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Boston Itinerary: How to Spend Five Days in Boston

One of the most historic cities in the United States , Boston is the city I called home for the first 25 years of my life.

More a collection of towns than a metropolis like New York , Boston is a city steeped in history (it contains a lot of historical firsts for the United States and played a pivotal role in its founding), delicious food, wide-open green spaces, first-rate museums, and warm, welcoming people.

Visiting Boston offers all the benefits of a big metropolis without the intensity and fast pace of New York.

Boston is easy to get around and compact, making it perfect for travelers. The subway will take you wherever you need to go.

So how many days do you need to visit Boston?

Most people visit for three to four days, and I think that’s a perfect amount of time. As someone who’s lived there, I can say that, since Boston is so small, you won’t waste a lot of time “in transit,” so you can pack a lot into your days. Obviously, you can spend longer here (slow travel is the best travel), but for the first-time visitor, three to four days is enough.

Here’s a suggested Boston itinerary that will allow you to see the best of Boston:

Table of Contents

Boston Itinerary: Day 1

Boston itinerary: day 2, boston itinerary: day 3, boston itinerary: day 4, boston itinerary: day 5, other things to see and do in boston.

• Boston Common
• Massachusetts State House
• Park Street Church
• Granary Burying Ground
• King’s Chapel Burying Ground
• Benjamin Franklin statue and the former site of Boston Latin School
• Old Corner Bookstore
• Old South Meeting House
• Old State House
• Site of the Boston Massacre
• Faneuil Hall
• Paul Revere House
• Old North Church
• Copp’s Hill Burying Ground
• USS Constitution
• Bunker Hill Monument

You follow a brick road through the city, and there are signs and historical markers all along the way. Given all the walking that’s involved, I would make this the main activity of the day. You’ll want to take your time and see all the sites thoroughly.

You can also take a guided tour from the visitor’s center. Tours run hourly between 11am and 1pm, with additional tours in the afternoon in the spring and summer. Tickets are $17 USD for adults, $15 USD for students and seniors, and $8 USD for children 6-12 (free for kids under 6).

4 S Market St, +1 617-523-1300, faneuilhallmarketplace.com. Open Monday-Saturday 10am-9pm and Sunday 12pm-6pm.  

Browse for Books Located a stone’s throw away from the Boston Common, Brattle Book Shop is a family-run used bookstore that dates back to 1825. It’s actually one of the oldest surviving bookstores in the country! It’s home to over 250,000 books, maps, postcards, and other odds and ends. In addition to used books, the store is also home to an impressive collection of first editions and antique books.

9 West Street, +1 617-542-0210, brattlebookshop.com. Open Monday-Saturday 9am-5:30pm.

Walk Around the Back Bay This area used to be an actual bay. Before the Europeans arrived, the indigenous population used the tidal bay to catch fish, as the bay drained completely during low tide. When the land was colonized, a dam was built and the tidal bay was eventually filled in, creating the Back Bay area.

The end of the Public Gardens meets Boston’s Back Bay, our version of New York’s SoHo and West Village. This is where Boston’s elite and wealthy live, and nearby Newbury Street is our Madison Avenue, with lots of expensive shopping and high-end eateries. It’s a beautiful space to stroll around, with pretty brownstones and tree-lined streets. You can still see plenty of old Victorian homes in this neighborhood that date back to the 19th century. ( Here’s a list of other neighborhoods worth checking out as well!

You’ll also find the Boston Public Library here. Opened in 1852, it’s one of the largest municipal libraries in the country, home to over 23 million items, with almost 4 million visitors each year.

206 Clarendon St, +1 617-536-0944, trinitychurchboston.org. The church is open for prayer and tours Tuesday-Saturday 10am-5pm and Sundays 12:15pm-4:30pm. Tours are $10 USD for adults, though it is free to enter for worship.

Head up to the Prudential Tower Head back toward Copley to see the Prudential Tower, colloquially known as “The Pru.” You can actually go up to the top and get a bird’s-eye view of Boston. There are 52 floors in the building, which was built in the 1960s. These days, it’s the second tallest building in the city (the John Hancock Tower is first).

800 Boylston St, +1 617-859-0648, prudentialcenter.com. Open daily from 10am-8pm (10pm in the summer). Admission is $34.99 USD for adults, with discount available for students, seniors, and children.

47 David G. Mugar Way, +1 617-626-1250, hatchshell.com. See the website for an up-to-date list of events.

1 Science Park, +1 617-723-2500, mos.org. Open Saturday-Thursday 9am-5pm and Fridays 9am-9pm. Admission is $29 USD for adults, with discounts available for seniors and children.  

1 Central Wharf, +1 617-973-5200, neaq.org. Open Monday-Friday 9am-5pm, weekends 9am-6pm. Admission is $34 USD for adults, with discounts available for kids and seniors.

See the Skinny House When you’re in the North End, visit 44 Hull Street. Known as “the Skinny House” (or the Spite House), this incredibly narrow house has a rather interesting history. Built after the Civil War, it was a passion project of Joseph Euestus, who came home from the war to find that his brother had taken over more than half of the inherited land they were meant to share. Joseph decided to build on the remaining land — which his brother thought was too small to build anything on. Joseph went ahead and built a narrow four-story home on the small slice of land to block his brother’s view.

Visit an Art Gallery or Museum Boston has a lot of great galleries and museums, so depending on your interest, you’ll want to check out some (or all) of the galleries and museums below. It will take more than an afternoon to see them all but you can always spread these visits out over a few days!

• Institute of Contemporary Art : If contemporary art is your cup of tea, this is for you. While it’s not my favorite style of art, I have to admit this place does put on some insightful exhibits. 25 Harbor Shore Drive, +1 617-478-3100, icaboston.org.
• Commonwealth Museum : This museum explores the history of Massachusetts. It’s actually really interesting and entirely underrated (especially if you’re a history nerd like me). 220 Morrissey Blvd, +1 617-727-2816, sec.state.ma.us/arc.
• Harvard Museum of Natural History : This natural history museum has exhibitions showcasing dinosaurs, animals, and minerals (including meteorites). It’s a great choice if you’re traveling with kids, though there is plenty of informative content for adults too! 26 Oxford St +1 617-495-3045, hmnh.harvard.edu.
• Harvard University Art Museums : Harvard actually has three art museums – the Fogg Museum, the Busch-Reisinger Museum, and the Arthur M. Sackler Museum. They are home to both modern and historical art exhibitions. See what exhibitions are running by checking their website. harvardartmuseums.org
• Museum of Fine Arts : This museum has an impressive collection of over 450,000 pieces of fine art. It also runs all sorts of art classes throughout the year, both multi-week classes as well as single-day workshops. If you’re looking to learn something new or improve your skills, check out the website for more details. 465 Huntington Avenue, +1 617-267-9300, mfa.org.
• Warren Anatomical Museum : Founded in 1847, this macabre museum is filled with Civil War–era medical tools as well as some unique (and perhaps unsettling) medical mysteries. It’s super weird but super neat. A definite must if you’re looking for an off-the-beaten-path museum! 10 Shattuck St, +1 617-432-6196, countway.harvard.edu/center-history-medicine/warren-anatomical-museum.
• Boston Tea Party and Ships Museum : This interactive museum is home to some historic ships that have been authentically restored to show you what life was like at sea during the Boston Tea Party. It also has a really informative documentary about the events that led up to the Tea Party and the American Revolution. Best of all, you can actually throw fake crates of tea into the river yourself to see what it was like! 306 Congress St, +1 617-338-1773, bostonteapartyship.com.
• Paul Revere House : Built in 1680, this is actually the oldest building in the entire city (it’s been renovated but it’s still the original building). The museum is filled with the family’s furniture and artifacts, giving you a sense of what life was like in Boston before the Revolution. 19 N Square, +1 617-523-2338, paulreverehouse.org.
• Museum of Bad Art : The name says it all! This is a museum filled with terrible art. The MOBA has rotating exhibits throughout the year, so there is always something new and terrible to behold. If you feel like a laugh, definitely check out this quirky gallery! 55 Davis Square, +1 781-444-6757, museumofbadart.org.
• Isabella Stewart Gardner Museum This museum is home to an amazing art collection of over 20,000 items, including European, Asian, and American art. Opened in 1903, the museum is made up of a wide-ranging collection of paintings, tapestries, decorative arts, and sculptures. It’s one of the best museums in Boston. Don’t miss it. 25 Evans Way, +1 617-566-1401, gardnermuseum.org.

Harvard University, +1 617-495-1000, harvard.edu/on-campus/visit-harvard/tours.

125 Arborway, +1 617-524-1718, arboretum.harvard.edu. Open daily 7am-7pm. Admission is free.

Take the Sam Adams Brewery Tour After four days of sightseeing, you deserve a beer or five. Luckily, this brewery is located near the Arboretum so it’s easy to visit and a great way to end your day. Sam Adams is a major brewer in Boston, and locals drink it widely and frequently. The brewery offers free tours, starting in mid-afternoon and departing every 45 minutes. You get a few free samples along the way. If you’re under 21, don’t worry. You can still go — you just can’t drink.

30 Germania St, +1 617-368-5080, samueladams.com. Tours are available Monday-Thursday and Saturdays 10am-3pm. On Friday, tours are available between 10am and 5:30pm. Their Sam Signature Experience is 45 min long and costs $10 USD.

4 Yawkey Way, +1 877-733-7699, mlb.com/redsox/ballpark. See the website for an up-to-date schedule.

(The Sox not in season? No worries. We have the Bruins, Celtics, and Patriots. No matter the time of year, you’ll be able to find a game to see!)  

Visit the Children’s Museum If you’re traveling with kids, this is a great place to spend part of your visit. It’s the second oldest children’s museum in the US and has permanent exhibits on health and exercise, construction, space, art, and diversity. It also has a real two-story house from Kyoto, Japan, that teaches kids about life there (it’s actually pretty cool!).

308 Congress Street, +1 617-426-6500, bostonchildrensmuseum.org. Open Wednesday-Sunday 9am-12pm and 1:30pm-4:30pm. On the first Saturday of the month, the museum opens at 10am. Admission is $20 USD for both adults and kids (free for infants under 12 months).

Charlestown Navy Yard, +1 617-426-1812, ussconstitutionmuseum.org. The ship is open Tuesday-Sunday 10am-6pm (with extended hours in the summer); the museum is open 10am-6pm (with extended hours in the summer as well). Admission is free, though the museum has a suggested donation of $10-15 USD.

Visit More Museums – With any extra time, visit more museums! There’s plenty of them to see! Try not to skip the big ones!

725 Commonwealth Avenue, +1 617-353-2630, bu.edu/astronomy/community/open-night-observatory/. Viewings are Wednesday evenings at 7:30pm in the autumn and winter and 8:30pm in the spring and summer. Make sure to get there 10 minutes early as they don’t permit entry once it starts.

See the Mapparium – Located in the Mary Baker Eddy Library, this three-story inverted globe serves as a giant map of the world that you can walk into via a glass bridge. It is constructed of over 600 stained-glass panels and shows the world as it looked in 1935.

200 Massachusetts Avenue, +1 617-450-7000, marybakereddylibrary.org. Open daily 10am-5pm. Admission to the Mapparium is $6 USD for adults, with discounts available for students, children, and seniors.

Head to Castle Island – Castle Island is located in South Boston and is famous for Fort Independence. When the fort was no longer needed for defense, it was actually used as the first state prison. The island covers 22 acres and has excellent beaches, as well as some running trails that are popular with the locals. There’s also an area for picnics and you can visit the old fort for free. The place gets pretty busy on the weekends during the summer, and you can often see school groups exploring the fort during the spring.

Relax at the Lawn on D – This massive green space is new to the city (when I was growing up, there was nothing in this area so you would never go there). There are all sorts of free activities happening year-round, from concerts to festivities and everything in between! There’s public seating, free Wi-Fi, art exhibitions, and a few games, like table tennis and bocce. To see what events are happening during your visit, check the website for details.

420 D St, +1 877-393-3393, signatureboston.com/lawn-on-d. Open Monday-Wednesday & Friday-Saturday from 7am-11pm and Thursday & Sunday from 7am-10:30pm (hours may vary for events). Admission is free.

Hike the Blue Hills – This park is a bit out of the way, but it’s definitely worth a visit if you want to get out and stretch your legs. The 7,000-acre park is home to over 100 miles of trails and offers some picturesque viewpoints. There are also plenty of activities to keep you entertained, such as boating, fishing, skiing, and rock climbing (depending on the season). It can get busy in the summer on the weekends, so just be sure to arrive early.

Tour the Custom House – Built in the 17th century, the Custom House is one of the most recognizable buildings in the city. In 1915, a tower was added to the building, making it the tallest building in the city at the time. The building is owned by Marriott Hotels now, though you can still take a free tour (by appointment) to go up to the observation deck on the 26th floor.

3 McKinley Square, +1 617-310-6300, marriott.com/hotels/travel/bosch-marriott-vacation-club-pulse-at-custom-house-boston. Tours are free though they are by appointment only.

Boston is a great city (and I’m not just saying that because I grew up there). I’ve never encountered a person who hasn’t liked it. This Boston itinerary will give you a good overview of the city at a relaxing pace. You’ll be moving around a lot, though, so make sure you get an unlimited “T” pass (subway/train pass). If you have more time, you can squeeze in some other activities .

But why rush such a beautiful place?

Take it slow. Mix and match the itinerary to suit your needs but this is how I’d structure my days if I was visiting Boston!

Book Your Trip to Boston: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe so you always know no stone is left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels.

For the best hostels, check out this post on the best hostels in the city.

If you want to know the best neighborhoods, here’s my guide to all the best areas in town !

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

• Safety Wing (best for everyone)
• Insure My Trip (for those over 70)
• Medjet (for additional evacuation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road. They will save you money when you travel too.

Want More Information on Boston? Be sure to visit our robust destination guide on Boston for even more planning tips!

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Disclosure: Please note that some of the links above may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I recommend only products and companies I use and the income goes to keeping the site community supported and ad free.

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Unlocking Beantown: Your Go-To Manual for Getting Around Boston

Navigate and enjoy Boston like a seasoned traveler! Learn how to get around the city using various transportation modes–from MBTA’s extensive network to hop-on and hop-off bus tours.

Are you thinking about visiting Boston? This city is a fantastic spot for tourists, and how to travel around Boston is super easy, even for first-timers.

Whether you want to hop onto the bus commuter rail for a city-wide tour or prefer to explore the city’s heart on foot, Boston has got all the options lined up for you. This guide will walk you through all the tickets you can purchase, handy commuter apps you can use to plan your trip, and various transportation modes available at your disposal.

Walking Around Boston

If you love to explore on foot, you’re in for a treat in Boston! This city is a walker’s dream, especially in downtown Boston. It’s so compact and super easy to stroll around. You can practically walk everywhere, exploring every nook and cranny at your own pace.

Additionally, Boston’s mostly flat terrain means you can wander around all day without getting worn out. It’s the perfect way to immerse yourself in the city’s vibrant history and culture, step by step.

Top Walking Tours in Boston

Walking tours are very popular in Boston. On top of the list is the iconic Freedom Trail Walking Tour . This 2.5-mile path winds through the city, letting you discover charming old buildings, serene churches, historic graveyards, and even a cool ship – all on foot.

The Boston North End Pizza – Walking Food Tour is an ideal choice for foodies. You will still visit historic Freedom Trail sites on foot. At the same time, you’ll stop by some of the best Italian restaurants in the country and the world!

Boston’s Bike Share Program

If you prefer two wheels over two feet, check out Boston’s bike share program. Mostly, renting a bike is done through a program called Bluebikes, which is the city’s official bike share system. It’s the go-to option for a green ride when getting around in Boston.

Get a head start by downloading the Bluebikes app. It’s your key to finding docking stations and checking bike availability. Plus, it’s how you’ll unlock and rent those two-wheelers.

Related Post: Boston Travel: Is Go Boston Pass Worth It?

While Bluebike hasn’t jumped on the e-bike bandwagon just yet (though they’re planning to in 2024), don’t worry. If you’re craving an electric boost, local businesses like Urban Adventours have got your back with e-bike rentals.

Pro tip: For Boston biking, always ride with the traffic flow, and make good use of those bike lanes. And remember, in most parts of Boston, especially the bustling business districts, biking on sidewalks is a no-go.

Boston Subway: The “T”

Ready to explore Boston on a budget? The subway Boston, affectionately called The “T”, is your go-to. It’s hands-down the best way to get around Boston without burning a hole in your wallet. The T offers a rainbow of routes, each with its own color and unique destinations:

• Red Line: Buzzing with activity, the Red Line connects you to the busiest spots in the city.
• Orange Line: This line takes you to exciting places like TD Garden and Faneuil Hall Marketplace.
• Blue Line: Take the Blue Line to reach the historic Revere Beach, perfect for a day of relaxation by the ocean.
• Green Line: Looking for a scenic spot? The Green Line takes you near Charles River. Rent a kayak, paddle away, or just enjoy a peaceful picnic by the water.
• Silver Line: Need to catch a flight? The Silver Line SL1 is your direct link to Logan International Airport, stopping at all terminals.

CharlieCard: Unlimited Subway and Bus Travel

Make your travels smoother with the Boston transit pass for tourists. Grab a CharlieCard offering 1-day or 7-day unlimited travel options on subway and local bus routes.

You can snag these passes from vending machines in subway stations. They’re a lifesaver, offering big savings and sparing you the hassle of buying individual tickets.

MBTA Commuter Rail

For those looking to explore beyond the city limits, the Massachusetts Bay Transportation Authority (MBTA) Commuter Rail is your golden ticket! It’s a key part of how to get around in Boston and its surrounding areas. Stretching across eastern Massachusetts and reaching into parts of Rhode Island, this rail system connects the region to the heart of Boston.

Whether you’re heading to quaint coastal towns or exploring diverse neighborhoods, the MBTA Commuter Rail makes it a breeze. It’s the ideal choice for covering longer distances, smoothly transporting you from North Station all the way to South Station and beyond.

And for those planning extensive travel, there’s a separate 1-day and 7-day pass for the commuter rail. While it’s a bit pricier than the CharlieCard, it’s totally worth it for the expansive coverage and convenience it offers. So, if you’re keen on discovering more than just the city’s core, this part of public transportation is your best bet.

MBTA Bus Service

Navigating Boston? The MBTA Bus Service is a go-to for both locals and visitors, making it an essential part of public transit in the city. With a handy CharlieCard, you’ve got a ticket to unlimited bus rides. But if you don’t have a CharlieCard, don’t worry. You can easily pay with cash or a card right on the bus.

Related Post: Boston Historical Sites: 21 Must-See Stops for History Buffs

The MBTA’s real-time bus tracking is available on their website, mbta.com. Checking this lets you know exactly when your bus will arrive, taking the guesswork out of your travel plans. Plus, their trip planner tool on the same site is super helpful for mapping out your commute.

If you’re more comfortable with Google Maps, it’s got your back too, offering reliable commute options whether you’re using the bus, subway, or commuter rail.

Boston Hop-On Hop-Off Tour by Old Town Trolley Tours

For a unique twist, why not try the Boston Hop-On Hop-Off Tour ? It’s a fantastic way to familiarize yourself with the city. Hop on and off at your own pace, and enjoy live narration from knowledgeable tour guides. It’s a perfect introduction to Boston, setting you up nicely on your first day in the city before you venture off on your own.

Ride Sharing and Taxis

When it comes to getting around Boston, ride sharing is a fantastic way to see the city. It’s particularly great if you’re journeying with friends, as the costs reduce significantly when you split them amongst your group.

Uber and Lyft are the most common ride-sharing services in the city, and they’re as reliable as they come. So whether you’re darting from one historic site to another or simply getting back to your hotel after a day of exploration, all of it becomes quick and hassle-free with ride sharing.

Renting a Car

Renting a car is a great idea if you’re looking to explore beyond the city’s public transit system. It’s particularly handy for reaching those charming small towns, serene beaches, or hidden rural gems in New England. If you’re traveling with family or a group, a car gives you the flexibility and space needed, especially for handling luggage, strollers, or other essentials.

Related Post: Things to Do at Night in Boston: 24 Nightlife Adventures

For seamless navigation, use Google Maps to plan your routes and explore how to get around Boston and its surroundings. Conveniently, car rentals are available at Logan International Airport, where you can pick up and drop off your vehicle. If you’re flying out from a different airport, no problem – you can return your car there too.

Travel tip: Car rentals usually require a credit card deposit as security. But here’s a travel hack—some of the best hotels in Boston offer complimentary airport transfers, and some even provide free shuttles to nearby attractions, helping you cut down on travel costs.

Plan Your Boston Trip with Ease

Now armed with all the information you need to get around Boston, remember to set out your itinerary in advance. Make sure to check out discount tickets on Tripster for savings on your travel expenses. You can bundle up and save more by combining your hotel stay with attraction tickets too.

For the ultimate Boston experience, don’t miss out on the Go Boston All-Inclusive Pass and Go Boston Explorer Pass. Not only will you secure great savings, but it’ll give you entry to your pick of Boston attractions and tours. Finding ways to save while seeing the best of Boston—the ultimate win!

What Did We Miss?

Do you have a Boston navigation tip to share? Leave us a comment below!

Written by Nicole King

There are only two things that make Nicole really happy–books and travel! When her head’s not buried in a book, she’s most likely...

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Connecticut , Maine , Massachusetts , New Hampshire , New York , Rhode Island , Vermont  ·  March 30, 2022

34 Awesome Road Trips From Boston & Best Itineraries (2024)

Boston is an amazing starting point for adventures all over New England and the Northeast. With so many options to visit tons of nearby coastal towns, exciting cities and plenty of quaint, charming villages, there are endless possibilities for road trips from Boston. And since I’ve been road-tripping and traveling all over the Northeast for over 10 years now, I know all the destinations that are worth your time.

This list includes destinations that are all individually under 6 hours from Boston, and if you’re looking for road trip itineraries that combine destinations from this list, be sure to scroll to the end for suggested itineraries to make the most of your road trip!

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 .

🚙 Need to rent a car for your epic road trip? I’ve got you covered! Click here to check the best prices on Discover Cars!

Best Road Trips From Boston

For this list, I’ve broken down the destinations into four categories: Coastal, City, Charming Towns and Luxury Getaways. For each destination, I’ve also included the time it takes to get there from Boston, highlights of the best things to do, what to expect once there, and nearby things to do.

Coastal Road Trip Destinations From Boston

1. plymouth, ma.

Distance From Boston: 40-50 minutes

If you’re looking for a quick, easy getaway from city life in Boston, a little road trip to Plymouth is a fun way to do that. While the town is known for its history dating back to the early 1600s, they are also lots of outdoor activities, parks and beaches, and combine that with a small-town feel, Plymouth makes for a lovely little escape from Boston.

Best things to do in Plymouth:

• Plimoth Patuxet Museum is a living replica of the original pilgrim colony settlement. If you’re a history buff, this is a must-see. You can even climb aboard the Mayflower II, an exact replica of the ship that brought the pilgrims to Plymouth.
• Plymouth Long Beach is a 3-mile long stretch of public beach that’s perfect for getting out by the water.
• Plymouth Farmer’s Market is held every Thursday from May through October, and was Yankee Magazine editor’s pick for best Farmer’s Market in 2018.
• Brewster Gardens is a tranquil, waterfront park that’s sure to invite lots of relaxation.
• Walk around the charming downtown to visit the shops and restaurants,
• Pop into Dirty Water Distillery for an artisanal spirits tasting.
• Go on a whale watch tour with Captain John’s Boat Tours .
• Spend the day getting pampered at Mirbeau Resort & Spa , and even stay for lunch or dinner, or the night for the ultimate day of relaxation.

Click here to book your stay at Mirbeau Resort & Spa!

Psst! I have an entire post on visiting Plymouth, MA , if you need more ideas!

2. Cape Cod, MA

Distance From Boston: 1-2.5 hours, depending on where you to choose to go on Cape Cod.

With over 500 miles of shoreline to explore, Cape Cod is the ultimate beach road trip from Boston because you can get there in about 2 hours and feel like you’re in a whole other world. There are 15 towns in Cape Cod to choose from for your visit, and more beaches than anyone can count. Fill your days being ocean-side, exploring beautiful little coastal towns, eating fresh seafood and taking in amazing sunsets.

Best Things To Do on Cape Cod :

• Visit The Cape Cod National Seashore
• Explore Chatham’s downtown
• Visit Provincetown and the Pilgrim Monument
• For more on the best things to do on the Cape, click the link below for my detailed travel guide.

You may also enjoy:

• Can’t Miss Things To Do When Visiting Cape Cod For The First Time
• Best Things To Do On Cape Cod For Adults
• Best Towns To Stay In On Cape Cod
• What To Pack For Cape Cod
• Unique Things To Do On Cape Cod

3. Nantucket, MA

Distance From Boston: 2-3 hours, which includes time to park at the ferry terminal, and ride the ferry.

Nantucket is a gorgeous island off the coast of Cape Cod bursting with charm and natural beauty. A day trip to Nantucket is common while visiting Cape Cod, but staying overnight for a night or two would be the best way to make the most of your road trip from Boston. This is a great island to explore if you’re looking for stunning beaches and a beautiful downtown area.

To get to Nantucket, you’ll need to take the ferry from Hyannis on Cape Cod. From there, you can choose between Hyline Cruises or Steamship Authority to get to Nantucket.

Best Things To Do on Nantucket:

• Explore the shops and restaurants in the main town.
• Visit Brant Point Lighthouse.
• Rent a moped to explore the local beaches and towns.
• For more amazing things to do on Nantucket, click the link below for my detail travel guide on a Nantucket day trip.
• The Best Nantucket Day Trip Travel Guide
• How Many Days Do You Need On Nantucket + Suggested Itineraries
• How To Visit All The Nantucket Lighthouses

4. Martha’s Vineyard, MA

Martha’s Vineyard is the other island off the coast of Cape Cod, and it’s more popular as an overnight destination, versus a day trip because it’s bigger. Comprised of 6 beautiful towns, Martha’s Vineyard is home to beautiful beaches, quaint Main Streets for shopping and dramatic cliff-lined shores.

To get to Martha’s Vineyard, you’ll need to take a ferry from either Woods Hole or Hyannis (both terminals located on Cape Cod). There is no benefit to picking one over the other, and it’s best to just pick whichever location is more convenient for you (usually it’s Hyannis for most people).

Best Things To Do on Martha’s Vineyard:

• Gingerbread Cottages in Oak Bluffs
• Edgartown downtown and lighthouse
• Aquinnah Cliffs and Gay Head Lighthouse
• South/Katama Beach
• For more information on visiting Martha’s Vineyard, click the link below for my guide on deciding between Nantucket or Martha’s Vineyard for a day trip.

You may also find these Martha’s Vineyard posts helpful:

• Is Nantucket or Martha’s Vineyard Better For A Day Trip?
• The Ultimate Martha’s Vineyard Day Trip Guide
• How To See Martha’s Vineyard Without A Car

5. Marblehead, MA

Distance From Boston: 40-50 minutes.

Marblehead is an adorable little coastal town along the North Shore of Massachusetts, and a very quick road trip from Boston. This is the place to come if you’re looking for historical homes, small-town charm, great seafood, dramatic, rocky coastline and options for beaches.

Best Things To Do in Marblehead, MA:

• Marblehead Lighthouse & Chandler Hovey Park
• Self-guided historical home walking tour.
• Take in the views at Castle Hill Rock.
• For more information on the best things to do in Marblehead, click the link before for my detailed travel guide.

Click here to read even more awesome things to do in Marblehead!

6. Salem, MA

Distance From Boston: 30-40 minutes.

Salem is another little coastal town along the North Shore of Massachusetts, and is known for being the premier New England destination for all things spooky. While visiting Salem in October is definitely a bucket list-worthy goal, it’s actually a really wonderful town to visit all year round. It’s very walkable with a variety of things to do, and makes for a great day trip, or a weekend getaway.

Best Things To Do in Salem, MA:

• Winter Harbor Park and Lighthouse
• Salem Witch Trials Memorial
• Salem Maritimes National Historic Site
• Essex Street Pedestrian Mall
• House of Seven Gables
• Peabody Essex Museum

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 😉

7. Rockport, MA

Distance From Boston: 50-60 minutes.

Rockport is one of my favorite coastal towns in all of New England. It has so much character, wonderful shops and restaurants, and really invites you to slow down a bit to take it all in. It’s a small town, and can be done in a day, but a weekend here would be a very relaxing road trip from Boston.

Best Things To Do in Rockport, MA:

• Visit Motif 1, the most painted building in New England, if not the country!
• Go for a scenic walk or hike at Halibut Point State Park.
• Meander through the shops on Bear Skin Neck.
• For more things to do in Rockport and the North Shore region, click the links below for my detailed travel guides.

Click here for more amazing things to do in Rockport!

Click here to read my travel guide on the best things to do on Cape Ann!

8. Newburyport, MA

Newburyport is a delightful little coastal town in Massachusetts that has a very traditional New England feel with beautiful homes at every turn, and an adorable little downtown area and waterfront park. Newburyport is also home to Plum Island, which is a gorgeous part of town with amazing beaches and wildlife sanctuaries.

Best Things To Do in Newburyport, MA:

• Visit Oldies Marketplace to look for antiques and treasures.
• Meander the streets of downtown to explore the beautiful storefronts.
• Take a leisurely stroll along the waterfront park.
• Pack a picnic or take a nature walk at Maudslay State Park , which has over 500 acres to explore.
• Head out on the open waters with Yankee Clipper Tours , and cruise around the Merrimack River and Newburyport Harbor.
• Drive over to Plum Island to visit Plums Island Beach, buy some handmade soaps at Plum Island Soap Co. , and walk the stunning nature trails at the Parker River National Wildlife Refugee .

Click here to read my full guide to visiting Newburyport & Plum Island!

9. Block Island, RI

Distance From Boston: 3-3.5 hours, which includes time to park at the ferry terminal, and ride the ferry.

Block Island is a beautiful island off the coast of Rhode Island with gorgeous beaches, walking trails, water activities, salt marshes, great restaurants and is overall a wonderful place to relax while appreciating the outdoors. This actually might be one of my top underdog suggestions for a weekend getaway from Boston.

It actually reminds me a bit of Prince Edward Island, so if you’re looking to live out your Anne of Green Gables dreams, but can’t make it to Canada, this is a great place to do that. There’s even a lovely hotel on the island called Avonlea.

To get to the island, you’ll need to drive to the Pt. Judith ferry terminal in Rhode Island. For more information on the ferry, click here .

Best Things To Do on Block Island, RI:

• Take in the views at Mohegan Bluffs.
• Rent a moped to explore the entire island.
• Spend some time swimming at Mansion Beach.
• Visit the island’s two lighthouses.
• Have lunch with a water view at The Oar .

Click here to read all my tips for taking a Block Island day trip!

10. Newport, RI

Distance From Boston: 1.5 hours, but always anticipate extra traffic crossing the Newport bridge.

Newport is a stunning coastal city in Rhode Island that’s the perfect destination for sailing, shopping, dining and being by the water. Even though it’s technically a city, I wanted to include it in the coastal destinations group because it definitely feels more like a resort waterfront town than a city.

With so many things to do, you could easily spend a weekend here, but Newport will also work for a day trip.

Best Things To Do in Newport, RI:

• Walk along Cliff Walk for amazing coastal views.
• Visit Bowen’s Wharf for shopping and dining.
• Grab a lobster roll at the Newport Lobster Shack .
• Walk over to Goat Island to see the lighthouse and take in views of the Newport Bridge.
• Sail around Narrangansett Bay with Sightsailing of Newport .
• Visit the unique shops along Thames Street.
• Grab lunch and cocktails at The Lawn at Castle Hill Inn , overlooking the water. Better yet, book an overnight stay for the ultimate Newport experience!

Click here to book your stay at The Castle Hill Inn in Newport .

Click here to read all my tips for taking a Newport, RI day trip!

Click here to read about all the best things to do in Newport, RI in the winter!

11. Mystic, CT

Distance From Boston: 1.5 hours

This adorable little town sits along Mystic River, and has an awesome mix of preserved maritimes history, small-town charm and nature. While Mystic is mostly visited for its quaint, waterfront downtown, it’s also home to parts of two bordering towns, Stonington and Groton, giving you opportunity to explore a few different coastal Connecticut destinations during your visit.

Best Things To Do in Mystic, CT:

• See penguins, beluga whales, sharks and sea lions at the Mystic Aquarium .
• Learn all about maritimes history at the Mystic Seaport Museum and Village , which is regarded as one of the best, if not the best, Maritimes museums in the country.
• Hit the trails at Bluff Point State Park.
• Take a sunset or moonlit cruise with Poet’s Lounge Sailing Charters .
• Grab a warm lobster roll, which originated in CT, at Ford’s Lobster in nearby Noank.

Click here to read about all the best things to do in Mystic, CT!

12. The Hamptons, NY

Distance From Boston: 5.5 hours if driving the whole way, 6 hours if you drive to New London, CT to take the ferry.

The Hamptons needs no introduction, as it’s become a famous summer destination in New York thanks to many celebrities calling it a secondary home. Sitting along the Long Island sound, you can expect gorgeous beaches, amazing shopping and restaurants, specialty food markets and farmer’s markets, wineries and plenty of opportunity for rest and relaxation.

The Best Things To Do in The Hamptons:

• Have a beach day and watch the surfers at Coopers Beach in Southampton.
• Go vineyard hopping, and taste some of the local wines. Channing Daughters Winery and Wölffer Estates are two great options.
• Take in the views at Montauk Lighthouse.
• Enjoy an afternoon of rest and restoration at the Montauk Salt Caves .
• Have some amazing and fresh seafood at Bostwick’s Chowder House in East Hampton.
• Rent a bike and ride along Gin Lane in Southampton for incredible views of the ocean, and to see some amazing houses.

13. Ogunquit, ME

Distance From Boston: 1 hour and 15 minutes

One of my favorite beach towns in all of New England is Ogunquit, which is one of the best places to visit in Maine in the summer , but it’s really fun in spring and fall, too. Offering both dramatic and rocky coastline that Maine is famous for, as well as a long, sandy beach that’s perfect for swimming, you’ll get the best of both worlds here. Ogunquit’s town is entirely walkable, so once you drive in, you’ll be able to leave your car behind and get almost everywhere by foot. There’s an amazing downtown scene with plenty of shops and restaurants, and you’re never that far from Ogunquit Beach.

Best Things To Do in Ogunquit, ME:

• Walk along Marginal Way, where you’ll get the most amazing views of the rocky coastline.
• Visit Perkins Cove to enjoy its charming shops and restaurants.
• Spend plenty of time at Ogunquit Beach, one of the best beaches in Maine.
• For more information on things to do in Ogunquit, click the link below for my detailed travel guide.

Click here to read about more amazing things to do in Ogunquit!

14. Kennebunkport, ME

Distance From Boston: 1 hour and 25 minutes

Just a short distance from Ogunquit is Kennebunkport, so these two destinations could easily be combined, and both are worth your time. Kennebunkport is full of character, and can be visited as either a day trip, or a weekend getaway, from Boston. Offering both beaches and a wonderful downtown scene, this is a great place to relax, unwind and enjoy being by the water.

Best Things To Do in Kennebunkport, ME:

• Visit Gooch’s Beach for a walk along the shore, or go for a swim.
• Have an authentic lobsterman experience with Rugosa Lobster Tours .
• Walk around the downtown and Dock Square shops.
• Grab an artisanal ice cream cone at Rococo Ice Cream .
• Have some craft cocktails and beer at Batson River Brewing and Distillery .
• Walk along Parson’s Way for amazing views of the dramatic coastline.
• Grab fresh seafood takeout from The Clam Shack .

Click here to see why Kennebunkport is one of the best Christmas towns in New England!

15. Bar Harbor/Acadia National Park

Distance From Boston: 4 hours and 45 minutes

One of the absolute best places to visit in all of Maine is Bar Harbor and Acadia National Park, and this will make an epic road trip from Boston. Bar Harbor is the adjacent town to Acadia, and where most people stay when visiting the park. Bar Harbor is a fun destination on its own because it’s full of character, and has great restaurants, and a beautiful harbor-side walking path and park.

Acadia National Park is one of the top destinations in all of New England, providing over 120 miles of hiking trails, and countless opportunities to take in some of the best and most incredible coastline views in the entire Northeast. In my opinion, this is one of the best roads trips from Boston you can take.

Best Things To Do in Bar Harbor & Acadia National Park:

• Walk along the Ocean Path trail inside Acadia, which is a flat, easy path along Shore Road that provides the most payoff for minimal effort when it comes to the most famous views in the park.
• Have lunch and popovers at Jordan Pond House inside Acadia, which offers views of the lawn and Jordan Pond.
• Drive to the summit of Cadillac Mountain inside Acadia for sunrise or sunset.
• Explore Bar Harbor’s downtown.
• Take a leisurely walk along Shore Path in Bar Harbor for the best views of the harbor.
• Visit Bass Harbor Lighthouse inside Acadia.

Tip : You’ll need to purchase a park pass to enter any attractions inside Acadia National Park. Park passes can be purchased online in advance by clicking here .

Psst! I have some posts on Acadia that you may find helpful, including my Acadia National Park Itinerary , and the Best Time To Visit Acadia National Park .

Luxury Road Trip Destinations From Boston

These destinations don’t have to be all about luxury, but since it’s nice to treat yourself every now and then, I wanted to include a few of my favorite luxury resorts that are easy road trips from Boston. If all you’re looking for is a little R&R and some serious pampering without having to leave the resort grounds, these are amazing places to visit.

16. Cliff House in Cape Neddick, ME

If you’re looking for the ultimate coastal Maine getaway to fully relax and recharge, then Cliff House will be the perfect road trip from Boston for you. This oceanfront resort sits atop 70 acres of cliffs, and offers incredible amenities that will allow you fully emerse yourself in Maine’s natural beauty without having to go far. Almost every square foot of this property has an ocean view, so there’s no way you can be stressed during your visit.

What To Expect During Your Stay At Cliff House:

• Beautifully-appointed rooms with a private terrace, and your choice of partial or full ocean views. Some rooms are also ocean-front.
• Complimentary coffee, tea and water stations on each floor.
• A full-service spa.
• Three oceanfront restaurants and a coffee cafe.
• Manicured gardens and pathways for relaxing walks.
• Two outdoor pools, two indoor pools and a hot tub.
• On-site shopping.

Click here to book your stay at Cliff House!

17. Ocean House in Westerly, RI

Distance From Boston: 1 hour and 45 minutes

For one of the very best luxury experiences in all of New England, Ocean House in Westerly, RI is a truly amazing destination. With the entire properly overlooking the Block Island Sound, it’s guaranteed you’ll be able to relax during your stay. Travel + Leisure has even named Ocean House as one of the top 100 hotels in the entire world.

What To Expect During Your Stay At Ocean House:

• Freshly designed and elegant coastal New England rooms and suites.
• Complimentary use of the hotels Mercedes-Benz convertibles for self-guided tours.
• Complimentary activities within the resort, such as daily yoga and cooking classes.
• Valet parking included in your room rate.
• Four on-site restaurants, and lobster dinners on the lawn during the summer.
• An on-site spa.
• Beautifully manicured lawns with yard games.
• Complimentary refreshments throughout the day.

Click here to book your stay at the Ocean House!

18. Mohonk Mountain House in New Paltz, NY

Distance From Boston: 3 hours and 45 minutes

If you’re looking for the ultimate road trip from Boston that combines hiking in the mountains with total relaxation, then Mohonk Mountain House is perfect for you. Located in the small college town of New Paltz, Mohonk Mountain House is right in the heart of the Hudson Valley of New York, and is surrounded by 40,000 acres of forest.

Overviews of the resort have been used in the Amazon Prime series Upload , and has long been rumored to be the inspiration behind Stephen King’s The Shining . But don’t let that scare you away! That only thing that will actually scare you once here is how amazing the views are.

If an overnight stay doesn’t work with your plans, guests can also purchase a day pass to the resort grounds, which allows you access to the hiking trails. This is a great way to enjoy the scenery without committing to an overnight stay.

What To Expect During Your Stay At Mohonk Mountain House:

• Traditionally-decorated rooms and suites that overlook the mountains. Most rooms also come with private balconies and rocking chairs.
• Lake Mohonk on the resort grounds.
• An all-inclusive stay where breakfast, lunch, afternoon tea and dinner, as well as all outdoor activities such as kayaks, row boats and canoes, are all included in the room rate.
• 85 miles of hiking trails right outside your door.
• Farm-to-table dining.
• Benches and chairs situated all over the resort grounds for moments of rest, and to clear your mind.

Click here to book your stay at Mohonk Mountain House!

Click here to read my detailed review of a Mohonk Mountain House Day Pass!

19. Mirbeau Spa in Rhinebeck, NY

Distance From Boston: 3 hours and 10 minutes

Mirbeau has a few locations throughout the Northeast, but my favorite of them all is in Rhinebeck, NY, a beautiful little town in the Hudson Valley. This particular Mirbeau Spa is one of the newer additions to their family, and is decorated in a modern, Parisian style, which makes it feel like a unique destination.

The spas at Mirbeau are really amazing. I’ve personally had massages and treatments at different locations, and they’ve always been consistent in quality (and, of course, relaxation). Guests are invited to walk around in robes, including at lunch, and the on-site hotel allows you to continue your relaxation journey into the evening for the perfect overnight stay.

What To Expect During Your Stay At Mirbeau in Rhinebeck, NY:

• A serene, calm spa atmosphere throughout the entire grounds.
• A relaxation room, aqua terrace and steam facility within the spa.
• Different spa packages to customize your stay that include dining options to make your visit stress-free.
• Luxurious and Parisian-inspired accommodations with options including in-room fireplaces and soaking tubs.

Click here to book your stay at Mirbeau in Rhinbeck!

Charming Small Town Road Trip Destinations From Boston

If you’re looking to visit some of the most charming towns in New England and New York for your road trip, I’ve got your covered! Here are the most adorable little towns to visit that make awesome road trips from Boston.

20. Saratoga Springs, NY

Distance From Boston: 3 hours and 15 minutes

While technically a city, Saratoga Springs’ historic downtown feels very much like a quaint village. Located in Upstate, NY and known for its horse racing track season, this destination has so much more to offer including a wonderful Main Street for shopping and dining, gorgeous parks, beautiful and historic architecture and live entertainment.

Best Things To Do in Saratoga Springs, NY:

• Walk around the grounds of Saratoga Spa State Park, which is a National Historic Landmark. You can enjoy a round of golf at an 18-hole championship course, have a picnic by the reflecting pool and admire the architecture of the Hall of Springs.
• July – Labor Day, visit the Race Track , and even try your hand at placing bets on the winner!
• Stroll through Congress Park, and find the mineral springs to taste the local water.
• Enjoy a healing bath at the Roosevelt Baths & Spa . The spa staff is trained on how to draw the perfect bath at just the right temperature, and the minerals in the waters have been said to have health benefits such as reducing sinus congestion and arthritis symptoms.
• Take in a live show at SPAC , one of the the country’s most renowned outdoor concert venues.
• Walk up and down Broadway, downtown’s main street, to visit the local shops and restaurants.
• Grab delicious cocktails with lunch or dinner at Morrissey’s Lounge & Bistro inside the famed Adelphi Hotel. Better yet, book an overnight stay at this Gilded Age-era boutique hotel, located in the heart of Saratoga’s downtown.

Click here to book your stay at the Adelphi Hotel in Saratoga Springs!

21. Skaneateles, NY

Distance From Boston: 5 hours and 20 minutes

Skaneateles is a lakeside town in the Finger Lakes region of Upstate, NY, and is a wonderful place to visit, especially in the Summer. With Skaneateles Lake right in the heart of downtown, and an adorable Main Street with really nice shops and restaurants, the quaintness of the town is perfect for rest and relaxation, but also offers plenty to do to keep from ever being bored.

Best Things To Do in Skaneateles, NY:

• Walk around Main Street to visit the boutiques.
• Sit and admire the views of the lake from the town’s many waterfront areas.
• Visit Anyela’s Vineyards to enjoy a tasting, or sip on a glass of wine and take in the peaceful views of the vineyards.
• Head out onto the lake for a boat tour.
• Grab dinner and drinks at the Sherwood Inn , located right in the heart of town, and just across the street from the lake.
• Spend the day getting pampered at Mirbeau Inn & Spa , the original Mirbeau location, which is home to a Monet-inspired garden and bridge.

Click here to book your stay at Mirbeau Inn & Spa in Skaneateles!

Click here to read more suggestions on the best things to do in Skaneateles, NY!

22. Lake Placid, NY

Distance From Boston: 5 hours

Known for hosting two Olympic games, Lake Placid in the Adirondack region of Upstate NY has so much more to offer (although, the Olympic sites are definitely worth visiting!). I personally love visiting Lake Placid in the winter because the alpine-inspired town really seems to come alive with apres-ski vibes, but it’s really a great destination all year round. While in Lake Placid, you’ll be surrounded by mountains and fresh air, and feel like you’ve truly escaped from every day life.

Best Things To Do in Lake Placid, NY:

• Walk around Mirror Lake, located in the heart of Lake Placid’s downtown.
• In the winter, enjoy skiing at Whiteface Mountain , and ice skating and a Toboggan Chute on Mirror Lake.
• Enjoy the miles of hiking trails in the nearby mountains.
• Walk around the alpine-inspired downtown village to visit the quaint shops.
• In the summer, go for a swim in Mirror Lake from the public beach area.
• Visit the Olympic sites, including the ski jump, ice arena and the Lake Placid Olympic Museum .
• Walk around High Falls Gorge, a 22-acre nature park with waterfalls.
• Grab drinks and lunch or dinner at The Cottage, a restaurant at Mirror Lake Inn Resort & Spa that sits right on Mirror Lake. Better yet, book an overnight stay, and also enjoy the on-site spa for the ultimate Lake Placid getaway!

Click here to book your stay at the Mirror Lake Inn Resort & Spa in Lake Placid .

Click here to read my post on all the best things to do in Lake Placid in the fall!

23. Hudson, NY

Distance From Boston: 2 hours and 45 minutes

Located in the Hudson Valley of New York, Hudson is known as being incredibly charming, and one of the best destinations for antiquing in the area. This is a great little town to visit if you’re looking to relax, enjoy a small-town atmosphere and see where the day takes you. Hudson is also a great destination if you’re looking to explore the entire Hudson Valley region.

Best Things To Do in Hudson, NY:

• Antiquing! There are countless antique shops in Hudson, and you’ll definitely want to check out The Antique Warehouse , which has over 300,000 sq. feet of treasures.
• Stroll down Warren Street, where most of the storefronts can be found.
• Take a boat cruise along the Hudson River with Hudson Cruises , which offers tours to the Hudson-Athens Lighthouse, and even murder mystery cruises!
• The Hudson Farmer’s Market is regarded as one of the best in the region, and is open every Saturday in-season, and also has a winter location February-April.
• Tour the local art galleries.
• Go for a nature walk in the Greenport Conservation Area, which is home to over 7 miles of trails, and is walkable from downtown Hudson.

Click here to read my post on the best things to do in Upstate New York in the fall!

24. Manchester, VT

This small little town in Southern Vermont is the perfect place to disconnect and relax. As you cross the New York/Vermont border, you’ll begin to see the tall mountains all around you, and instantly feel more at peace. In fact, you’ll be able to see the surrounding mountains from everywhere in downtown Manchester. And with everything to do from shopping and dining to hiking and nature walks, you’re sure to find something that everyone in your group will enjoy.

Best Things To Do in Manchester, VT:

• Hike or drive up Mt. Equinox, the tallest mountain in the Taconic Range, and enjoy the incredible views from above.
• Browse through Northshire Bookstore , an amazing independent bookstore that’s been in business since 1976. Here, you’ll find new and used books, a wonderful children’s section, and unique Vermont-inspired gifts and souvenirs.
• Visit Hildene , the Lincoln family estate, where visitors can tour the gardens, walking trails, farm land and indoor exhibits, and enjoy sweeping views of the Vermont countryside.
• Rent a tube at Vermont River Runners and take a relaxing water tube ride along the Battenkill River, which is perfect for a warm summer day.
• Grab a sandwich as big as your head at Zoey’s Deli . I also love their homemade chips!
• Hike the Lye Brook Falls trails to visit a beautiful waterfall. The trailhead is a short 5-minute drive from town center.
• Go for a dip in the Dorset Marble Quarry for a unique swimming experience!
• After your swim, visit the Dorset Union Store , a quintessential Vermont country store.

Click here for an awesome Vermont covered bridges tour itinerary!

25. Woodstock, VT

Distance From Boston: 2.5 hours

Of all the Vermont towns on this list, I think Woodstock might be my favorite. I love them all, but there’s something about Woodstock that just screams New England charm, and perfectly balances being a town that caters to tourists, while not losing any of the local character. It’s one of those idyllic towns you’ll daydream about moving to.

Best Things To Do in Woodstock, VT:

• Walk through the truly adorable village and enjoy the local shops and coffee cafes.
• Head over to the Woodstock Middle Covered Bridge, located right in the village, for a picture-perfect Vermont moment.
• Get your hands muddy with a pottery workshop at Farmhouse Pottery .
• Drive to nearby Quechee and visit the Simon Pearce Restaurant & Mill , and take in a live glass-blowing demonstration, as well as lunch overlooking the gorge.
• Head over to Quechee Gorge Village after Simon Pearce for some antiquing.
• Visit Billings Farm & Museum to tour a working dairy farm, gardens and orchards, and see live demonstrations. The grounds here are truly spectacular!
• Hike Mount Tom for stunning views of Woodstock from above.
• Best Places To Stay In Vermont In The Fall
• Best Things To Do In Woodstock, VT
• Best Winter Getaways In New England

26. Stowe, VT

Distance From Boston: 3 hours and 20 minutes

Stowe is an adorable little village in Northern Vermont that I love to visit, and it always puts a smile on my face. Even though it’s a well-known ski destination in the winter months, it’s a great little place to visit year-round will lots of outdoor activities and perfect Vermont scenery all over, including some beautiful covered bridges.

Best Things To Do in Stowe, VT:

• Hike Mount Mansfield, the highest mountain in Vermont, or drive the auto road to the summit.
• See if you believe in ghosts at Emily’s Covered Bridge. Legend says it’s haunted by a girl who hung herself on the bridge after her boyfriend never came to meet her.
• Walk the Stowe Recreation Path, a 5.5-mile long paved path that goes through beautiful scenery throughout the village. The path can be accessed from several locations in the village.
• Connect to the Quiet Path along the Rec Path, which is reserved for walkers only (meaning, no bikes wizzing by you). It meanders through parts of Mayo Farm, and is a very relaxing way to spend an afternoon.
• Go hiking at Smuggler’s Notch State Park.
• Visit the nearby Ben & Jerry’s Factory for a tour.
• Explore Sterling Falls Gorge.
• In the winter, hit the slopes at Stowe Mountain Ski Resort.
• Pick up some chocolates from Lake Champlain Chocolates.
• Best Things To Do In Stowe, VT
• Best Stops To Make When Driving From Boston to Stowe, VT
• Best Things To Do In Vermont In The Winter

27. Greenwich, CT

Distance From Boston: 3 hours

Greenwich is an absolutely beautiful town that sits right on the border of New York, and also very accessible to Manhattan. I love coming to this idyllic little town when I want a day of relaxing, shopping, dining, being outside, visiting the beach and enjoying the gorgeous scenery.

Best Things To Do in Greenwich, CT:

• Shop the stores along Greenwich Avenue.
• Enjoy a serene walk through the Donald M. Kendall Sculpture Gardens in nearby Purchase, NY.
• Meander through Montgomery Pinetum, a public park that’s very relaxing, and also has beautiful ponds, nature trails and gardens with an educational center and greenhouse.
• Head to the Lobster Bin for an amazing lobster roll on-the-go.
• Spend some time at the beaches along Greenwich Point Park.
• Admire the architecture of the historic district buildings.

28. Jackson, NH

Let’s head to the White Mountain National Forest in New Hampshire! One of the best towns to stay in is Jackson, where you’ll find a lovely downtown and Main Street, an iconic red covered bridge, and endless opportunities to explore the White Mountains region, including lots of hiking and outdoor activities. While it’s most popular during the winter for skiing, and the fall for foliage season, Jackson can be enjoyed year-round.

Best Things To Do in Jackson, NH:

• Visit Honeymoon Bridge, the town’s famous red covered bridge.
• Drive to the summit of Mount Washington, the highest peak in New England.
• Hike the Glen Ellis Falls Trail.
• Explore the downtown shops and restaurants.
• In the winter, go skiing at Black Mountain. In the summer, the mountain offers horseback riding and lots of hiking trails.

You may also like: The best things to do in New England in the fall!

City Life Road Trip Destinations From Boston

Even though you’re road-tripping from a city already, it’s still exciting to explore a new one. There are quite a few cities that make for amazing road trips from Boston, and many of them can be combined with other destinations from this list to offer the best of city life, and coastal or small-town living.

29. Portsmouth, NH

Distance From Boston: 1 hour

This charming little city is just a short drive from Boston, and definitely feels more like a town than a city. Portsmouth is a port-side city with a gorgeous downtown filled with quaint shops and boutiques, and is known as being a huge foodie destination. This is a great city to visit if you’re looking for a lot of character, and lots of options when it comes to being outside, dining and shopping.

Best Things To Do in Portsmouth, NH:

• Grab some fresh and delicious pastries from Elephantine Bakery , and be sure to enjoy them just outside the cafe in the most adorable little courtyard.
• Shop the boutiques in downtown Portsmouth.
• Walk along Prescott Park, which has over 10 acres of waterfront gardens and paths, and is home to live entertainment in the summer months.
• Take a dip in the water at Great Island Common Park.
• Go brewery hopping, as Portsmouth is home to five breweries.
• Enjoy a drink at the Book & Bar , a combined bookstore, cafe and bar.
• Head out onto the water with Portsmouth Harbor Cruises .
• Visit Portsmouth Harbor Lighthouse.

30. Providence, RI

Providence is the capital of Rhode Island, and also home to famed schools Brown University and the Rhode Island School of Design. It’s also a really fun city to be a tourist! With Providence River running through the city, you still have opportunities to feel like you’re connected to nature, and with tons of restaurants, shops, nightlife and history, this destination makes for an amazing road trip from Boston.

Best Things To Do in Providence, RI:

• Visit The Arcade , the country’s very first shopping mall designed with Greek revival architecture, and now home to some awesome boutiques and art galleries.
• Visit the Roger Williams Park Zoo , which is the third oldest zoo in the country, where guests can feed giraffes and other farm animals, and see over 160 different species while visiting. You can also jump on the Explore and Soar ride, which is a fun zip ride and train excursion through the forests.
• Enjoy a leisurely walk along the Providence Riverwalk.
• During the summer, experience WaterFire, where braziers are set with bonfires in the middle of the river.
• Take in the exhibits at the RISD Museum of Art.
• Take a Venetian gondola ride along the river at Waterplace Park.
• Do a self-guided historical walking tour along Benefit Street to see some of the city’s most historic houses and buildings.
• Take a boat tour along the Providence River.

Click here to read my post on the best day trips from Providence!

31. Portland, ME

Portland is an exciting waterfront city in Maine that sits on a peninsula along Casco Bay, and provides the best of both worlds as far as being a city destination that’s also coastal. With things to do outdoors along the dramatic coastline, to an amazing restaurant and food scene, Portland has a little something for everyone during your road trip from Boston.

Best Things To Do in Portland, ME:

• Portland Head Lighthouse is a must! It’s the most famous lighthouse in Maine, and one of the most iconic in all of New England. Nearby, you can also visit Spring Point Ledge Light and Bug Light, and do a mini lighthouse tour without leaving the city!
• Visit one of my favorite breweries in New England, Bissell Brothers . They also get bonus points for being close to the waterfront at Thompson’s Point.
• Meander around Old Port to see the city’s fishing industry come to life.
• Walk along the lively waterfront scene on Commercial Street for shopping, dining and water views.
• Tour the open waters on a beautiful Schooner tour with Portland Schooner . They also invite you to pack a picnic with beer and wine to enhance your experience.
• Tour the Portland Arts District, which is filled with art galleries, museums and theaters.
• Take a culinary tour of the city and learn the very best places to eat, led by a local. Click the link below to book your tour, or learn more info.

Click here to book your walking culinary tour in Portland!

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32. New York City

Distance From Boston: 3 hours and 45 minutes (but always allow extra time for traffic)

New York City needs no introduction, and if you’ve never been to the city that never sleeps, this is an absolute must if you’re looking into road trips from Boston. Below is a list of my absolute favorite things to do when I visit NYC, which includes the best things to do for first-time visitors.

The Best Things To Do in New York City:

• Walk the Brooklyn Bridge and visit DUMBO for sweeping views of both the Brooklyn and Manhattan bridges.
• Get bagels at Brooklyn Bagel (the best in the city).
• Visit Central park, and be sure to stop at Bow Bridge, Belvedere Castle and The Mall walkway.
• Grab a slice of pizza at Joe’s (150 E 14th St.)
• Explore the MET Museum and Cloisters.
• Take the Staten Island Ferry for views of the Statue of Liberty (this is free and way better than the official tours, which are super crowded!).
• See a broadway show.
• It’s touristy, but I love going to the top of the Empire State Building.
• Walk around the West Village for amazing streets and brownstones.

33. Burlington, VT

Burlington is a small and beautiful city in Northern Vermont that sits along Lake Champlain, and is wonderfully diverse, exuberant and also very relaxing. This is a great destination if you’re looking for a small-town feel set in a bigger city, waterfront and outdoor activities, an art scene and plenty of amazing restaurants.

Best Things To Do in Burlington, VT:

• Walk around Church Street, a pedestrian-only area lined with unique shops and restaurants.
• Stroll around the waterfront to admire the views of Lake Champlain, as well as the Burlington Breakwater Lighthouse.
• Bike the Burlington Bike Path, a beautiful path along the lake that’s over 7 miles long.
• Go kayaking or stand up paddleboarding on the lake.
• Head to nearby Shelburne to tour Shelburne Farms , one of my favorite things to do in all of Vermont! There are tons of hiking and walking trails through the 1400-acre picturesque grounds, and you can stop to sample their homemade cheeses and baked goods along the way.
• Take in the art scene on the South End, which is loaded with galleries and shops.
• Get a taste for the local brews with a Sip of Burlington Beer Tour. Join a small group for dinner, and learn from a local brew expert as you taste all the different beers that are brewed nearby. Click the link below to learn more, or book your tour.

Click here to book your Beer of Burlington experience!

34. Philadelphia, PA

Last but most definitely not least on our round-up of the best road trips from Boston, is the city of Brothery Love, Philadelphia. Philly is Pennsylvania’s largest city, and is deeply rooted in history, but there are all kinds of things to do from exciting nightlife and amazing food to parks and waterfront activities.

Best Things To Do in Philadelphia, PA:

• Run up the Rocky Steps at the Philadelphia Museum of Art, and snap a picture with the Rocky statue. A bit touristy, but if you’re a fan of the movie, you gotta go for it.
• Speaking of the Philadelphia Museum of Art , after your Rocky moment, be sure to visit. They have an amazing American art collection, as well as works by famed impressionists Renoir, Degas and Monet.
• Tour Independence Hall, regarded as the birthplace of the United States, and where the Declaration of Independence was debated by our Founding Fathers.
• Venture just outside the city to visit Longwood Gardens, an expansive garden oasis filled with both indoor and outdoor gardens and, and beautifully designed grounds.
• Grab a Philly cheesesteak at Woodrow’s Sandwich Shop .
• Stroll along the Delaware Riverfront to explore Cherry Street and Race Street Piers, and take in amazing views of the Benjamin Franklin Bridge.
• Hop on a BYOB trolley tour of the city, hosted by hilarious guides that share historic and entertaining information, and take you to some of the top sites in the city. Click the link below to learn more, or book your tour.

Click here to book your Historically Hilarious Trolley Tour in Philadelphia!

Road Trip Itinerary Options

If you’re looking to combine towns from this list into longer roads trips, or are wondering which towns are close enough to combine together to maximize your time and cover the most ground, I’ve got you covered! Below you’ll find suggested itineraries with different routes you can take while planning the best road trips from Boston.

Option 1: Massachusetts North Shore Road Trip From Boston

For this route, you’ll head north from Boston and visit the following destinations:

• Newburyport & Plum Island
• Portsmouth, NH

Days Needed For This Route: 2-4 . If you’re looking for an easy road trip from Boston with lots of options, this is an awesome route to take. You can do it in as little as 2 days for a weekend trip, or add on two additional days to take your time and explore each town.

Option 2: Cape Cod & The Islands Road Trip From Boston

For this route, you’ll head south from Boston and visit the following destinations:

• Martha’s Vineyard

Days Needed For This Route: 7-8 days. Because this route requires ferries from Cape Cod to the islands, and with Cape Cod being a larger region to explore, I recommend a week.

If you have less time, the islands could be done as day trips, and you could attempt this route in about 5 days . If you have 10 days, I would suggest spending one night in Plymouth, 5 days on Cape Cod, two nights on Nantucket and two nights on Martha’s Vineyard for the ultimate Cape Cod road trip.

Option 3: Boston To Bar Harbor Road Trip

This route will take you up the coast of Maine and stop in these destinations:

• Newburyport, MA
• Ogunquit, ME
• Kennebunkport, ME
• Portland, ME
• Bar Harbor, ME

Days Needed For This Route: 7-10 days. I suggest this much time because your final destination, Bar Harbor, is home to Acadia National Park, and there’s so much to see and do just in the park. And each stop along the way is a very worthy destination to spend at least one night in.

If you’re very short on time, you can do this route in 4 nights with this itinerary:

• On your way to Ogunquit, pass through Newburyport and spend 2-3 hours there. Arrive in Ogunquit late afternoon to spend the night.
• The next day, spend the morning in Ogunquit, and then drive to Kennebunkport to spend about 3 hours exploring there. Drive to Portland, and spend the night.
• The next day, spend your morning in Portland, and then drive to Bar Harbor to arrive by mid-afternoon. Spend 2 nights in Bar Harbor.
• Drive back to Boston.

I have a detailed Boston To Bar Harbor, Maine Road Trip Itinerary if you’d like more help with planning!

Option 4: Vermont Road Trip From Boston

For this route, you’ll head northwest of Boston, and drive through the best towns in Vermont from this list. You’ll cover these destinations:

• Manchester, VT
• Woodstock, VT
• Burlington, VT

Note : This route isn’t as direct as the other routes, and will include 6.5 hours of driving time to get from Boston to Burlington, stopping at the other destinations along the way. But then you can drive direct from Burlington to Boston on your way home, which will only take 3.5 hours.

Days Needed For This Route: 3-5 days . This could easily be a long weekend itinerary if you don’t stop in each town overnight, and just visit Manchester and Stowe for a few hours each. You could, of course, take your time, and do up to 5 nights for this itinerary.

Option 5: Rhode Island & Coastal Connecticut Road Trip From Boston

This route will take you southwest from Boston, and you’ll visit these destinations:

• Providence, RI
• Newport, RI
• Block Island, RI
• Westerly, RI

Days Needed For This Route: 3-6 days . This is another itinerary you could also do in a weekend if you only spend a few hours in Mystic, as a day trip from Newport, and skip going to Block Island. To visit all these destinations, you’ll need about 5 days, but 6 would be ideal to not feel rushed.

Tip : If you wanted to extend your road trip further along this route, there is a ferry that leaves from New London, CT, and goes to the Hamptons!

Option 6: Boston To New York City & The Hamptons Road Trip

This route will take you to these destinations:

• Rhinebeck, NY
• New Paltz, NY
• New York City
• The Hamptons
• Optional add-on: Philadelphia, PA

Note : The route from Boston to The Hamptons, while making all the stops in the Hudson Valley in-between, is not direct, and will take about 7.5 hours without stops, so I highly suggest you stop overnight in at least one of the towns to break up your drive. If you wanted to visit Philadelphia, this would be the route you would want to add that destination to, as you will have to drive through NYC to get there.

Days Needed For This Route: 1 week. To do this route in 7 days, I would suggest spending a few hours each in Hudson and Rhinebeck, then spend the night in New Paltz (splurging at Mohonk Mountain House is definitely worth it!). Then drive to NYC the next day, and spend 3 nights there. Then drive to The Hamptons, and spend 3 nights. If you want to add Philadelphia, you’ll want to add an extra night or two.

If you’re short on time and want to do this route in fewer days, I would suggest spending a night in the Hudson Valley (same as above), spend 3 nights in NYC, but include a day trip to The Hamptons. Or, if The Hamptons is of more interest to you, you could spend one night in NYC, and spend a night or two in The Hamptons. And then drive back to Boston.

The other option is to drive direct from Boston to New York City, and leave out the Hudson Valley towns entirely. On that route, your focus would be New York City and The Hamptons.

What Towns Are 1 Hour From Boston?

Plymouth, Salem, Rockport, Newburyport are all within an hour from Boston, and make for wonderful road trips or day trips from Boston.

Towns not mentioned on this list that are also an hour or less from Boston that are perfect for a road trip are Scituate, Gloucester, Manchester-By-The-Sea and Essex, all of which are located in Massachusetts.

What Cities Are 6 Hours From Boston?

New York City, Portsmouth, NH, Philadelphia, PA, Portland, ME, Burlington, VT and Providence, RI are all within 6 hours or less from Boston, and are all included on this list as amazing road trips from Boston.

Is Boston Close To Niagara Falls?

Boston is over 7 hours from Niagara Falls, and for that reason, didn’t make this list of road trips. But if you have extra time, it could be added to a road trip itinerary for Skaneateles, NY and the finger lakes region.

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That’s A Wrap On The Best Road Trips From Boston

As you can see, Boston is really an incredible gateway to all of the Northeast, making it easy to take lots of different road trips. Whether you want to explore the coast of Massachusetts and Maine, go cute-town-hopping through Vermont or visit as many cities as you can, you’re now ready to plan which of these road trips from Boston is perfect for you.

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The 16 best day trips from Boston

Take a break from city life and visit these nearby New England destinations—no packing required

While many of us could easily spend every waking moment in Boston, it can be refreshing to escape the city for 24 hours or so. Fortunately, this picturesque New England region offers an array of potential day trips from Boston, including quaint seaside villages, historic towns and stunning mountain vistas. So grab your pals or significant other, and hop on a ferry, train or automobile to one of these lovely destinations. Once you're back in town, you'll once again feel ready to take advantage of the  best Boston attractions ,  best free things to do in Boston  and  best museums in Boston . And when you need a little longer time away check out our list of the best weekend getaways in New England . RECOMMENDED: The Best Hotels in Boston

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Best day trips from Boston

1.  Newport, RI

The Newport mansions of the Gilded Age still impress with their grandeur—just as they were built to do. If you have time to only tour one estate, check out The Breakers . Near the International Tennis Hall of Fame , the Audrain Auto Museum houses a seasonally rotating display of incredible cars inside a gorgeous Art Deco building.

Take the Cliff Walk, which has stunning views of the ocean, or relax at the public Easton’s Beach . Stroll past cool shops and eateries on narrow Thames Street. On Marlborough Street, dine at the White Horse Tavern , which claims to be America’s oldest restaurant, or duck over to The Reef at Howard Wharf for dinner and drinks with a view. Near the harbor, Bowen’s Wharf’s buildings date back to the 1700s, now offering an inviting maze of restaurants and shops. Stroll over the causeway to Goat Island where the Newport Harbor Lighthouse is overlooked by the upscale Gurney’s Resort.

2.  Portland, ME

​​Maine's largest city, located about a two-hour drive north of Boston, attracts epicureans from around the country to its cobblestone streets. Wander the charming, hilly Old Port district, where every kind of boutique imaginable touts colorful wares. Pop into one of the many quaint pubs and dimly lit cocktail bars, like the excellent Jewel Box or Blyth & Burrows —the latter of which pairs the best in innovative mixology with equally scrumptious small plates. In the West End arts district, enjoy the I.M. Pei-designed Portland Museum of Art and the State Theatre , which hosts national acts, both musical, comedic and theatrical.

The food scene here lives up to the hype:   Cong Tu Bot for nationally celebrated Vietnamese fare;  Green Elephant for an inventive vegetarian meal;   Evo Kitchen + Bar for progressive twists on Mediterranean cooking; or  Union , a vibrant locavore haunt located at  The Press Hotel , whose historic building was formerly the home of the Portland Press Herald.

3.  Newburyport, MA

The Newburyport Historic District, which encompasses most of the downtown, is listed in the National Register of Historic Places. This treasure trove of well-preserved, Federal-period architecture includes the notable Cushing House Museum & Garden , home of statesman Caleb Cushing, and the Custom House Maritime Museum , which also unravels local history. The beautiful Waterfront Park and boardwalk has regular concerts during warmer months.

Catch a play or see a show at the Firehouse Center for the Arts , grab a gourmet sandwich and bottle of wine at Joppa Fine Foods ,  relax with excellent cocktails and modern Middle Eastern bites at Bar25 ,  dine on classic seafood at The Black Cow  or head to the Newburyport Brewing Company ,  offering a friendly tap room and beer garden.

Newburyport includes part of neighboring, sedate Plum Island , a barrier island overlooking salt marshes.

4.  Gloucester, MA

Shipbuilders and fishermen put Gloucester on the map, and both industries still exist there today —just  on a smaller scale. The Fishermen’s Memorial on Gloucester Harbor honors all those lost at sea, including the Andrea Gale and its crew, the real-life victims of The Perfect Storm . Check out the Cape Ann Museum , which has an amazing collection of art and artifacts specific to Gloucester and its surroundings.

Across narrow Main Street, you can savor straight-off-the boat seafood at the chic basement restaurant  Tonno . Oak to Ember  will impress with its menu of hearty, wood-fire-cooked dishes and thoughtful cocktails. Or, if you're more about ocean views, head to the Beauport Hotel , whose 1606 Restaurant has a great deck overlooking the water. Next door to the hotel, Beauport Cruise Lines offers seasonal jaunts around the harbor.

5.  Salem, MA

Salem is forever linked to its horrifying and fascinating 1692 Witch Trials. The curious flock to the home of presiding Judge Corwin, which today is a museum known as The Witch House . Halloween is a big thing here—so are new age and cult shops. On a less spooky note, the Peabody Essex Museum houses a wonderful art collection, and Salem is the birthplace of Nathaniel Hawthorne, author of The House of the Seven Gables. You can even tour the house he may have been writing about, the 350-year-old Turner-Ingersoll Mansion.

Though it only dates back to 1930, Pioneer Village —a 10-minute drive from downtown, in Forest River Park—reenacts early 17th-century colonial life. Eat like a local at Ledger or Settler , or nerd out with old school arcade games and pinball machines at Bit Bar . 

6.  Provincetown, MA

Creative, sassy P-Town—located only a 90-minute ferry ride from Boston—is an artsy LGBT hotspot. It’s got a great mix of galleries, restaurants and nightlife hangouts. Lined with dozens of colorful shops, friendly eateries and local businesses, Commercial Street is the bustling heart of the town. Seek out one of the many events and festivals that fuel the thriving arts scene.

The famous and seasonal  Lobster Pot is the biggest name in town for classic lobster rolls and fresh seafood treats. Climb the 252-foot granite Pilgrim Monument for dramatic harbor views, then escape to Race Point Beach to enjoy the sights, sounds and smells of the open ocean.

Eat innovative seasonal dishes at Strangers & Saints and great seafood at Mac’s Fish House , which has crispy fish and chips and Happy Hour dollar oysters. Explore the beautifully barren Outer Cape’s stretch of the Cape Cod National Seashore , including Truro’s picturesque Highland Light .

7.  Ogunquit, ME

Set on the breathtaking Maine coast, Ogunquit is a popular, classic beach town with a quiet ambiance, particularly in the cooler months when crowds disappear. But it’s also a historic arts community; the Ogunquit Museum of American Art was started in the 1950s by native artist Henry Strater, a student of Ogunquit’s Perkins Cove artists colony.

Wander the galleries around town, explore the Barn Gallery on Shore Road and get tickets to a show at the Ogunquit Playhouse —which boasts eight decades of professional theatre and summertime children’s productions—or another summer stock theater.

8.  Watch Hill, RI

A coastal village that’s part of the town of Westerly, Watch Hill has one of the best beaches on the East Coast, and celebrity glamour to spare. Get to town early and take a walk out on the Napatree Point Conservation Area , where  you’ll find the remains of Fort Mansfield and lots of beautiful birds like osprey and piping plovers.

After your nature walk, head into the charming town for a stroll and some shopping. The kids will love the vintage carousel, and be sure to have lunch at the Olympia Tea Room (supposedly Taylor Swift’s fave—you can take a peek at her house from afar, too, because it’s hard to miss). Finish the day with cocktails at the gorgeous Ocean House , where you can have a drink and a bite to eat.

9.  Concord, MA

Stroll to the Old North Bridge and explore the Minute Man National Historical Park’s five-mile Battle Road Trail, dedicated to the Battle of Concord (April 19, 1775), where militia engaged with British troops and ignited the Revolutionary War. The 19th-century Transcendentalist movement and its influential authors and thinkers—Ralph Waldo Emerson, Henry David Thoreau and Bronson Alcott—were rooted in Concord, and the Concord Museum is a good place to connect the dots. Located just outside of Concord Center are Walden Pond , which honors Thoreau’s famed naturalist journal, and Orchard House , where Louisa May Alcott wrote Little Women 150 years ago.

Pick up a picnic lunch at The Concord Cheese Shop . The Saltbox Kitchen’s tasty dishes and small-batch brewery are both fueled by produce from its nearby Saltbox Farm. For dinner, Woods Hill Table  also sources from their own farm at Woods Hill in Bath, NH, and the sleek, seasonally-focused 80 Thoreau is worth the day trip alone.

10.  Providence, RI

Providence is a foodie’s dream. Why does this small capital city have so much kitchen talent? Nearby Johnson & Wales University’s College of Culinary Arts is a major factor. Hemenway’s downtown is the grand dame of area seafood restaurants;  Waterman Grille is a vibrant jewel on the East Side near Brown University; and Aleppo Sweets is a lauded Syrian bakery and cafe—just to name a few spots. Federal Hill, the city’s impressive Italian neighborhood, is also loaded with Italian eateries and shops. 

Waterplace Park is a lovely gathering spot, and it anchors the city’s annual WaterFire program, which runs from spring through late fall; braziers along the Providence River are lit at sunset and stoked with aromatic wood by black-clad figures on boats, while themed music plays.

Providence is home to the notable Trinity Repertory Company , and The Strand Ballroom & Theatre, one of the nation’s best rock venues. The Rhode Island School of Design’s museum includes one the country’s finest university art collections.

11.  Mystic, CT

Settled in 1654, Mystic was once a shipbuilding seaport village. Now, it's a quintessential New England town, packed with mom-and-pop shops and activities for the whole family to do. 

During warm weather, spend a few hours on the sea with a day sail or sunset cruise from Argia Mystic Cruises , or visit the famous Mystic Aquarium or the Mystic Seaport Museum .  

After working up an appetite, stroll through the village to see the famous weighted Bascule bridge . P ick up a sweet treat from award winning Sift Bake Shop  and  splurge on a Connecticut lobster roll at the The Shipwright's Daughter  or a hearty, grass-fed burger at the Engine Room .  And, if you must eat pizza in Mystic, head to Nana’s Bakery and Pizza for inventive takes on personal pies.

12.  Falmouth, MA

Falmouth is nestled on the southwestern part of Cape Cod, 20 miles south of the Sagamore Bridge. Lined with great beaches, cool boutiques and relaxing spots to eat and drink, it's also one of The Cape’s easiest towns to get to. Do breakfast or lunch like a local at The Pickle Jar Kitchen .

The Falmouth Museums on the Green brings 1700s Cape Cod to life; the Federalist home of Dr. Francis Wicks is wonderfully preserved and packed with original artifacts. The Shining Sea Bike Trail ,  which hugs the coast and brings you past lovely views of both the Vineyard Sound and Buzzards Bay, runs from Falmouth to Woods Hole. The trail’s name comes from “America the Beautiful,” the famous poem by Katherine Lee Bates, a Falmouth native. (Though once a railroad, the path follows ancient Wampanoag Indian trails.) One more highlight: the Woods Hole Oceanographic Institution Ocean Science Discovery Center .

13.  Lexington, MA

The best part of taking a day trip to Lexington? You can easily do it by bicycle by traveling down the Minuteman Bikeway , which begins in North Cambridge and runs right through the leafy suburb, some 15 miles northwest of Boston. This posh town is most famous for its historic Battle Green , where the bloody Battle of Lexington took place and patriotic Minute Men engaged the British Army on Lexington Common. Many of the original homes flanking the battleground are preserved, including one that serves as a visitor’s center.

Stroll Lexington Center’s mom-and-pop shops, enjoy homemade ice cream at Rancatore’s or dine at il Casale   from local chef Dante de Magistris, who draws from his family’s roots to make handmade pastas, delicious sfizis and classic dishes, all in a rustic-chic atmosphere. For an elegant Sunday brunch or dinner, The Inn at Hastings Park’s Town Meeting Bistro  is a modern pleasure involving sleek, seasonal dishes.

14.  Kittery, ME

Kittery, while most famous for its shopping, has so much more to offer. First stop: Bob’s Clam Hut , a 60-year-old roadside diner that serves incredible fried clams, sustainable local fish and amazing milkshakes. Next stop? Yes, shopping at the adjacent Kittery Premium Outlets , whose stores include everything from discounted Calvin Klein to Lindt chocolate.

Also known for the historic Portsmouth Naval Yard —which is in Kittery, not neighboring Portsmouth, NH—this sleepy town includes Tributary Brewing Company , which has a cool tasting room and live music on weekends.

The heart of Kittery Foreside, which is the downtown area, is Wallingford Square and it's dotted with all kinds of restaurants including the sleek bistro Anneke Jans  and casual asian eatery  Anju Noodle Bar . Or  stop by Lil’s Café , a quaint spot set in a former bank whose old walk-in safe is now its Vinyl Vault, a small alcove with used records for sale. Lil’s bakery downstairs turns out some of the best pastries in New England and excellent chai, too.

15.  Washington, CT

For a small town in rural Connecticut, Washington has a big reputation for its arts and architecture. The Judy Black Memorial Park and Gardens is set in a once-abandoned gas station and boasts lovely landscaping and revolving art exhibits.

Every July, the Litchfield Jazz Festival takes place at venues around town and world-renowned modern dance company Pilobolus holds its Five Senses Festival . In September, Gilmore Girls fans take over—the town inspired the beloved TV program’s fictional Stars Hollow. Surrounded by colonial architecture, you can shop at unique boutiques and treat yourself to dinner (and a room, for a real spurge) at the historic, luxurious Mayflower Inn .

16.  Stockbridge, MA

Just off I-90, Stockbridge is the gateway to the beautiful Berkshires, part of the Taconic Mountains. Main Street is home to the venerable Red Lion Inn , a one-time frontier town tavern that maintains a casual eatery called Widow Bingham’s Tavern, as well as a gorgeously original main dining room with traditional favorites and an award-winning wine list.

Nature and art dominate the area: Just off Park Street, behind Main Street, take the wooden footbridge and walk the Laurel Hill Association’s beautiful trails. Visit the Norman Rockwell Museum and see where the renowned illustrator and artist lived and worked. Nearby, visit Chesterwood , the home of the Lincoln Memorial sculptor Daniel Chester French, and Naumkeag , a Gilded Age architectural masterpiece. A few miles away in Lenox is the Tanglewood Music Center , the Boston Symphony Orchestra’s summer home. Nearby, you can take a guided tour of Edith Wharton’s home, The Mount , and learn about the woman behind the building and the books.

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Beyond Boston

10 day trips from boston by train—local’s guide.

The nice thing about Boston is that you don’t need a car to go to some pretty cool places. This is all thanks to the Commuter Rail, which will take you to many towns within a couple hours of the city. As the name suggests, the train is mainly for commuters, but it also runs on the weekends.

After living in Boston for a few years, I’ve done some decent exploring of the area and want to share my favorite day trips for those looking for a short getaway.

These day trips range from cities to seaside villages to the countryside. They’re fitting for really any traveler—solo travelers, couples, friends, and families.

This post was written in 2019 and has been updated for 2023.

Table of Contents

How to Get to These Boston Day/Weekend Trips

All of these trips are accessible by the Commuter Rail, on different lines. I’ll be sure to specify which line and direction to take, and which station to leave from. You can always check up-to-date schedules on the  Commuter Rail site .

I highly recommend going on the weekend, as you can use the $10 unlimited Weekend Pass, cutting your transportation costs in half. Otherwise, most of these tickets cost around $20 roundtrip. With the Weekend Pass, you can take as many trips as you want for $10. You could even do one day trip on Saturday, and one on Sunday, if you’re feeling especially motivated 🙂

To be extra prepared, you can download the MBTA mTicket app, where you can purchase your tickets on your phone. You can also buy tickets on the train, but you’ll need to pay cash, and it may be more expensive (it’s unclear if Weekend Passes can be purchased on board). I’ve always used the app, and it’s super convenient.

Day Trips from Boston Without a Car

Note that this post contains affiliate links, meaning that I earn a small commission on any bookings you complete. This doesn’t cost you any extra, and it’s a great way to support my blog.

1. Providence, RI

How to get there:  take the Providence/Stoughton line towards Wickford Junction Train station in Boston:  South Station, Back Bay, Ruggles Distance:  1 hour

While the rest of these destinations are in Massachusetts, one of my favorite day trips is actually in Rhode Island. Being from the Midwest, I always found it mind-boggling that you could drive an hour in the Northeast, and end up in a different state!

Providence is just an hour from Boston by train, and it’s a charming riverfront city. With a population of under 180,000, Providence is highly-walkable, but be prepared for some hills!

Here are some top things to do in Providence:

Wander through the prettiest little library, the Providence Athenaeum . This library basically screams “insta-worthy.” It’s full of cozy reading corners and study spaces; you’ll probably spot some Brown University students, who are known for frequenting the Athenaeum. The best part is that visiting is free to the public—you even can bring dogs inside!

After visiting the Athenaeum,  take a stroll along Benefit Street  (right in front of the Athenaeum). This street is known for its lovely houses. You can also  walk around the campus grounds of Ivy League school Brown , which is just up the hill.

One of the most famous Providence attractions is  WaterFire . There are many braziers along the river, which are basically metal containers used to burn firewood. WaterFire is an evening event where all these braziers are lit up. It’s a bit of a strange experience, and feels kind of creepy at times (almost like a satanic ritual haha). The music was spooky, and the people lighting the fires are often dressed in all black. Regardless, the riverfront is especially beautiful with the light of the fire. The event also brings together community vendors, residents, and tourists. In typical years, WaterFire is scheduled about every other Saturday from late May to early November.

Active travelers will appreciate the East Bay Bike Path,  which also offers views of the city and riverfront. You could rent a bike, or go on a run.

Finally,  if you’re looking for a delicious vegan meal, check out Veggie Fun . It sounds like a sketchy restaurant, but the food is well-balanced, it’s conveniently located downtown, and the setting is modern. The seitan spareribs are so savory and filling, and I highly recommend them!

Looking to stay longer than a day, and need a place to stay?  You might like this  historic apartment near Brown and RISD , or if you’re feeling extra adventurous,  this yacht in a private marina .

How to get there:  take the Newburyport/Rockport line towards Newburyport or Rockport Train station in Boston:  North Station Distance:  30 minutes

Salem is notorious as the  location of the 17th century Salem Witch Trials.  Nowadays, the small town really plays up this haunted/witchy reputation, and there are countless witch museums, haunted houses, dungeons, and witch souvenir shops. You can even take a ghost tour . I’m not a huge fan of “haunted” things, so I have a whole guide on  non-witchy things to do in Salem .

I do think the history of the witch trials is important to learn and understand, so if you haven’t been to the  Salem Witch Museum , you might want to visit. The exhibits are educational, rather than spooky.

My absolute favorite thing to do in Salem is  go to the Salem Willows Park and Arcade,  which is on a little peninsula about 1.5 miles from the town center. You can play classic games like Skee ball, coin pusher, air hockey, and Deal or No Deal.

At the park, you’ll also find plenty of vendors selling comfort food, like ice cream, pizza, fries, and Chinese takeout. You can stroll along the marina, have a picnic, and watch the sunset.

In the town center, there’s no shortage of cute shops and restaurants though. I personally love the stores  Oak + Moss  (pictured above) and  Mark Your Spot —they’re incredibly aesthetic. For vegan-friendly pizza in a fun, retro setting, I recommend  Flying Saucer Pizza Company . It’s a little pricey, but the portions are massive!

Looking to stay longer than a day, and need a place to stay?  You might like this  historic cottage near the town center .

3. Gloucester

How to get there:  take the Newburyport/Rockport line towards Rockport Train station in Boston:  North Station Distance:  1 hour 15 minutes

Gloucester is a small seaside town best known for its beaches, whale watching expeditions, fishing, and seafood.

Some popular beaches include:

• Wingaersheek Beach
• Good Harbor Beach
• Half Moon Beach
• Niles Beach

All of these beaches are at least couple miles from the town center, so expect a longer walk, or be ready to take an Uber/Lyft. Some, like Wingaersheek and Niles, offer residents-only parking on certain days—if you’re driving, be sure to double-check. Even if there is public parking, you may have to pay $30+ per car!

I’ve only been to Wingaersheek, and I especially liked it for its exposed rocks at low tide.  The rocks would create little pockets of water which were fun to wade in, and you could also spy the minnows darting around. The tide changes daily, so  check tide reports  if you want to visit at low tide.

After swimming and wading at Wingaersheek, we walked to  Jones Salt Marsh , which was about a mile away. The marsh is a popular boating and fishing destination, but it’s also just a lovely place to watch the sunset.

Many people come to Gloucester to whale watch,  as it’s conveniently located between two feeding grounds. I went on a trip a couple years ago, and it was really cool to see the whales in their natural habitat. If you do go, be sure to choose a responsible operator with a naturalist on board, such as 7 Seas Whale Watch .

Looking to stay longer than a day, and need a place to stay?  You might like this  beach house  that’s only a short walk to Good Harbor or  this apartment  with a great porch view of the harbor.

4. Newburyport

How to get there:  take the Newburyport/Rockport line towards Newburyport Train station in Boston:  North Station Distance:  1 hour 10 minutes

Newburyport is a charming, historic city right next to the ocean. The cobblestone streets and colonial architecture take you back to another era.

You can walk and relax along the Waterfront Park , which has benches and shade. After that, walk down State Street and Water Street for local shops and cafes.

Newburyport seemed to be committed to sustainability, as there were many low-waste, Fair Trade, and vegan-friendly places.

I really liked Green House Goods , which was full of zero waste goodies. There was also Sea Bags, which had totes made from used sails.

For food, I had a vegan bowl and cookie at NU Kitchen . The bowl was good and filling, but the cookie was gluten-free so it wasn’t as chewy as I wanted. If you like coffee, Plum Island Coffee has Fair Trade roasts.

For some beautiful colonial architecture, make sure to stroll down Inn Street .

Finally, Plum Island is a popular beach destination. I didn’t find the beach particularly impressive (the water was also super cold and brown), but the area seemed quite lovely and it might be worth going to a different part of the beach (I went to the northernmost point). There’s no public transport here, so you’ll have to take an Uber or rent a bike.

Looking to stay longer than a day, and need a place to stay? Check out this charming 1789 home .

How to get there:  take the Newburyport/Rockport line towards Newburyport Train station in Boston:  North Station Distance:  50 minutes

Ipswich is another seaside town best-known for its beaches, farms, and history . The Commuter Rail takes you to the town, and from there, you can explore on foot or take the Ipswich Explorer shuttle .

The Ipswich Explorer costs $1.50 one-way and you can pay via your CharlieCard or in exact change.

The Crane Beach route of the shuttle takes you to to the following places:

• Crane Beach —beautiful, white-sand beach with a concession stand and bathrooms. The walk-on fee is $2 (which is much better than the $40 parking fee).
• Russell Orchards —farm with seasonal fruit picking, animals, and local goals for sale.
• Wolf Hollow —gray wolf sanctuary

There is also an Essex route that will take you to:

• Essex Shipbuilding Museum
• Famous seafood restaurants like Woodman’s
• River cruises and antique shops

The town itself is also quaint and has lovely restaurants and shops. In particular, I liked Sandpiper Bakery , which had a refreshing tofu sandwich and tempting pastries.

Looking to stay longer than a day, and need a place to stay? Stay in this modern home near the beach .

6. Rockport

How to get there:  take the Newburyport/Rockport line towards Rockport Train station in Boston:  North Station Distance:  1 hour 30 minutes

Rockport is another seaside village, and it’s just a hop away from Gloucester. You get a totally different vibe from this town though—it feels like more of an artisan’s community. Rockport is perhaps best known for its independent art galleries and local goods. One of the most famous shops is  The Pewter Shop , which offers products made by artists in Boston. The exterior of the shop is a popular photo op, with its red siding and bright blue door.

If you like sweets, you’ll want to stop by  The Ice Cream Store , which has another Instagram-famous façade. There are unfortunately no vegan flavors, but there is shaved ice that should be dairy-free (there are  plenty of vegan ice cream spots in Boston  anyways). There’s also the  Rockport Fudgery , with a lovely pastel storefront.

After walking past all the adorable shops, you’ll find yourself at  Bearskin Neck, a rock-covered peninsula . There’s not much to do there, but there are a couple cafes overlooking the water.

Unlike Gloucester, Rockport isn’t known for its beaches, but there is  Front Beach  just a short walk from the shopping district. On the way there, you might stop by  Bullseye Books—Flyboys,  which offers vintage books; along with the old-time music, you’ll feel like you’re back in the 70s.

Finally, it’s not a trip to Rockport without taking a photo of  Motif No. 1 , a red fishing shack that is reportedly the most-painted building in the world. With the ships in the marina, the fishing shack makes for a lovely seaside scene.

I also want to add that the best time to visit Rockport is in the summer, followed by the spring and fall. In the winter, many shops and restaurants are closed, though you can still find some things to do (I went in January). Just a heads up for y’all!

Looking to stay longer than a day, and need a place to stay?  You might like this  cottage near the town center  or this  quaint beach cottage .

7. Plymouth

How to get there:  take the Kingston line towards Kingston  (NOTE: the Plymouth stop was unfortunately suspended in April 2021 and may not be reinstated . You can, however, take an Uber/Lyft from Kingston for the remaining 5 miles).

Train station in Boston:  South Station Distance:  1 hour 30 minutes

You’ve probably heard of Plymouth (also spelled “Plimouth”) from your elementary school history lessons on the Pilgrims. This town is known as being the first landing spot of these English settlers.

For your local history fix, visit the  Plimouth Plantation.  There, you’ll find a  living history exhibit—the Wampanoag Homesite.  There, you’ll be able to see typical 17th-century Wampanoag homes, and Native employees practicing traditional skills like belt weaving. The  Plimouth Plantation website  has a section for how to interact with the Native People in a culturally respectful way.

In a similar vein, you’ll be able to visit a  17th-century living history English settlement.  There will be “Pilgrims” going about their daily lives in historical costumes, and you can speak to these employees to learn more about life as a settler.

Tickets to Plimouth Plantation are a little pricey, but you can also buy a combination ticket that will grant you entry to the  Mayflower II  and  Plimouth Grist Mill . The Mayflower II is a replica of the original Pilgrims’ ship, and the Grist Mill is a reproduction of a 17th-century, water-powered mill.

Before leaving town, take a gander at the original Plymouth Rock. It’s nothing special—it’s literally a small rock with 1620 engraved on it—but it’s kind of cool to see the landing site of the Pilgrims.

Looking to stay longer than a day, and need a place to stay?   Search for available hotels in Plymouth .

8. Manchester-by-the-Sea

How to get there: take the Newbury/Rockport line towards Rockport Train station in Boston:  North Station Distance:  50 minutes

Manchester-by-the-Sea is a small, seaside town that was the filming location of the eponymous movie.

The biggest draw of Manchester-by-the-Sea is Singing Beach , a beach that gets its name from the unique sand that creates squeaking sounds when you step on it with enough force (you kind of have to give it a kick while stepping). The beach is unique not only for its sand, but its otherworldly feel. The rocks and trees that line the beach aren’t typical of New England shorelines; in fact, the rocks reminded me of a beach in Montenegro.

The beach is a 20-minute walk from the Commuter Rail station, and the walk-on fee is $10 per person. It’s actually much more convenient to take the Commuter Rail into Manchester-by-the-Sea to go to the beach, as beach parking is expensive and sometimes only open to residents.

The town itself doesn’t have much to offer, besides a few restaurants and a grocery store, but it’s charming. Plus, it’s convenient to grab some snacks on your way to the beach.

Looking to stay longer than a day, and need a place to stay? Stay in this historic apartment in the town center.

9. Wachusett Mountain

How to get there:  take the Fitchburg line towards Wachusett; requires a 10ish minute Uber ride from the Wachusett stop, though there are free weekend morning shuttles during ski season (also some Wednesday afternoons)

Train station in Boston:  North Station Distance:  1 hour 40 minutes

Waschusett Mountain is probably best-known for its  skiing , but the area offers outdoor activities in all seasons. In warmer months, you can go  hiking  on the mountain, or go  kayaking  in the nearby lakes.

The area is quite rural, so getting around without a car is a little trickier. I’d recommend taking an Uber/Lyft to the mountain from the train station, and then walking around the countryside the rest of the day.

If you time your trip right, you might also be able to catch one of the many festivals on the mountain, featuring great eats and live music. Some popular events include Oktoberfest, Applefest, and Boofest.

I think Wachusett Mountain is probably more fitting for a weekend getaway than a day trip; there’s not a lot to do outside of the mountain, so it’s really a place to unwind. There are also so many cute apartment rentals!

If you’re looking for more places to stay,  you might check out this  house near a lake . Or, you might like this large  lake house with canoes and a grill .

How to get there:  take Lowell line Train station in Boston:  North Station Distance:  40 minutes

Lowell is a sleepy former industrial town. Its old manufacturing sites were actually turned into the Lowell National Historical Park . You can walk along the canals (or take a boat ride) and visit the water-powered mills and learn about the Industrial Revolution.

Another way Lowell is distinctive is its high Cambodian population, which is the second-largest in the US. In some parts of town, it feels like you’re walking through a different country, thanks to the Southeast Asian grocery shops and locals playing traditional Cambodian games in the parks. If you like Southeast Asian food , you won’t be disappointed. I ate at Simply Khmer and found it good.

Other popular attractions include Mill No. 5 , which is an indoor streetscape with historic storefronts; nowadays the stores range from sweets shops to art stores. In a similar vein, if you like record shops, there are three within a few blocks of each other.

Finally, if you’re a distance runner, you may want to check out the Baystate Marathon and Half Marathon in October. It’s known as a fast and flat course, and I did the half in 2021 and found it well-organized.

Looking to stay longer than a day, and need a place to stay? The UMass Lowell Inn and Conference Center is well-located.

Map of These Boston Day Trips by Train

Here’s a map of these day trips so you can situate where they are and potentially plan a couple stops in one day.

I hope you learned about some new places to check out! If you know of other Boston day trips by train, I’d love to hear from you in the comments!

You might also like these posts: Berkshires Travel Guide: An Outdoorsy Weekend Itinerary Best Hikes in Maine’s Acadia National Park

16 thoughts on “ 10 Day Trips from Boston by Train—Local’s Guide ”

wonderful. just what we were looking for, as we are planning a trip to Boston, without a car, and wanted some side-trip options. this is perfect. thank you

So happy it could help!

This was very helpful. Thank you for putting it together.

Where is the best to stay in Boston to be closest to the trains?

You’ll want to be close to North Station or South Station, depending on the places you want to go (different routes start at different stations).

Thank you for the suggestions. I travelled out to Providence and had a great day based on your suggestions.

I’m so glad to hear it! Thank you for letting me know 🙂

Thank you for the information. It was very interesting. We are planning on visiting May 2023

Glad it could help! I hope you enjoy your trip!

I want to go May of 2023 also, I am in need of cost friendly rooms but also want to be near train station and downtown if that’s possible. Help this weary traveler.

Have you seen my post on where to stay in Boston? It may help! https://roamingboston.com/where-to-stay-in-boston/

Wow, this is an amazing post! Thanks to you, I think I’ve just stumbled upon my new favourite library – the Providence Athenaeum. I would love to explore the Athenæum’s storied history, beautiful collections, and Greek Revival building as well as pick up a book or two written by Edgar Allen Poe. Thanks for sharing and have a good day 🙂 Aiva xx

I’m glad you enjoyed the post! Thanks for stopping by 🙂

Thanks for the great post! I’m planning a trip to Boston soon and this was really helpful. I’m looking forward to taking some of these day trips by train.

What is the easiest way to get from the airport to the north station? We’re spending our first night in Salem after we arrive.

I would recommend taking the Silver Line to South Station and then taking the Orange Line to North Station from there. If you put it into Google Maps, you’ll get real time info on schedules. You can also take an Uber/Lyft. Enjoy Salem!

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One-Day Itinerary

Day Trips From Boston

Sam Adams Brewery Tours

Top Things to Do

Free Things to Do

Things to Do With Kids

Skiing Near Boston

Beaches Near Boston

Hikes Near Boston

Boston Public Garden

Museums in Boston

Fenway Park Guide

Shopping in Boston

The Best Time to Visit Boston

Weather & Climate

Neighborhoods to Know

Driving in Boston

Public Transportation in Boston

Getting Around Boston: MBTA "T" Subway System

Navigating the MBTA "T" Subway System and More

Elijah-Lovkoff/Getty Images

One of the most daunting parts of visiting Boston for the first time is figuring out how to navigate the city’s public transportation: the Massachusetts Bay Transit Authority’s (MBTA) subway and bus system, commonly known as the “T.” However, once you get a lay of the land and try it out a few times, you’ll likely find that it’s an easier — and more affordable — way to get around. Parking can be hard to come by, so you’ll be happy not having a car if you plan on staying in the city.

How to Ride Boston’s T (Subway and Busses)

The T is the United States’ oldest subway system, which started running back in 1897. It’s not particularly nice, but it will conveniently get you from one point to another within the city so you can see even more than you could by foot (though Boston is a walkable city). It also comes in handy during winter months when walking isn’t enjoyable.

• Fares : A single ride CharlieTicket for the bus is $2 and the subway is $2.75. However, you’ll save on each ride if you load money onto a CharlieCard (for example, save 50 cents per ride on the train). Do some research and determine if it make sense to purchase a 7-day unlimited pass, which you can use on both the trains and busses. There are also monthly passes available if you’re in town for an extended stay. Children under 11 who are with an adult ride for free, along with military personnel, police officers, firefighters and government officials. Reduced fares are available to students and seniors.
• Types of Passes: There are two types of passes and the best option for you depends on how often you’ll be riding the T, along with the modes of public transportation you want to take. First is the CharlieCard, which is ideal for those that plan on taking the bus and/or train frequently and will give you discounted one-way fares. Oftentimes a CharlieTicket is best for visitors, as they can be bought at any train station and loaded with cash or passes as you need them. While you won’t get discounts this way, they’re also valid on the Commuter Rail and Ferry and will allow you to ensure you aren’t spending more than you need on public transportation.
• Hours of Operation: Hours will vary depending on the line and station you plan on traveling on, but for the most part, you’ll find that the T runs from 5 a.m. to somewhere between midnight and 1 a.m. Don’t wait until it’s getting close to 1 a.m. to head to the train or bus though — that’s recipe for missing the last one from your station. Boston bars typically stay open until 2 a.m., so if you plan on staying out until they close, you’ll need to take an Uber, Lyft or taxi home.
• Subway Lines: The T consists of five separate lines, each of which connects at several locations within the city. The Green Line began as America’s first underground subway system in 1897. Today, the line consists of four separate branches (be sure to get on the right one). The other lines are the Red Line, Blue Line, Orange Line and Silver Line. The main stations that you can connect from one line to another are North and South Stations, as well as stops like Park Street and Downtown Crossing.

Map out your travels using the MBTA trip planner website , which will help you determine the best options for trip, as well as real-time departure and arrival information.

Where and How to Buy Passes for the Boston MBTA Trains & Busses

There are lots of ways to pay for your MBTA train and bus passes, most of which can be purchased online or at MBTA train stations throughout the city. These are the places you can purchase them, including which options accept cash:

• Fare vending machines: Fare vending machines can be found at all subway stations, as well as at the Lynn and Worcester/Union Commuter Rail stations. Here you can buy or renew CharlieTickets and CharlieCards, including 1-day, 7-day, cash value and monthly passes. These machines accept cash and major credit and debit cards, though keep in mind that some will be marked as not accepting cash.
• Retail sales locations: There are select stores in the Boston area and even Providence, RI where you can purchase a CharlieCard and add cash value or a pass to it or add to an existing CharlieCard or CharlieTicket if you already have one. Plan ahead and find a retail store closest to you . These locations accept cash or credit/debit cards.
• Online: If you already have a CharlieCard or order one ahead of your Boston trip, you can register for a MyCharlie account and easily add cash value or passes online. This can also come in handy because it protects you if you happen to lose your card somewhere along the way. Sign up for MyCharlie here — or you can load money onto an existing card here without logging in .
• At street-level stops along the Green Line or Mattapan Trolley: If you’re riding either of these lines, you can add up to $20 cash value on your CharlieCard or CharlieTicket right onboard at these street-level trolley stops. Note that this option does not apply to 1-day, 7-day or monthly passes. To pay at a street-level stop, you’ll need to use cash or coins.

Other Transit Options

• Airport Transit : There are two free MBTA options to get from Logan Airport to Boston. First, take the MBTA Silver Line SL1 Bus, which will go to South Station, which connects to the Red Line, Commuter Rail and several busses. Or you can opt for the Blue Line via a free Massport shuttle bus, which will take you right from the airport terminal to Airport Station on the Blue Line. Alternatively, there is a scenic water taxi that will take you to various destinations along the waterfront, but it’s not the easiest option if you’re traveling with luggage.
• Ferries : The MBTA has two ferry lines that travel to Boston, including the Charlestown Ferry and the Hingham/Hull Ferry, both of which are popular among commuters who live in these areas. Both go to Boston’s Long Wharf, which is easily accessible to many of the city’s hotels and attractions. If you’re looking to visit Boston area beaches, you may want to use the Hingham/Hull Ferry to get to South Shore towns.
• Commuter Rails to Nearby Suburbs: If you’re not renting a car, the Commuter Rails are a great way to get to Boston area suburbs. There are several lines to choose from that will take you in any direction. Rates will depend on where you are traveling to, as they are priced by zone.
• Ubers, Lyfts and Taxis: It should come as no surprise that there is an abundance of Ubers, Lyfts and taxis in the city of Boston. Ride-sharing services are oftentimes more affordable than taxis, though some prefer the convenience of picking up a taxi at a designated taxi stand.
• Bike Sharing: An increasingly popular way to get around Boston is through the city’s Blue Bikes bike share program . There are over 1,800 bikes at 200 stations throughout the city and it’s easy to use – simply become a member online, buy a pass from the app or a kiosk and pick up a bike in a location that’s convenient to you. When you’re done, find a drop-off location, check it in and you’re good to go.
• Car rentals: Car rentals are certainly available in Boston, especially by Logan Airport , but think about if you’ll truly need one before you book. Most Boston neighborhoods lack ample parking, especially without a resident sticker, so you may end up paying a good amount of money to park it. There are plenty of other ways to get around the city without a car. If you plan on spending a decent amount of time outside the city, then a car rental may be necessary. But you could also explore services like ZipCar to use one for a day, for example, which may offer cost savings.

Tips for Getting Around Boston

• Winter weather causes delays. Bad weather — especially snow — typically impacts public transportation, so plan for delays and resulting crowds. Unfortunately, this is due to the MBTA’s old infrastructure in many cases.
• Apps will help predict timing, especially for busses. The MBTA has gotten much better about providing riders with real-time updates on wait times for the trains, but apps can also be helpful. There is an MBTA-endorsed Transit App , as well as others that riders find helpful like the MBTA Bus app.
• Hours of operation end between midnight and 1 a.m. Don’t wait until 1 a.m. to catch the last train or bus — you’ll likely miss it.
• Taking the T can help avoid traffic. With the exception of the Green Line, which is above-ground for much of its path, the T is underground, helping you avoid traffic during peak hours.
• Avoid renting a car unless you plan to leave the city.  You'll find it's both easier and more affordable, as public city parking can be hard to come by and expensive.
• Plan ahead to determine if your best bet is public transportation, walking or Uber/taxi. Google Maps comes in handy here, as you can play out your options to determine which will be faster. It really depends on where you are going and what day of the week or time you’re traveling.
• Think through the best MBTA pass to ensure you get the best cost savings. As mentioned earlier, this depends on how often you’ll be using public transportation, as well as what you plan to see while you’re in town and the number of days you’re visiting for.
• Compared to other major cities, the T is affordable. Keep that in mind if you’re used to NYC fares, for example. Again, do the math before deciding how to get around the city.
• Pay attention to inbound vs. outbound when taking the T. It’s easy to get caught riding in the wrong direction if you don’t look at the map and enter the station on the correct side.

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52 Best Weekend Trips and Getaways from Boston

Outdoor adventures.

PHOTO BY TRENT BELL

1. Peak’s Island, Maine

Two hours by car

Different Strokes | If the idea of wearing a tank top seems profoundly depressing, skip the sports club in favor of an upper-body workout that’ll replace the reflection in the gym mirror with a view of Maine’s wild and rocky coast. And thankfully, there’s little exertion in getting there. Drive up Friday night; stay at Portland’s Regency Hotel (two hours from Boston); then catch the nearby ferry at 9:15 a.m. to Peaks Island, where the affable staff of Maine Island Kayak Company will escort you to a kayaker’s paradise. After an introductory paddling course, a primer on the vagaries of ocean weather, and some disclaimers, you’re ready to slide into a single-person sea kayak and head for open water. You’ll first need to get your heading: Peaks Island, just off Portland’s coast in Casco Bay, is one of the area’s dozens of small islands, many of which are public. Some feature Civil War–era forts, sea birds, and coastal flora and fauna. Expeditions are led by registered Maine guides—in other words, experienced outdoorspeople who know their way around a compass and can handle almost anything Mother Nature tosses their way. Although the company does offer half-day excursions (sans meals, $65 per person), we recommend a full-day jaunt ($115 per person), which allows plenty of time to practice maneuvering. Meanwhile, if you’ve already got kayaking chops and want to spend as much time near the water as possible, opt instead for the two-night camping trip.

Maine Island Kayak Company, Kayak Beach, Peaks Island, Maine, 207-766-2373,  maineislandkayak.com . Stay: Portland Regency Hotel, 20 Milk St., Portland, Maine, 207-774-4200,  theregency.com .

2. Stowe, Vermont

Three hours, 45 minutes by car

It’s All Downhill | Singing, dancing, precious urchins mugging for the camera…and yet, you don’t see much mountain biking in The Sound of Music. But the state-of-the-art trails at Stowe’s Trapp Family Lodge (owned and operated by the movie’s same family) make the hills come alive—with the grunts and groans of cyclists testing their mettle on more than 25 miles’ worth of track.

700 Trapp Hill Rd., Stowe, Vermont, 800-826-7000, trappfamily.com .

3. Lake Champlain, Vermont

Peak Experiences | You’ve seen fall foliage from the car, the hiking trail, and the boat—now how about from the sky? Parafly Paragliding offers classes in the Lake Champlain valley; on a cloudless day, you’ll get 360-degree views of the fiery sugar maples stretching clear to the northern border.

116 Waybury Rd., Colchester, Vermont, 802-879-3507, paraflypg.com . Stay: Willard Street Inn, 349 S. Willard St., Burlington, Vermont, 802-651-8710, willardstreetinn.com .

4. Craftsbury Common, Vermont

Four hours by car

Cause A Row | The Craftsbury Outdoor Center almost kisses Canada, but it’s still close enough for a two-day escape. The rustic resort sits on a long, narrow lake surrounded by farmland, and is the perfect place to explore the rarefied world of sculling. Craftsbury offers intensive, all-inclusive weekend programs for every level, some of which come with yoga classes. Bonus: It also rolls out running camps, and has arguably the finest cross-country skiing trails in New England.

535 Lost Nation Rd., Craftsbury Common, Vermont, 802-586-7767, craftsbury.com

5. Charlemont, Massachusetts

Two hours, 45 minutes by car

See the Forest for the Trees | Zipline tours got their start in Central America in the 1970s, but it’s only been in recent years that they’ve hit New England in a big way. Most are in the northernmost part of the region, though two Charlemont-based companies are competing to be the go-to source in Massachusetts. Zoar Outdoor Canopy Tours emphasizes the educational aspect, with guides who describe the local foliage and fauna. Meanwhile, Berkshire East goes for the thrill, with two 2,000-plus-foot ziplines that plunge downhill at 50 miles per hour.

Zoar Outdoor Canopy Tours, 800-532-7483, zoaroutdoor.com ; Berkshire East, 413-225-2425, berkshireeast.com . Stay: Warfield House Inn, 200 Warfield Rd., Charlemont, 888-339-8439, warfieldhouseinn.com .

6. Block Island, Rhode Island

One hour, 45 minutes by car to ferry

Natural Selection | Afternoon sun glistening on the clay bluffs, seagrass waving on a stretch of reclaimed farmland—nearly half of Block Island is designated as conservation land, and the other half is so picturesque that it might as well be. With 10 compact square miles of land area, you can bike anywhere in under 20 minutes, so it’s easy to spend all weekend on two wheels.

Stay: Hygeia House, 582 Beach Avenue, Block Island, Rhode Island, 401-856-9920, thehygeiahouse.com . See Block Island Ferry schedule at blockislandferry.com .

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12+ Best Day Trips from Boston

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What are the best day trips from Boston? Have I got the post for you! Boston is a brilliantly situated city, surrounded by seaside towns, cool beaches, and natural wonders. Whether you’re staying in downtown Boston or out in the suburbs, whether you’re traveling with kids or on your own, there’s so much to see throughout Massachusetts and beyond.

And if there’s anything I know like the back of my hand, it’s Boston day trips — the ones that are worth it (Newburyport! Providence! Portland!), and the ones that are bad ideas.

Planning your trip to Boston last minute?

Boston is very popular and books up quickly year-round. Book ahead to avoid disappointment!

🦞 Top Day Trips from Boston:

• Salem in a Day from Boston: Witches Tour (My top recommendation!)
• Martha’s Vineyard Day Trip from Boston (LONG trip, but great place)
• Boston to Newport, RI Day Trip (Elegant mansions!)

🛌  Top-Rated Hotels in Buenos Aires:

• The Liberty Hotel (Former jail and super trendy!)
• Boston Park Plaza (Super nice and not too $$)
• Oasis Guest House (Great budget option)

🚗 Renting a car in Boston? Find deals on car rental rates here.

I grew up 20 minutes outside Boston — Reading, specifically — and spent several years living in Boston as an adult. Today, I spend much of the year in the Boston area with my family. I feel very lucky to be from New England, which is filled with fabulous places to visit, from my beloved Portsmouth, New Hampshire, to Provincetown, the funky tip of Cape Cod.

While most of these Boston day trips require a car, several of them can be done with public transportation. Read on to see which day trips from Boston are best for you.

I would like to acknowledge and honor the Massa-adchu-es-et (Massachusett), Pawtucket, Pokanoket, Wôpanâak (Wampanoag), Nauset, Pentucket, Abenaki/Abénaquis, Wabanaki and Mohican people, the Indigenous stewards and traditional owners of the unceded land now known as the Greater Boston area.

This post was last updated in March 2024.

Table of Contents

Best Day Trips from Boston

There are lots of day trips from Boston — but which ones are best? It all depends on what you’re looking for as a traveler.

My top three Boston day trips are the seaside town of Newburyport ; Provincetown , the funky tip of Cape Cod; and one of my favorite small cities, Portsmouth, New Hampshire .

North of Boston, I recommend Crane’s Beach in Ipswich . South of Boston, I recommend Duxbury Beach in Duxbury .

If you want to do a day trip from Boston on public transportation, I recommend the seaside town of Newburyport by train, the foodie city of Portland, Maine , by train, and the fun Cape Cod town of Provincetown by ferry.

Check out the deCordova Sculpture Park in Lincoln , spend the day in York, Maine , or have a fun beach day in Duxbury .

In winter many smaller towns in New England are virtually closed down. I would bundle up and visit another busy, active city like Portland, Maine or Providence, Rhode Island .

There’s a lot to consider, so here are my four big tips:

Tip #1: Don’t go overboard with history-oriented day trips if you’re not into history.

Yep, we’ve got a lot of wonderful historic sites in New England, and most travel writers tend to disproportionally play them up, but not everyone is up for doing historic day trip after historic day trip. I know I’m not.

Tip #2: Don’t just visit other cities.

Portland, Portsmouth, and Providence are great, but if you’re in Boston, you’re already in a city, and you shouldn’t miss out on the other side of New England: small towns and areas of natural beauty.

Tip #3: Keep your destinations within a two-hour drive.

If not, you’ll be spending a huge chunk of your day driving. Each destination I’m listing here is within a two-hour drive of Boston, with the occasional exception noted.

Tip #4: Make sure you have the right train station.

Boston has two main train stations: North Station and South Station. Trains to northern destinations depart from North Station; trains to southern destinations depart from South Station. There is also Back Bay Station, which is the first stop after South Station, so if you’re staying around Back Bay, you can just hop on the train there. Buses depart from South Station Bus Terminal.

Newburyport, Massachusetts

If you’re looking for quintessential New England seaside towns, Newburyport is one of my absolute favorites. This is small town New England at its best. Located north of Boston on a convenient commuter rail line, Newbury has a lovely waterfront, a beautiful downtown area with lots of fun shops, and easy access to the beach and wildlife at Plum Island.

Best things to do in Newburyport: This is a nice town for just walking around, and I encourage you to go in without too big of an agenda. Walk along the waterfront, browse the treasures at Oldies Marketplace , visit the Custom House Maritime Museum or Cushing House (the Museum of Old Newbury) , or even go on a food tour with Taste Newburyport .

Plum Island, a barrier island along the coast, is technically split between the towns of Newburyport, Newbury, Rowley, and Ipswich. You can stake out a nice spot on the beach — but Plum Island really excels at wildlife. Check out the bird life at Parker River National Wildlife Refuge , go kayaking, ride your bike along the trails, and enjoy the atmosphere.

There are plenty of dining options in Newburyport, but if you want a really local spot, head to The Grog . There’s nowhere else I go in town. This hole-in-the-wall pub has dollar oysters (you need to ask for them!), lots of interesting beers on tap, and delicious appetizers, including a nice chowder.

How to get from Boston to Newburyport: Newburyport is about a 45-minute drive from Boston. The train from Boston (North Station) to Newburyport takes one hour. If you’re heading to Plum Island, you’ll want to have a car.

Provincetown, Massachusetts

If you’re looking for a summertime day trip that combines a nice beach and an active town, both classic New England style and modern hotspot, Provincetown is the perfect choice! P-Town, a popular summer destination and legendary LGBTQ summer getaway, is at the very tip of Cape Cod.

Normally, I don’t recommend doing a day trip to Cape Cod during the summer because you’ll inevitably be sitting in hours of traffic at the Sagamore Bridge. But Provincetown is the one exception — because you take the ferry! The fast ferry runs direct from Boston to Provincetown from mid-May through mid-October, and it only takes 95 minutes each way. You can check the ferry schedule here.

In Provincetown, you can have a beach day or an exploration day — or a little bit of both!

Best things to do in Provincetown: Enjoy relaxing at Racepoint Beach, check out the Pilgrim Monument and Provincetown Museum (the only permanent exhibition that tells the story of the Pilgrims’ arrival from the point of view of the Wampanoag), explore the shops and galleries on Commercial Street, go wine tasting at Truro Vineyards (just south of Provincetown in North Truro), try beers at the Provincetown Brewing Company , see a Zoe Lewis show .

See the full list of things to do in Provincetown here .

If you’re going to eat, check out The Lobster Pot — check out their Portuguese soup with red beans, kale, linguica, and chorizo, featured by Anthony Bourdain on Parts Unknown . Southeast Massachusetts is home to a big Portuguese community, so take advantage!

How to get from Boston to Provincetown: The fast ferry takes 95 minutes and departs from the World Trade Center in Boston’s Seaport District. That’s the only way I’d recommend doing a day trip, as the drive to Provincetown takes 2.5 hours without factoring in the bottleneck at the Sagamore Bridge.

Want more? See my full Provincetown guide here!

Martha’s Vineyard

Is it possible to do a day trip from Boston to Martha’s Vineyard? Yes, it is, but it’s best done as a tour from Boston . Honestly, I highly recommend staying at least overnight, or for a few days, but if all you have is a day, you can absolutely make it happen.

I absolutely love Martha’s Vineyard and especially love exploring it by car. Just keep in mind that if you visit during the summer months, there can be a TON of traffic heading down the Cape. I would not do this from Friday through Sunday during the summer months.

Best things to do in Martha’s Vineyard: Start in the beautiful town of Oak Bluffs and visit all the colorful gingerbread houses, followed by a spin on the carousel. If you don’t have a car, I recommend renting a bike and riding down to Edgartown , which is SUCH a beautiful town. From Edgartown you can take the Chappy Ferry to Chappaquiddick Island , which is perfect to explore by bike.

And if you have time in the evening, I highly recommend checking out the stunning Aquinnah Cliffs and/or Moshup Beach, my favorite beach in Martha’s Vineyard, late in the afternoon, followed by sunset in the fishing village of Menemsha. And another lovely town to explore is Vineyard Haven , with lots of cute shops and the Black Dog.

How to get from Boston to Martha’s Vineyard: If you’re doing a day trip from Boston to Martha’s Vineyard, I strongly suggest you book this tour . With limited time, it will be far easier if you have professionals taking you directly.

Otherwise, you can drive to Woods Hole on Cape Cod (80 minutes, but longer during the summer), and take the Steamship Authority ferry to either Vineyard Haven or Oak Bluffs on Martha’s Vineyard (one hour). This ferry allows cars.

Portsmouth, New Hampshire

Portsmouth is one of my favorite places to take people visiting New England for the first time. It simultaneously has the feeling of a small town and a medium-sized city, all perched on New Hampshire’s brief sliver of coastline, a stone’s throw from Maine. It has a funky, almost bohemian feel in some parts. Throw in fresh seafood and surprisingly few tourists and you’ve got a great spot for a day trip from Boston.

Portsmouth is on a lovely stretch of waterfront, just across the water from Kittery, Maine , so it pairs well with the south coast of Maine. I often pair a day trip to Portsmouth with a visit to The Maine Diner in nearby Wells, Maine, one of my favorite restaurants on the planet.

Best things to do in Portsmouth: Portsmouth, like Newburyport, is the kind of destination that lends itself to walking around and exploring. Browse the Portsmouth Book & Bar bookstore while enjoying a coffee or beer, explore the shops on Market Square, check out the Strawbery Banke Museum and its historic homes, take a self-guided tour of the Black Heritage Trail of New Hampshire , try some beers at the Portsmouth Brewery , and walk across the bridge into Maine (fun if you’ve never walked into another state before!).

As for where to eat, there are tons of spots! My favorite is The Friendly Toast , a joyful diner-like spot serving up creative dishes. River House is a great spot for dining right on the water. Portsmouth Brewery has a great menu of American comfort classics.

How to get from Boston to Portsmouth: Portsmouth is about an hourlong drive from Boston. There are also buses that take an hour and 20 minutes from South Station Bus Terminal.

See more on my sister site, New Hampshire Way:

• 27 Fun Things to Do in Portsmouth, NH
• Best Portsmouth NH Restaurants
• Best Bars in Portsmouth, NH
• Best Portsmouth, NH Hotels and B&Bs

South Coast of Maine

Ever wanted to visit Maine? You can absolutely do that on a day trip from Boston! Maine’s south coast is closer to Boston than you’d think. (So close, in fact, that some people refer to the south coast as “North Massachusetts.” Hehe.) Even so, you’ll see that Maine has a personality all its own, where life is slower, houses are brighter, and relationships are strong.

Ideally, I recommend visiting a few destinations in a single day trip. Morning in Kennebunkport, late lunch at the Maine Diner in Wells, and an afternoon and evening in Ogunquit would be lovely! Here are destinations in southern Maine worth visiting, from north to south:

Kennebunkport — Most famous for its longtime summer residents, George and Barbara Bush, Kennebunkport is one of the classic beauties of southern Maine. The town is beautiful on its own; it’s also home to Gooch’s Beach, a few nice museums, food tours , and trolley tours .

Wells — Home to a lovely stretch of beach and one of my favorite restaurants on the planet, The Maine Diner . They make the best seafood chowder IN THE WORLD, a fantastic lobster pie, a hot lobster roll with butter, blueberry pie, and a dish my friends and I swear we’re going to order someday, the Clam-o-Rama. Everything here is good, even if you don’t eat seafood.

Ogunquit — An artsy, colorful village and popular LGBTQ vacation spot, home to nice beaches and a rocky cove, Ogunquit is one of the most photogenic spots in a very photogenic state. Come here to enjoy the beach, hang out at the bars, explore the shops, or catch a show at the Ogunquit Playhouse. You can see my full guide to Ogunquit here.

York — Home to a large, calm beach, a picture-perfect lighthouse, a carnival-like fun park, and one of the coolest candy stores around, York makes an especially good choice for families with young kids. It’s good for a brief drop-in or a lazy day away. You can see my full guide on York, Maine here .

Kittery — At the southern edge of Maine, Kittery is most famous for its outlet shopping and pretty waterfront. It’s right next door to Portsmouth, New Hampshire, so these destinations pair well together. You can see my full guide to Kittery here.

Portland, Maine, is just north of Kennebunkport but it’s more of a standalone destination. See more on that below .

How to get from Boston to Maine: Kennebunkport is about a 90-minute drive from Boston; the other towns are closer. This is one Boston day trip I recommend doing by car as there are lots of small towns to see and the public transport connections aren’t the best.

Read More: My Guide to Ogunquit, Maine

Salem, Massachusetts

The city of witches. The city of history. The city that welcomed my 12-year-old great-grandfather when he arrived on a boat from Sicily at age 12, alone. Salem is a very popular day trip from Boston, especially for people looking for historic and/or educational day trips. And the Salem Witch Trials of 1692 have led to a community of witches, Wiccans, and those interested in the occult today, making it a strange blend with the maritime history!

I’ve written a full guide to visiting Salem if you’d like more in-depth information!

I think Salem is worth visiting if you’re really into history or you’re visiting during October, when Haunted Happenings brings a full month of celebrations. And Halloween night in Salem is a TON of fun! Beyond that, I would go with somewhere else on this list. On the North Shore, Newburyport and Rockport are much nicer. Even Marblehead, next door to Salem, is nicer.

Best Things to Do in Salem: Check out the Salem Witch Museum , visit the House of the Seven Gables , get a tarot or palm reading , visit the Peabody Essex Museum , go on a ghost tour .

How to get from Boston to Salem: If you want a guided tour, I highly recommend this Salem day trip from Boston from Walks . Salem is about 30 minutes from Boston, either by driving or by train from North Station. You can also get there by ferry on Boston Harbor Cruises. Check the ferry schedule here.

25 Spooky, Historic Things to Do in Salem, Massachusetts

Lexington and Concord, Massachusetts

Yes, the shot heard ’round the world was first fired from Lexington and Concord, starting the American Revolution. Massachusetts bleeds Revolutionary War history, and Lexington and Concord are great towns to explore that time period — as well as literary history. These towns were home to Louisa May Alcott, Ralph Waldo Emerson, Henry David Thoreau, and more.

If you’re into history of this time period — or craving a break from Boston’s crowds and skyscrapers — Lexington and Concord, two historic towns side by side, make a lovely Boston day trip.

Best things to do in Lexington and Concord: Check out Walden Pond , a natural escape where Thoreau wrote Walden ; dive into American Revolution history at Minuteman Historic Park ; see Louisa May Alcott’s home at Orchard House ; tour the Battle Green , where the shot heard ’round the world was fired; check out Lexington’s historic buildings like Buckman Tavern and Hancock-Clarke House.

For food, continue the historic theme at Concord’s Colonial Inn , which dates back to 1716 and has two restaurants serving classic Yankee dishes alongside more modern offerings.

How to get from Boston to Lexington: Lexington is about a 20-minute drive from Boston; there are public transportation connections that take closer to an hour. I recommend doing Lexington and Concord by car because the attractions are pretty spread out.

Rockport, Massachusetts

If you’re looking for a visually stunning small seaside town in Massachusetts, you’re going to love Rockport . This little town on Cape Ann, the “other” cape in northeast Massachusetts, makes a beautiful day trip. There’s a reason why North Shore residents treasure Rockport as a lovely weekend getaway.

My favorite fun fact about Rockport is that it was the filming location for Sandra Bullock and Betty White’s small Alaskan village in the movie The Proposal ! Seriously! It’s worth watching before you go to Rockport. Bearskin Neck, a tiny neighborhood of shops perched on the edge of town, could surprisingly look like a fishing village anywhere.

Best things to do in Rockport: Photograph all the fishing boats and painted cottages; check out the shops and art galleries on Bearskin Neck, sample all the fudges of Rockport Fudgery , relax on the beaches, take a walk along the rocky coastline at Halibut Point State Park , go on a Cape Ann whale watch . Also, don’t overlook Gloucester, the town next door and a short drive away!

As for where to eat in Rockport, the quintessential experience is getting a lobster roll at Roy Moore Lobster Co . and eat it while looking over the water. Alternatively, head to the Azorean Restaurant and Bar in nearby Gloucester to enjoy flavors of Portugal’s Atlantic archipelago.

How to get from Boston to Rockport: Rockport is about a 50-minute drive from Boston. You can also take the train from Boston (North Station) to Manchester (50 minutes) and from there take the connecting shuttle to Rockport (28 minutes).

Read More: 27 Fun Things To Do in Rockport, MA

Newport, Rhode Island

Newport may be another seaside New England town — but this one is a hell of a lot fancier. Newport is famous for its mansions, sailing, and history as one of the see-and-be-seen destinations among the American elite. During the Gilded Age, Newport became THE summer destination of America’s greatest thinkers, with a party scene to match.

But is a destination for famous rich people in the 1900s worth visiting today? Absolutely. Newport today has lots of historical sites to explore, but at its heart it’s a modern city. You come here for beaches and breweries, donut shops and Instagrammable cliff walks. And, of course, mansions that make you want to sing, “My God, this house is freakin’ sweet!”

Best things to do in Newport: Go on the Cliff Walk , a 3.5-mile journey along the coastline, passing some of the biggest mansions; visit The Breakers , the most insane mansion in all of Newport; chill out on the beaches; try beers at Newport Brewing Company or wines at Newport Vineyards ; explore the (much smaller!) colonial-era homes of The Point; visit the Newport Art Museum ; watch the sunset over Naragansett Bay.

For eating, Jo’s American Bistro does a fabulous lobster carbonara and features a $20.95 prix fixe menu Sunday to Thursday — great value if you’re doing a day trip from Boston during the week.

How to get from Boston to Newport: Newport is about a 1.5-hour drive from Boston. I highly recommend this day trip from Boston , which includes transportation and the mansions.

There is a bus departing South Station that takes 2.5 hours. You can also take the train from South Station to Providence, then a bus to Newport, but I think that’s too much of a hassle for a day trip.

White Mountains, New Hampshire

If you’re looking for a fall foliage day trip from Boston, the White Mountains are my top recommendation. This is one of the most gorgeous fall getaways in New England, but most outsiders haven’t even heard of it. But it also makes a great trip in late spring or summer, with tons of great outdoor activities.

(If you’re visiting the White Mountains for fall colors, keep in mind that the White Mountains are further north and at a higher altitude than Boston, so the leaves change earlier. Peak foliage tends to be the first week of October. See more on that in my Best Time to Visit Boston post.)

I grew up camping in the White Mountains every summer — specifically, at White Lake State Park in Tamworth. If you want to go chill out at a lake for a day, this is a great spot! It gets busy on summer weekends but it’s mostly quiet the rest of the time.

Note that the White Mountains are the only day trip I recommend that is more than two hours from Boston. If you’re up for a BIG day in beautiful nature, I think it’s worth it. If that’s a bit far for you for a day trip, consider staying overnight.

Best things to do in the White Mountains: Explore the cute downtown of North Conway ( Zebs General Store is a must), drive the Kancamagus Highway and explore the stops, hike through the Flume Gorge or Lost River Gorge , do a canopy tour at Alpine Adventures , take the Mount Washington Cog Railway up Mount Washington. Or just drive around, listening to music and admiring the scenery.

How to get from Boston to the White Mountains: North Conway is about a 2.5-hour drive from Boston; Lincoln is about a two-hour drive (and literally right on route 93). Though there are some buses to North Conway, this is one day trip that is best done by car.

• 30 Unforgettable Things to Do in the White Mountains
• 31 Fun Things to Do in North Conway, NH
• Hiking the Appalachian Trail in New Hampshire
• Complete Guide to Driving the Kancamagus Highway, NH

Portland, Maine

It’s far more than just “the other Portland” — Portland, Maine, is one of the emerging foodie destinations of the United States. If you love cities but feel like Boston is a bit overwhelming and large, Portland might be more your speed! Especially if you love to taste the local libations. It’s the best of a small city and a fishing village, all rolled into one.

My friends and I decided to plan our friend’s bachelorette in Portland on a whim — none of us were too familiar with the city. It turned out to be a fabulous idea and became one of our favorite getaways. You can read about that trip here.

Best things to do in Portland, Maine: Go mead tasting at Maine Meadworks , spirit tasting at Maine Craft Distilling , and kombucha tasting at Urban Farm Fermentory ; check out the Portland Head Light lighthouse; explore the Old Port, downtown Portland’s quirky shops and boutiques; go on a lobstering tour by boat; visit the Portland Museum of Art ; go on a Portland food tour.

As for where to eat in Portland — well, you’ve got plenty of choices. I especially recommend Duckfat for sandwiches and fries and the Holy Donut for potato donuts (trust me, they’re great). If you’re looking for a truly special dinner, Fore Street serves hyper-local fine cuisine and serves especially good seafood. Book early.

How to get from Boston to Portland: Portland is a 1-hour and 45-minute drive from Boston. There are also trains (two hours, departing from North Station) and buses (2.5 hours, departing from South Station Bus Terminal).

Providence, Rhode Island

Yet another fabulous New England city in a smaller package — one with a distinctive artistic flair. Providence, home to the Rhode Island School of Design, is a great place to visit and an underrated gem of New England. Sure, it’s got history, pretty neighborhoods, interesting restaurants and some memorable celebrations. But it stays firmly under the radar — and likes it that way.

If you’re visiting Providence in the summer, see if you can time your visit to see Waterfire , a festival in downtown Providence where artistic fire installations erupt over the water and local businesses open for celebration. This takes place several times during the summer months, so double-check the datess before you go!

Best things to do in Providence: Visit the RISD Museum , the Museum of the Rhode Island School of Design; fall in love with the Providence Athenaeum , a stunning library straight out of Beauty and the Beast ; go on a Providence brewery crawl ( see a map of local breweries here ); go Italian food-hopping in the Federal Hill neighborhood; take a long walk through Roger Williams Park, the largest and best maintained park in town.

Food-wise, don’t forget to try Rhode Island-style calamari and coffee milk (yes, it’s like chocolate milk, but with coffee-flavored syrup), my two Rhode Island favorites! If you want to go fancy, I recommend Persimmon ; if you want to go funky, I recommend the Peruvian and Bolivian Los Andes ; if you want to go cheap and fun, go for Korean food at Den Den .

How to get from Boston to Providence: Providence is about an hour’s drive from Boston, but the train from South Station takes closer to 38 minutes. There are also hourlong buses from South Station Bus Terminal.

Cape Cod, Massachusetts*

Should you do a day trip from Boston to Cape Cod — or down the Cape, as we Bostonians say? I actually don’t recommend doing so during the summer months.

Cape Cod is a summer destination, for obvious reasons. It’s all about beaches and ice cream stands and bike rides. And it is best explored by car, giving you the freedom to explore small towns at your own pace.

But what other guides don’t tell you is that summer traffic bottlenecks up at the Sagamore Bridge, which could add hours to your trip in either direction. It’s one of Boston’s dirty secrets. Do you want to be stuck in bumper-to-bumper traffic twice in a single day?

If you’re going to do a day trip to Cape Cod during the summer, I recommend the aforementioned day trip to Provincetown by boat. That’s a nice, traffic-free journey from Boston that won’t slice hours off your trip.

If you’re visiting more in the off-season — say, May through early June, or September or October — a Cape Cod day trip is much more doable, but know that it won’t be in full summer mode.

Best things to do in Cape Cod: The Cape is another place that lends itself to wandering and seeing what you find. Go find your perfect piece of beach on the Cape Cod National Seashore ; go on a catamaran sailing trip , rent a bike and head down the Cape Cod Rail Trail , catch a Cape Cod Baseball League game, see a movie at the Wellfleet Drive-In , check out the Sandwich Glass Museum .

Food-wise, why not try out some fabulous Wellfleet oysters right at the source? Check out The Impudent Oyster in Chatham, The Wicked Oyster in Wellfleet, and The Naked Oyster in Hyannis.

How to Get from Boston to Cape Cod: Hyannis is about a 1.5-hour drive from Boston if there’s no bridge traffic. There is also a two-hour, 20-minute train to Hyannis from South Station; it also stops at Buzzards Bay and Bourne.

Beach Day Trips From Boston

If you’re looking for a fun beach day trip, and somewhere nicer than Boston’s T-accessible beaches like Revere Beach or Carson Beach, consider taking a day trip to one of the NICE ones!

You don’t even have to go down the Cape — there are a lot of nice beaches on the North Shore (north of Boston) and the South Shore (south of Boston). Here are some worth considering:

Best Beaches North of Boston

Here they are, from south to north:

Singing Beach in Manchester-by-the-Sea — A gorgeous beach with “singing” sand that’s also accessible by train from Boston! No car necessary! (It’s about a half-mile walk from the station to the beach.)

Crane’s Beach in Ipswich — One of the most beloved beaches in New England, long and expansive with soft sand.

Wingaersheek Beach in Gloucester — One of my high school favorites, with fabulously clear water (by New England standards, at least) at low tide and lots of big rocks to climb.

Salisbury Beach in Salisbury — A long, endless-seaming beach with big waves, right next to the New Hampshire border.

Best Beaches South of Boston

Here they are, north to south:

Nantasket Beach in Hull — A narrow beach on a wispy peninsula near Boston Harbor, a really good choice if you want to pair your beach day with a lively boardwalk-type atmosphere.

Duxbury Beach in Duxbury — One of the most solid all-around beach options in the area, and if you’re there, you might as well try their trademark oysters!

Horseneck Beach State Reservation in Westport — Buzzards Bay is one of the big Massachusetts secrets — it’s the Cape, but before the Sagamore Bridge, so no bottleneck to get there! Soft white sand greets you here.

Museum Day Trips From Boston

Yes, Boston has some of the best museums in the United States — but there are plenty of excellent museums outside the city, too! Here are some of the notable ones that I recommend doing as a day trip from Boston:

New England Whaling Museum in New Bedford, Massachusetts — This is a surprisingly lovely museum that isn’t so much about hunting whales as about the entire seafaring industry over several centuries. (And a spectacular wedding venue! I was a bridesmaid in a wedding here.)

Norman Rockwell Museum in Stockbridge, Massachusetts — One of my personal favorite museums in Massachusetts, this museum is a monument to the quintessential New England illustrations and journey to activism of Norman Rockwell.

Plimoth Patuxet Museums in Plymouth, Massachusetts — Formerly Plimouth Plantation, this historic site brings to life Plymouth Colony and the Indigenous peoples who called this area home. (Nearby Plymouth Rock is often cited as the most underwhelming site in Massachusetts, so be prepared for that.)

Naismith Memorial Basketball Hall of Fame in Springfield, Massachusetts — If you’re a basketball fan in the least, come down to where basketball was invented! This museum has a massive collection of memorabilia.

deCordova Sculpture Park and Museum in Lincoln, Massachusetts — A really fun place to visit on a nice day, deCordova is the largest sculpture park in New England, featuring giant works of art over 30 acres.

Old Sturbridge Village in Sturbridge, Massachusetts — A living museum that brings the late 1800s to life, costumed historians showing you what life was like more than 100 years ago.

Peabody Essex Museum in Salem, Massachusetts — Whether you do the full Salem day trip or not, PEM is one of the hidden gems on the North Shore, with a lovely collection of global art, as well as local treasures.

Shopping Day Trips from Boston

Are you here to do some serious shopping? You’ve got options. A lot of people from Massachusetts customarily head to New Hampshire to make big purchases, as there’s no sales tax there. The Mall of New Hampshire and the Mall in Rockingham Park are popular for this reason. (The people at the Apple Store in Nashua practically know me by name at this point.)

But there are some destinations near Boston that work as day trips or half-day trips on their own.

Wrentham Village Premium Outlets — The Wrentham Outlets usually get all the attention, thanks to their high-end shops. Here you have designer outlets like Armani, Gucci, and Ferragamo as well as more mainstream outlets like Gap, Express, and Adidas.

Kittery Outlets — In Maine’s southernmost town, next door to Portsmouth, New Hampshire, this small outlets collection includes primarily mainstream shops like Nike, Ann Taylor, and Lululemon, with cool additions like Le Creuset. Not quite a standalone destination but it pairs well with a trip to Portsmouth or southern Maine.

Merrimack Premium Outlets — These outlets in Merrimack, New Hampshire, have the bonus of no sales tax! Mainstream stores include Bath and Body Works, J. Crew, Kate Spade, the Disney Store, and more.

Boston Day Trips to Avoid

Do not take a day trip to Acadia National Park in Maine. Not only is it WAY up north, way beyond a doable day trip, it also books out several months in advance. My suggestion? Plan a longer road trip up to Acadia and back.

Do not take a day trip to Burlington, Vermont. I love that little city, but it’s four hours away. If you go, go for the weekend, not a day trip.

Do not take a day trip to the Berkshires. Some people do it, but I think it’s a bit too far, with the POSSIBLE exception of Stockbridge , which is 2.5 hours by car and right off the Mass. Pike. Other destinations like North Adams, Williamstown, and Great Barrington are much further.

The Berkshires are wonderful — but it’s much better if you stay for a few days, or overnight. Be sure to check out my ultimate travel guide to the Berkshires , which will help you plan an awesome trip!

Do not plan a Connecticut casino day trip unless you know what you’re in for. Mohegan Sun and Foxwoods brand themselves as sexy resorts — but I find them depressing, smoky, and the furthest thing from sexy. If you’re expecting the party vibes of Las Vegas, you’ll be disappointed.

And be especially careful about planning trips in the winter. Some of these destinations get very quiet — especially the small seaside towns. And if it’s going to snow, don’t go anywhere ! You don’t want to be caught up in a nor’easter when you’re far from home.

Best of Boston:

• What NOT to Do in Boston
• Where to Stay in Boston: Best Neighborhoods & Hotels
• 40+ Fun Things to Do in Boston at Night
• Best Time to Visit Boston
• 24 Interesting Things to Do in Cambridge, Mass.
• 21 Best Museums in Boston

Cape Cod & the Islands:

• Which of the Towns of Cape Cod is Best for You?
• 24 Fab Things to Do in Cape Cod
• 22 Fabulous Things to Do in Provincetown, MA
• Which Of The 6 Martha’s Vineyard Towns Is Best For You?
• A Guide to Oak Bluffs, MA — Home of the Gingerbread Houses
• A Guide to Edgartown, MA — Prettiest Martha’s Vineyard Town
• A Guide to Vineyard Haven, MA — Authentic Town on Martha’s Vineyard

Western Massachusetts:

• 33 Best Things to Do in the Berkshires
• Best Towns in the Berkshires, Massachusetts
• 24 Cool Things to Do in Lenox, MA
• 12 Fun Things to Do in Stockbridge, MA

North Shore:

• 27 Fun Things to Do in Rockport, Mass.
• 25 Spooky, Haunted Things to Do in Salem, Mass.

Have you been to Boston? Do you have any day trip recommendations? Share away!

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Mayor Wu Announces Return of Playoff Hub on Canal Street

Canal Street to close to vehicular traffic for upcoming Bruins and Celtics home playoff games

Mayor Michelle Wu, in partnership with Downtown North Association, today announced the return of the Boston Playoff Hub on Canal Street, creating a car-free zone for fans to gather before and during home playoff games at TD Garden. The return of this pedestrian zone builds on Mayor Wu’s commitment to reimagining Boston’s streets and transforming public space in a way that’s enjoyable for residents, small business owners, and visitors.

“We’re thrilled to give Boston fans an opportunity with both the Bruins and the Celtics in the playoffs this year to come together safely, cheer on their favorite teams, and support our local businesses,” said Mayor Michelle Wu . “I’m grateful to our partners for working with us to bring back the Playoff Hub, creating a joyful experience for our hockey and basketball fans. I encourage everyone to come out before and during the playoff games to build community and support our teams.”

“This is a really great thing for us to be doing to ensure we are encouraging local fans to support small businesses while celebrating Boston’s legacy as the city of champions at the teams’ doorstep! Our fans show up for our iconic teams year after year, so I can’t wait to take part in these festivities as we root for the Celtics and Bruins to take it all the way,” said District 8 City Councilor Sharon Durkan.

The Playoff Hub will be free and open to the public, providing more space for residents and visitors to gather outdoors and celebrate Boston’s home teams. Canal Street will be closed from noon on game days, through one hour after the game ends. Parking regulations will be posted ahead of the first Bruins playoff game on Saturday, April 20. Vehicles in violation of posted regulations will be towed. 

“We are looking forward to creating vibrancy and camaraderie on Canal Street,” said Segun Idowu, Chief of Economic Opportunity and Inclusion . “Activating this space will give visitors and residents the opportunity to support local businesses while supporting Boston’s sports teams.” 

"We are grateful to Mayor Wu and the City of Boston for bringing back the Playoff Hub on Canal Street," said Glen Thornborough, president of TD Garden and COO of Boston Bruins . "With both teams in the playoffs, it's a great opportunity for fans to gather before games and bring the palpable energy from TD Garden out into the community.”

“There’s nowhere quite like TD Garden, especially on Celtics and Bruins gamedays,” said Rich Gotham, President of the Boston Celtics. “We extend our appreciation to Mayor Wu and the City of Boston for bringing back the Playoff Hub on Canal Street, which creates a space outdoors for fans to continue cheering on both teams and support local businesses throughout the playoffs.”   

“The Downtown North Association is excited to see the return of Canal Street as the Playoff Hub,” said Jay Walsh, Executive Director of Downtown North Association. “We look forward to welcoming Bruins and Celtics fans to the area and to create a festive atmosphere.  We are grateful to Mayor Wu and our members look forward to what will hopefully be lengthy playoff runs for both teams.”  

The first Bruins playoff game will be on Saturday, April 20. The first Celtics playoff game is Sunday, April 21.

• Last updated: April 19, 2024

Red Sox 1B Triston Casas on rib injury: ‘I…

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Patriots udfa tracker: center, cornerback added after draft, red sox 1b triston casas on rib injury: ‘i pretty much created a car crash within my body’.

Triston Casas first felt the discomfort after a swing against Ben Lively during last Wednesday’s shutout of the Cleveland Guardians at Fenway Park. The Red Sox first baseman thought it was an abdominal issue, but after trying to tough it out for a few days it eventually became clear this wasn’t an injury he could play through.

Now Casas is likely to miss several months with what the club described as a rib fracture, though after a series of examinations he likened to an anatomy lesson, Casas explained his injury is actually a bit more complex than a simple bone break.

“No ribs were fractured, it’s not a bone thing, it’s more of a cartilage thing,” Casas said in the Red Sox clubhouse Friday afternoon. “So there’s the rib cage and there’s the sternum, and there are pieces of cartilage that connect the two, and that’s what was torn.”

Casas said he was told by the doctors that his injury is much more common in football and hockey players, and he was asked if he’d been involved in any collisions that would merit some pain in his midsection. When he told them no, the doctors chalked it up to his being so big and rotating so fast so many times when he swings that his body couldn’t hold up.

“I pretty much created a car crash within my body, and it was a matter of time before this happened,” Casas said. “He said it was something similar to like a pitcher needing Tommy John, just an inevitable thing that was going to happen sooner or later.”

The good news is this injury isn’t any better or worse than if he’d fractured a bone or pulled a muscle, as all would have a similar timetable of several months. The bad news is there isn’t anything he can do but wait for the cartilage to heal, and there isn’t much clarity over how long that could take.

“They said anywhere from three weeks to six weeks to nine weeks, they don’t know, it’s just depending on how my body is feeling,” Casas said. “Right now I’m still in pain to breathe, my lungs are still hitting my midsection. I’m still getting to like 75% capacity without pain, so the first step is to feel good breathing before I can move to cardio and then I’ll move into more anaerobic exercises and progress as I go there.”

Even still, Casas said he’s optimistic he’ll be back in time to play a meaningful portion of the season, and that once the injury heals it shouldn’t take long to get back into game shape.

“It’s not something he said I’m going to need to manage, he says once it mends correctly I’ll be able to hit the ground running and keep going,” Casas said. “There won’t even need to be a rehabilitation process, just a strengthening process of the abdominal area to continue my swing progression.”

As for whether there’s concern he could suffer an injury like this again — much like some pitchers need Tommy John surgery more than once — Casas said his understanding is that once the cartilage heals, his whole abdominal area should be more durable, making a recurrence less likely down the road.

“Hopefully with all the blood and enzymes and nutrients that’s going to my rib cage hopefully it heals and mends stronger,” Casas said. “Typically whenever you get injured it comes back a little stronger, so my hope from all of this is I come back swinging the bat faster and a little more durable and I’m hoping my body can grow into my midsection so I can continue playing the game healthy like I know I can.”

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Debate over how to classify rideshare drivers isn’t just about pay. It’s also about their safety.

LYNN — Driving for Uber or Lyft can be a terrifying experience sometimes. You don’t really know who you’re picking up, or what condition they’ll be in when they climb into your car. There’s no barrier between the front and back seats. So much can go wrong.

And drivers live in a corner of the economy where workers have few rights and protections. Some live in daily fear of being kicked off their apps without notice, which makes them even more vulnerable.

“Drivers have to get our background checks, so that the passengers are safe with us,” said Magaly, 52, who has been driving full time for four years. “They should do the same for us, because I don’t feel safe.”

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A couple of years ago, after Magaly refused to give her phone number to a passenger she’d picked up outside a Lawrence bar, he unleashed a torrent of profane insults. When they arrived at his destination, he refused to get out at first, lunging at her and grabbing at her bra. He also threatened to report her to the company. When she called to report the incident, she said the company apologized and said they would never match her with that passenger again.

“They should have suspended him,” Magaly said, speaking Spanish through a translator. “Other drivers wouldn’t be safe with this guy.”

The mother of two asked that her full name be withheld because she’s afraid speaking publicly will get her in trouble with the ride-hail companies.

One afternoon in January, Victoria, 45, was attacked by a man because he didn’t like the route she was taking.

“He said so many insulting things to me,” said the slight woman, a widowed mother of three young adults. “Then he was manhandling my arm, shaking my arm so I couldn’t drive. As if hitting me would get me on the right road.”

She pressed the emergency button on her rideshare app and was told to call 911. When the police arrived, they coaxed her passenger out of her car, but seemed uninterested in pursuing the matter further, she said. Shaken, Victoria drove right home.

“I was such a wreck,” she said. “I felt so humiliated.”

That is not even her worst experience. A couple of years ago, she picked up two drunk men from Back Bay who groped at her breasts and thighs as she tried to drive. She got out of her running car at a red light, leaving the men and her phone inside it. A passerby called 911 and the men fled. She doesn‘t believe police ever pursued the matter. She has never driven at night since, instead working the less well-paying hours from 5 am to 5 p.m., six days a week. She worked as a paralegal before coming here from the Dominican Republic, and would gladly do other work here, but her English is not good enough for most jobs, she said through a translator.

Elizabeth, 33, picked up a customer in Quincy one afternoon who repeatedly asked her how much it would cost to have sex with her.

“I immediately started shaking, and I remember thinking, ‘How am I going to defend myself? The only thing I can do is crash this car,’” she said through a translator. She drove him to his home but he refused to get out, until she threatened to call 911.

She, too, asked that her full name not be used, because she is afraid her rideshare companies will freeze her access to the apps, even temporarily, as they do sometimes when a customer complains. She thought about calling the police after the incident, but didn’t want to cause trouble.

“They are always telling us how each customer is so important,” she said.

These are the people at the center of the battle over gig workers in Massachusetts. Some unions, including 32BJ SEIU, are pressing legislation that would allow them to organize those workers. Other unions , and legislators including Senator Lydia Edwards, are pushing measures that would go further, classifying drivers as employees, so they qualify for many more protections. As they have in other states , the rideshare companies are pouring millions into combating that reclassification effort, advocating for ballot questions that would keep drivers as independent contractors.

The rideshare companies argue that contractor status allows their drivers to maintain independence and flexibility. It also protects the companies’ bottom lines. Edwards cites numbers from an upcoming state auditor’s report showing that, based on drivers’ $1.4 billion in gross earnings in Massachusetts last year, the companies avoided paying some $47 million to unemployment insurance, family medical leave, and other contributions required of companies with employees.

“It’s not flexibility they care about, it’s profit,” said the East Boston Democrat.

In statements, Uber and Lyft said they care immensely about the safety of their drivers, and are regularly introducing measures to better protect them. They also say serious incidents are extremely rare — though rare in an industry this big means thousands of cases nationally each year.

Each company has introduced in-app emergency buttons that allow drivers and riders to make direct contact with security consultants or emergency responders, and real-time tracking that will set off an alarm if a ride veers off course or is stopped for too long. Uber is expanding its verification of rider identities , and Lyft has introduced a feature called Women + Connect that matches women and nonbinary drivers with more women and nonbinary riders. Both companies say riders are in fact suspended for serious or multiple offenses, and that drivers are never penalized for bringing safety concerns to them.

This is all great. But to take advantage of many of the features that protect them — particularly when it comes to getting their harassers or attackers banned — drivers need to feel secure enough to pursue complaints against passengers. And according to these women, and to the unions and legislators trying to protect them, they simply do not: The gig economy can be a cruel, capricious place, where pay and conditions are subservient to the whims of the market and the moment, and where even companies with good intentions owe drivers nothing.

Unions and labor laws exist to make sure companies do the right thing by their workers. Having union backing would mean drivers wouldn’t be alone when trouble arises with passengers, or the company. They’d have access to advocates who could challenge the companies for kicking them off the apps, for example, and to counselors and legal help during crises.

“They need a collective voice to improve wages and working conditions,” said Mike Vartabedian, an official at the International Association of Machinists, which backs legislation to unionize the workers.

Edwards says they need more than that — employee status, which would give drivers and other gig workers access to labor laws, and protections against harassment and discrimination.

“When you rely on the kindness of a corporation, you’re basically saying we should trust them and their bottom line to do right by workers,” said the senator. “I’m saying we should trust the law.”

Victoria will take whatever help she can get.

“We need somebody who can stand up for us,” she said. “Right now, we have nobody but ourselves.”

Globe columnist Yvonne Abraham can be reached at [email protected] .