to do in Portsmouth in one day .

28. Providence Rhode Island (1 Hour Drive)

Nicknamed the “cooler city” by GQ, Providence is one of the  best towns on the East Coast . Providence is home to an Ivy League college, design schools, and a culinary institute. 

The city is a hodgepodge. It combines big city sophistication with small town charm. It has a vibrant local culture, celebrated restaurants, and sparkling waterfront parks. Providence is full of historic Yankee monuments, but also has a young and funky vibe.

Providence is an easy day trip from  Boston , less than an hour away. But this little jewel box of a city is often overlooked by travelers and definitely underrated. So much the better for its admiring visitors.

Be sure to explore Providence’s Little Italy on Federal Hill. Then, head to the East Side to encounter Providence’s Colonial past. Benefit Street is a bucolic 1.2 mile walk that’s an architectural showcase.

You’ll see some of the most beautiful Federal era architecture in the United States. You’ll also find the lovely campus of Brown University.

And you can’t leave Providence without visiting the fabulous  Rhode Island School of Design Museum . A major cultural institution in the United States, RISD houses over 100,000 works. It’s one of the best small museums in the world .

READ: 1 Day Itinerary For Providence

29. Provincetown Massachusetts (2 Hour Drive Or Ferry)

Do you want to combine a day at the beach with great art? head to Provincetown. The pretty town is tucked away on the far end of Cape Cod.

It’s been attracting artists and creative types for more than a century. Eugene O’Neill wrote his first play here. Modern art luminaries like Helen Frankenthaler, Marsden Hartley, and Hans Hofmann had studios here.

Nowadays, there are 60 art galleries scattered down Provincetown’s picturesque streets. It’s the perfect place for art lovers on the East Coast.

The town’s premiere art venue is the Provincetown Art Association and Museum on Commercial Street. The museum highlights local and New England artists with single artist and themed shows.

The Schoolhouse Center for Art & Design is home to several galleries as well. The Silas-Kenyon Gallery focuses on contemporary art. If you like vintage photography, head to the Driskel Gallery.

The big ticket art festivals you should have on your radar are the Spring Arts Showcase Weekend in May and the Fall Arts Festival in September and October. There’s also an International Film Festival in June.

Don’t forget to eat some lobster, preferably at the Lobster Pot . You can go wine tasting at  Truro Vineyards  or sip craft beers at the  Provincetown Brewing Company .

If you visit Provincetown in the summer, you could spend hours in traffic at the Sagamore Bridge if you drive. But you can also take the Providence Ferry . The fast ferry runs direct from Boston to Provincetown from mid-May through mid-October. It’s only 95 minutes each way.

30. Rockport Massachusetts (55 Minute Drive)

I f a stunning seaside town is on your Boston day trip agenda, head to Rockport. This little town is on Cape Ann, the “other” cape in northeast Massachusetts. There’s a reason why North Shore residents treasure Rockport as a lovely weekend getaway.

There are plenty of things to do in Rockport. Stroll around and admire all the fishing boats and painted cottages. Check out the shops and art galleries on Bearskin Neck, a cute area perched on the edge of town.

Sample some fudge at Rockport Fudgery , eat lobster rolls, relax on the beaches, or take a walk along the rocky coastline at  Halibut Point State Park . You can even go on a  Cape Ann whale watch .

31. Rye New Hampshire (1:10 Hour Drive)

Another good beach option is Rye. The picturesque town of Rye is home to the best beach on the 18 mile long New Hampshire shoreline.

First settled in 1623 on Odiorne Point, Rye is the birthplace of New Hampshire. Rye is largely undeveloped because it’s subject to strict zoning laws.

Rye is a serene contrast to the more frenzied Hampton Beach down the road. In Rye, the tide is small and rolling. It’s a perfect place for a beginner surfer.

You can also take a scenic drive down Route 1A past Millionaire’s Row and ogle at Rye’s breathing early 20th century mansions.

32. Salem Massachusetts (45 Minute Drive)

Even if you haven’t traveled in Massachusetts , you’ve probably heard of Salem. Known as the “Witch City,” Salem is a beautiful seaside town and an easy day trip from Boston.

In Salem, you can learn about Salem’s creepy past as the “witch capital” of the United States. Salem embraces its notorious past, when the infamous 17th century Witch Trials defined the town.

Salem is replete with whimsical magic shops, all things haunted horror, and ghostly tour options. Many of Salem’s top attractions are devoted to its witchy history. This means that the best time to visit Salem in during Halloween.

Salem is also famous for its beautiful 17th century Colonial and Georgian architecture and delicious seafood. Essex Street is the historic cobblestoned district, with the original brick  Old Town Hall .

Old Town Hall dates from 1816. The second floor still stands as a public hall and the first floor is used as a public art space.

If you’re a literary fan, you should visit the  House of the Seven Gables . Built in 1668, it’s one of the oldest Colonial mansions still standing in the United States. Nathaniel Hawthorne immortalized the house in his 1851 novel of the same name.

Inside, you’ll find a recreation of the secret staircase from the novel. The house where Nathaniel Hawthorne was born is also on the property.

Click here to buy ferry tickets to Salem.

There are some excellent guided tours in Salem. If you’re a history buff and want to take a witchcraft trials walking tour, this is an excellent guide . If you’re staying overnight in Salem, you can also take this haunted history nighttime tour or this ghosts of Salem walking tour .

33. Stellwagen Bank National Marine Park (30 Minute Drive)

Want to view some of the most massive animals on the planet? The  Stellwagen Bank National Marine Park  is one of the best whale watching spots in the entire world. It’s a wild ocean destination not far from Boston, just 37 miles away.

The sancturay has an extremely productive and diverse environment, which encourages a wide mix of marine wildlife.

Each summer, around 50 recognized humpbacks return. You can also spot dolphins and seals. There are plenty of whale spotting tours available in the area departing from Gloucester or Provincetown. Click  here  for a list of boat tour operators.

34. Stockbridge Massachusetts (2 Hour Drive)

Stockbridge is the quintessential New England town. It’s one of my favorite day trips from Boston.

Stockbridge was settled in 1734 by British missionaries. It’s blessed with simple charm and a fabulous line up of cultural attractions.

Three of the greatest American artists and authors called Stockbridge their home — Edna St. Vincent Millay, Herman Melville, and Norman Rockwell. One of America’s greatest treasures is the  Norman Rockwell Museum .

Rockwell was one of the greatest artists and illustrators in American history. Stockbridge was Rockwell’s long time residence and what he called his “best studio yet.”

You can also visit  Chesterwood , the home of Daniel Chester. It’s a 1920s Colonial Revival house.

It comes complete with the soaring studio of the legendary sculptor and landscape architect. Chester created the statue of President Lincoln seated in the Lincoln Memorial in Washington D.C., and you’ll see plaster models in the museum.

Every summer, Stockbridge (along with Lenox) hosts the Tanglewood Music Festival. It’s a series of concerts across all musical disciplines.

Stockbridge is also home to one of the Berkshires Gilded Age “cottages,”  Naumkeag . You can tour this quirky 44 room mansion designed by Stanford White, a famed starchitect of the time.

 35. White Mountains, New Hampshire (2 Hour Drive)

It’s a hike to get to the White Mountains from Boston. But it’s worth the long drive to spend a day immersed in nature.

The White Mountains are New Hampshire’s premiere attraction. It’s the best day trip from Boston for fall foliage .

The White Mountains are incredibly beautiful, with plenty of natural wonders. They’ve long attracted vacationers, photographers, and adventurous hikers and skiiers. Mount Washington is the Northeast USA’s peak of superlatives. 

The sinuous Kancamagus Highway in the White Mountains is the granddaddy of New England drives. It’s a scenic 35 mile stretch of highway. You’ll be dazzled by the incredibly unspoiled scenic views along the way.

There a few pullouts for trailheads, providing great photo and hiking 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.

 In Crawford Notch State Park , 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.

Don’t leave without experiencing the  Mt Washington Cog Railway . It’s a historic train ride up to the summit of Mt. Washington. The mountain is the tallest one in the northeastern United States at 6,289 feet.

Aside from driving around soaking up the scenery, you can explore the cute downtown of North Conway, relax at  White Lake  in Tamworth, do a canopy tour at  Bretton Woods , go on a  waterfall hunt  near Conway. 

36. Worcester (1 Hour Drive)

Right in the heart of Massachusetts, Worcester is one of the best day trips from Boston. Worcester is the second largest city in Massachusetts after Boston. It’s just an hour away from Beantown.

Once in Worcester, take a gander through the huge exhibitions at the  Worcester Art Museum . You can easily spend a good few hours inside. The museum has works of Impressionism, Roman mosaics on the Renaissance Court floor, medieval armor, and Paul Revere’s silver collection.

Be sure to visit the  Bancroft Tower . On the National Register of Historical Places, it’s been around in Worcester since 1900. This fantasy medieval castle was built on a whim to honor a US Navy pioneer. It’s a miniaturized castle in the middle of a park.

At night, you can take in a theater or music performance at the elegant Hanover Inn, Mechanics Hall, or Tuckerman Hall.

I hop you’ve enjoyed my guide to the best day trips from Boston. You may enjoy these other New England travel guides:

• 3 day itinerary for Boston
• 1 day in Hanover New Hampshire
• 35 Landmarks in Boston
• 10 day itinerary for New Hampshire
• Berkshires Road Trip Destinations
• Hidden Gem Towns on the East Coast
• 10 day itinerary for coastal Maine
• 7-10 day itinerary for Vermont
• One week itinerary for southern New England
• Fall foliage road trip in New England

If you’d like to take some day trips from Boston, pin it for later.

4 thoughts on “35+ Amazing Day Trips From Boston Massachusetts”

Nice collection of day trips, but with the review of Salem, MA I can’t believe you left off both the Peabody Essex Museum (one of the best art and culture museums in New England) and no mention of any of the NPS sites and all the maritime history this city has.

I know the Peabody Essex Museum is amazing. I’ve written about it in my Salem article and in my article on the best museums in New England. I will add something here. But with a round up post, you can only write so much for each town.

This was definitely a trip down memory lane. I lived in New England for 23yrs and visited many of these destinations. You certainly did a great job on the history. I especially enjoyed the colorful pictures. I am drooling over just the thought of the lobster rolls on the Maine and New Hampshire coast.

I would love a lobster roll right now!

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Last Updated on July 4, 2023 by Leslie Livingston

17 Memorable New England Day Trips Perfect for Every Season

Looking to explore new places without the time and cost of an overnight stay? New England day trips are the perfect hassle-free way to discover unfamiliar towns and destinations while creating lasting memories. You’d be surprised by the interesting things you can find just a short drive from home. It’s a convenient travel option that won’t kill your car’s mileage or your budget. 

Growing up as a Rhode Island native, I’ve taken my fair share of day trips throughout New England, making for some of my best childhood adventures and cherished family time. Using my expertise, I’ve created a list of the best New England day trip destinations perfect for a long weekend or spontaneous excursion.

Most of these New England day trips are within a two-hour drive from central Massachusetts. Whether it’s enjoying a scenic drive to Brattleboro, Vermont, or revisiting American history at Old Sturbridge Village in Massachusetts, the opportunities are endless. 

New England Day Trips

Don’t know which location would suit you best? I’ve got you covered. Here are my top picks to help guide you on your next day trip. Let the fun begin. 

• Best for families: Mystic, CT
• Best for nature lovers: Berkshires, MA
• Best seaside day trip: Newport, RI
• Best for history lovers: Salem, MA or Plymouth, MA
• Best for relaxation: Litchfield, CT

Day Trips in Massachusetts

Most day trip destinations in Massachusetts are no more than a two hour drive from southern Vermont or New Hampshire, Boston, Providence, or Hartford.

Known for its spooky history, Salem Massachusetts offers a great experience for Halloween lovers or those looking to immerse themselves in early American history. Fall is the ideal season to visit, with the leaves changing and lively parades and events. If busy crowds aren’t for you, the summer months are equally enchanting with waterfront views. Conveniently located an hour from central Massachusetts, this city attracts visitors from around the country. 

One of the main tourist attractions is the Salem Witch Museum , telling the history of the 1692 Salem Witch Trials. Along with the museum, Salem features the Salem Witch Trails Memorial , honoring the victims, and The Witch House , once home to Judge Jonathan Corwin, who had an active role in the trials (and recognizable from the movie Hocus Pocus.)

Additionally, the Pickering Wharf Marina is a beautiful spot to dine by the water at restaurants like Sea Level Oyster Bar, Finz Seafood & Grill, and Village Tavern. The area has a variety of shopping opportunities and evening entertainment. Before heading home, stop by Goodnight Fatty for delicious freshly baked cookies, soft-serve ice cream, or a combination of both. It’s the perfect way to end the day and treat yourself for all the walking. Be warned, the bakery operates exclusively on Fridays through Sundays.

Read more: Bewitching Things to do in Salem, MA

Boston stands as a beloved city, renowned for its esteemed education, historical sites, successful sports teams, and delicious cuisine. No matter your interests, Boston has something for everyone to enjoy. The best time to explore the city’s signature highlights is from late spring to early fall, offering the perfect temperature before the start of New England’s unpredictable weather.

A Boston Duck Tour is an excellent way to kick off your trip, providing an introduction to the city. The tour features both land and water sightseeing, offering insight into major attractions. Sites include a visit to the historic Old State House, the Charles River, and America’s first public park and botanical garden. After the tour concludes, consider revisiting your favorite locations to get a closer look. For a memorable dining experience, head to Boston Burger Company for lunch or dinner.

This local gem’s extensive menu of juicy burgers like the Green Monstah to freak frappes like Dough My Goodness . With multiple locations across the Boston area, you can easily savor their flavors no matter where you are. If you’re on the go, Faneuil Hall Marketplace stands as another must-visit destination. Stop to shop at boutiques, explore the diverse food options at Quincy Market (my favorite is Mmmac N’ Cheese), and watch lively street performances. Faneuil Hall adds flavor to your day and is a welcoming all-in-one environment.

Surrounded by beautiful homes, rich American history, and friendly locals, Plymouth Massachusetts is the ideal getaway for history nerds, seafood lovers, and anyone eager to learn more about culture. September through November is the optimal time to visit this coastal town to take in fall foliage and explore well-preserved artifacts.

A prominent attraction drawing many to Plymouth is The Mayflower ll . This historical replica mimics the boat that transported the Pilgrims from England to America. Take a tour above and below deck to see the challenging conditions travelers endured during their 66 days at sea. You can also visit the Plimoth Patuxet Museum to learn about the day-to-day life of Patuxet people or stroll through a recreation of a 17th-century Colonial village.

In close proximity, Plymouth Rock stands as a landmark where the Pilgrims stepped ashore. Embraced by the beautiful harbor, this iconic rock is a site worth seeing, especially if you happen to be in the area. Enjoy waterfront shopping at Miller’s Country Store , renowned for its saltwater taffy, or savor fresh seafood takeout like clam chowder from Wood’s Seafood , Plymouth is an unforgettable destination. 

Read more: Things to do in Plymouth, MA

Cape Cod is a popular summertime destination known to have some of New England’s best beaches. From nature reserves and wildlife sanctuaries to small towns and shopping, Cape Cod offers a range of experiences for those who love the outdoors or those looking for some fresh seafood. Just under two hours from central Massachusetts, a day trip to Cape Cod guarantees an adventure that will leave you eager for more. 

Cape Cod’s sandy beaches are the perfect way to relax. If you’re looking for spots to sunbathe, Coast Guard, Head of the Meadow, Nauset, and Marconi Beach are the best for getting a tan. For those not interested in soaking in the sun, Race Point and Herring Cove are better options, common for water-related activities like kayaking and paddleboarding. These beaches are part of The Cape Cod National Seashore , covering 40,000 acres with stunning landscapes, dunes, and a refreshing ocean breeze. It’s the perfect paradise for watching the sunset or sunrise.

Downtown Provincetown is another lively option to explore, coming to life with shopping and dining, it will just take a bit longer to get there. Stop by Commercial Street to take home a souvenir and grab a sweet treat at Fudge Factory which has an assortment of candies, chocolates, and even icecream. Finish off the day with dinner at Jimmy’s HideAway for fresh sea catches or Provincetown Brewing Co. for craft beer and burgers.

Read more: Favorite things to do on Cape Cod

Old Sturbridge Village

Explore New England during the 1830s at Old Sturbridge Village . Spanning more than 200 acres of land with 40 historical buildings, this museum offers an immersive experience for both children and adults. To avoid crowds, late spring is the ideal time to visit, with warm temperatures for walking along the nature trails and exhibits.

December is also a great time as the museum offers special events like Christmas by Candlelight where guests can join in on holiday traditions. Just a half-hour drive from central Massachusetts, Old Sturbridge Village encourages guests to take part in hands-on learning. 

Get a glimpse into the early years of the nation, where you can see the day-to-day lives of small-town villagers. Costumed historians will teach you about village life, from farmers to blacksmiths, all ready to answer your questions. Don’t miss the opportunity to check out the countryside, home to a variety of farm animals including cows, goats, chickens, pigs, and more.

Enjoy a horse-drawn wagon ride and savor a delicious meal at either the Bullard Tavern Cafe, with options like paninis, salads, and chicken tenders, or the Ox & Yoke Cafe, known for its baked goods. If you’re looking for a change of scenery outside the village, stop by Publick House for classic comfort food or Enrico’s Brick Oven Pizzeria for a hot slice. 

Located in the heart of central Massachusetts, Worcester is seeing a renaissance with the new baseball stadium, breweries, and restaurants downtown. With a blend of cultural attractions, historical landmarks, and scenic parks, Worcester offers an array of experiences to choose from. While visitors are welcomed year-round, I recommend planning a visit during the summer season to take advantage of the warm weather and daylight.

Green Hill Farm Park is a great spot to meet farm animals such as llamas, miniature horses, and alpacas or enjoy a summer barbeque at one of its picnic tables. The EcoTarium is another great option to explore nature and wildlife further. This engaging science museum is an interactive learning environment expanding across three floors of exhibits, ranging from live animal habitats to a planetarium. Its 45-acre campus is designed to captivate visitors of all ages. The museum also features an outdoor park, train rides, and a history collection of more than 50,000 species.

If shopping is on your agenda, look no further than Crompton Collective , where locally crafted treasures await. From an extensive collection of jewelry and home decor to vintage clothing, this unique shop is stocked with items waiting to find the right home. Finish your trip with an American classic, hot dogs, and ice-cold chocolate milk from George’s Coney Island . This Worcester landmark has been around for generations and is loved for its old-fashioned diner style. The giant neon sign marks the spot for quick, delicious, and budget-friendly food.

Recognized as America’s oldest seaport, Gloucester, Massachusetts, draws visitors to its coastal community with its rich fishing history, stunning beaches, and delicious seafood. Whether you’re a fisherman, outdoor adventurer, or foodie, this day trip offers experiences to fit your interests. Located just about an hour and a half away from central Massachusetts, Gloucester is an ideal destination to explore the region’s fishing and whaling history. Given its seaside setting, Gloucester is best to visit during the summer season. 

Whale watching is a top attraction for visitors to Gloucester. Both Seven Seas and Cape Ann whale watching present the opportunity to see marine animals in their natural habitat. As many whale species migrate to Gloucester’s shores, whale watching offers an excellent way to get a better understanding of marine mammals’ behavior. Humpback whales are commonly found alongside potential sightings of dolphins and sharks.

Take a break from sailing the seas to explore the Eastern Point Lighthouse . Along the rocky shoreline, the lighthouse is a breathtaking sight to see. While the lighthouse itself is fenced off, you can walk along the seawall for a closer look. The view gives a glimpse of the Boston skyline, making for a great view to capture photos, especially during sunset. Parking is available for $10.

Grab a bite to eat at Seaport Grille for lunch or dinner. Their menu includes options that cater to everyone’s palates, featuring dishes like mouthwatering lobster mac and cheese, scallops, and margarita pizza. 

Read more: Things to do in Gloucester, MA

Springfield

Springfield is a large yet quiet city that is surrounded by American history, artistic expression, and sports culture. Best for basketball lovers and families, Springfield serves as a great day trip. Located an hour away from central Massachusetts, its accessible location ensures visitors can explore its attractions year-round. I suggest planning a visit during the fall season to watch the leaves change color and to take in the crisp autumn air. 

Known as the birthplace of basketball, Springfield is home to the Naismith Basketball Hall of Fame , a must-visit destination for fans of men’s and women’s college and professional basketball. Spread across three floors, the hall showcases a collection of jerseys, shoes, and informative videos about the sport’s history. One noteworthy exhibit is dedicated to Kobe Bryant, designed by wife, Vanessa. After exploring, guests can practice their skills on the hall’s basketball and browse the gift shop for memorabilia.  

The Amazing World of Dr. Seuss is another captivating experience for visitors in Springfield. Transporting guests back to childhood, this museum will make you feel like you’re inside the whimsical world of Dr. Seuss’s famous stories. With colorful rooms and life-sized statues, the Seuss Museum appeals to more than just children.

A ticket purchase grants you access to five museums, including The Amazing World of Dr. Seuss Muesuem, George Walter Vincent Smith Art Museum, Springfield Science Muesuem, Michele and Donald D’Amour Museum of Fine Arts, and Lyman and Merrie Wood Museum of Springfield History.

Before heading home, indulge in a delicious burger at Plan B or enjoy the community vibe and great food at White Lion Brewery . You may also want to make a pitstop at the Yankee Candle Village to stock up on gifts and explore the elaborate Christmas village.

Read more: Things to do in and near Springfield, MA

This mountainous retreat is loved by many New Englanders for its natural beauty and abundance of outdoor adventures, but it is also known for its arts and culture. Whether you’re drawn to skiing, hiking, or art museums, the Berkshires make for a remarkable day trip experience.

Summer welcomes outdoor concerts and symphony performances, while spring showcases blooming flowers and hiking trails. In winter, the landscape transforms into a snowy wonderland, perfect for snowshoeing, skiing, snow tubing, or cozy evenings by the fireside. Fall invites visitors to pumpkin patches and apple orchards. Located just an hour and a half from central Massachusetts, the Berkshires are the perfect destination for nature enthusiasts and those looking for a reset.

Those looking for art and culture and plan a stop at Edith Wharton’s The Mount or spend a day engaged with the immersive contemporary art at Mass MoCA . If you prefer to be active, take on the treetop aerial adventure course at Ramblewild or climb Monument Mountain .

In the winter, Jiminy Peak offers skiing, snow shoeing, and a thrilling mountain coaster. Enjoy snow tubing or night skiing at Bousquet Mountain and take on the slopes at the local’s favorite, Berkshires East .

If you’re feeling hungry, stop by Baba Louie’s in Great Barrington for sourdough pizza, pasta, or salads. Craving something sweet? Chocolate Springs in Lenox is the shop to cure your craving with a tempting selection of treats, including chocolate-covered pretzels, marshmallows, truffles, and more.

Read more: Things to do in the Berkshires with kids

Day Trips in Connecticut

An hour-and-a-half drive from central Massachusetts, Mystic Connecticut, is a great day trip spot for family fun and historians. Home to some of Connecticut’s most visited attractions, this charming town boasts a plethora of shopping, dining, and interactive experiences. Travelers come to its scenic shores to explore the vibrant streets, vineyards, and neighboring towns.

Step back in time and experience life in a 19th-century village at Mystic Seaport or enjoy shopping at the forty small shops and eateries at Olde Mistick Village .

Nearby, the Mystic Aquarium awaits, where you can witness marine life including penguins, beluga whales, and sharks. The aquarium features both indoor and outdoor exhibits, some of which allow you to touch fish like stingrays and crustaceans.

Start your trip with something sweet from Sift Bakery (featured in the Hallmark Movie Mystic Christmas ) and end it at Red 36, an outdoor restaurant and bar overlooking the Mystic River, for an all-around perfect day.

Read more: Things to do in Mystic, CT with kids

Litchfield, Connecticut is a small town located within a two-hour drive from central Massachusetts. Surrounded by farms, nature reserves, historic inns, and wineries, it creates the perfect space for relaxation and serenity. This countryside is a haven for introverts and can be used as a romantic escape for couples seeking uninterrupted quality time. The most popular to visit is during the early summer to early fall months, drawing people with its sunny days and warm temperatures.

Ripley Waterfowl Conservancy is an excellent starting point for your trip, home to more than 80 species of rare and endangered birds. Spanning 150 acres, this conservation works to protect more than 400 birds year-round, while conserving wetlands and educating visitors on the importance of protecting feathered friends. Frolick through the fields and learn about the adorable ducklings’ habitat. You could also hike up to the top of Mt. Tom in Litchfield to find some of the prettiest fall views in Connecticut from the old stone tower at the summit.

The Litchfield Distillery is another attraction to visit during your trip. Sample some of the Baker brothers’ 18 award-winning spirits, ranging from vodka and whiskey to bourbon and gin. Enjoy a complimentary tour to get a behind-the-scenes look into how they make their drinks and taste-test different flavors to find your favorite. On certain weekends, you can also enjoy live music outside at nearby Hopkins Vineyards .

For a quick bite to eat, visit The Pantry for baked goods, sandwiches, and salads, or sit down at the Market Place Tavern , in the oldest building in town. For delicious ice cream, line up at Arethusa Dairy for fresh, homemade deliciousness.

Day Trips in Rhode Island

Discover the hidden gems tucked within Rhode Island’s creative capital, Providence. Filled with prestigious universities, historic districts, and a talented artistic community, this small city carries metropolitan power without the overly crowded streets. Located within a 45-60 minute drive from central Massachusetts, Providence is a destination that attracts foodies and art lovers.

As a college student familiar with the Providence area, I recommend visiting during the spring when the weather warms up, just in time for events like WaterFire or enjoying a stroll through scenic landscapes.

A day trip to Providence with kids calls for a visit to Roger Willams Park Zoo , one of the oldest zoos in the country. With more than 100 species from across the globe, including monkeys, giraffes, and cheetahs, the zoo offers an immersive wildlife experience. Little kids will also enjoy the Providence Children’s Museum .

Another highlight for many visitors is the RISD Museum . Co-founded with the Rhode Island School of Design, this art museum has a collection of thousands of artworks ranging from modern art made by students to ancient textiles. With its rich history and diverse pieces from artists around the world, the RISD Museum makes for an educational adventure through art and culture.

For authentic Italian cuisine, head to “Little Italy,” commonly known as Federal Hill. This Italian neighborhood is decorated with Italian flags to represent its cultural heritage. Here you’ll find fantastic restaurants and bakeries serving traditional Italian goods like gnocchi and pastries like cannolis. One of my personal favorites is Costantino’s Venda Bar & Ristorante.

Read more: Things to do in Providence, RI

Known as the “City by the Sea”, Newport is a popular summer destination for its sandy beaches, yacht-filled harbors, and relaxation. Surrounded by some of the state’s wealthiest residential properties and beautiful beach houses, Newport will transport you to island time the moment you cross the Newport Bridge.

Just an hour and a half from central Massachusetts, Newport makes an unforgettable day trip, whether you’re a history nerd or an avid beachgoer. Surprisingly, Newport isn’t just a summer hotspot, turning into a winter wonderland with holiday lights, festivals, and plenty of opportunities for ice skating. 

A must-see attraction during your visit to Newport is the Newport Mansions . Built during the Gilded Age, these historic estates have more than 250 years of American history. Each mansion offers a glimpse into the luxury lives of the families who once lived in them, through its interior design and astounding architecture. The Breakers is one of the most popular mansions followed by Marble House, The Elms, and Rosecliff.

Bowen’s Wharf is another Newport specialty that offers a little bit of everything. Whether you’re looking to shop or try one of their exquisite dining options, the wharf’s friendly environment helps you immerse yourself in Newport’s lifestyle. With its old-town charm, Bowen’s Wharf is great for sunset views over the marina, refreshing drinks, and fresh seafood. This is also the spot to jump on board a sailing vessel for a ride around the harbor. End your day with a quick walk to Kilwin’s on Thames Street for some homemade ice cream.

Read more: Things to do in Newport, Rhode Island

Beloved for its state parks, coastal cliffs, and marshlands, Jamestown serves as a wonderful destination for a scenic day trip. Its seemingly quiet roads offer the perfect opportunity for a relaxing day by the water. From swimming and biking to fishing and kayaking, this island has a rich marine history and natural beauty that make it a must-visit destination, especially during the summer months. A little under an hour and a half away from central Massachusetts, Jamestown is for anyone who appreciates the great outdoors.

Beavertail State Park is a staple of Jamestown. Home to the third oldest lighthouse in the United States, it has played a crucial role in guiding ships and sailors to safety. The rocky coastline surrounding the lighthouse is great for hiking and climbing, although watch your step because the rocks can be slippery. Watch sailboats pass by, fly a kite, or bring a picnic to enjoy as you admire the view. 

Fort Wetherill State Park is another popular attraction found on 100-foot-high granite cliffs. Originally built as a military fort to protect the Narragansett Bay, Fort Wetherill now invites the public to explore its historic grounds. The park’s old war bunkers are decorated with colorful graffiti art, adding personality. Bring your fishing poles to cast out along the saltwater shorelines or a camera to capture memories of this beautiful town.

Work up an appetite? Visit JB’s on the Water for a classic New England lobster roll or Slice of Heaven Cafe for coffee and pastry.

Day Trips in New Hampshire

Portsmouth New Hampshire is a favored location for its historical sites, waterfront eats, and tax-free shopping opportunities. Just an hour and a half drive from central Massachusetts, Portsmouth invites visitors to enjoy a night out on the town or a leisurely day exploring the beautiful scenery.

Whether you’re a food enthusiast, trailblazer, or a lover of learning, Portsmouth makes for a memorable day trip. The spring and summer months are the best times for seasonal activities.

The Portsmouth Naval Shipyard is the start of Portsmouth’s rich history, home to the USS Albacore, a groundbreaking creation by the U.S. Navy for testing modern submarine features. Renowned for setting an underwater world speed record, the vessel invites guests to explore its interior. Move from room to room listening to the audio stations including crew member stories about their experiences at sea.

If you’re looking to get some fresh air, Prescott Park is the place to be. Spanning ten acres, the park is surrounded by trees and showcases a stunning garden with vibrant flower beds. Visitors can enjoy a view of the Memorial Bridge while unwinding on a bench or strolling along the pathways. If you are visiting with kids, you will want to spend time exploring the nearby Strawbery Banke Museum or walking the Portsmouth Black History Trail .

When you get hungry, you have plenty of options to choose from, including popular Flatbread Company for wood-grilled pizza or Row 34 for fresh oysters and seafood.

Read more: Things to do in Portsmouth, NH

Day Trips in Maine

Portland, Maine packs a whole lot into its three-mile-long peninsula. Despite being smaller than some other cities on the East Coast, there are plenty of reasons to travel up north, including the history, landmarks, artisan breweries, and delicious food .

Portland, which is only two hours away from central Massachusetts, comes alive with a packed social calendar, especially in the summer months of June through August. Whether you’re a foodie, nature lover, lone explorer, or a family looking for excitement, Portland has you covered.

No trip to Portland is complete without two things, a stop at Portlandhead Light for the view of the lighthouse and to scramble on the rocks, and a lobster roll. You can even try to catch some yourself on a lobster boat tour (and then the Portland Lobster Company will cook it up for you if you get lucky!)

Want to stay out of the crowd and save money? No issue, the Portland Freedom Trail offers a free, self-guided tour passing thirteen significant locations one being the local Underground Railroad. Kids will enjoy Children’s Museum and Theater of Maine , while adults may want to join a Portland beer tour .

After a long day, Portland’s Bar Futo , is a great dining spot that serves a variety of skewers and tiny plates such as charred shishitos and Maine uni with potato mochi. They specialize in Japanese binchotan cooking. Not to mention, the Big Mac skewers will leave your mouth watering! Of course, kids might prefer a stop at Duckfat for those amazing french fries and milkshakes.

Read more: Things to do in Portland, Maine

Day Trips in Vermont

Brattleboro.

An hour and a half from central Massachusetts, Brattleboro, Vermont, is tucked away in the charming countryside along the banks of the Connecticut River and attracts a wide range of artists and creatives. Travelers can (and should) flock to Brattleboro in all four seasons; spring is sugar season and summer bring ideal weather, while crisp fall vistas showcase the beautiful foliage and the winter months bring snowshoeing and ice fishing.

Downtown Brattleboro is bursting with opportunities to express your creative side with workshops for all ages and interests including woodworking at Hatchspace , pottery at the Wheelhouse Clay Center , and glass blowing at Fire Arts Vermont . You can even try your hand at circus arts or watch a performance at the New England Center for the Circus Arts .

If you are looking for local products, the Robb Family Farm is the place to get maple syrup, as well as maple sugar candy and maple cream. During the summer months, take home fresh fruits and vegetables at the Brattleboro Farmers Market. Stop into Tavernier Chocolates for hand-crafted chocolates showcasing local ingredients. Or pop into the Grafton Village Cheese shop for a wonderful cheese tasting.

Work it all off by hiking the trails at the Retreat Farm and enjoy the food truck events they host in the summer. Finish it all up with a cold, local craft beer at either Whetstone Brewery or Hermit Thrush .

Fuel up for your adventures or car ride home at The Marina. This waterside restaurant offers canopy-shaded seating on the outdoor deck and water views are available from almost every seat inside as well. A juicy burger and seafood specialties like Rachael Ray’s beloved grilled, lime-marinated shrimp are among the many options available on its vast menu.

Need more ideas?

• Best kid-friendly museums in New England
• 110 Things to do in New England with kids
• Massachusetts bucket list
• Rhode Island bucket list

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Marissa is a lifelong Rhode Island resident and is currently a senior at Johnson & Wales University studying digital media and communications. She has a passion for storytelling and enjoys bringing experiences to life through her writing. Marissa has also written for Rhode Island Monthly and WPRI 12, and is the Media and Entertainment Editor for the Campus Herald at Johnson & Wales University.

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Publish Date: February 10, 2024

16 thoughts on “17 Memorable New England Day Trips Perfect for Every Season”

How about surfing day trip in Narragansett? A lot of people are saying that Narragansett offers the best surf in New England so it’s worth checking out. There are also a lot of day trips that you can do in and around Narragansett is surfing is not your thing. 🙂

My daughter tried surfing there this summer and loved it.

My hubby and I have wanted to do a New England raodtrip for quite awhile – these look like a whole bunch of fun spots to hit!

Let me know if you do as I would be happy to make some great food recommendations too.

Great list of ideas for day trips! We haven’t done Old Sturbridge Village yet and we need to get on it! We’d also love to see Salem! I love exploring in our own backyard! So much to see.

New England is so rich in history and outdoor adventure for sure!

The only one we haven’t visited is Old Sturbridge. Great list otherwise! I grew up in Plymouth and now we drive between Newport RI and Plymouth every summer week!

Any favorite restaurants in either?

Quito’s seafood in Bristol. Down on Thames St.over looks the water. So yummy!

We actually did a few of these when my son was 3 and I was pregnant with my daughter. Seems a lifetime ago, and I’d love to go back and tour New England anew! Great suggestions!

GREAT LIST! I’ve been wanting to plan a few staycation trips for spring break in a couple of weeks, and this is going to be super helpful!

Cool — maybe you can suggest some others in CT for a summer list.

Honestly you ROCK! I have started to plan for Summer road trips and was looking for 1 to 2 day trips to enjoy with the family.

I am so glad! Hope this helps. I think I’ll do another for summer.

What a great list! We have been to a more than a few and agree – great places. And love the Jamestown idea – that might be our next trip! We also like Providence (agree – fantastic food) and have spent lovely days in Newport, RI, too.

Newport is definitely a good one, although a bit more fun as it gets warmer.

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Best weekend getaways in new england.

Known for its historical roots, rugged landscape, savory seafood and rich sports culture, New England is home to a variety of vacation destinations. But with so many picture-perfect towns spread from the coast to the mountains, it's hard to decide where to head for a weekend getaway. That's why U.S. News took into account sights, culture, food and more to determine the best weekend getaways in New England. Cast your vote below to help us decide next year's ranking. Considering a fall trip to New England? Read our top travel tips »

Newport, RI

Portland, me, martha's vineyard, acadia national park, kennebunkport, white mountains, block island, the berkshires, sugarloaf mountain.

Visitors heading to Newport, Rhode Island, will be treated to breathtaking coastal vistas, glamorous seaside homes and top-notch sailing. Soak up some sun at Easton's Beach, or enjoy the sound of crashing waves while strolling the scenic Cliff Walk. If you'd rather treat yourself during your trip, hit up Thames Street, a bustling strip with delicious eateries, small boutiques and historic Colonial structures. Don't forget to save time for a tour (or two) of Newport's elaborate mansions, including The Breakers and Marble House.

An ideal destination for foodies and culture hounds, Portland, Maine, is filled with award-winning restaurants, museums, breweries, art galleries, boutiques and more. Spend some time wandering the cobblestone streets of the historical Old Port, where boats line the harbor and seafood is aplenty. Or, venture southeast of the city to Cape Elizabeth to snap a picture of the iconic Portland Head Light – one of the most photographed lighthouses in America – and hike or picnic in Fort Williams Park.

A popular summertime island retreat for New Englanders and politicians alike, Martha's Vineyard appeals to all types of travelers. Fly or take the ferry from the mainland to explore the Massachusetts island's six towns and numerous beaches. Don't miss the colorful gingerbread cottages in Oak Bluffs, the fresh seafood in the village of Menemsha or the boutiques in Vineyard Haven. While the island's eastern side is walkable, it's best to take a bus or car to the dramatic Aquinnah Cliffs on the more rugged western side.

Many pass through Bar Harbor on their way to Acadia National Park , but this charming seaside town is definitely worth a stop. Located on Maine's Mount Desert Island, Bar Harbor is bursting with locally owned boutiques, fresh seafood restaurants and gorgeous coastal views. Walk the scenic Shore Path for views of Frenchman Bay and multimillion-dollar mansions, or take a ride on a lobster boat to learn about the craft firsthand. While the town is popular in summer, its smaller crowds and vibrant foliage in autumn make it equally appealing during the shoulder season.

For a quintessential New England getaway, head to this Massachusetts peninsula known for its laid-back vibe. Vacationers can bask in the sun somewhere along Cape Cod National Seashore's 40 miles of sand before digging into a plate of fried clams or retreating to a quaint bed-and-breakfast . When planning your visit, keep in mind that each Cape Cod town is a little different. You'll find upscale shops in Chatham, historical landmarks in Sandwich, sky-high sand dunes in Wellfleet and a thriving LGBTQ community in Provincetown. Cape Cod's ample restaurants, boutiques, art galleries and ocean views are enough to keep you busy for days.

In the mood for an adventure? This more than 47,000-acre national park in Maine, one of the state's top attractions , is perfect for hiking, biking and rock climbing, among other outdoor activities. Your top priority should be to hike 1,530-foot-tall Cadillac Mountain – it's the first spot in the country to catch a sunrise from October to March. If you're not a fan of hiking, rent a car and make the drive along the 27-mile Park Loop Road. You'll pass the dramatic edge of Otter Cliffs and the cave at Thunder Hole, as well as other wonders visible from the road's pull-off observation areas.

The largest city in New England is fairly compact and walkable – perfect for sightseeing in just a few days. History buffs can follow the Freedom Trail to learn about the American Revolution before stopping for a beer at the historic Bell in Hand Tavern. Foodies can get a taste of Italy in the North End or indulge in some fresh oysters and clam chowder in the Seaport District. Meanwhile, fashionistas can browse the many shops on Newbury Street, and souvenir hunters can visit Faneuil Hall Marketplace. No matter your interests, your trip to Boston would not be complete without visiting Fenway Park.

Despite its small size, Nantucket has no shortage of activities. Board a ferry from Cape Cod or fly into the island's airport to enjoy a unique Massachusetts vacation. Visit Cisco Brewers for private brewery, vineyard and distillery tours, or simply enjoy the food trucks and live music. While Nantucket is a walkable island, many visitors enjoy renting bikes or mopeds to explore the area, especially tiny Siasconset Village. You'll want to also save time for watching the sunset at Madaket Beach on the island's west coast.

It doesn't get more relaxing than Kennebunkport, Maine. You can lay on sandy beaches, stroll through quaint boutiques and sample local specialties like lobster rolls, oysters and blueberry pies. There are also plenty of unique ways to see the town, including on foot during a food tour, by boat while on a lobster boat tour and by trolley with Intown Trolley. Plus, you can stop along the way to take pictures of Walker's Point – the Bush family compound. Keep your eyes peeled for other famous faces, as Kennebunkport is a popular celebrity vacation destination.

Although Stowe's small-town charm and dramatic vistas make it a beautiful destination year-round, snow lovers won't want to miss this Vermont retreat in all its winter glory. Stowe is dubbed the "Ski Capital of the East," but this New England hideaway is also ideal for snowboarding, snowshoeing and dog sledding. If you'd rather visit during the warmer months, consider hiking the Stowe Recreation Path or driving the Auto Toll Road to the top of Mount Mansfield for unbeatable views of the Adirondack Mountains. Whichever season you prefer, fans of "The Sound of Music" can't miss a visit to Stowe's Trapp Family Lodge.

If historic walking tours, charming bistros and tax-free shopping describe your ideal New England weekend, book your ticket to Portsmouth, New Hampshire, today. Take a narrated boat tour of the Isles of Shoals, or spend the day exploring Market Square, the gem of downtown Portsmouth. For a breath of fresh air, sink your toes in the sand at nearby Wallis Sands State Beach or stroll through the gardens at Prescott Park. Time your visit for summer to attend the Prescott Park Arts Festival, which transforms this beautiful green space into a vibrant outdoor performance venue.

Whether you're looking for a quiet mountain hideaway or an activity-filled weekend, potential abounds in the White Mountains. Designated as a protected national forest, the White Mountains cover parts of New Hampshire and Maine. Take the scenic route along the Kancamagus Highway, and consider stopping at a campground along the way. If you're visiting in summer, hike, drive or take the Mount Washington Cog Railway to the summit of its namesake for spectacular views. In winter, shred powder on some of the best ski slopes in New England before curling up with a cup of hot cocoa at a bed-and-breakfast.

Walk any direction on Block Island and you'll end up at a free public beach. This oasis off the southern coast of Rhode Island features 17 miles of shoreline, as well as old-fashioned cottages and two historical lighthouses. Take in sweeping ocean views from Mohegan Bluffs, or look for animals at Block Island National Wildlife Refuge. If you want an adrenaline rush, try snorkeling in the island's crystal-clear waters, biking around its picturesque perimeter or hiking its Clayhead Trail. A quick ferry ride from the mainland will take you to Block Island, making it an easy weekend retreat.

The rolling mountains of the Berkshires attract everyone from artists to nature lovers to city dwellers looking for an escape. This region of western Massachusetts has long been a culture and history hub. Charming towns like Great Barrington and North Adams draw visitors with their quaint main streets and historic homes. The town of Lenox is home to the famous Tanglewood concert venue, while the town of Pittsfield boasts many theaters and art galleries. You'll find a variety of festivals to attend in summer, vivid foliage in fall and plenty of skiing in winter.

Situated in western Maine's Carrabassett Valley, Sugarloaf Mountain has a lot to offer travelers looking for an exciting weekend getaway in New England. In winter, enjoy a range of cold-weather activities – including cross-country skiing, snowboarding, snowshoeing, ice skating, tubing and more – at the mountain's namesake ski resort. In summer, take advantage of the warmer temperatures by mountain biking, zip lining or hiking sections of the famous Appalachian Trail.

About 20 miles northeast of Boston, this Massachusetts town is best known for the witch trials of the late 17th century, which you can learn all about on a historical walking tour. For an even bigger dose of local culture, visit in October when the town hosts Halloween-themed events all month long. You'd also be remiss to skip top sights like the Peabody Essex Museum and The House of the Seven Gables, the setting of Nathaniel Hawthorne's 1851 novel of the same name.

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31+ Ideas For Family Day Trips in New England

Posted on Published: 03/21/2023

Summer is a great time for a day trip, although you may be up for a day trip any time of year. If you, like me, live in the Northeast, there are so many options for New England day trips, including a bunch of quaint New England cities and towns .

Here are some great ideas including destinations and attractions that you may consider for family day trips in New England. If I’ve missed your favorite, leave me a comment below, and I’ll update the post.

This post includes affiliate links. A purchase/click through one of these links may result in a commission paid to us at no additional cost to you.

Admission to some of these attractions was offered on a complimentary basis for review. All opinions are my own. Please review the specific attractions’ websites before departing for your day trip, as operating days and hours are always subject to change.

Day Trips in New England

Learn about history.

New England offers many historical attractions, so head out and do some learning on your vacation. Of course, Plimoth Patuxet Museums is a popular spot for anyone looking to learn about Plymouth. Old Sturbridge Village in Sturbridge, MA is another living history museum that is great for families to visit.

These living history museums can be a great way for kids to learn about history without even realizing it. If you visit Plimoth Patuxet Museums, you can also purchase tickets to the Mayflower II, a replica of the original Mayflower. While I don’t necessarily think it’s an essential add-on, it is an option.

To learn about United States history, you can also check out the Freedom Trail in Boston, as well as the Boston Tea Party Ship and Museum . For something a little different, head south to Fall River, MA to Battleship Cove , where you can explore the USS Massachusetts.

Salem, MA is another of my favorite places to visit for a day trip. This town by the water is the home of the Salem Witch Trials. In addition to the various museums dedicated to this history, you’ll also find historic homes, shops, restaurants, museums, and more.

Salem is especially busy in October, before Halloween. But, it can be a fun place to visit any time of year, especially in the summer.

Visit the Beach for a Day Trip in New England

Beach days are always fun in the summer, and New England is filled with dozens of them. Whether you visit a saltwater ocean beach, like Horseneck Beach in Westport, MA, Ogunquit Beach in Ogunquit Maine , or Nantasket Beach in Hull, MA, or a pond or lake, a day at the beach can be a great way to cool off in the heat.

Remember that the most popular beaches can fill up in the summer months, so arrive early and check online to learn about what facilities are offered.

In the summer, you may consider taking a day trip down to Cape Cod , where you’ll find miniature golf courses, delicious restaurants, and of course, world-class beaches. Again, these beach parking lots fill up quickly on peak days, so you’ll want to arrive early. 

If you are staying at a hotel or vacation home in Cape Cod, Martha’s Vineyard or Nantucket can be a great day trip. You’ll just want to book your ferry in advance because they sell out in the busy months.

Go to a Museum

New England, especially the Boston area, is home to numerous fantastic family museums. With younger kids, check out the Boston Children’s Museum in Boston , the  Children’s Museum in Easton , MA or the Discovery Museums in Acton , MA.

There are also so many fantastic art museums in New England. Art lovers will enjoy the Yale University Art Gallery in New Haven, CT , the Boston Museum of Fine Art, the Peabody Essex Museum in Salem, MA, and the or the Portland Museum of Art in Maine .

For more of a science and/or natural history experience, there are options in Cambridge, MA (the Harvard Museum of Natural History ), Boston (the Boston Museum of Science),  New Haven, CT (the Yale Peabody Museum of Natural History ), and the Montshire Museum of Science in Vermont.

The Newport Mansions in Rhode Island are a fun place to visit, even if you are traveling with kids. These homes, which are the former summer homes of many famous families, offer audio tours. The Breakers has a family audio tour that is especially great for kids. You can also take a walk along the Cliff Walk for beautiful views. There’s also Fort Adams State Park in Newport, which offers gorgeous views.

West of Boston, you’ll find the Basketball Hall of Fame in Springfield, MA. You may also consider the Amazing World of Dr. Seuss Museum, which is also in Springfield. 

Check out more things to do in New Haven, CT , and Portland, ME .

Get Great Prices While Outlet Shopping

With the back-to-school season coming up, it may be a good time to start shopping. There are lots of outlet malls in the New England area. My favorites are Settlers Green in North Conway, MA, the Wrentham Premium Outlets in MA, the outlets in Kittery, Maine , and the Merrimack Premium Outlets in NH.

Remember that there’s no sales tax in New Hampshire, so if you are planning to buy lots of things, it may be worth it to go to one of the New Hampshire outlet malls for shopping. 

Go to an Aquarium

The New England area offers several world-class aquariums. Right in downtown Boston, you’ll find the Boston Aquarium. It’s located right on the water and also offers an IMAX theater. 

There’s also a wonderful aquarium in Mystic Connecticut – the Mystic Aquarium. Although it’s smaller than the Boston Aquarium, it’s got some great exhibits including my favorite – the beluga whales pictured above! The Mystic Aquarium has both indoor and outdoor exhibits that are great to visit in the spring and summer months. Mystic is a great New England town to visit.

Visit a Theme or Water Park

Story Land (Glen, NH), Six Flags (Agawam, MA), Santa’s Village (Jefferson, NH), and Canobie Lake Park (Salem, NH) are just four of the theme/amusement parks that you can visit with your kids this summer in New England.

There are also several outdoor waterparks, like Water Country (Portsmouth, NH), Whale’s Tail ( Lincoln, NH ), and Water Wizz (East Wareham, MA).

Younger kids will love visiting the Edaville Family Theme Park. However, in recent years it has had a limited opening, and it’s unclear if it will be reopening in the summer or just for the holiday season.

Shop at Boutiques

My daughter and I love shopping at small boutiques, and there are lots of quaint shops throughout New England. Some of our favorite places to walk around and shop are Portsmouth, NH, Portland, ME , Rockport, MA, Chatham, MA, and Newport, RI. In the summer, it can be nice to enjoy the outdoor weather as you go from store to store.

Have an Outdoor Adventure

New England is home to so many fantastic places for outdoor adventures. I love Purgatory Chasm State Reservation in Massachusetts and the many hiking trails in the White Mountains of New Hampshire and the Green Mountains of Vermont. In the summer, you can also take a boat ride or a Whale Watching tour, or even visit a cranberry bog for more outdoor fun.

I’d definitely recommend taking a day trip over to the Boston Harbor Islands, where you can swim, explore, and learn about nature in this state and national park. Before you take the public ferry, look at their website to see the different islands to visit. They are all different and have various activities so you’ll want to know in advance which one you plan to visit.

If you enjoy skiing, there are so many options, especially in Maine, New Hampshire, and Vermont. Some of these mountains offer summer activities as well.

One of the more popular summer destinations is Cranmore Mountain in North Conway, NH, which has a mountain adventure park. It includes a chair lift ride, a seated zip ride, and a mountain coaster.

Another popular spot for a family vacation is Acadia National Park, located in Maine. It’s more of a drive from the Greater Boston area, but worthwhile if you haven’t been to that part of the state. If you are driving from Boston, you will probably want to stay overnight at least to make the drive worthwhile.

What is your favorite New England day trip?

See more New England vacations here .

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Saturday 1st of July 2017

I think you meant Glen, NH (not, MA) for Story Land! Also- the Tanger Outlets in Tilton, NH are awesome-great, great deals and many high-end Brand Name Store (e.g. Coach, J. crew, Banana Republic to name a few). They also have a nice catergory variety for a one-stop shopping experience' from Bath & Bodyworks to an Old Navy Outlet to several children's clothing stores (Gymboree, The Children's Place, Carters, etc.) to a few different shop options for underwear/lingerie, and (not nearly last) right within the plaza lot are a choice of dining options for you (and the family) too! Speaking of family, there's an outdoor playground situated in a main corner between two long Store-strips for when the kiddos get restless! While you're in the area, Laconia offers up the country's (world's?) largest arcade complete with a full bowling alley, small diner/restaurant, and Bingo hall! Of course now I have to mention Weir's beach- a beach with a strip, boardwalk with more arcades, ice cream shops, and (one of the last standing) drive in movie theatres! I could go on and on and on; the entire surrounding area is surrounded with entertainment for families of all kinds and interests!

Jodi Grundig

Tuesday 4th of July 2017

Thanks so much for your comment. You are right - it is definitely Glen NH! Thanks for that. I haven't been to the Tanger Outlets in Tilton, NH in years - but I definitely remember it being a great spot (and you can't beat tax-free)! I also have such fond memories of Weir's Beach because we used to go when I was a kid, but I haven't been back with my kids.

Adventures in New England

A local's guide to savoring the history, culture, food and nature of the Northeast USA

15 Fabulous Day Trips in Connecticut

Connecticut is in southwestern New England. It has a big city, fancy suburbs of New York City, a pretty coastline, and rural farmland. I did my residency in Hartford and lived just north of that area for about 5 years. Since Connecticut borders Rhode Island, I still visit often for day trips. Below are a few of my favorite Connecticut day trips.

Table of Contents

The historic boating town of Mystic has an aquarium, cool balancing bridge, colonial seaport, and quaint downtown.

Read on for more things to do in Mystic, Ct.

Hike to Hublein Tower, Simsbury

A 1.25-mile hike through Talcott Mountain’s woods brings you to this tower with sweeping views of Connecticut, including Hartford.

Talcott Mountain is one of my top ten New England family hikes.

West Hartford Center

If you are in the mood to spend a day shopping and eating, West Hartford is the place to be. Here you can find almost any store you can think of. My favorite Connecticut restaurant, Restaurant Bricco , is on LaSalle Road.

New Haven is the Ivy League school’s home, Yale, and the home of some delicious wood-fired pizza. There is some controversy about who has the best, but the original is at Frank Pepe Pizzeria Napoletana. There are often long lines, so it is good to show up right when they open. One of their most popular pizza is the white clam. While in town, visit the museums of Yale, such as the Yale Peabody Museum of Natural History.

Southwestern Connecticut

If you want to explore Connecticut’s rural side, try a road trip around the southwest corner of the state where you can drive past farms, go antiquing, visit wineries, and hike to waterfalls.

Read more about spending a day in rural southwestern Connecticut.

Connecticut Wine Trail

You can see the whole state, as well as have an amazing day visiting Connecticut’s 40 wineries, but of course, you would need a designated driver and drink safely.

You can read about my day with the girls at Jonathan Edwards Vineyards.

A Day at Lavender Pond Farm, Killingworth

If you are in Connecticut in June or July, spend a peaceful day among the blooming, fragrant stems. The farm has chairs and games to play as well. This farm is on my list of the best flower fields around New England.

Clyde’s Cider Mill, Old Mystic

If you are visiting in the fall, be sure to join the party at Clyde’s Cider Mill, where you can see cider being pressed by a room-sized antique press and eat apple cider donuts. Right up the road, visit Whitehall Cemetery with graves dating back to the 1600s.

Sharpe Hill Winery, Pomfret

Start your day at the Lavender Hill Alpaca Farm in Voluntown. After getting your fill of these frilly-headed animals. Then take a hike around the Connecticut Audobon Society Bafflin Sanctuary. End your day with a wine tasting and dinner in Sharpe Hill’s beautiful old barn.

Lake Compounce

Read more about spending a day at Lake Compounce, the oldest continually running amusement park in the United States.

Devil’s Hopyard

Devil’s Hopyard is one of my favorite picnic spots in New England. On the two-mile hike, you can see a waterfall, covered bridge, and sweeping green views.

Explore the Connecticut River Valley

Take a boat ride on the river, explore Gillette Castle, take a train ride, or shop and eat in the charming town of Essex.

Read on for how to spend a day in this area.

Visit Old Saybrook

Get a spa treatment at the Saybrook Point Resort and Spa. Walk through the Monument Park. Enjoy lunch on Main Street. A few of my favorite restaurants are the Penny Lane Pub or Liv’s Oyster Bar. Finish your day with a walk by the ocean or a peek at the Lynde Point Lighthouse.

Spend a Day at the Florence Griswold Museum, Old Lyme

Around the turn of the twentieth century, Florence Griswold was running a boarding house on the Lieutenant River banks drawing painters to the area. This was the Lyme Artist Colony, the beginning and hub of American Impressionism. The house is open for touring, as well as a garden and a museum housing a large collection of impressionist paintings. Be sure to leave time for lunch on the veranda overlooking the river.

Mark Twain House

This gothic-style house in Hartford is where Samuel Clements raised his family. There are three buildings to tour, including the house.

I hope you enjoyed this list of day trips in Connecticut. I will continue to add to it as I think of more.

Did I miss any of your favorites? Please let me know in the comments.

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7 thoughts on “15 Fabulous Day Trips in Connecticut”

I live in Boston, these are some really great things to see in CT. I love Mystic, it’s one of my favorite towns in New England. I actually wasn’t aware if the Lavender Fields, I’m going to need to check those out some year.

Those are some great ideas for day trips. I think I should like to do them all – from the lavender to antique hunting to the wine trail. Mystic has always been intriguing to me, and those waterfalls in Devil’s Hopyard looks so scenic.

I have only done Mystic and its outdoor seaport museum in my only day in CT and I really do need to go back to the state to check out the natural beauty (or maybe the changing of the colours in the leaves in the fall). I am loving the waterfalls in Devil’s Hopyard and would defo want to check these out. One place I would like to go is Hartford for a bit of history, as the founder of the town is from a town very near to my home in Hertford, in the UK. 🙂 So there is a little bit of a connection for me, not much, but its enough for me to get myself into gear and visit CT again 🙂

That is cool that you live near our founder. I didn’t know the origin of the name Hartford.

I have never been to Connecticut and this post makes me want to spend a week just exploring the day trips. I would first explore Devil’s Hopyard. A two-mile hike isn’t too bad especially if you get views of a waterfall and bridge. I’ll have to see if it’s pet-friendly too. I’m sure my pup would enjoy this hike as well.

This is a part of the US I’d really like to explore more! I didn’t know that Connecticut had a winery scene but checking out some of them sounds like a lot of fun! Mystic also looks like an interesting little town. I checked out your other post and the drawbridge does look unique with those concrete slabs!

There is also. Harkness park in Waterford Connecticut. it’s a mansion that used to Belong to a rich family. there is Alot to see. it’s surrounded by the ocean. flower gardens . it’s beautiful. Look it up!

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20 Best Weekend Getaways in New England

From charming small towns to mountain escapes, these are the best places in New England for a weekend trip.

Anne Olivia Bauso is a travel writer and hotel expert based in New York City. She has written hundreds of hotel reviews, from 5-star Ritz-Carlton properties to treehouse eco-resorts in the jungle.

With prettier-than-a-picture countrysides, cliff-lined coasts under the watchful beams of centuries-old lighthouses, and countless small towns to stumble upon, New England is a region that merits a lifetime of getaways, weekend or otherwise. Whether you’re looking for a quick escape from the city or a romantic trip, here are 20 of the best weekend getaways in New England.

Block Island, Rhode Island

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With its towering bluffs, plains filled with native shrubs, and grand Victorian-style hotel , Block Island looks like it could really be in England. The cedar-shingled saltbox houses are what clue you back to the fact that we’re in New England, not some wind-swept corner of the U.K. Located 13 miles off the coast of Rhode Island, this quintessential seaside getaway is just as much about cruising down country lanes and walking through open heathland as it is visiting the beach.

Mad River Valley, Vermont

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Below the famous Sugarbush and Mad River Glen ski areas, the Mad River Valley is a particularly pretty nook of Vermont. And that’s on top of a surprisingly glam history (Sugarbush was once dubbed “Mascara Mountain” by Vogue due to all the fashionable model types frequenting its slopes). The skiing’s still good around these parts, but there’s also fun off-the-slopes stuff like mountain biking, farm stand shopping, and summer concerts.

Nantucket, Massachusetts

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Reverence for this 50-square-mile fleck off the coast of Massachusetts runs deep, especially when it comes to summer getaways. But forget the cars and chain restaurants that clog your typical beach scene. Instead, hop on a bike or island shuttle to visit historic lighthouses (the still-in-use Brant Point dates back to 1746!), grand homes built for whaling captains, and laid-back beaches. Refuel every few hours with a lobster roll or perfectly prepared bay scallops before spending the night at a waterfront resort like the White Elephant Nantucket .

Newport, Rhode Island

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Fans of HBO’s Gilded Age owe themselves a trip to Newport, the summer vacay spot of choice for the late-19th-century elite. Take a stroll down the Cliff Walk to see Newport’s lavish mansions on one side and the Atlantic Ocean crashing against rocks on the other. The 3.5-mile path works up an appetite, so you’ll be ready to feast like a Vanderbilt: do the (BYOB!) brunch at Cru Cafe or go big with lobster mac ‘n’ cheese at local landmark, Brick Alley Pub.

Sugar Hill, New Hampshire

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City folk looking for a slow pace and gorgeous scenic views find lots (and lots) to love in Sugar Hill. The sight of brilliant fall colors or fields blanketed in deep purple lupines — set against New Hampshire’s rugged White Mountains — is like a massage for your optic nerves. At Harman’s Cheese & Country Store, scoop up crackers and a hunk of aged cheddar to stash in your pack before hiking to Bridal Veil Falls (via the family-friendly Coppermine Trail) or summiting Mount Lafayette (Skookumchuck Trail is a toughie, but it’s well rated by hikers). 

Camden, Maine

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Often called one of the most beautiful small towns in the U.S. , Camden is a popular filming location for TV shows and Hollywood films. After enjoying a big bowl of haddock chowder on the harbor, peep the handsome Queen Anne-style houses in the historic district or make your way up to the top of Mount Battie, where the view inspired Maine native Edna St. Vincent Millay to write one of her finest poems. And remember, it’s not a trip to Maine without some quality antiquing: peruse the treasures inside Antiques at 10 Mechanic.

Martha’s Vineyard, Massachusetts

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Think of it this way: getting there is half the fun. Sure, the ferry to Martha’s Vineyard, sister island to Nantucket, can be a bit of a test for landlubbers, but once you disembark, you’ll find a treasure trove of seaside villages, bike paths, and A+ lobster rolls. First stop: Waterside Market, where yummy breakfast sandwiches are served all day (or opt for lobster salad on brioche straight out of the gate), then grab a cab or bike over to Oak Bluffs for beach time and frozen drinks at Nancy’s. Spend a day in pristine little Edgartown, with its indie shops (Edgartown Books is a real treat, as is the hidden cafe behind it), raw bars, Greek Revival mansions, and charming boutique hotels like Faraway Martha's Vineyard .

Lakes Region, New Hampshire

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Woods, rocky summits, and hundreds of lakes and ponds set the scene for this ridiculously pretty area surrounding Lake Winnipesaukee, New Hampshire's largest lake. Set in the White Mountain foothills, the region seduces leaf-peepers, walkers, boaters, cyclists, and off-roaders in search of abundant outdoor activities.

It’d be a shame not to get on the water in the warmer months, so hop aboard one of M/S Mount Washington ’s daily scenic cruises for a mimosa and postcard-worthy views of the surrounding mountains. Hikers have 28 miles of trails to explore at Castle in the Clouds and boundless views to enjoy at the top of Belknap Mountain, the highest peak in the area.

Woodstock, Vermont

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Dotted with old covered bridges, quaint cafes, and Victorian homes, Woodstock is the epitome of an idyllic New England town. At Billings Farm and Museum, say hi to the Jersey cows and draft horses, enjoy a maple sundae, and grab some smoked cheddar to go (it’ll make a tasty trail snack). Prue and Paul fans: Hop over to the neighboring town of Norwich to channel your inner Great British Baking Show contestant with a pie- and-tart-making class at King Arthur Baking Company.

Great Barrington, Massachusetts

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Part of the Berkshires, Great Barrington looks straight out of a Louisa May Alcott novel. Everywhere you look are storybook old buildings now housing bakeries, upscale grocers, and farm-to-fork restaurants. (During the holidays, the town looks like the real-life version of a snow globe.) See what’s going on at Mahaiwe Performing Arts Center, a 1905 theater hosting everything from classic flicks to big-name bands.

Bar Harbor, Maine

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Once upon a time (in the late 1800s), Bar Harbor was a summer oasis for the Vanderbilts, Rockefellers, Astors, and other VIP members of society looking to beat the heat. The appeal of this place takes no imagination; Bar Harbor is a quaint small town on Frenchman Bay and a gateway to Acadia National Park. Take a warm-up stroll along Bar Harbor’s shore path before diving into moody Acadia, where rocky shores and 150 miles of hiking trails await.

Portsmouth, New Hampshire

Drive about an hour north of Boston, and you’ll find the darling town of Portsmouth. Kick off a walking tour at Market Square, hit the Portsmouth Harbor Trail, and dedicate a couple of hours to Strawbery Banke Museum — an outdoor museum with historic structures and costumed actors bringing three centuries of history to life. Reward yourself with the oyster happy hour and a cold local Smuttynose at Row 34 before moving on to dinner at Black Trumpet, a bistro and wine bar.

North Adams, Massachusetts

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Art lovers have streamed into North Adams since 1999 when Mass MoCA opened in a previously abandoned 19th-century mill. Bed down at the art-filled Hotel Downstreet or The Porches Inn, a series of Victorian homes that once housed textile workers. The draws of this small Berkshires city don’t end with Sol Lewitt’s wall drawings and Michael Oatman’s installation art, on view at Mass MoCA. Outdoor options include seeing the continent’s only natural white marble arch at Natural Bridge State Park and hiking Mount Greylock, the highest mountain in Massachusetts. 

Westerly, Rhode Island

Westerly may not have quite the vacay clout as Newport or the Vineyard, yet the coastal town balloons in the summer with beachgoers looking to hit Narragansett Bay and Misquamicut State Beach. For a quintessential New England weekend getaway, spend at least an afternoon in the ocean-view neighborhood of Watch Hill, visiting its 1850s lighthouse and walking along the pristine beach at the Napatree Point Conservation Area.

Provincetown, Massachusetts

Journey to the farthest-flung tip of Cape Cod, and you’ll be rewarded with some of the area’s best stretches of sand, cool boutiques and art galleries, and an enchantingly funky and bohemian vibe. This LGBTQ-friendly town has something for every mood, whether it’s drag karaoke, dance parties, and pub crawls that strike your fancy or catching the sunset on Herring Cove Beach.

Jackson and North Conway, New Hampshire

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These sister towns in New Hampshire’s pretty Mount Washington Valley make a popular getaway, thanks to their waterfall hikes, scenic drives, small-town shopping scene (Schartner Farms has a drive-up, honor-system jam stand — how cute is that?), and big-box outlets. 

On the highway between the two towns is Sunrise Shack, an old-school drive-in restaurant that's now a roadside staple for truly enormous breakfasts. After a summer swim at Echo Lake State Park or a challenging hike on Mount Chocorua, indulge in the biggest cone you’ve ever seen at Trails End Ice Cream.

Mystic, Connecticut

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History lovers looking for a fun-filled weekend getaway in New England will likely love this former shipbuilding hub. The Mystic Seaport Museum is a fascinating jumping-off point, with its million-plus artifacts depicting the town’s nautical life — you can even test out your sea legs on vessels like the Charles W. Morgan, the last wooden whaling ship that remains in the world today.

Appreciate the Long Island Sound and Fisher’s Island views at Bluff Point State Park and feast on some of the best seafood around at Oyster Club. Our perfect meal? Smoky Rhode Island clam chowder, dashi-buttery roasted oysters, and the homemade bucatini.

Montpelier, Vermont

Nestled in the foothills of the Green Mountains, the country’s smallest state capital by population brims with opportunities for nature activities, from hiking up the 4,000-foot peak of Camel’s Hump to whitewater rafting on the Winooski River. Of course, no trip to this neck of the woods is complete without a taste of what it does best. At Morse Farm's and Bragg Farms' maple sugar houses, you can sample the Vermont specialty in the form of maple cookies, kettle corn, or “creemee” (Vermontese for soft serve).

Kennebunkport, Maine

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Like Mystic, Kennebunkport boomed as a shipbuilding hub during New England’s maritime heyday. The coastal town’s nautical vibe lives on, with glossy Italian-built yachts bobbing in the harbor and authentic schooners sailing toward the Atlantic. Kennebunkport swells in the summertime with New Englanders flocking to its beaches, but the town’s boutiques, cafes, and art galleries have year-round appeal.

Litchfield, Connecticut

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Litchfield is a small town that more than carries its weight on the history, charm, and scenic beauty fronts. This picture-book spot in rural western Connecticut (birthplace of Revolutionary leader Ethan Allen and abolitionist Harriet Beecher Stowe) has an oak-shaded town green and hundreds of historic buildings. The vast Topsmead State Forest is a favorite area for hiking and picnicking and was originally the summer estate (complete with a Cotswold-style cottage and formal gardens) of banking heiress Edith Morton Chase.

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 quite a few fall foliage road trips and even more fall getaways. It took me a while, but I’ve finally put together the perfect itinerary for you based on real experience.

This post details the best places to visit in New England during fall foliage season that are worth the hype, 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!)
• Best Time To Visit Acadia National Park

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! It’s one of the first places in the U.S. to see the sunrise, depending on the time of year, and starting October 7 through March, it’s the very first spot in the country to see the sun come up. 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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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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10-Day New England Road Trip Itinerary

• New England offers a variety of destinations for a memorable road trip, including Boston, Cape Cod, Providence, and more.
• Boston, Massachusetts, is one of the best New England road trip stops, known for its historical landmarks and museums, although it can be pricey and congested.
• Bar Harbor, Maine, is a must-visit when road-tripping New England in 10 days; it's perfect for nature enthusiasts, as it's home to Acadia National Park, while Portland, Maine, is a charming waterfront city with a blend of history and innovation.

The moniker of New England brings a great deal of curiosity to those looking for a new area of the world to explore. As a collection of states spanning Maine, Connecticut, Massachusetts, Vermont, Rhode Island, and New Hampshire, ample opportunities exist to take in all the area has to offer through an old-fashioned road trip.

Deciding on a route that will accommodate the top destinations New England has to offer is half the battle. The 10-day road trip below combines heritage, entertainment, and cultural opportunities to ensure a well-rounded and memorable vacation. All that's left to do is to buckle up and enjoy the adventure yet to come!

Related: These Are The 14 Most Beautiful Places To Live In New England

Boston, Massachusetts

Boston has exceptional museums, restaurants, and landmarks to visit on a road trip.

Boston is the start for those looking to road trip New England in 10 days; it's one of the oldest cities in the United States and bears much historical significance. Founded in 1630 by John Winthrop , the area was brought forward by Puritans settling in the new country of America.

Today, the capital of Massachusetts is known for its European feel; plus, Boston's many famous landmarks are a major draw for tourists, like the Bunker Hill Monument , the home of Paul Revere, Fenway Park (the home of the Boston Red Sox) , The Freedom Trail , and Boston Common . Visitors to the area can partake in tours of the U.S.S. Constitution , The Boston Tea Party Ships and Museum , and Old North Church .

Boston is known for being quite pricey when it comes to accommodations and entertainment, so it's best to budget accordingly. Parking and traffic can also be a challenge. However, Boston is a walkable city, so it's easy to leave one's vehicle behind and explore on foot.

Cape Cod, Massachusetts

Enjoy fantastic restaurants, hundreds of miles of seashore, and historic museums.

Many look at Cape Cod, Massachusetts, as an idyllic and tranquil seashore destination that allows for adequate relaxation and an opportunity to take in the historical and cultural significance of the area. Located on Route 6A, a historic highway that has achieved National Scenic Byway Status , Cape Cod is home to many different lighthouses, whale-watching recreation, optimal hiking and birdwatching, and multiple art museums.

Those who stop in Cape Cod can particularly enjoy the Cape Playhouse for local theater performances and the Cape Symphony for timeless musical concerts.

• Distance: 70 miles from Boston
• Road Trip Length: Approximately 90 minutes

Providence, Rhode Island

Locals refer to providence as "the creative capital" due to its small-town charm and simultaneous big-city vibes.

Although it is well-known as the smallest state in America, Rhode Island isn't one that should be ignored. The tiny spot on the map packs in over 400 miles of coastline, earning Rhode Island the nickname "The Ocean State" . Located next to the Atlantic Ocean, vacationers will have their fair share of freshly caught seafood to enjoy during their visit.

Besides food, there are plenty of fun things to do in Providence as part of a New England road trip itinerary; stop at the Roger Williams Park Zoo for a day of exploring or go for a ride with Providence Kayak . Locals and guests alike will also appreciate the many local boutique shops and community events.

• Distance: 82 miles from Cape Cod

Related: 10 Beautiful Coastal Stops On A Road Trip In New England

New Haven, Connecticut

The ultimate blend of college town and seaside retreat.

New Haven, Connecticut, is the perfect blend of a college town and a seaside retreat. Younger generations come to advance their education while families, retirees, and vacationers appreciate the beauty the Long Island Sound provides to the area. With the addition of Yale University , the Ivy League establishment has brought multiple museums to the city, including the Yale University Art Gallery, Yale Center for British Art, and the Yale Peabody Museum.

Other points of interest within New Haven include public parks. Two of the most popular recreational areas include East Rock Park and Lighthouse Point Park . Another top contender is Edgerton Park , which is built on a demolished historical estate.

• Distance: 102 miles from Providence
• Road Trip Length: Approximately one hour and 45 minutes

The Berkshires, Massachusetts

Discover this mountain area's museums, orchards, breweries, wineries, and festivals.

There are many small towns and villages that make up the area that is called The Berkshires in Massachusetts. For those looking to learn more about the area, The Berkshires boasts over 100 cultural attractions . People visit the mountain area throughout the year, enjoying various recreational activities in different seasons.

There are many local festivals to take part in during a visit. Depending on the timing of the visit, there are ample orchards, breweries, and wineries to enjoy. Visitors also rave about the local boutique shopping, the Susan B. Anthony Birthplace Museum , Edith Wharton's Home , and Berkshire Art Museum .

• Distance: 78 miles from New Haven

Brattleboro, Vermont

Experience farm-to-table restaurants, a focus on all things local, and beautiful landscapes.

Another one of the fun stops on a New England road trip is the town of Brattleboro, previously known as Brattleborough , which is most commonly known to locals by the simple nickname of "Bratt".

One of the unique aspects of Brattleboro is that it's home to one of the top circus performance schools, NECCA . Visitors can also participate in activities frequently hosted on Retreat Farm ; this farm conservation effort is on 500 acres of forests, farms, trails, and waterways. Whether it's a guided round of "Hike and Seek" or craft beer and cheese tastings, people of all ages are bound to find a suitable activity.

• Distance: 93 miles from The Berkshires

Brattleboro, Vermont, is known as "one of the best small towns in America" and was the winner of the 2023 Strongest Town Award .

Burlington, Vermont

For those keen on ice cream and teddy bears, this stop is a dream come true.

The city of Burlington, Vermont, has an array of attractions to enjoy in a day when visiting as part of a New England 10-day road trip itinerary. The city boasts tons of amenities that suit any age; people can easily pack their days full of fun activities and sightseeing between the beautiful beaches, the various breweries, parks, and shopping centers.

Just a short drive away, road trippers can find the iconic Ben and Jerry's ice cream factory and the Vermont Teddy Bear Factory . Both attractions offer tours for a nominal fee. Visitors should not forget to check out the flavor graveyard at Ben and Jerry's, where the company has laid to rest their retired ice cream combinations.

Plus, a visit to Burlington isn't complete without checking out the Church Street Marketplace shopping center and the scenic overlooks sprinkled throughout the area.

• Distance: 151 miles from Brattleboro
• Road Trip Length: Approximately two hours and fifteen minutes

Related: 10 Cozy Towns To Retire To In Vermont

Bar Harbor, Maine

Although this leg is by far the lengthiest, a pit stop in this coastal town opens up acadia national park.

Home to Acadia National Park, the coastal area of Bar Harbor is outstanding for nature enthusiasts and is easily one of the best stops on a New England road trip route. Visitors have endless opportunities to enjoy hiking, swimming, biking, running, and more during a short stay in Bar Harbor. For those who aren't inclined to participate in such activities, the views of Acadia National Park are also worth the long drive.

Nature aside, Bar Harbor offers much more for locals and tourists to enjoy during their time in the city. The Seal Cove Auto Museum is a top destination, as well as The Natural History Center . Visitors can also enjoy a guided tour of the area through Oli's Trolley and participate in one of the many ghost walks that uncover the past of Bar Harbor.

• Distance: 339 miles from Burlington
• Road Trip Length: Approximately six and a half hours

Portland, Maine

By blending the present with the past, this waterfront city offers a combination of charm and innovation.

Next on the 10-day road trip itinerary for New England is Portland in Maine , which has a history of agriculture and shipbuilding; those two elements are still very present today. Nestled on a peninsula that enters the Casco Bay, visitors will be mystified by the laid-back approach to life that the locals enjoy. The waterfronts are home to many fishing piers that bring fresh seafood to the top-notch restaurants in the city, and the historical homes pay homage to the area's past.

Visitors can hop on a ferry that takes them around Casco Bay. A visit to Portland's many attractions , such as the Portland Observatory and Portland Museum of Art, gives a unique perspective to the cultural scene that is very prevalent in the area. To learn more about the beginnings of Portland, guests should pop into the Maine Historical Society for insight into the early days.

• Distance: 175 miles from Bar Harbor
• Road Trip Length: Approximately three hours

Portsmouth, New Hampshire

Take a break from the car with a visit to this walkable, historic city on the seacoast.

This walkable city on the coast is another one of the fantastic New England road trip stops. As one of the oldest cities in the United States, Portsmouth was settled in the early 1600s by founder John Mason. Today, the area has many attractions that speak to its unique elements and humble beginnings.

Visitors can enjoy the Strawberry Banke Museum, the Seacoast Science Center, and a tour of the Portsmouth Historic Sites, which include the former residences of prominent navy commanders and officials. Other noteworthy activities include a ride on a Portsmouth harbor cruise or taking in a show at The Music Hall.

• Distance: 52 miles from Portland
• Road Trip Length: Approximately one hour

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460 Years Ago, Shakespeare Was Born Here. Or Somewhere.

Every year, millions flock to Stratford-upon-Avon, England, to visit the house known as Shakespeare’s Birthplace. But was he really born there? A whole industry depends on it.

By Elizabeth Winkler

Sometime in the late 18th century, a sign appeared outside a shambly butcher’s hut in the English town of Stratford-upon-Avon: “The Immortal Shakspeare was born in this house,” it announced, using a then common spelling of his name. Devotees began making pilgrimages — dropping to their knees, weeping, singing odes: “Untouched and sacred be thy shrine, Avonian Willy, bard Divine!”

A tradesman grew rich selling carvings from a local mulberry tree, like pieces of the true cross. Some skeptics suspected that the sign was part of a scheme to bring visitors to Stratford; others wondered if it had been hung by the property’s occupant. A local antiquarian criticized the whole scene as “a design to extort pecuniary gratuities from the credulous and unwary.”

Pilgrims flocked to the house, and it became a site so hallowed that one visitor warned that the veneration of Shakespeare threatened to eclipse that of God:

Yet steals a sigh, as reason weighs/ The fame to Shakespeare given,/ That thousands, worshippers of him,/ Forget to worship Heaven!

About 250 years after its break from the Catholic Church, England had its own Bethlehem and manger.

The problem: No one really knows where Shakespeare was born.

Mock Tudors and magic wands

Stratford-upon-Avon lies two hours northwest of London in the Midlands, more or less the heart of England. Today, it is one of Britain’s most popular tourist destinations, drawing up to three million visitors a year. The Birthplace is its main attraction, followed by the cottage reputed to be the place where Anne Hathaway, Shakespeare’s wife, grew up.

Stratford exudes Elizabethan kitsch, with souvenir shops and half-timbered buildings. ​​In the 19th century, the Victorians tried to make Stratford look more “authentic,” which has left it teeming with mock Tudors.

It’s a town whose economy and identity revolve around Shakespearean fervor, which peaks every year on April 23, the date celebrated as Shakespeare’s birthday. It is also, conveniently, St. George’s Day , honoring the patron saint of England.

On my first visit in June 2021, I passed the Hathaway Tea Rooms and a cafe called the Food of Love, a cutesy name taken from “Twelfth Night” (“If music be the food of love, play on”). Confusingly, there were also several Harry Potter-themed shops. Stratford and Hogwarts, quills and wands, poems and spells . Then again, maybe the conflation was apt: Wasn’t Shakespeare a sort of boy wizard, magically endowed with inexplicable powers?

On Henley Street, I arrived at the Birthplace, a half-timbered house yellowed with age. Today, it looks like a single detached building, but it was originally a row of tenements. John Shakespeare bought one tenement on the street in 1556, though he also bought property on nearby Greenhill Street, which could just as easily have been the site of his son’s birth. He bought the property thought to be the Birthplace in 1575, 11 years after his son was born.

Those who believe in the Birthplace point to a record from 1552 showing that a John Shakespeare was fined for keeping a dung heap somewhere on Henley Street. It doesn’t specify the location, but that dung heap has fueled a theory that he must have been living there at the time of his son’s birth, perhaps as a renter.

Similarly, the claim for the authenticity of Anne Hathaway’s Cottage rests on a record that a John Hathaway leased the 90-acre farm on which the building stood 13 years before Anne was born in about 1556. The cottage may well be linked to the Hathaways, but there is no proof that Anne actually grew up in it, just as there is none that Shakespeare was born in the house on Henley Street.

Together, these traditions have sustained Stratford’s tourist industry, worth about $315 million in 2019, before the pandemic. But they have not convinced many skeptics over the years.

“Stratford permits — indeed encourages — one of the biggest frauds in England to rage unchecked,” the journalist Bernard Levin railed in The Daily Mail in 1965. “I mean those two monumental frauds, ‘Shakespeare’’s Birthplace and Anne Hathaway’s Cottage.”

It didn’t help that hucksters have found ways to make the story profitable. In the early 19th century, a tenant of the Birthplace named Mrs. Hornby ran a lucrative hustle showing and selling Shakespeare’s “relics” to gullible visitors. The relics were eventually exposed in an 1848 article in Bentley’s Miscellany , which observed that four different chairs, each purporting to be “Shakespeare’s chair,” had been sold over the years, each made by a well-known local craftsman.

I entered through the Shakespeare Centre, a strange museum that acts as an antechamber to the Birthplace. There were no books owned by Shakespeare or letters in Shakespeare’s hand, because none are known to exist. Instead, a glass case displayed eight Shakespeare busts dating from 1844 to 2000. Another case featured a Shakespeare beer mug (1933), Shakespeare playing cards (1974) and a Shakespeare action figure made in China (2003).

Inside the Birthplace, I went from room to room with the other visitors. Guides regaled us with tales of Shakespeare’s childhood — how he played and ate and dreamed in these rooms. Of course, his childhood is actually a yawning blank: From his baptism in 1564 to his marriage in 1582, there are no records of him. In one room, a table displayed books, quills and ink, indicating a family of learning — but his parents signed documents with a mark, like many illiterate people in Tudor England.

The other visitors murmured to one another in reverent museum whispers and nodded at the guides. I thought of how, in the late 19th century, a Birthplace custodian named Joseph Skipsey resigned his post after a few months, explaining that “not a single one of the many so-called relics on exhibition could be proved to be Shakspere’s” and that “the Birthplace itself is a matter of grave doubt.”

The power of popular faith

Efforts to preserve the property as the official Birthplace began in 1847, when it was put up for sale. In response to fears that P.T. Barnum was going to buy it and make it part of a show, a committee was formed to “save” the house for the nation, and the group began to solicit donations.

Not everyone was convinced. “The extraordinary sensation caused by the purchase of this shabby sausage-shop deserves a prominent place amongst popular delusions,” declared the 1848 Bentley’s Miscellany article . A writer for another British periodical mocked the gullibility of a nation pouring forth funds to buy a “rubbishing mass of lath and plaster in which the Poet was no more born than was the Man in the Moon himself.”

But the belief had already become an article of faith, strengthened by its own repetition. The Birthplace was a better shrine for the very absence of evidence — for the faith it required of its visitors — the publisher Charles Knight wrote at the time. That same year, the committee secured the Birthplace at auction for 3,000 pounds, worth about $323,000 today .

The “shabby sausage-shop” made an uninspiring temple. So the adjoining premises were demolished, walls moved, floorboards replaced, new doorways and staircases created. Its new stewards transformed it into the large, comfortable home of a prosperous Elizabethan family, leaving the cellar as “the only portion which remains as it was,” as the scholar Sidney Lee wrote in 1901. What emerged was less a Tudor dwelling than a Victorian imagination of one.

The committee became the Shakespeare Birthplace Trust , the group that still runs the site, and maintains its authenticity. “We know that, to the best of our current understanding, the building includes the surviving fabric of a property that is traditionally and intimately associated with Shakespeare and his family,” said a spokesman for the trust.

The trust went on to acquire more properties, including Anne Hathaway’s Cottage, a thatched farmhouse where visitors are invited to “relive Shakespeare’s love story.”

A temple to baby Shakespeare

“This is the room where we believe William Shakespeare was born in April 1564,” read a sign in the Birthroom. Next to the bed stood a cradle laid out with blankets and a tiny pillow, encouraging visitors to imagine the baby genius mewling by his parents’ side. For the Victorians, the Birthroom offered the mystical possibility of contact with the poet. Visitors recorded melodramatic accounts of what they felt on entering the room: They burst into tears. They fell down. They kissed the floor. Those desiring a more extended communion spent the night.

Others were unimpressed. “If I were to allude to Stratford, it would not be in connection with the fact that Shakespeare came into the world there,” wrote the novelist Henry James after visiting. “It would be rather to speak of a delightful old house near the Avon which struck me as the ideal home for a Shakespearean scholar.”

But the fantasy is resilient. In a 2023 PBS documentary, “ Making Shakespeare: The First Folio ,” the scholar Michael Dobson, director of the Shakespeare Institute, stood in the Birthplace, gushing over “the very room in which Shakespeare was born.”

I shuffled around the cradle with the other visitors, unsure of what to do. Were we supposed to genuflect? Kiss it? After an appropriate amount of staring, we moved on.

To exit, I had to pass through the gift shop, where any lingering sense of piety dissipated in a tidal wave of consumerism. Visitors were loading up on Shakespeare T-shirts, breakfast teas and tea towels. Shakespeare rubber ducks and windup toys. Shakespeare Christmas ornaments, baby onesies, tote bags and luxury chocolates. Belief is good business.

When I returned to Stratford last February, little had changed since my first visit. The Shakespeare Centre was now showing modern artists’ interpretations of the poet, including a Surrealist painting of a masked figure that suggested the mystery surrounding him. The trinket stands were still hawking their modern versions of those 18th-century mulberry tree carvings. Faith in the traditions is bound up with desire — the need to believe.

Where was “the Immortal Shakspeare” really born? Stories are usually more seductive than the truth.

Sheelagh McNeill contributed research.

Elizabeth Winkler is a journalist, a critic and the author of “ Shakespeare Was a Woman and Other Heresies: How Doubting the Bard Became the Biggest Taboo in Literature .”

Follow New York Times Travel on Instagram and sign up for our weekly Travel Dispatch newsletter to get expert tips on traveling smarter and inspiration for your next vacation. Dreaming up a future getaway or just armchair traveling? Check out our 52 Places to Go in 2024 .

Open Up Your World

Considering a trip, or just some armchair traveling here are some ideas..

52 Places:  Why do we travel? For food, culture, adventure, natural beauty? Our 2024 list has all those elements, and more .

Mumbai:  Spend 36 hours in this fast-changing Indian city  by exploring ancient caves, catching a concert in a former textile mill and feasting on mangoes.

Kyoto:  The Japanese city’s dry gardens offer spots for quiet contemplation  in an increasingly overtouristed destination.

Iceland:  The country markets itself as a destination to see the northern lights. But they can be elusive, as one writer recently found .

Texas:  Canoeing the Rio Grande near Big Bend National Park can be magical. But as the river dries, it’s getting harder to find where a boat will actually float .