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21 Magical Winter Things to Do in Boston—Local’s Guide

Boston is known for its harsh New England winters, from bone-chilling temperature to knee-deep snow. But, the season can also be really magical with the holiday lights, snow sports, markets, and warm drinks.

After living in Boston for three winters, I’m happy to report that it’s not all gloom and doom, and there are many things to look forward to. In this post, I’ll share some of the best things to do in winter in Boston, organized in two sections by outdoor and indoor activities.

Table of Contents

Outdoor Things to do in Winter in Boston

1. go ice skating.

Frog Pond in the Boston Common is perhaps the best-known ice skating option in the city, but did you know that you can go skating indoors for FREE in the city’s public rinks? If you don’t own skates, many public rinks let you rent them for a low price. Just call ahead to ask, and double-check their online schedules for public skating hours.

Here are Boston’s public indoor ice skating rinks. They’re located across the city and beyond, so you may even have one in your neighborhood!

• EHO – Charlestown
• Steriti – North End
• Devine – Dorchester
• Murphy – South Boston
• Bajko – Hyde Park
• Reilly – Brighton

The outdoor ice skating rinks in Boston include:

• Frog Pond – Boston Common
• Skate @ Canal District Kendall – Cambridge
• The Rink at 401 Park – Fenway
• Kelly Outdoor – Jamaica Plain (public – free admission with rentals for a small fee)

Just keep in mind that non-public rinks charge both an admission and rental fee. Some rinks may also require online reservations.

Frog Pond is the most classic option, and for good reason. You get to skate right in the Boston Common with the city as your backdrop. That said, it’s also the most crowded. The ice gets scratched up easily, and it can be hard to get around if you need to hold onto the edge of the rink.

Skate @ Canal District Kendall is right near the Kendal Square T stop, giving you access to lots of great restaurants where you can grab a bit after your skate session. They also offer private and group lessons.

The Rink at 401 Park is hosted by REI and is located between Time Out Market Boston, home to several food vendors, and Trillium Fenway, a brewery. There are also several popular restaurants and bars in the area, and Fenway probably has the most active nightlife of these non-public outdoor rinks.

Kelly Outdoor Rink is close to the Stony Brook T stop, and admission is free, with rental skates costing just a few bucks. There’s not as much nearby, but if you take a 15-minute walk to Hyde Square, you’ll find some great local restaurants.

2. Enjoy a holiday cruise around the Boston Harbor

Available in December, this holiday cruise is the perfect way to get in the festive mood. Listen to holiday tunes while sipping hot cocoa and admiring the Boston skyline at night. Tickets cost $37-56 per person.

3. Wander in the snow

Boston Public Garden and Louisburg Square in Beacon Hill

There’s nothing more magical than walking through downtown Boston in the freshly-fallen snow. Stop by the Boston Common, Public Garden, Beacon Hill, and Back Bay for the best snowscapes.

See my guide to the most Instagrammable places in Boston for more photo spot suggestions.

4. Enjoy the SoWa Winter Festival

Home to art studios and boutiques in old warehouses, SoWa is a neighborhood in the South End that’s about as hipster as you can get. Every winter, they have a festival that includes an expansive holiday market, live music, art galleries, and food trucks.

The holiday market is indoors in SoWa’s Power Station, an old power plant turned event space. The industrial and modern interior is especially charming with the light displays. There are countless vendors, ranging from local foods to upcycled clothing. On the second floor, there’s a bar with live music. Tickets cost $10 at the door (paid by card only), and it’s certainly worth a visit.

If you stop by the Winter Festival on a Sunday, you should also stop by the SoWa Vintage Market for some unique knickknacks.

5. Visit Snowport

Snowport is another winter festival, but in Seaport, also an up-and-coming neighborhood in Boston. Their holiday market is outdoors and features similar small businesses, but there’s a larger emphasis on food and drink that you can buy and enjoy in heated tents.

Outside of the holiday market, there’s also a tree market that will deliver your tree to your home, as well as a a place to go curling. Don’t forget to take a stroll along the Boston Harbor as well and snap some shots of the skyline!

6. Admire the holiday lights or go to a Christmas tree lighting

Go on a walk through the city and admire the beautiful light displays. Some popular spots include:

• Christopher Columbus Park—the archway is covered in lights and is very romantic
• Faneuil Hall—go shopping or grab a bite to eat while admiring the indoor and outdoor decorations
• Commonwealth Avenue Mall—the trees with holiday lights frame the Public Garden perfectly
• Somerville Illuminations Tour (the locals are known for elaborate lighting displays)
• ZooLights at Stone Zoo

If you’re looking for impressive Christmas tree displays and lightings in particular, here are some to look out for:

• Light Up Seaport (there is also a Menorah lighting)
• USS Constitution tree lighting
• Faneuil Hall tree lighting
• North End tree lighting

A great bonus is that many of these events come with free food or drink and music!

7. Go skiing

You don’t need to drive to the mountains to hit the slopes! The Blue Hills are only a 20-minute drive from the city. If you don’t have a car, Wachusett Mountain  is accessible by the Commuter Rail in about 2 hours (there’s a  free shuttle  from the Fitchburg station during ski season).

Of course, you’ll get better slopes and views if you make it out to bigger mountains. So, if you’re looking for extra adventure, check out popular skiing destinations Stowe in Vermont and Bretton Woods in New Hampshire.

8. Eat in an igloo

If you’re looking for a special dining experience, you can eat in a cozy igloo with the Boston skyline as your backdrop at the Envoy Lookout Rooftop Bar . They also have igloos along the Boston Harbor. Be ready to stomach a steep price, however—reservations are $400-500 for two hours, and the igloos can sit up to 8-10 people.

For a more affordable, but still special, winter outdoor dining experience, check out Bow Market’s firepit tables in Somerville’s Union Square. The cost is $5 per person. Make sure to dress extra warm since you won’t be in an enclosed space. A great benefit, however, is that you can order from any of the restaurants in Bow Market (I highly recommend the poutine at Saus, and they even have a vegan option).

9. Shop small at Bow Market

Speaking of Bow Market, there’s no better place to buy local gifts. This up-and-coming shopping and dining space is located in a former storage building. The market is dedicated to small, unique shops including a quirky gift store, vintage shop, clothing boutiques, and more.

10. Go sledding

The thick snow may be the bane of every Bostonian’s existence as they walk or drive, but there’s no doubt that the snow makes for great sledding. Grab your family or friends and head over to these popular sledding spots:

• Corey Hill Park (Brookline)
• Arnold Arboretum (Jamaica Plain)
• Danehy Pond (Cambridge)
• Flagstaff Hill (Boston Common)
• Sugar Bowl at Jamaica Pond

11. Visit the New Hampshire Ice Castles

While not in Boston, these awe-inspiring Ice Castles are just a 2-hour drive away in rural New Hampshire. Made entirely of thousands of hand-placed icicles, the Ice Castles are a work of art that you can physically explore through its caverns, tunnels, archways, and slides. If you have kids, they’ll certainly be delighted.

Beyond the Ice Castles, there’s also an enchanted forest walk and small tubing area that’s included in admission, which costs $20-27 per person.

If you can make it out for an entire day and also do a winter hike in the White Mountains, the Ice Castles are worth the trip. See my full review of the New Hampshire Ice Castles for more photos and info.

Indoor Things to Do in Winter in Boston

After you enjoy the outdoor activities, come inside and warm up with these wintery things to do!

12. Have a drink at cozy cafe

Grab a hot cocoa to warm your hands and body. If you’re looking for cafe suggestions, Tatte Bakery is one of the prettiest local cafe chains in the city, and they offer a mouth-watering selection of pastries. They can be found all over Boston and the surrounding suburban cities.

Cafe SuSu on Newbury Street is another aesthetic spot, and it’s actually located inside a suit store! It’s a great place to go after doing some holiday shopping in Back Bay.

13. Enjoy a festive performance

If you want a more classic experience, you could enjoy The Nutcracker or the Holiday Pops by the Boston Symphony Orchestra. If you want something a little different, try The Hip Hop Nutcracker or “A Very Postmodern Christmas” by Postmodern Jukebox.

Check the schedule of winter performances over at Boston Theater .

14. Dig for thrifted gems at The Garment District

The Garment District is a secondhand clothing store in Cambridge known for its $2/pound used clothing selection. If you’re looking for adventure (and aren’t too afraid of germs), you can sift through mounds of clothing of all sizes and styles.

If you prefer a more curated selection, they also offer vintage styles on your traditional clothing racks, but at a higher price point. They also typically offer a special section for ugly holiday sweaters!

15. See a movie at an indie theatre

Spice up your typical movie-going experience by going to Coolidge Corner Theatre  in Brookline or  Somerville Theatre in Davis Square. These independent theatres have beautiful interiors with the classic red curtains.

Both theatres are located close to T stops and have a great selection of nearby restaurants and shops.

16. Make art in a pottery or paint studio

Winter is the perfect time to work on creative pursuits indoors. Whether you’re new to art or more experienced, going to a pottery or paint studio lets you make art in a structured environment while spending time with loved ones. In fact, it makes for a great Boston experience gift .

For pottery, Clayroom in Brookline is a studio where you can paint a pre-made piece of pottery, ranging from household items like plates and mugs to decorative figurines. Once you’re done painting, the studio will fire the pottery for you, and you’ll be able to pick it up later.

For painting, Muse Paintbar in Assembly Row has an instructor guiding everyone step-by-step through a preselected painting. There is food and drink available for purchase, and all ages are welcome at most events (just double-check the listing). Afterwards, grab a bite to eat at the many nearby restaurants, or go shopping at popular retailers.

17. Go rock climbing or bouldering

When it’s harder to exercise outside with the winter cold, going rock climbing and bouldering is a fun way to stay active. Here are some gyms in the city:

• Central Rock Gym  has locations in downtown Boston, Fenway, Cambridge, and neighboring towns
• Rock Spot Gym  is accessible from South Boston
• Boston Bouldering Project  is in Somerville

Many of these places offer day passes with gear rentals for around $30, and there are climbing routes of all difficulty levels.

18. Try an escape room

Another way to work both your body and mind is to tackle an escape room. One of the best options is  Boda Borg  in Malden, which has over 20 “quests” that are basically mini escape rooms. You can try each room multiple times, with some being more intellectual and others more active.

Some other more traditional escape rooms include:

• Escape the Room  (Downtown Crossing)
• Trapology  (Downtown Crossing)
• Room Escape  (Chelsea)
• Boxaroo  (Government Center)
• Room Escapers  (Downtown Boston)

Keep in mind that most escape rooms require a group of at least 2-3 people. Costs usually range from $30-50 per person.

19. Hunker down in a board game cafe

If you’re tired of being stuck inside at home, but still want to stay cozy, venture out to a board game cafe. You can spend all day playing classics or learning new games while sipping hot drinks or snacking on comfort food.

Knight Moves is a homey spot in Brookline that has over 2000 games. The board game cafe is also near Coolidge Corner, a bustling suburban center with several shops and restaurants.

Tavern of Tales  is another option, but you must reserve a room, which can be pricey unless you have a large group.

20. Explore a new museum

Boston is known for its many museums, ranging from science to art. When the weather outside is cold and dreary, exploring a new museum is one way to lift your spirits. Some popular options include:

• The Isabella Stewart Gardener Museum  (art museum in the style of a Venetian palace with a lush courtyard)
• Institute of Contemporary Art , which overlooks the Boston Harbor in the trendy Seaport neighborhood
• Museum of Fine Arts
• Museum of Science
• Boston Children’s Museum
• Harvard Museum of Natural History
• Harvard Art Museums

If you have a local library card, you may be able to get free or discounted passes to some of these museums. Check out your library’s website for more details on picking up these passes!

21. Eat at an indoor market

As you’re wandering around the city in the cold winter weather, you may want to grab a quick drink or bite to eat. Here are some indoor markets where you’ll find a wide variety of cuisines.

• Time Out Boston (Fenway)
• Quincy Market (Downtown Boston)
• Boston Public Market (Downtown Boston

For more ways to stay warm and entertained in the winter, check out my full post on indoor things to do in Boston .

Let us know if you have any other suggestions you’d add to this list. Stay warm and cozy this winter!

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18 Best Things to Do in Boston in Winter (2024)

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Winter in Boston can be a bit daunting with its frosty temperatures, but it also brims with wonder and charm. As a local, I’ve crafted this guide to highlight the very best things to do in Boston in winter. My curated list features some enchanting activities: from admiring the dazzling holiday lights across the city to gracefully ice skating in Boston Common. And of course, I’ve also included several indoor activities, so you can stay warm and cozy amidst the Boston winter, like on a delightful hot chocolate crawl through some of Boston’s most inviting cafes.

This guide promises a journey through the best of Boston’s winter offerings. Embrace these experiences, and you just might find yourself agreeing that winter in Boston is the best time of year!

Table of Contents

18 Best Things to do in Boston in Winter

1. admire the city of boston aglow in holiday lights.

One of the most spectacular ways to experience Boston in the winter is to get outdoors. It may be chilly, but step outside to admire the lights all around, and you will be entranced. Here are a few places in Boston where you can see gorgeous, cheerful holiday lights.

• Downtown and the Back Bay

All through winter, much of downtown Boston is twinkling. Lights adorn trees, lamp posts, and buildings, making evening walks even more inviting. Take a stroll on the Boston Common, where trees are lit up in a host of different colors, (and check your travel dates to see if your trip coincides with the incredible Boston Common Tree Lighting! Cross over into the Public Garden, where the illuminated bridge and trees are absolutely romantic. Walk along the Commonwealth Avenue Mall, adjacent to the Public Garden, and you’ll be surrounded by sparkling lights that will inspire a sense of magic and wonder in you.

• ZooLights at the Stone Zoo

If you’re an animal lover, you won’t want to miss ZooLights at the Stone Zoo in Stoneham , a northern suburb of Boston. An evening trip is doubly delightful! Not only will you get to see the animals that make this space spectacular (some highlights are lions, flamingos, and Arctic foxes), but the lights will put you in festive spirits. If you don’t have access to a car but want to immerse yourself in the world of animals, visit the Franklin Park Zoo, located in Boston.

• Faneuil Hall Marketplace

Faneuil Hall hosts a spectacular light and sound show called “Blink!” during the holiday season. The marketplace is decked out with thousands of lights, and the show features animated lights synchronized to music.

Heading to Boston in search of the Christmas spirit? Don’t miss our guide to all the amazing things to do to get into the festive season and celebrate a Boston Christmas !

2. Go ice skating

In the winter in Boston, is there a better way to spend time outside than to ice skate? With numerous public, low-entry fee outdoor ice rinks, there are ample opportunities to admire the city on skates, whether you can nail a double-axel or you’re holding the sides of the rink closely. The Frog Pond on Boston Common offers daily skating with views of the Massachusetts State House and brick-lined Beacon Hill. This is a popular spot where families love to skate. Don’t forget to grab a hot cocoa after your turn on the ice.

If you’re in Cambridge (directly across the Charles River from Boston), try out the under-the-radar Skate @ Canal District Kendall , where you’ll be gliding across ice in the city’s innovation district. No need to pack skates for your trip – rentals are available at all of these locations

3. Keep cozy on a Hot Chocolate Crawl!

It’s no secret that it can get pretty cold during the winter in Boston. But that’s no problem when you’ve got a warm cup of something delicious! So put your puffy coat on and get ready to check out some (or maybe all of) Boston’s best hot chocolate havens!  Here are 5 must-visit spots I recommend.

• Thinking Cup (Back Bay, Downtown, North End)

A Boston staple, Thinking Cup serves delectable French hot chocolate. This liquid chocolate is so richland creamy that you’ll want to savor every sip slowly in Thinking Cup’s cozy digs. With three locations – Back Bay, Downtown, and the North End – you have no excuse not to stop by and have sip!

• Cacao, Jamaica Plain

This neighborhood favorite is steeped in positivity and intoxicatingly good scents. Their Dulche de Leche hot chocolate is creamy and dreamy on a chilly day! If, like many Bostonians, you enjoy an icy treat even on the frostiest of days, try the iced mocha at Cacao during your next winter trip to Boston!

• L.A. Burdick Handmade Chocolates, Downtown Boston and  Harvard Square

This stylish yet down-to-earth spot has carefully crafted specialty hot chocolates across the taste spectrum. Your palette will be pleased with any of the artisanal goods you encounter at L.A. Burdick Handmade Chocolates !

• Gates Commes des Filles, Somerville

This authentic French chocolate shop (it’s name translates to “spoiled like girls”) is located in Somerville’s hip Bow Market. The signature hot chocolate at Gates Commes des Filles is crafted with incomparable homemade whipped cream. With an owner who studied at the Cordon Bleu in Paris, you know the drinks will be tres bien !

• Brothers & Sisters, Brookline Village

An amazing array of seasonal lattes and other hot beverages (try the mulled cider or honey pumpkin latte!) await you at this local gem! Located immediately west of Boston, Brothers & Sisters Coffeehouse and Cafe is a community-driven small business with endless charm. Other great coffee shops in Boston can be found on this list.

4. Immerse Yourself in Boston History on the Freedom Trail

Covering 2.5 miles of terrain and marked in inlaid bricks, the Freedom Trai l is a walking path connecting 16 sites of historic importance in Boston. Beginning at the Boston Common downtown and winding all the way to the Bunker Hill Monument in Charlestown, you’ll enjoy it whether you’re a complete history buff or if fun facts are more your thing. Stop in at a visitor center at Boston National Historical Park at Faneuil Hall or the Charlestown Navy Yard for programs on the 17th-19th centuries and information about the area.

Also near the start of the Freedom Trail is the Boston African American National Historic site, where you can learn about the abolitionists of Beacon Hill and the ways people of color shaped Boston.

Looking for a guided tour of Boston? This list has some great options!

5. Hop on an Old Town Trolley Tour

If you want to see everything without trekking around town, winter bus tours are an excellent option. Old Town Trolley operates 90-minute guided tours most Thursdays through Sundays in the winter months. Visitors will see and learn the significance of Boston’s most famous sites all from the comfort of an enclosed trolley. Gotta stay warm during a Boston winter!

Ding ding! Get your Boston trolley tour tickets here!

PS: If you’re visiting December 2nd & 3rd, 2023, you could join in on the Mayor’s Enchanted Trolley Tour , a festive tradition that’s been going on for 27 years!

6. Visit some of Boston’s best museums

Visiting some of Boston’s many terrific museums is one of the top things to do in any season. But when you want an excuse to get away from the winter cold, these seem even better! A few recommendations:

• Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum , situated in the Fenway neighborhood, offers an unparalleled museum experience. The lush courtyard is a popular photo spot that will instantly transport you to the world of the museum’s eponymous founder. Take a tour with a docent or explore on your own and be swept away by the worldly collections and uniquely designed rooms.

• The Museum of Science 

With 130,000 square feet of exhibit and gallery space, the Museum of Science offers hours of entertainment for visitors of all ages. Among its permanent exhibits are real dinosaur fossils, New England habitats, an interactive Hall of Human Life, and Nanotechnology. Plus, new exhibits rotate through several times a year, so there’s always something exciting happening.

Boston Travel Tip: Grab a Go Boston Card or CityPASS if you’ll be visiting either of these museums (or others!). Both cards offer great discounts on some of Boston’s top attractions.

7. Head to the symphony

There is always a full calendar of events offered by the Boston Symphony Orchestra , so be sure to check out what’s coming up on the BSO calendar during your winter in Boston trip. If you’re visiting Boston in December, don’t miss the annual Holiday Pops selection of concerts. No matter what performance you enjoy, you’re going to swoon over the gorgeous interior of Symphony Hall.

8. Cozy up with a good book

Is there anything better to do on a snowy day than to curl up with a good book somewhere warm and inviting? I’ve got some recommendations for you on exactly where to do that:

• Boston Public Library 

Book lovers and design aficionados will swoon over the beauty of the Boston Public Library in Copley Square. Art and Architecture Tours, led daily, are an excellent break from the chill outside and offer a chance to learn about an institution central to Boston’s past and present. From the enchanting Bates Hall reading room to the iconic lions outside the entrance to the courtyard at its heart (not to mention the thousands upon thousands of books), you will be enchanted by the Boston Public Library.

• Beacon Hill Books & Cafe

Just steps away from the cobblestone streets of glorious Beacon Hill, you’ll encounter a small bookshop. Beacon Hill Books & Cafe is an unassuming spot, but there are wonders within! This multi-story bookshop is not only filled to the brim with excellent books and cozy spaces to read them, but they have a children’s section that is truly enchanting.

Are you a true book worm? Check out more of Boston’s best literary sites !

9. Experience winter at the Boston Seaport aka Snowport

One of the most magical winter things to do in Boston is to go somewhere that will transport you into a winter wonderland. That place just might be Snowport.

There is so much going on this time of year at the Seaport, with a full calendar of events, rooftop igloos, free curling lanes, lights galore, and perhaps best of all, the Holiday Market.

2023 will be the 3rd year of the Boston Winter Holiday Market at Snowport , and this year it will feature more than 120 vendors, an abundance of food including a new custom cocktail bar from Tuscan Kitchen, and even more festive decor than ever before. It sounds like this is one of top things to do this holiday season in Boston.

10. Visit a chocolate factory

Take a tour of the Taza Chocolate Factory – no golden ticket required! You will satiate your sweet tooth and learn something new at this Somerville spot. On a tour, you’ll learn about the chocolate-making process and have the possibility of seeing it get made. And yes, there are samples, complete with chocolate guides who will let you know what you’re tasting. This is a sweet idea for a Boston winter date!

11. Enjoy a show at the Coolidge Corner Theatre in Brookline

A local favorite, the Coolidge Corner Theatre has been around for nearly 100 years. Today, this nonprofit cinema features everything from cult cinema to big screen classics. Its art deco appearance and community-driven spirit make it a true treasure. It’s the perfect place to go for an evening activity or an extra cold or rainy winter day in Boston. 

1 2. Nosh on a gourmet grilled cheese at Roxy’s

Roxy’s Grilled Cheese sandwiches are melt-in-your-mouth amazing. These delectable melts contain so much more than cheese and bread. Try “The Allston” for a savory sweet treat or the “Green Muenster Melt” for a smoky bacon-filled dream dinner. Don’t just grab some tasty grub though. Head into the back room and you’ll step into the A4cade, an arcade and bar complete with everything from PacMan to pinball.

You Might Also Like: Weekend in Boston Itinerary

13. Find a treasure at The Garment District, Kendall Square

For the funkiest finds around, head to this “alternative department store.” Garment District , in Kendall Square, is part costume shop, part thrift shop, and part new clothing store, this place is a whole lot of fun. No matter your style, you can spend hours trying clothes and costumes on at this fun Cambridge shop.

14. Attend the SoWa Winter Festival

Every Sunday, Bostonians and visitors flock to the South End neighborhood to visit the SoWa Open Market. Here, you’ll encounter an engaging shopping experience, featuring local artists, plus food and beverage vendors. In winter, this transforms into the SoWa Winter Festival , a 15-day celebration where hundreds of vendors gather to make, sell, and share. Whether you are looking for holiday gifts or for a treat for yourself, shopping at SoWa supports local artists and offers countless unique treasures, in a beautifully illuminated space. Sounds like the perfect winter in Boston activity!

15. Eat your fill of incredible Italian food in Boston’s North End

To me, hearty Italian fare goes hand-in-hand with wintertime. Who doesn’t love a heaping bowl of pasta on a cold day? Piping hot bread savored as the winter winds whip outside? Italian cuisine is an ultimate comfort food.

In Boston, the North End is home to some of the most amazing Italian restaurants anywhere. The North End is very cool and absolutely worth a visit in general, but there’s no denying that FOOD is one of its major draws.

If you want to stuff your face on some epic meals, check out our list of the Best North End Restaurants in Boston . You won’t regret it.

Consider yourself a foodie? A Boston food tour is a perfect idea for you. Check out our whole list of Boston food tours to consider. Bon appetit!

1 6. Pamper Yourself at G20 Spa

For the perfect cold weather activity in Boston, head indoors to warm up and pamper yourself (and your date, perhaps?) at G20 Spa , one of the top spas in Boston. There are all the traditional spa treatments plus some interesting extras like an Experience Room for aromatherapy-infused steam sessions, Flotation Pod, Salt Cave, Fireside Lounge, and so much more. A couples day at the spa could be the perfect romantic thing to do on a Boston winter’s day!

17. Catch views of the Boston skyline in wintry wonder

No matter where you are in Boston, you’ll get amazing views from the vantage point of a rooftop. Restaurants , bars, and other venues offer indoor and outdoor spaces where you can admire the city in its winter finest! While shorter days can sometimes be a bummer, your spirits will be lifted when you catch the sunset and all the angles of “the Hub” from one of these spots. PS: These are all great options for Boston winter date ideas!

• Après…@ Deck 12

The much-anticipated Après…@ Deck 12 at YOTEL is making its grand return for the 2023 winter season. This innovative rooftop bar offers a cozy après-ski experience right amidst the urban buzz of Boston. Guests stepping onto Deck 12 will be greeted with an environment meticulously crafted to resemble a classic winter resort. The space boasts elements like heated gondolas, chair lifts, and snug Adirondack chairs, plus a winter-inspired menu that includes warming beverages like hot cocoa and creative specialty cocktails, along with indulgent comfort foods. YUM.

PS: This is quite close to Snowport, so consider visiting the holiday market and then popping over here après!

• Lookout Rooftop & Outlook Kitchen at the Envoy Hotel

Views and cocktails from Lookout Rooftop are superb. Pair the panoramic views of Boston Harbor from the indoor lounge or outdoor heated igloos with one of the unique craft cocktails, and the only chill thing will be the vibe!

• Dorchester Brewing Company 

Here’s a place you can grab a beer AND a view. On an industrial stretch of road in Boston’s biggest neighborhood, Dorchester Brewing Company is unassuming at first. But take a look up and you’ll notice its expansive roof deck and greenhouse-style rooftop beer hall, dubbed the “Hopservatory.” Order a house- or locally-brewed beer, wine, and cider on tap and admire skyline views of Boston from the south. Also featured on the main level of DBC are a game room and a barbecue joint, where you’ll find a menu that meets most dietary needs and desires. This is another great date spot for a fun Boston winter date night!

Situated on the outskirts of Harvard Square in Cambridge, Daedalus will delight your senses all around. Although the rooftop is just one story above ground, the backdrop of Harvard’s stately campus combined with gentle lighting and intentional greenery will lift your spirits into a mellow ambiance. The casual restaurant features interesting New American cuisine plus a bar on each level. It also has heated dining pods bestowed with twinkling lights, so no matter the weather, you’ll be comfortable. 

18. Discover the winter night sky at Coit Observatory

Okay, so you’ll be looking a *bit* above the Boston skyline when you visit the Coit Observatory – up at the stars, to be specific. This observatory at Boston University hosts Public Open Nights every Wednesday evening from 7:30 – 8:30 in the winter. Depending upon the night and the weather, you’ll have a chance to learn about and view stars, constellations, planets, the moon, and astronomical occurrences, and take a look at them through a telescope. Tickets are free but must be reserved in advance.

Where to Stay in Boston in Winter

• The Liberty Hotel

The Liberty Hotel is a unique boutique hotel that makes the perfect spot to stay in Boston during your next winter trip because it’s easily walkable to lots of great Boston things to do. It’s also a site with some pretty neat history, as it was once the historic Charles Street Jail; this is one of the coolest places to stay in Boston in winter and beyond!

Click Here to Check Prices & Book!

• The Verb Hotel

If you’re into funky, retro homage boutique hotel experiences, The Verb Hotel has you covered. This hip place to stay in Boston features rock and roll memorabilia everywhere you turn and is quite literally just steps to Fenway Park!

• The Fairmont Copley Plaza

If you’re planning a romantic winter getaway in Boston, consider booking a room at The Fairmont Copley ! This gorgeous luxury hotel is the perfect place to shack up with your sweetheart on those cold winter Boston nights.

Whatever you end up doing and wherever you end up staying during your winter trip to Boston, stay warm and have a good time!

Boston Winter FAQs

Is boston worth visiting in winter.

You may not think of winter as prime time to visit New England , but truth is, it’s gorgeous up here. With snow-dusted streets, charming holiday storefronts, and welcoming restaurants and shops to warm up, it is truly a winter wonderland in this region of the country.

And while yes, it can be quite cold, there are still many advantages to visiting Boston in winter, including fewer crowds, off-season pricing, and the charm of a snowy cityscape.

How cold does Boston get in winter?

Boston experiences cold and often snowy winters, with temperatures typically ranging from chilly to downright cold. Here is a breakdown of the typical winter temperatures in Boston:

• December: High temperatures range from around 40°F (4°C) to lows of 26°F (-3°C).
• January: High temperatures average around 37°F (3°C) and can drop to lows of 22°F (-6°C).
• February: High temperatures continue to be cold, averaging around 39°F (4°C), and lows can dip to 24°F (-4°C).

Boston in December, January, and February is also quite likely to have snow, with the city receiving approximately 44 inches each year.

If you choose to visit Boston in winter be prepared for cold weather, potentially icy conditions, and the need for appropriate clothing such as warm coats, hats, gloves, and insulated footwear. Winter storms can also impact travel plans, so it’s a good idea to monitor the weather and check for any potential disruptions if you plan to visit during this season.

Editor’s Note : You don’t need a car in Boston with its terrific public transportation system, but visiting in winter is even more reason not to rent a car, as you’ll have to contend with potential winter driving conditions. I can tell you, Boston is no picnic driving in any season, but winter is particularly stressful! – Amy

More Boston & Massachusetts travel guides:

• 10 Awesome Things to Do in Boston with Kids
• 10+ Essential Things to Do in Boston for First Timers
• Where to Go for the Best Breakfast in Boston
• 10 Ideas for a Festive Christmas in Massachusetts

A Complete Guide to Visiting Boston in the Winter, From a Local

By Author Meg Frost

Posted on Last updated: March 9, 2024

Categories Massachusetts , United States of America (USA)

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Boston in the Winter can be a wonderful time to visit, as long as you plan accordingly.

I’ve lived in this historic city for 20 years now, so I have an insight into all the best winter activities and tried-and-true tips on how to deal with the weather.

If you’re planning to visit Boston in the Winter, here’s my comprehensive guide to help you with weather tips, a packing list, and a curated selection of activities you don’t want to miss.

Weather in Boston in the Winter

A Winter trip to Boston is sure to include chilly weather with a chance of snow. Here’s what you can expect month by month, from December through February.

Weather data courtesy of the National Oceanic and Atmospheric Administration’s National Centers for Environmental Information.

Average temperatures in Boston in December typically range from 30°F to 45°F. That’s a decent range, so to narrow it down, the average temperature in December 2023 was 40°F.

The beginning of the month usually starts pretty mild, but as the month progresses, the temperatures start to drop.

Sometimes you’ll get snow, although usually it’s just flurries. That doesn’t mean there won’t be a big snowstorm though!

January brings the full blast of winter to the city! Average temperatures range from 24°F to 36°F, and we usually get a good snowstorm or two.

Every few years, though, we get blasted with a blizzard in January or February, with temps dropping even lower.

February is much like January. Average temperatures range from 26°F to 37°F and there’s bound to be a snowstorm or two.

I highly recommend getting a travel insurance policy that covers inclement weather. There’s a higher chance this time of year that you’ll have to move your trip due to ice or snowfall.

What to pack for Boston in the Winter

If you’ve decided to brave the cold and visit Boston during the winter season, packing smart is essential.

To put it simply, layering is your best friend. Here’s a comprehensive packing list to ensure you’re prepared:

• Comfortable walking shoes or boots : Make sure they are warm, comfortable for lots of walking, and have a good grip. It’s best if they’re waterproof, too. Most of all, pack a minimum of two pair!
• Hats, gloves, and scarves : These warm layers can be added or removed as needed.
• Winter coat : A waterproof coat is best, in case you get met with snow or rain, but above all, make sure it’s warm!
• Casual layer-able clothing : Unless you have a fancy event to attend, you can stick to casual wear. Bring clothing that you can layer so you don’t get too hot or cold.
• Warm socks : Opt for moisture-wicking materials that dry quickly, like wool.
• Lip balm and moisturizer : The dry winter air is no joke here. Moisturize, moisturize, moisturize!
• Small backpack or day bag : Bring something easy to carry and will fit what you need for the day.
• Camera or smartphone : You’ll want to record all of your fun memories!
• Portable phone charger : Stay charged up throughout the day with a power bank.
• Waterproof, insulated snow boots : Check the weather before you leave, as this might be overkill.
• Thermal underwear : If you’re not used to the cold, you may want to wear thermals under your clothes for added warmth.
• Hand and toe warmer inserts : These are great to have on hand if you’ll be outside lots.

Things to do in Boston in December

Boston goes all out in December when it comes to the Winter holidays! There’s no shortage of events for Christmas, Hannukah, and Kwanzaa!

Here are my top picks for things to do in Boston in December.

Shop for the holidays

Get your holiday shopping done in style along Newbury Street in Boston’s Back Bay. This famous shopping street is lined with boutiques, art galleries, restaurants, plus many of your favorite chain stores.

For a more festive atmosphere, check out the Seaport Holiday Market at Snowport and the SoWa Winter Festival in the South End.

These vibrant pop-up markets offer unique, handcrafted gifts and plenty of snacks from local vendors.

See the holiday lights

Boston twinkles with festive lights during the holiday season.

Explore places like the Boston Common, the Commonwealth Avenue Mall, Copley Square, and Faneuil Hall Marketplace, which are adorned with a myriad of holiday displays that add a warm glow to chilly evenings.

Each year, a giant Christmas tree is lit up on Boston Common, as well as a large menorah, accompanied by live music and other festivities.

Want to make a night of it? Check out the Holiday Lights Trolley , which takes you around the city to see the best light displays.

It’s BYOB for 21+ and includes a pit stop at the Snowport market for the afternoon run and Encore Casino for the evening run.

See a holiday show

There are always several good shows running throughout the area that celebrate Christmas. Here are my top recommendations:

• Holiday Pops featuring the Boston Pops Orchestra and Tanglewood Festival Chorus
• Langston Hughes’ Black Nativity – a retelling of the Nativity with a Black twist, such as Gospel music
• The Nutcracker featuring the Boston Ballet
• The Slutcracker – An 18+ burlesque version based on the original ballet

First Night Boston

Ring in the new year on December 31 at First Night Boston.

This free event includes live music, ice sculptures, a parade, fireworks, and other family-friendly fun.

Activities take place throughout the city at key spots like the Boston Common, City Hall Plaza, Downtown Crossing, and the Rose Kennedy Greenway.

For more details about this year’s city-wide party, check out the First Night Boston website.

Things to do in Boston in January

Start the new year with a winter vacation to Boston in January! Here are a few fun events to check out this month.

Boston Celtic Music Festival

This festival features traditional Irish, Scottish, and Cape Breton music, as well as dance performances and introductory music classes.

Also known as BCMFest, it usually takes place over a weekend in mid-January. For more information, check out the festival’s Facebook page .

Boston Wine & Food Festival

The Boston Wine & Food Festival is a culinary extravaganza put on by the Boston Harbor Hotel.

Each weekend, from mid-January through March, there are wine tastings, seminars, tastings, and themed brunches and dinners.

Check out the festival’s website for more information, including how to make reservations or buy tickets.

Things to do in Boston in February

Whether you’re in town for the Super Bowl or a romantic getaway, here are the top fun things to do in Boston in February.

Boston Beanpot Hockey Tournament

The Beanpot Hockey Tournament has been a Boston institution since 1952!

This tournament features the men’s and women’s hockey teams from 4 major colleges in the area: Boston University, Boston College, Harvard University, and Northeastern University.

The men’s teams typically face off on the first 2 Mondays of February at the TD Garden, while the women’s teams play on the first 2 Tuesdays with the location rotating each year between the 4 schools.

Black History Month Film Festival

Another excellent film festival in Boston in February is the Black History Month Film Festival.

Hosted by The Boston Globe, this event includes virtual and in-person film screenings and discussions featuring films that “celebrate the lives, culture, and creativity of Black Americans,” as the festival’s site states.

For more information on dates and a schedule, check out the festival website .

Boston Science Fiction Film Festival

Each February, Sci-Fi film fans flock to Somerville Theatre for screenings, panel discussions, parties, and premieres.

Recently, an online component was added on Filmocracy so fans worldwide can join in, even if they can’t make it to Boston.

Check out the festival website for dates and schedule.

Things to do in Boston in the Winter

Even with Winter’s bite, the city of Boston comes to life with seasonal events and activities that celebrate this special time of year.

Here are more must-do activities that will make your winter visit to Boston memorable, no matter when you visit during this season.

Celebrate Chinese New Year

Boston’s Chinatown hosts a Chinese New Year celebration, complete with a lion dance parade, cultural performances, and a street fair.

The date varies but typically occurs between the end of January and the end of February. The Chinese Consolidated Benevolent Association of New England (CCBA) is a good source for celebration dates and information.

Outdoor dining (hear me out…)

Yes, that’s right – you can dine outdoors in Boston in the winter ! There are a handful of spots that have heated igloos and yurts for outdoor dining that also provide a bit of privacy.

Here are a 5 top spots to consider:

• 75 on Liberty Wharf
• The Anchor Boston in Charlestown
• The Bowery Bar in Dorchester
• Deck 12 in Seaport
• Lookout Rooftop Bar at the Envoy Hotel

Ice skating

Embrace the season with ice skating. The Boston Common Frog Pond and the Rink at 401 Park offer picturesque outdoor locations for a spin on the ice.

Skate rentals are available at both locations, so no worries if you don’t have a pair of your own!

Taza Chocolate Factory Tour

Venture on a behind-the-scenes tour to learn about Taza’s stone-grinding techniques and sample their delicious chocolates.

This is a perfect indoor activity for a brisk winter day or a unique date activity!

Black Heritage Trail

The Black Heritage Trail is a 1.6-mile walk through the Beacon Hill neighborhood that highlights over a dozen important sites in Boston’s Black history and heritage.

The walk can be self-led via an audio tour from the NPS app or you can join a guided tour through the National Park Service during the Summer .

Boston Bruins & Celtics games

We’re a bit obsessed with our professional sports teams here in Boston.

If you’re visiting during the winter months, you can catch a Boston Bruins hockey game or Boston Celtics basketball game, both held at the TD Garden.

You can catch the home game schedules here: Boston Bruins | Boston Celtics.

Explore Boston’s finest museums

If outdoor activities aren’t your thing, dive into Boston’s rich history and renowned museums.

Here are the top spots to hit up this time of year:

• Boston Children’s Museum – Definitely check out their Snowmazing! indoor playground!!
• Institute of Contemporary Art – Contemporary art museum with stunning views of Boston Harbor.
• Isabella Stewart Gardner Museum – Be sure to check out their holiday courtyard garden on display from December-January.
• Museum of African American History – Learn about African American history from the 18th and 19th centuries.
• Museum of Fine Art – Browse the permanent and visiting fine art exhibitions from around the world.
• Museum of Science – Super fun, immersive museum with an IMAX theater.

What are your favorite things to do in Boston in the Winter?

Boston in the Winter brings lower crowds and for some, a romantic snowy backdrop.

On the other hand, the weather can be a turn-off for some. But if you pack smart and plan lots of indoor activities, you’ll have a great time.

Just be sure to book refundable hotels and transportation and make sure your travel insurance covers cancellations or rescheduling fees due to inclement weather.

About the author

Meg Frost is a Boston-based travel blogger that helps people embrace technology to make vacation planning and traveling wicked easy, affordable, and fun.

She holds an M.A. in Journalism from Northeastern University and B.S. in Communication & American Studies from University of Miami.

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The Wild Trek

22+ Best Things To Do In Boston In The Winter From A Local

Boston in winter is a magical experience. The city comes alive with holiday decorations, seasonal events, and plenty of indoor and outdoor activities. Whether you’re a local or a visitor, you’ll find no shortage of ways to embrace the chilly weather.

Today I’m sharing everything you need to know about visiting Boston in the winter from a local perspective, as well as 22+ best things to do in Boston during the winter season!

Why Visit Boston In Winter?

Visiting Boston in the winter is an experience. And while Boston is beautiful during all four seasons, there are plenty of reasons to go in the winter specifically.

One of the best things about visiting Boston in winter is that you’ll encounter fewer tourists. This means shorter lines at popular attractions and a generally less crowded experience as you explore the city. Boston can get  pretty packed in the summer, making it hard to actually experience history.

Plus, winter is generally considered the low season for tourism in Boston, so you’re more likely to find better deals on flights and accommodations. Many attractions also offer off-season pricing . The price differences can be huge.

Boston in winter is not short on things to do. From ice skating at Frog Pond to holiday markets and seasonal concerts, the city offers a host of winter-specific activities that you won’t find during other times of the year. Because we’re used to winter up here, we have  tons of activities that you can  only do during the winter. Hey, we need to get through the cold months somehow. And Boston has a rich array of indoor activities, from museums to historic sites and theaters . Winter is a great time to explore these options without feeling like you’re missing out on outdoor activities.

If you come during the holiday season , Boston is something to behold. With tree lighting ceremonies, holiday markets, and decorations all around, the city becomes a winter wonderland. If you love the holidays, Boston in winter is a perfect fit.

And if you’re a fan of winter sports like skiing, snowboarding, or sledding, there are several places within a short drive from Boston where you can hit the slopes or find a good hill for some classic winter fun. I  love how close Boston is to all New England winter sports because you can experience the winter city magic and do the rural New England thing all in one trip.

Lastly, Boston is a walkable city, and its public transportation system is efficient. Even in winter, the city is easy to get around, whether by foot or by using the T (subway). One of the perks of being a smaller city is that it’s not hard to get somewhere, even during chilly winter days.

Best Things To Do In Boston In The Winter:

Here are some of my favorite Boston winter activities that you’ll  definitely want to schedule in.

22. Ice Skating

Ice skating is one of those activities that epitomizes Boston in winter. Whether you’re a local looking for a seasonal activity or a visitor wanting to embrace the winter chill, strapping on a pair of skates is an ideal way to do it. Here’s the scoop on ice skating in Boston, including some top spots to check out.

No discussion about ice skating in Boston would be complete without mentioning Frog Pond. Situated in Boston Common, the city’s historic park, Frog Pond is transformed into an outdoor skating rink every winter. It’s perfect for skaters of all ages and skill levels. Rentals are available, and there’s a café where you can grab some hot cocoa or a snack.

This is my #1 recommended area to ice skate in Boston. Everyone should go to Frog Pond once!

Frog Pond generally opens for the winter season from late November or early December through March, weather permitting. The rink has specific hours for public skating, which can vary depending on the day of the week and whether there are any special events or private bookings.

Kendall Square Community Ice Skating:

Located in Cambridge, not too far from downtown Boston, the Kendall Square rink offers another outdoor skating experience. This rink is less crowded than Frog Pond, making it a good option if you’re looking for a more relaxed environment. They also offer skate rentals and lessons if you’re a beginner.

Steriti Memorial Rink:

Located in Boston’s North End, the Steriti Memorial Rink is an indoor option that offers free public skating. It’s particularly popular among locals and offers a view of the Boston Harbor. It’s a good alternative if you’re looking for a place to skate without braving the outdoor chill.

Warrior Ice Arena:

If you’re a hockey fan, you might want to check out Warrior Ice Arena , the practice facility for the Boston Bruins. The arena is open to the public for skating at certain times and offers a high-quality ice surface. It’s located in the Boston Landing area, which has restaurants and shops to explore before or after your skate.

21. Visit Faneuil Hall Marketplace

Faneuil Hall Marketplace is one of the prime spots to visit in Boston in winter. The historic area is transformed with twinkling lights and holiday decorations. Street performers often brave the cold, providing free entertainment as you stroll around. Don’t forget to grab some hot cocoa or mulled wine from one of the many vendors.

Shopping:   Faneuil Hall Marketplace is also a shopping destination. The area is dotted with a variety of shops, from major retail chains to quirky, independent boutiques. Whether you’re looking for souvenirs, fashion, or unique crafts, you’re likely to find it here.

Food: One of the main attractions of visiting Faneuil Hall is the food. Quincy Market , located just behind Faneuil Hall, is home to a bustling food court that offers an extensive range of options, from classic New England dishes like clam chowder and lobster rolls to international cuisine. It’s a fantastic place to grab a quick, affordable meal in the heart of the city. Outside, in the North and South Markets, you’ll find even more dining options, including sit-down restaurants and pubs where you can take a breather and soak in the atmosphere.

Winter events: Faneuil Hall is not just a summer attraction; it has a year-round appeal. In winter, it transforms into a festive wonderland complete with holiday decorations and seasonal events like the “Blink!” light and sound show. There’s often a large Christmas tree, making it a focal point for holiday celebrations in Boston.

20. Catch a Celtics Game

Sports are a big deal in Boston, and winter is basketball season. Catching a Celtics game at TD Garden is an electrifying experience and a perfect way to escape the winter chill. The crowd is passionate, and the energy is high, making it one of the best indoor activities in Boston in winter.

The Celtics play right at TD Garden , which is super centrally located and is also North Station (perfect if you’re taking the train in or out). So you can catch a game and do a few other activities if you plan right!

If you’re not from the Massachusetts area, then I  highly recommend seeing a Celtics game . There’s nothing like the New England sports atmosphere (we’re pretty intense) and the whole thing is a wild experience.

19. See The Nutcracker Ballet

When it comes to cultural activities that capture the magic of Boston in winter, seeing a performance of “The Nutcracker” ballet is near the top of the list. Performed annually by the esteemed Boston Ballet and various other local companies, this classic Tchaikovsky ballet has become a cherished holiday tradition for many Bostonians and visitors alike.

The primary venue for the Boston Ballet’s rendition of “The Nutcracker” is the historic Boston Opera House , located in the heart of the Theater District . The Opera House itself is worth a visit, boasting grand architecture and opulent interiors that set the stage for a night of elegance and enchantment. It’s one of the fanciest spots in Boston!

Tickets for “The Nutcracker” typically go on sale in the late summer or early fall and can sell out quickly, especially for popular dates close to Christmas. It’s advisable to book your tickets well in advance. The ballet usually runs from late November through December, offering multiple performances each week, including matinees that are perfect for families. Even if you’re not a huge fan of the ballet, I highly recommend going to see the Nutcracker just to experience the Opera House atmosphere! Plus, you get to dress up, which you won’t find many other places in Boston (it’s a casual city, especially in the chilly winter months).

18. Walk The Freedom Trail

Boston in winter offers a unique opportunity to walk the Freedom Trail with fewer crowds. The 2.5-mile trail takes you through 16 historical sites, offering a glimpse into America’s past. While it may be chilly, a winter walk along this route offers a quieter, more reflective experience.

Many of the sites, like the Massachusetts State House , Paul Revere’s House , and the Old North Church , are just as captivating in winter. Some of them have indoor areas where you can escape the cold for a bit while learning about the American Revolution and Boston’s role in it.

To enjoy the Freedom Trail in winter, it’s essential to dress warmly. Layering is key, as are waterproof boots, gloves, and a hat. Boston winters can be quite cold, with temperatures often dropping below freezing, especially in the evenings. I recommend insulated snow boots that are easy to walk in and a puffer coat, or at the very least a heavy wool coat with layers. But make sure to check the weather before you go: Boston in the winter fluctuates like crazy!

You can do the trail yourself since it’s pretty easy, but you won’t get much info about the history of the buildings. If you’re a history buff, I recommend doing a guided tour , which in my mind is worth it, but then again I’m obsessed with Boston History!

Check out some of the top tours here.

17. Go Museum Hopping

Boston is home to a wide range of museums that cater to all kinds of interests, from art and history to science and technology. If you’re looking to engage in a cultural exploration of the city, museum hopping is a great way to do it. Here’s a brief rundown of some must-visit museums and what you can expect at each.

Museum of Fine Arts (MFA)

What to Expect : The MFA is one of the largest and most comprehensive art museums in the U.S. It boasts an extensive collection that spans multiple continents and centuries, from Ancient Egypt to modern American art.

Details : Located in the Fenway-Kenmore neighborhood, it’s accessible via the Green Line’s Museum of Fine Arts stop. General admission is $25 for adults, but there are discounts for seniors, students, and youth.

Isabella Stewart Gardner Museum

What to Expect : This museum offers a unique blend of art, architecture, and horticulture. The Venetian-style palace surrounds a beautiful courtyard garden.

Details : It’s a short walk from the MFA, so you can easily visit both in one day. Admission is $20 for adults, and if your name happens to be Isabella, you get in for free!

The New England Aquarium

What to Expect : This is a must-visit for marine life enthusiasts. Highlights include a giant ocean tank, a penguin exhibit, and a variety of hands-on activities.

Details : Located on the Central Wharf, it’s easily accessible from the Blue Line’s Aquarium station. Tickets are around $32 for adults and $23 for children.

Museum of Science

What to Expect : A perfect destination for families or anyone interested in science and technology. The museum offers interactive exhibits on topics like physics, biology, and astronomy.

Details : Situated near the Charles River, you can get there via the Green Line’s Science Park/West End station. General admission starts at $29 for adults and $24 for children.

The USS Constitution Museum

What to Expect : This maritime museum offers an in-depth look at the history of the USS Constitution, the world’s oldest commissioned naval vessel still afloat.

Details : Located in the Charlestown Navy Yard, it’s a bit of a trek but worth it for history buffs. Admission is by donation, so you pay what you can.

The Institute of Contemporary Art (ICA)

What to Expect : If modern art is more your style, the ICA is the place to go. The museum features rotating exhibits of contemporary artists and offers stunning harbor views.

Details : Situated in the Seaport District, it’s accessible via the Silver Line’s Courthouse station. Admission is $15 for adults, and free for everyone on Thursdays from 5 to 9 p.m.

Boston Children’s Museum

What to Expect : This is an ideal spot if you’re museum-hopping with younger kids. The museum is designed to be interactive and educational, with exhibits on everything from science and culture to environmental awareness.

Details : Located on Children’s Wharf along Fort Point Channel, it’s close to the Red Line’s South Station. Admission is $18 per person, but they offer $1 admission every Friday from 5 to 9 p.m.

16. Winter Food Tour

When it comes to experiencing Boston in winter, food is an essential part of the journey. The city’s culinary scene offers a blend of traditional New England fare and innovative cuisine that can warm you up on the coldest winter days. Here’s how to go on a winter food tour in Boston, featuring some iconic foods and where to find them.

New England Clam Chowder

What to Expect : A creamy, hearty soup filled with clams, potatoes, and onions. It’s a quintessential comfort food for Boston in winter.

Where to Go : Legal Sea Foods in the Seaport District or Quincy Market is a popular choice for an authentic bowl of clam chowder.

Lobster Roll

What to Expect : Fresh lobster meat served in a grilled, buttered roll. It’s a luxurious treat that’s delicious year-round.

Where to Go : Neptune Oyster in the North End is well-known for its high-quality lobster rolls, albeit at a premium price.

Boston Cream Pie

What to Expect : A two-layer sponge cake filled with cream and topped with chocolate glaze. It’s so iconic, it’s the official dessert of Massachusetts.

Where to Go : The Omni Parker House in Downtown Boston is where this dessert was invented, so it’s a must-visit for the real deal.

Baked Beans

What to Expect : Navy beans slow-cooked with molasses and pork. It’s an old-school dish that’s rich in flavor and history.

Where to Go : Durgin-Park in Faneuil Hall used to be the go-to, but since it’s closed, you can head to places like Union Oyster House for a traditional take on this dish.

What to Expect : A crispy pastry tube filled with sweet ricotta cheese, often garnished with chocolate chips or pistachios.

Where to Go : Mike’s Pastry or Modern Pastry in the North End are both famous for their cannolis and usually have lines out the door, even in winter.

Roast Beef Sandwich

What to Expect : Thinly sliced roast beef piled high on an onion roll, usually accompanied by BBQ sauce, mayonnaise, and cheese.

Where to Go : Kelly’s Roast Beef in Revere Beach is an institution for this local favorite.

Sam Adams Beer

What to Expect : While not a food, no trip to Boston is complete without trying a locally brewed Sam Adams.

Where to Go : The Sam Adams Brewery in Jamaica Plain offers tours and tastings, perfect for warming up on a cold winter day.

If you want to get going on your food tour earlier in the day, then try out a classic Boston brunch . There are tons of breakfast spots in Boston and this is a huge event during weekend winter days!

15. Harbor Cruise

Believe it or not, harbor cruises aren’t just for summer. Some operators offer winter wildlife cruises, a unique way to experience Boston in winter. You’ll have the opportunity to see seals, sea birds, and the breathtaking skyline, all while bundled up and sipping hot tea or coffee.

Several companies offer a variety of harbor cruises , even during winter. Whether you’re interested in history, sightseeing, or just enjoying the sea air, there’s likely a cruise for you. Some popular options include:

• Sunset Cruises : Catch the early winter sunset over the harbor.
• Historical Cruises : Learn about Boston’s maritime history.
• Dinner Cruises : Enjoy a meal as you take in the city skyline.

Most of the winter cruises leave from Long Wharf or Rowes Wharf, both of which are easily accessible via public transportation. If you’re driving, parking is available but can be pricey.

During the holiday season, some companies offer special-themed cruises, such as New Year’s Eve cruises with fireworks or Valentine’s Day cruises for couples. These tend to sell out quickly, so booking well in advance is recommended.

14. Visit the Boston Tea Party Ships & Museum

The Boston Tea Party Ships & Museum is not your typical museum experience. You’ll have the opportunity to participate in reenactments, explore authentically restored tea ships, and even throw replica tea crates into the harbor just like the Sons of Liberty did back in 1773.

The museum has a series of exhibits and interactive displays that offer insights into the events, people, and ramifications of the Boston Tea Party. One highlight is the “Eleanor,” one of the museum’s restored ships where you can experience firsthand what it was like to be part of the protest.

The museum is located on Congress Street Bridge in Boston, just a short walk from the South Station, making it easily accessible via subway, bus, or even a leisurely stroll if you’re already downtown.

While the museum is indoors, the ship exhibits can get chilly in winter, so dress warmly. But the wintertime also tends to be less crowded, so you can explore at a more relaxed pace.

Adult tickets are around $30, and discounts are available for children, seniors, and military personnel . Operating hours can vary by season, so it’s best to check the official website for the most current information.

13. Brewery Hopping

Boston isn’t just famous for its historic sites and seafood; it’s also a burgeoning hub for craft beer enthusiasts. Brewery hopping is an excellent way to get a feel for the local scene, and doing it in winter gives you an excuse to sample some of the darker, richer brews that pair well with chilly weather.

Boston breweries offer a wide range of beers, from hoppy IPAs to robust stouts. In winter, you’ll find seasonal offerings with flavors like cinnamon, ginger, and chocolate. Many breweries also have indoor taprooms and even fire pits to help you shake off the cold.

Samuel Adams Brewery

What It’s Known For : Being one of the pioneers of the American craft beer movement.

Winter Specials : Look out for winter lagers and seasonal ales.

Location : The brewery is located in Jamaica Plain, and they offer tours and tastings.

Harpoon Brewery

What It’s Known For : Their flagship Harpoon IPA and a wide variety of other styles.

Winter Specials : Try their Winter Warmer, a spiced ale that’s perfect for the season.

Location : Located in the Seaport District, they also have a beer hall where you can pair a fresh pretzel with your brew.

Trillium Brewing Company

What It’s Known For : Innovative, high-quality beers, including hop-forward and experimental brews.

Winter Specials : Seasonal stouts and barrel-aged offerings.

Location : They have multiple locations, but the Fort Point location is a popular choice.

Dorchester Brewing Company

What It’s Known For : A focus on traditional styles, as well as some fun experimental brews.

Winter Specials : Expect darker, richer brews during winter.

Location : Located in Dorchester, this brewery also has a spacious taproom.

Night Shift Brewing

What It’s Known For : A wide range of unique and flavorful beers.

Winter Specials : They often release special brews during the holiday season.

Location : Their taproom is in Everett, a short drive from downtown Boston.

12. Beacon Hill Exploration

Beacon Hill , with its gas-lit streets and Federal-style row houses, is one of Boston’s most iconic neighborhoods. Exploring it in winter adds a layer of charm that makes it feel like you’ve stepped into a real-life snow globe.

In winter, the snow adds a picture-perfect touch, especially in the evenings when the gas lamps are lit. You’ll feel like you’ve stepped back in time.

Start your exploration with a visit to the Massachusetts State House , recognizable by its gleaming golden dome. While the exterior is impressive in its own right, the interior is open to the public and offers historical and architectural intrigue.

One of the most photographed streets in the U.S., Acorn Street is particularly enchanting in winter. The cobblestones and historic homes take on a magical quality when dusted with snow.

This is Beacon Hill’s main thoroughfare, filled with boutique shops, cafes, and antique stores. It’s a great place to grab a hot chocolate or a warm meal. In winter, many of the shops have festive window displays.

Lastly, Beacon Hill is adjacent to Boston Common , the oldest public park in the U.S. In winter, the park is transformed into a winter wonderland, complete with ice skating at Frog Pond.

11. Attend a Boston Pops Concert

When it comes to cultural experiences in Boston, attending a Boston Pops concert ranks high on the list. The Pops are renowned for their blend of classical music and popular tunes, and there’s no better time to experience their magic than during the winter season, especially around the holidays.

The Boston Pops Orchestra , usually just called the “Pops,” is famous for making orchestral music accessible to the general public. In winter, their repertoire often includes holiday classics, traditional pieces, and even some contemporary hits. It’s not uncommon to hear Tchaikovsky’s “Nutcracker Suite” one moment and a jazzy rendition of a holiday pop song the next.

Conducted in the historic Symphony Hall , decorated to the hilt with festive ornaments and lights, the atmosphere is nothing short of magical. The Holiday Pops concerts often feature sing-alongs, special guest appearances, and even a visit from Santa Claus.

Located in Boston’s Back Bay area, Symphony Hall is considered one of the world’s best concert halls, acclaimed for its superb acoustics. The grand interior, with its intricate moldings and chandeliers, adds a sense of occasion to any concert. This is one of the must-see shows in Boston during winter!

10. Hot Chocolate Tour

What’s better than hot chocolate in winter? Not much! Boston has several cafes known for their delicious hot cocoa. Take a self-guided tour or just visit a few places to find your favorite hot chocolate in Boston in winter. Some of my personal favorite spots include:

L.A. Burdick Chocolate

What It’s Known For : Their “Drinking Chocolate” is made from shavings of real chocolate rather than cocoa powder.

Location : Located in the heart of Harvard Square in Cambridge, it’s easily accessible via the Red Line.

Tip : This place is often busy, especially on weekends, but the wait is worth it.

Flour Bakery + Cafe

What It’s Known For : A traditional hot chocolate that hits all the right notes—rich, creamy, and perfectly sweet.

Location : They have multiple locations, but the one in the South End is particularly cozy.

Tip : Pair your hot chocolate with one of their mouth-watering pastries.

What It’s Known For : Italian-style hot chocolate, which is on the thicker side and can be customized with flavored syrups.

Location : Multiple locations throughout Boston, including Back Bay and Downtown Crossing.

Tip : Opt for the whipped cream on top; you won’t regret it.

Tatte Bakery & Café

What It’s Known For : Offering a decadent “Nutella Hot Chocolate.”

Location : With locations in Beacon Hill and Kendall Square among others, it’s easy to incorporate into your Boston itinerary.

Tip : This spot is also known for its pastries, so consider a combo for the ultimate treat in a French-style cafe.

Thinking Cup

What It’s Known For : Their Valrhona Hot Chocolate is made from Valrhona chocolate and steamed milk.

Location : Conveniently situated along the Freedom Trail, near Boston Common.

Tip : This café also specializes in coffee, so it’s a good option if your group is split between coffee and hot chocolate lovers.

Max Brenner

What It’s Known For : A chocolate-focused restaurant offering an entire menu of hot chocolate variations.

Location : Located in the Back Bay area.

Tip : Try their “Mexican Spicy Hot Chocolate” for something a little different.

9. Boston Winter Village

This seasonal pop-up features a mix of shopping, dining, and entertainment, all designed to celebrate Boston in winter. Think of it as a winter fair with a variety of activities, from ice maze explorations to shopping for winter apparel.

Imagine twinkling lights, holiday decorations, and the buzz of holiday shoppers all set to the soundtrack of classic winter songs. That’s Boston Winter Village for you. A mix of local artisans, food vendors, and various activities make this a one-stop destination for winter fun.

The village is populated by a variety of kiosks and small pop-up shops, many of which feature local artisans and makers. From handcrafted jewelry to unique Boston souvenirs, there’s a little something for everyone on your gift list. And winter treats are aplenty here. From hot chocolate and mulled wine to food trucks serving up seasonal favorites like roasted chestnuts, the Boston Winter Village is a foodie’s paradise.

One of the highlights is usually an outdoor skating rink. Even if you’re not a skater, it’s fun to watch others take to the ice. Rentals are available, so you don’t have to lug your own skates around the city.

Weekends often feature live entertainment, ranging from local school choirs to professional musicians. The vibe is festive, adding an extra layer of holiday cheer to your visit.

Boston Winter Village is usually set up in a central downtown location, often near City Hall Plaza, making it easily accessible by public transportation. If you’re already downtown for other activities, it’s a convenient stop.

8. Check Out One of Boston’s Famous Speakeasies

Boston has a rich history that stretches back to the days of Prohibition, and its modern-day speakeasies pay homage to this clandestine era. These speakeasies are all the rage in Boston right now, and are super popular (and cozy!) spots in the winter.

What It’s Known For : Despite its simple name, Drink offers a complex cocktail experience with bartenders who are more like mixologists.

Location : Situated in the Fort Point neighborhood, near the Seaport.

Tip : There’s no menu here; you tell the bartender what you like, and they whip up a custom cocktail for you.

Yvonne’s

What It’s Known For : Yvonne’s offers an opulent experience with a modern twist on the classic supper club. The atmosphere is a mix of vintage and trendy, featuring intricate chandeliers and plush seating, making it a stylish take on the speakeasy concept.

Location : Situated in Downtown Crossing, just a short walk from the T station.

Tip : Don’t just stick to drinks; their small plates menu is well worth exploring. The “Grilled Lollipop Lamb Chops” and the “Baked Oysters” are must-tries.

What It’s Known For : This place is famous for its creative cocktails and laid-back atmosphere.

Location : Tucked away in Union Square in Somerville, just a short trip from downtown Boston.

Tip : The entrance is a bit hidden, situated at the back of a hallway behind a café. Look for the door marked “Backbar.”

Wink & Nod

What It’s Known For : A sultry, underground lounge setting with plush seating and mood lighting.

Location : In the South End, accessible via the Orange Line at Back Bay Station.

Tip : They frequently rotate their food menu by hosting different chefs, making each visit unique.

The Hawthorne

What It’s Known For : An upscale speakeasy that feels like someone’s stylish living room, complete with bookshelves and comfy chairs.

Location : In Kenmore Square, easily accessible from the Green Line.

Tip : Their cocktail menu is extensive but don’t skip their small bites, which are just as impressive.

Brick & Mortar

What It’s Known For : This speakeasy focuses on classic cocktails with a modern twist.

Location : Located above Central Kitchen in Cambridge’s Central Square.

Tip : The entrance isn’t obvious; it’s an unmarked door next to a hardware store.

What It’s Known For : Not quite a speakeasy in the traditional sense, but its basement location and vintage vibe give it a hidden-away feel.

Location : Nestled in the downtown area, close to Park Street Station.

Tip : Try their signature comfort foods like mac and cheese.

7. Visit the Public Library

When people think about things to do in Boston in winter, visiting a library might not be the first thing that comes to mind. However, the Boston Public Library is no ordinary library; it’s a historic landmark, an architectural wonder, and a cozy sanctuary all rolled into one.

The Boston Public Library isn’t just a place to read or borrow books. It’s home to stunning architecture, historical collections, rotating exhibits, and even a café . The library offers a tranquil escape from the bustling city outside, making it a perfect spot for a quiet afternoon.

Seriously, if you’re a fan of dark academia , then you’ll want to check out the Boston Public Library simply because it’s gorgeous! Boston is a collegiate historical city and that’s clearly reflected here.

The McKim Building, the older part of the library, is known for its grandeur and Renaissance Revival architecture. When you walk into Bates Hall, you’ll be stunned by the high, coffered ceiling, the rows of green-shaded lamps, and the sense of tranquility that pervades the room.

The modern counterpart to the McKim Building, the Johnson Building is all about contemporary comforts. It’s bright, open, and home to a variety of resources, including computers, an expansive children’s library, and popular fiction and non-fiction titles.

The Boston Public Library’s main branch is located in Copley Square, easily accessible by taking the Green Line to Copley Station.

6. Shop on Newbury Street

If you find yourself in Boston in winter and have a penchant for shopping, you absolutely must stroll down Newbury Street. Known as Boston’s most famous shopping street , Newbury has a little bit of everything—from high-end boutiques to popular chains, vintage stores, and even some cute cafés for when you need a shopping break.

Newbury Street is a shopper’s paradise. It’s home to a variety of retail experiences, ranging from luxury brands like Chanel and Gucci to local boutiques that offer something uniquely Bostonian . You’ll also find home decor shops, bookstores, and plenty of beauty and skincare options.

The atmosphere is part of what makes shopping on Newbury Street so enjoyable. Cobblestone sidewalks, historic brownstones, and trees strung with fairy lights make it a charming place to be, even more so when there’s a blanket of snow on the ground.

All that shopping can make you hungry. Luckily, Newbury Street has an array of food options. Grab a quick bite from a food truck, settle in for some fine dining, or warm up with a hot drink from one of its many cozy cafés.

Even if you’re not a big shopper, I recommend that you walk down Newbury Street and enjoy the atmosphere. This is one of the prettiest spots in Boston in the winter!

5. Take a Tour

Boston is a city rich in history, culture, and stunning sights that can be enjoyed all year round. If you’re visiting Boston in winter, taking a guided tour can provide you with a deeper understanding and appreciation of the city’s many attractions. Here are some of the best tours to consider when you’re in Boston during the colder months:

Freedom Trail Tour

What It Is : A guided tour along the 2.5-mile-long Freedom Trail that takes you through 16 historical sites.

Why It’s Great in Winter : The winter snow adds an extra layer of charm to this historic walk. Just bundle up and maybe grab a hot cocoa beforehand!

Trolley Tour

What It Is : A hop-on, hop-off trolley service that covers Boston’s major attractions.

Why It’s Great in Winter : It’s a quick way to see the sights without spending too much time in the cold. Some even have heated trolleys!

Harbor Cruise

What It Is : A boat tour that gives you fantastic views of the Boston skyline and harbor area.

Why It’s Great in Winter : While many harbor cruises run only in warmer months, some specialty winter cruises offer breathtaking views of the snowy cityscape.

Brewery Tour

What It Is : Visit some of Boston’s best breweries to learn about the beer-making process and sample some local brews.

Why It’s Great in Winter : A brewery tour is an indoor activity, making it perfect for a chilly day. Plus, many breweries offer seasonal winter ales.

Haunted Boston Ghost Tour

What It Is : This evening walking tour takes you through some of Boston’s most haunted sites while telling tales of the city’s eerie past.

Why It’s Great in Winter : The early sunset and chilly weather add to the spooky atmosphere.

Fenway Park Tour

What It Is : A behind-the-scenes tour of Boston’s iconic baseball stadium.

Why It’s Great in Winter : While there’s no baseball in winter, the stadium tour is still available and much less crowded.

Food Tour of the North End

What It Is : Sample some of Boston’s best Italian food as you stroll through its oldest neighborhood .

Why It’s Great in Winter : The hearty Italian fare will warm you up in no time.

4. See the Tree Lightings

One of the most festive activities to do in Boston in winter is attending one of the many tree-lighting ceremonies. The city is home to several grand trees that are illuminated in spectacular fashion. From the ceremony at Boston Common to others in different neighborhoods, it’s a twinkling way to ring in the holiday season.

3. Skiing and Snowboarding

If you’re a winter sports enthusiast, you’ll be thrilled to know that Boston in winter offers relatively easy access to a variety of skiing and snowboarding options. While the city itself doesn’t have ski slopes, there are several excellent resorts and mountains within a couple hours’ drive. Here are some of the best spots to consider:

Wachusett Mountain

Location : About an hour and a half from Boston.

What’s Special : A solid mix of beginner, intermediate, and advanced runs. They also have night skiing, so you can hit the slopes after the sun sets.

Loon Mountain

Location : Around two hours north in New Hampshire.

What’s Special : Known for its expansive terrain and excellent snow conditions. It’s bigger than many of the closer resorts, offering a broader range of trails.

Sunapee Mountain

Location : Also about two hours away, in New Hampshire.

What’s Special : Sunapee is great for families and offers a balanced variety of trails for skiers and snowboarders of all levels.

Blue Hills Ski Area

Location : Just 30 minutes from downtown Boston.

What’s Special : While it’s smaller and has less challenging runs, it’s the closest option for a quick day trip to scratch that skiing itch.

If you’d prefer to go for a weekend, there are plenty of awesome mountains in New Hampshire , Vermont , and Maine that are a few hours’ drive.

2. Go Sledding

When the first big snowfall hits, one of the simplest and most enjoyable winter activities in Boston is sledding. Grab your sled, or even a cafeteria tray if you’re a college student looking for a cheap thrill, and head to one of the city’s many parks that become sledding havens in the winter. Here are some top spots to consider:

Boston Common

Location : Central Boston

What’s Special : This iconic park offers multiple hills suitable for all age groups. The Frog Pond area is a popular sledding spot, offering easy slopes for younger kids.

Larz Anderson Park

Location : Brookline

What’s Special : Known for having one of the largest and steepest hills in the Boston area, it’s perfect for those looking for a little more speed and excitement.

Arnold Arboretum

Location : Jamaica Plain

What’s Special : This park is ideal for sledding among beautiful, snowy trees. The sloping terrain provides plenty of options for sledders of various skill levels.

Prospect Hill Park

Location : Waltham

What’s Special : With multiple hills and an incredible view of the Boston skyline, Prospect Hill offers a sledding experience that’s both fun and scenic.

1. Visit Nearby Small Towns

One of the cool things about being in Boston in winter is that you’re not far from some quintessentially New England small towns that look like they’re straight out of a holiday card. A quick drive can transport you to charming locales where you can experience a different, more relaxed vibe. Here are a few spots worth the trip:

Location : About 30 minutes north of Boston.

What’s Special : Known for its witch trials, Salem offers history, museums, and a charming downtown area. In winter, the crowds are smaller and the vibe is cozier. See the top things to do here , as well as some awesome Salem restaurants here .

Location : Roughly 30 minutes west of Boston.

What’s Special : The town is rich in literary history, being the home of authors like Thoreau and Emerson. Walden Pond is particularly peaceful in the winter months.

Newburyport

Location : About an hour north of Boston.

What’s Special : This coastal town is beautiful in winter. With fewer crowds, you can really enjoy the boutiques and seafood restaurants at a leisurely pace. Plus, Newburyport offers some cozy, historic hotels that you won’t want to leave!

Check out our favorite things to do in Newburyport here , and our top Newburyport restaurants here.

Location : An hour and a half north of Boston.

What’s Special : Known for its art galleries and Bearskin Neck , a scenic stretch of old fishermen’s shanties converted into shops, Rockport offers a serene oceanfront experience in winter with plenty of things to do and delicious restaurants.

FAQs About Visting Boston In Winter:

Just how cold does boston get in the winter.

Boston winters can vary, but they’re generally cold. Temperatures can range from mild to quite chilly. Here’s a general idea:

• Average High: Around 41°F (5°C)
• Average Low: Around 28°F (-2°C)
• Average High: Around 36°F (2°C)
• Average Low: Around 22°F (-5°C)
• Average High: Around 39°F (4°C)
• Average Low: Around 25°F (-3°C)

Snowfall is also common, especially in January and February. The city can receive anywhere from a light dusting to several inches of snow in a single storm.

Wind chill can also be a factor, making it feel colder than the actual temperature. It’s not unusual to have days where the wind chill dips into the single digits or even below zero in Fahrenheit, particularly in January and February.

Basically, Boston in the winter is pretty chilly. It won’t be as cold as, say, Canada, but you  will want to bring tons of layers. Even for a night out at a bar, everyone will be dressed in sweaters.

What should I pack for Boston in the winter?

Boston in winter is chilly, often snowy, and sometimes downright freezing. But that doesn’t mean you have to sacrifice style for warmth. Here’s how you can look chic while braving the Boston cold:

Wool Coat : Go for a classic wool coat that reaches at least down to your thighs. Black, navy, or camel tones are versatile and timeless.

Puffer Jacket : For especially cold days, a sleek puffer jacket can be both warm and stylish. You’ll see a lot of  long puffer coats in Boston, usually in darker colors.

Leather or Suede Boots : Knee-high or ankle boots with a good grip are perfect for navigating the city streets.

Sneakers : A pair of stylish yet functional sneakers can be great for days when you’ll be doing a lot of walking but the weather is dry.

Snow Boots : Of course, you’ll see plenty of snow boots in Boston. I love a good low pair of snow boots that are cute and comfortable.

Sweaters : Pack a variety of knits, from chunky turtlenecks to slim cashmere pullovers. We pretty much wear sweaters everywhere in Boston in the winter, from museums to pubs.

Long-Sleeve Tees : These are great for layering under sweaters and jackets. Stick to neutral colors to maximize outfit combinations.

Accessories

Beanie or Fedora : A cute hat can keep you warm while also upping your style quotient. I personally wear a knit beanie everywhere I go – this is a staple.

Scarf : Go for a large, cozy scarf that can double as a wrap. Plaid or herringbone patterns can add some texture to your look and are pretty common.

Leather Gloves : They’re warmer than you think and way more stylish than chunky knit ones. This is the “upscale chic” city vibe for Boston in winter.

Lastly, you’ll want to bring nice sunglasses and simple jewelry. You’ll see most people wearing leggings or jeans tucked into boots just about everywhere, though you can get away with a tweed skirt and tights if the weather is more mild.

Guys tend to dress pretty casual and preppy, with simple jeans, workboots or snowboots, henleys, puffer coats, or wool coats (when they’re feeling fancy).

Is Boston walkable in the winter?

Boston is definitely a walkable city, even in the winter months. The compact layout of the city makes it convenient to go from one neighborhood to another on foot, and many attractions are clustered close together.

Boston gets its fair share of snow, and while the city is generally good at clearing main roads, you might find some smaller streets and sidewalks that are icy or slushy. Be careful when walking, and it’s advisable to wear boots with good grip.

Also, daylight is limited during winter; the sun sets as early as 4:30 p.m. in the deepest winter months. If you plan to walk around, either make the most of the daylight hours or stick to well-lit areas if you’ll be out in the evening.

Boston’s public transportation system, known as the “T,” is generally reliable and can be a great way to cover longer distances or to give yourself a break from the cold. Just be aware that inclement weather can sometimes cause delays. So plan in about 30 minutes anytime you want to take the T, even if it’s supposedly a short jump (there’s almost  always at least one delay).

While Boston is walkable, it’s worth noting that it’s also an old city with cobblestone streets, which can be a bit tricky to navigate in icy conditions. If you or someone in your group has mobility issues, extra caution will be needed. And you  won’t want to wear heels

Cozy Boston Hotels During The Winter:

When you’re visiting Boston in winter, a cozy hotel can make all the difference. Nothing beats returning to a warm, inviting space after a day of exploring the chilly city. Here are some hotels that offer that extra level of coziness you’ll crave during your winter getaway.

The Liberty Hotel

Location : Beacon Hill What’s Special : Situated in a converted jail, The Liberty offers a unique blend of historical charm and modern luxury. With warm fireplaces in the lobby and plush bedding, it’s a cozy spot to unwind.

Location : Beacon Hill What’s Special : This boutique hotel takes luxury to the next level. Each room features a fireplace, and you’ll have access to complimentary hot chocolate and warm cookies in the lobby.

Boston Harbor Hotel

Location : Waterfront What’s Special : Want to enjoy waterfront views without braving the cold? The Boston Harbor Hotel offers just that. Its rooms are designed to make the most of the views while keeping you snug and warm.

Omni Parker House

Location : Downtown What’s Special : Known as the longest continuously operating hotel in the U.S., Omni Parker House has a rich history and classic New England charm. It’s famous for its Parker House Rolls and Boston Cream Pie.

Location : Back Bay What’s Special : Sustainability meets luxury at The Lenox . The hotel features eco-friendly amenities, but what makes it a winter haven are the real wood-burning fireplaces in some rooms.

So, there you have it—a comprehensive guide to making the most out of Boston in winter. Despite the cold and snow, this historic city has a unique charm that truly comes alive during the winter months. From festive tree lightings and holiday markets to world-class museums and cozy hideaways, Boston offers a multitude of experiences that cater to all kinds of interests.

Visiting Boston in winter lets you see the city in a different light—literally and figuratively. The shorter days make the city lights glow brighter, and the snow-draped architecture turns familiar landmarks into postcard-worthy scenes. Yes, it’s cold, but with the right gear and a hearty New England spirit, you’ll find the city to be just as welcoming in winter as in any other season.

So, if you’re wondering whether to visit Boston in winter, the answer is a resounding yes. With a little preparation and an open mind, you’ll find that Boston’s winter offerings are as rich and rewarding as those of any other season. Get ready to layer up, step out, and dive into a winter wonderland like no other!

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Backpacking in the USA , Winter Travel

Boston in winter: the ultimate guide .

I visited Boston many years ago, just for a day trip, so following the success of the guest post about Free Things to do in Boston, I asked Tegan and Alex from Why Not Walk to share their top tips for visiting Boston in Winter and they certainly came through!  Check out their ultimate guide to visiting Boston in winter:  

Boston is the capital of Massachusetts and is one of the oldest municipalities in the United States.  Famous for its history, whale watching tours and delicious food, Boston is a wonderful city to visit at any time of year, but here is why you should visit Boston in winter to make the most of the special winter activities and events.

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Know Before You Go to Boston

Before travelling to Boston, make sure you book accommodation and popular attractions ASAP as hotels and tickets can sell out.

🛌 MY FAVOURITE ACCOMMODATION IN BOSTON:

$$ The Revolution Hotel : creatively designed rooms great for groups

$$ The Verb Hotel : a music-themed boutique hotel near Fenway Park

$ HI Boston Hostel : a modern hostel with private and dorm rooms

⭐ TOP 3 BOSTON ACTIVITIES TO BOOK IN ADVANCE:

1. Guided Walking Tour of the Freedom Trail

2. Boston Tea Party Ships and Museum Interactive Tour

3. Boston Fenway Park: Guided Ballpark Tour

Find Deals to Book Your Trip

Flight Deals

Hotel Deals

Group Tours

Winter Weather in Boston

Many dismiss Boston as too cold in the winter for a visit, picturing howling winds and icy roads. However, given that Boston is a coastal city, its proximity to the Atlantic Ocean truly gives it the best of both worlds: it’s much more temperate than the rest of the state and region in the wintertime, but still gets to enjoy several gorgeous, fluffy snowfalls each year.

That said, average winter temperatures in Boston hover around or just below freezing, with January typically being the coldest month.  January also usually gets the most snow, although you can expect some snow from November through to April.

Why Visit Boston in Winter?

Boston is bursting with fun things to do all year, but we would argue the wintertime is an extra special time to visit.  Stroll along romantic cobblestone streets, stop for a hot chocolate or perhaps some outdoor ice skating, and enjoy Boston’s wealth of museums, local breweries, charming neighborhoods, sports teams, and more.

Read on for all our best tips for the ultimate winter visit to Boston, and for more Boston tips for any time of year, check out Why Not Walk’s Boston-area landing page here .

What to Wear in Winter in Boston

Layers, layers, layers! We cannot stress this enough. While Boston’s temperatures aren’t quite as cold as people like to think they are, what we do have in spades here is wind. The downtown and Seaport areas, in particular, are known for wind tunnels that can get fairly brutal due to their tall buildings, so we definitely recommend a scarf and gloves, as well as a jacket with a hood or a beanie or hat.

As Boston is a walking-heavy city, you should definitely bring warm and comfortable shoes, preferably waterproof ones. We especially recommend boots (like Uggs or Timberlands) and of course some nice, thick socks. 

As for a coat, down or alternative down is the way to go. You’ll see many Bostonians rocking the knee- or ankle-length coats. This isn’t totally necessary if you usually live in warmer climes, but definitely make sure to bundle up, and plan a mix of indoor and outdoor excursions for each day. 

YOU MAY ALSO LIKE: Free Things to do in Boston Massachusetts

Things to Do in Boston in the Winter

You could live in Boston for years (like we have) and still not experience everything Boston has to offer. Boston has something for everyone, from the history aficionado to the sports fanatic to the autumnal leaf-peeper.

Here are some of the top things to do in Boston at any time of year: 

• Boston’s “Little Italy” North End Pizza & History Walking Tour
• Boston History & Highlights Walking Tour
• Day Trip Tour to Quincy and Plymouth
• Boston Duck Boat Tour with Cruise Along Charles River
• Guided Walking Tour of Harvard University Campus

You can browse more tours and attractions in Boston here, or enjoy some of the best free things to do in Boston . While you’re visiting Boston, plan an epic East Coast road trip , as well!

FIND A TOUR IN BOSTON

While visitors flock to Boston and the region in the fall to see autumn foliage , we’d argue that a beautiful snowfall gives the leaves a run for their money. If a winter “city break” is what you’re after, Boston will not disappoint. Keep reading for all the best tips on the best things to do in Boston in winter, the city’s top winter attractions, and a sample Boston 2 day itinerary. 

Recreate the Boston Tea Party

Yes, it’s probably the most touristy thing to do in Boston, but if it’s your first time in the city then learning about the famous Tea Party at the interactive museum is a fun way to forget the weather!  This ships and museum tour runs several times a week even in the winter and allows you to travel back in time to 1773 to be part of the famous Boston Tea Party and the events leading up to the American Revolution.

You can explore fully restored replicas of the Tea Party ships, take part in an interactive museum tour and re-live the events of the day with live actors and 3D holograms.  You’ll even have the chance to throw your own tea overboard! 

Money Saving Tip

Visit the museums in boston.

Wondering what to do in Boston when it snows?  When the weather is poor, getting inside and visiting some of Boston’s incredible museums is a great way to keep warm and dry and learn something at the same time!

The Museum of Fine Arts (Back Bay/Fenway) houses over 450,000 works of art at the world’s 17th-largest museum. 

The Isabella Stewart Gardner (near the MFA): Once the home of notable Bostonian Isabella Stuart Gardner, the house and artwork were turned into a museum under the terms of her will. The ISG gained notoriety for a 1990 art heist that remains unsolved to this day. Don’t miss the gorgeous courtyard in the center.

The Boston Science Museum (Lechmere): though a bit dated, science fans will enjoy the Science Museum’s many exhibits and indoor zoo.

The Museum of African American History (Downtown): Don’t miss a visit to New England’s largest museum dedicated to preserving and honoring African-American history, located in the African Meeting House– the oldest Black church building in the U.S.

The Institute of Contemporary Art (Seaport): If modern and contemporary art is more your scene, the ICA does not disappoint. It also has lovely views of the Harbor area, and its neat architecture is an exhibit unto itself.

Check Out Vintage Movies, Glamorous Shows and Improv Comedy

These are some of our favorite places for a more unique Boston experience, especially during the winter!

Watch vintage movies (often in 35mm!) at Brattle Theatre (Harvard Square) or the Coolidge Corner Theatre (Brookline.) Coolidge Corner is the oldest Art Deco theatre in the area, built in 1933.

Get dressed up for a show at the Boch Center or the Emerson Colonial Theatre . You will be awe-struck at the beautiful decor, sweeping ceilings, and enormous chandeliers. All 3 of these theatres opened in the early 1900s and are some of the oldest continuously operating theatres in the region. You can also enjoy Boston’s premier symphonic ensembles at the Boston Symphony Orchestra (Fenway.)

Alternatively, laugh ‘til your sides hurt at a comedy show at ImprovAsylum (North End.)   

Warm Up with Hot Chocolate

Any excuse for a tasty hot chocolate is fine by me, and these tasty treats will warm you right up on a cold Boston winter day!

The Mexican hot chocolate at Ogawa Coffee House is absolutely decadent, and its location in downtown Boston is perfect if you’ve just gone ice skating at the Frog Pond (more info on that below!)

Located in the swanky Back Bay, LA Burdick offers all sorts of artisanal chocolate offerings, including hot chocolate.

If you don’t want to choose just one, check out seasonal Hot Chocolate Flights at The Met Back Bay . You can even ask for yours to be spiked!

If you like to combine your cocoa with Christmas carols, this cruise on Boston Harbor takes in the beautiful sights of the Boston Skyline while listening to Christmas music and carols as you sip on your cocoa. 

Bonus: If hot chocolate isn’t for you, and you’re more in the mood for normal chocolate, check out the Chocolate Factory Tour at Taza in Somerville.

YOU MAY ALSO LIKE: Things to do in Orlando in Winter

Ice Skating and Winter Sports in Boston

The ultimate Boston winter experience is outdoor ice skating at the Boston Common Frog Pond . The Common is the “Central Park of Boston,” and is located in the heart of downtown. Tip: if you go after sundown, there are twinkly lights all over the park that really set the scene! There is also seasonal ice skating at City Hall Plaza ’s Boston Winter installation, as well.

If indoor ice skating is more your scene, check out the Steriti Ice Rink in the North End. Admission is free, and you can rent skates for a few dollars. Pair this with a visit to the North End (Boston’s Italian neighborhood) and Boston Harbor afterwards. 

If you don’t want to splurge on (very pricey) hockey tickets, you can watch the Boston Bruins practice at Warrior Ice Arena. 

Enjoy the Red Sox stadium tour without the crowds– it’s available year-round!

If you are interested in attending sporting event while you are in town, check out the TD Garden calendar for Bruins and Celtics tickets, as well as concerts! 

Brewery + Distillery Tours

What better way to warm up on a wintery day in Boston than with a tasting of your favorite tipple?  You could join a tour that takes in three of the top breweries in town , or check out our recommendations below:

Sam Adams (Jamaica Plain): Sam Adams is definitely touristy, but worth a visit if you’re visiting Boston for the first time, or if you’re interested in how one of the nation’s largest breweries operates. The tour is free (make sure to reserve ahead of time), and you get samples and a free small glass with your tour. Sam Adams recently opened a new taproom in the Faneuil Hall area as well. 

Harpoon Beer Hall (Seaport): Harpoon wins “best brewery tour” in our book, hands down. Harpoon is a super fun atmosphere– they’re employee-owned, make amazing pretzels with their leftover beer byproduct, and their beer hall in the Seaport can’t be beat. Definitely sign up for their brewery tour– it costs $5, but includes some time at the end for unlimited samples! 

Boston Harbor Distillery (Dorchester): Their table-side tasting tour offers several samples and a history of their operation for $20/pp. They also have a VIP tour ($50/pp), offering a “back-room of whiskey-making” experience. Also in Dorchester is Bully Boy Distillers , which is worth a look too.

You should also check out these beer and brewery tours that are guaranteed to keep you warm and tipsy!

Explore Beautiful Wintry Neighborhoods in Boston

There are some lovely neighborhoods in Boston where you can talk a stroll, no matter what the weather.  Just wrap up warm and enjoy!

Beacon Hill

Located right behind the Boston Common with Charles Street as its main drag, don’t miss a visit to Beacon Hill while in Boston. Characterized by its cobblestones and mix of Victorian- and Federal-style brick row houses and antique black streetlamps, Beacon Hill is so charming and picturesque – and quintessentially Boston.

Don’t miss the State House with its gold dome, especially beautiful when covered in snow, and Acorn Street, one of the U.S.’s most-photographed streets.  

Likely Boston’s most “fancy” neighborhood, Back Bay is also home to beautiful architecture, as well as a large shopping district including Newbury Street and the sparkly Prudential Center. The Commonwealth Avenue Mall, leading up to the Public Garden, is beautiful in any season.

Boston’s Italian district is also Boston’s first neighborhood, continuously inhabited since 1640. The North End is adorned with narrow, winding streets and some of Boston’s oldest surviving architecture. Don’t miss American Revolution hero Paul Revere’s house and the infamous Old North Church (of “one if by land, two if by sea notoriety), both on the Freedom Trail.

Places to Check out Snow in Boston

If snow is what you’re after, you have a good chance of seeing it between December and March, with January and February usually clocking in as the coldest and greyest months with the most chance for that sort of precipitation. There is sometimes snowfall as late as April, to the delight of visitors and chagrin of locals.

Top Tip: If you want to increase your chances of seeing snow, plan a quick day trip to Western Massachusetts and the Berkshires while you’re in Boston, as they have fairly constant snow cover and are only about 2 hours away.

Closer by, the towns surrounding Boston are excellent places to enjoy a fresh snowfall – Brookline and Chestnut Hill, in particular, have beautiful Victorian architecture and stately homes that make a gorgeous backdrop for photos, and their wonderful reservoirs and parks are at their most impressive when covered in snow. 

Holidays in Boston

Boston really gets into the swing of the holiday spirit during the winter, check out the variety of holiday-themed pop-ups at bars around the city, including the Tiki bar Christmas pop-up at Shore Leave (South End), Pop-up igloos at the Envoy Hotel (Seaport) and a Hanukkah-themed pop-up at Backbar (Somerville).  You can even get your fix of Holiday movie-themed cocktails at Precinct Kitchen & Bar (Back Bay)!

Christmas in Boston

Holiday and Christmas lights appear all around the city during the winter.  The Boston Common is festooned with twinkling lights, as well as a lighting ceremony for a huge Christmas tree. Visit Faneuil Hall downtown, to see Quincy Market decorated with lights and decorations, and book tickets to see the Nutcracker ballet at the Boston Opera House.  

New Year’s Eve in Boston

First Night Boston is the city’s biggest New Year’s Eve celebration.  It is family-friendly and alcohol-free so if you are visiting Boston with kids then they will love it!  There are fireworks over Boston Common at 7pm, and another spectacular display over Boston Harbor at midnight. 

You can watch a parade, admire ice sculptures, watch a pyrotechnic show and catch some live music performances.  It is one of the best things to do in Boston in December, and a wonderful way to welcome in the New Year.  This website has more details about the events.

Want More Winter Travel Ideas?

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• Lake Louise in Winter

How to Spend Winter in Boston 2 Day Itinerary

If you need some more tips for things to do in Boston during the winter, this Boston itinerary has more suggestions for you! 

Boston in Winter Itinerary Day 1

Start your day in Copley Square, visiting its churches and the Boston Public Library , and exploring the Back Bay neighborhood.

Tip: the BPL is one of Boston’s best-kept secrets. Built in 1888, its interior is absolutely gorgeous. Don’t miss the 2nd floor Bates Room for old-school study vibes, or the outdoor courtyard in the middle (follow the signs on the ground floor.)

Meander along Newbury Street, perhaps stopping in one of its chic eateries for brunch as you walk along. Newbury Street also has Boston’s most upscale shopping, if that’s in your budget. Pop over a block to the Commonwealth Avenue Mall promenade for a snowy stroll.

Continue down to the Prudential Center, a shiny shopping center where you can thaw for a little bit on a chilly day. For a lovely Italian market experience, check out Eataly. 

If you’re in the mood for some seafood for lunch, check out Saltie Girl . If that’s a bit out of your budget, enjoy locally-sourced DIY bowls at Dig Inn .

In the afternoon, take the green line or a ride-share a few stops to the Fenway area to visit the Fenway Baseball Stadium, the Museum of Fine Arts, and the Isabella Stuart Gardner Museum. If you’re not feeling too cold, the Fens area of the interconnected parks known as the Emerald Necklace is lovely in the winter.

In the evening, check out the South End for trendy eateries and bars. Stop into the Beehive for a drink and live jazz music, or Barcelona Wine Bar . If you decide to stay in the Copley area, Lolita is another favorite, for frozen margaritas and other cocktails in what we like to call a “dungeon-glamour” locale.

Lastly, a favorite bar in Seaport is Drink , for really neat DIY cocktails. Here’s how it works: you sit down at the bar, tell the bartender what combination of flavors and liquors you like (e.g. vodka and citrus, or “drinks that don’t taste like alcohol,” or rum and bitter), and they make you a surprise. It could be a bartender invention or an obscure combination – you never know!

Boston in Winter Itinerary Day 2

In the morning, take the MBTA’s green line or a ride-share to the Boston Common to start the Freedom Trail : a 2.5 mile walking tour of Boston’s esteemed role in the history of the United States. Pair the Freedom Trail with its sister tour in Beacon Hill, the Black Heritage Trail .

For a full, step-by-step guide to both trails (plus bonus local content!), check out Why Not Walk’s definitive guide to the Freedom Trail . We recommend allotting at least a half day for the Freedom Trail. While it can theoretically be done in about 1.5 hours, you will definitely want to spend longer at various sites!

The Freedom Trail ends in Charlestown, at the Bunker Hill Monument and the USS Constitution. You can spend some time exploring the area, or make your way back downtown for lunch.

For quick bites downtown, check out Sam LaGrassa’s for sandwiches, Dig Inn for locally-sourced bowls (if you didn’t go to the Back Bay location yesterday!), or Clover Food Lab for vegetarian-friendly fare. In nearby Chinatown, there are delicious dim sum and dumpling restaurants galore. One particular favorite is Gourmet Dumpling House .

Alternatively, there is something for everyone at Faneuil Hall Marketplace, which is a stop along the Freedom Trail if you’d like to take a break then. Here, you can sample Boston’s famous lobster rolls (we recommend hot rolls more than cold!) drizzled with fresh butter or clam chowder in a bread bowl. Note: For a less-touristy place to try lobster rolls, there’s always Yankee Lobster in Seaport.

In the afternoon, tour the North End, Boston’s quintessential Italian neighborhood. We hope you saved some room from lunch, because you can’t miss sampling hand-made Italian cookies, cannoli, gelato, and other treats here. Don’t miss the epic Mike’s Pastry versus Modern Pastry cannoli battle, at the very least.

You can stay in the North End for dinner too, choosing one of many restaurants (you can’t go wrong!) such as Regina’s for pizza, or Trattoria Monica , Giacomo’s , or Antico Forno for pasta and other Italian fare. Note that Giacomo’s does not take reservations, so you will likely have to start lining up at around 3PM or earlier to get in for dinner. This may not be worth it if you’re on a tight schedule.

In the evening, enjoy the downtown Boston bar scene at classy Yvonne’s or the Marliave , or the really fun dive bar Biddy Early’s . Watch live Irish music with the Guinness on tap flowing at Black Rose . If breweries are more your scene, check out Harpoon or Trillium in the Seaport, Dorchester Brewing Company in Dorchester, or Lamplighter in Cambridge.

Where to Stay in Boston This Winter

After a long day of exploring Boston, Massachusetts, you’re going to need somewhere to rest your head and get energized for the next day.

Here are a few great options for hostels and hotels in Boston for your visit:

HI Boston Hostel : This modern, environmentally friendly hostel is near Boston Common, Chinatown, the subway and most of the city’s sights. Dorms feature individual lockers and personal shelves, reading lights, and power outlets. You’ll get lots of privacy balanced with common spaces for socializing when you stay here. >>>CHECK PRICES

The Verb Hotel : A small, music-themed boutique hotel near historic Fenway Park. Fans of rock ‘n roll will love the funky decor and party atmosphere. Plus, it’s literal steps from some of Boston’s best restaurants, shopping, and activities. >>>CHECK PRICES

The Godfrey Hotel Boston : Stylish, sophisticated, and centrally located, this hotel provides excellent access to just about everything a guest would want to do in Boston.  >>>CHECK PRICES

If you’d like more options, you can browse all hostels in Boston on Hostelworld , or find great value hotels on Booking . There are also various options for Airbnbs in Boston too, take a look at some of the rental homes available here .

BROWSE HOTELS IN BOSTON

Travel Tips for Boston

We hope this post has inspired you to book your winter vacation in Boston this year!  Be sure to check out these extra travel tips to help you plan the best trip to Boston you can:

Getting There

• Use Skyscanner to find cheap flights to your destination.
• Public buses are the cheapest ways to get to your accommodation from the airport, but a shared shuttle transfer is quicker and cheaper than a taxi - you can pre-book those on GetYourGuide or Viator
• Try Omio for booking trains and Busbud for buses including Greyhound and Flixbus.

Where to Stay

• For hotels, I use Booking.com to check reviews and find the best deals on hotels and apartments wherever I'm travelling to.  Hotels.com is another good site.
• If you're on a tight budget, use Hostelworld to find the best hostels all over the world

• Get a quote for car hire with Discover Cars who compare car rental deals from many companies so that you can choose which is best for your trip.

Book Tours and Activities

• I use GetYourGuide or Viator to book everything from skip-the-line entry tickets to food tours as I can compare options from several companies and choose the best one for me
• If you're staying in a hostel, check out their tours and activities which are usually free or very cheap - and a great way to meet people!  

Get Travel Insurance

• Unfortunately, things can and do go wrong when you travel.  I never leave home without travel insurance, so consider getting insurance for your trip to cover things like adventure sports and activities as well as emergency medical, lost luggage, stolen items, trip cancellation and more.  
• Get a quote for your trip from True Traveller if you're based in the UK, or World Nomads or SafetyWing which both offer travel insurance for backpackers and long-term travellers.  Alternatively, use a comparison site like Travel Insurance Master to find the best cover for you.

Check Your Travel Documents

• Don't forget to check the validity of your passport and any other documents for your trip.  Use iVisa to check if you need a visa to visit your destination, and get up to date official travel advice from your government, for example on the Department of State website in the US or the UK government website .

Get Cheap Currency

• When travelling abroad, using a travel bank account like Wise means you get great deals on foreign currency - including a fee-free transfer of up to £500 when you use this link to sign up . 

Top Money Saving Tip for Backpackers

• Work exchanges are a great way to travel for longer and extend your trip as you can save a ton of money on accommodation.  Get an extra $10 discount on Worldpackers here or learn more about work exchanges .

About the Authors

Tegan George & Alex McKenzie

Tegan and Alex are travel, hiking, and biking enthusiasts currently based in Boston, USA. There is nothing they love more than exploring new places by walking, and they have visited over 30 countries together since they met in 2015. Their love for “walking the world” led them to found Why Not Walk , a travel guides site. Follow them on Instagram , Facebook , or Pinterest to start planning your next adventure.

If you’re looking for travel insurance for your trip to Boston, get a quote now from World Nomads .

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Just to let you know, this post may contain paid or affiliate links, which help to maintain Tales of a Backpacker and give me the chance to keep travelling, and to keep creating awesome content for you!  I only recommend goods and services I believe are useful and reliable.

Hi! I'm Claire Sturzaker, a 30-something foodie traveller who loves to enjoy the best of a destination without breaking the bank. I'm here to help you and all women backpackers to plan their best budget travel adventure. I am an avid supporter of female solo travel, and took my first solo trip 20 years ago! I love to write about travel, hostels, backpacking and van life.

1 thoughts on “ Boston in Winter: The Ultimate Guide  ”

Nice post Tegan and Alex. Super comprehensive guide here. Well done. I am heading to Middleton in under 2 weeks for a month long trip, about. We will miss Boston during winter but may take a trip into town as we will be about 30 minutes outside of Beantown.

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The 15 Best Things to do in Boston in the Winter

There’s nothing like Boston in the winter . And that’s coming from someone who spent two weeks trapped in her freshman-year dorm because the snow was piled higher than the front door.

But it’s also coming from someone who has fond memories of dancing around the Public Garden in her pajamas in the snow after the Patriots won the Super Bowl and who spent many a night strolling through the Boston Common, loving the way the holiday string lights seemed to dance around her.

Winter in Boston can be brutal. But it’s also incredibly magical. I’ve compiled a list of some of the most magical things to do in Boston in the winter, from ice skating on an iconic pond to getting in on the sports culture. Stick to this list, and you’re bound to fall in love with Boston in the winter just as much as I have.

Disclaimer: This post may contain affiliate links. If you make a purchase or booking through one of our links we may earn a small commission (don’t worry, it’s at no extra cost to you).

15 Fun Things to do in Boston in the Winter

1. go ice skating on frog pond.

When the weather heats up, the Boston Common Frog Pond becomes a place where all the kids play around in the shallow pool, trying to cool off. But when the snowy season starts, Frog Pond becomes one of the best winter activities in Boston. 

Though there are other places to go ice skating in Boston, Frog Pond is likely the most iconic. There are few things better than gliding on the ice with the string lights twinkling on the trees all around you.

2. Join the Beacon Hill Holiday Stroll

If you’re experiencing a Boston winter, visiting Beacon Hill is simply a must-do. As the freshly fallen snow begins to build on the famous cobblestone streets, there’s a certain magic to this historic district.

Beacon Hill also offers one of the best things to do in Boston during winter, the Beacon Hill Holiday Stroll . At the start of December, Charles Street is closed to vehicles, creating an enchanted evening where guests can listen to Victorian carolers, enjoy sampling seasonal treats, and experience some festive fun.

Take the Beacon Hill History Walking Tour

3. Have a Board Game Night at Knight Moves

Over in Brookline, you’ll find a place that’s perfect to spend a cozy night in. Knight Moves is a board game cafe, and having a board game night here is one of the most fun things to do in Boston in the winter.

Grab a comfy sweater, call up your friends, order yourself a hot chocolate, and pick from their vast collection of board game titles. Whatever you’re in the mood for, you’ll find it here. Whether you’re looking for a quest that will take hours to finish or a short game you can play over and over again, the game you want is likely in their collection, which features over 600 titles.

4. Go Tree Lighting Hopping on the Enchanted Trolley Tour

The Mayor’s Enchanted Trolley Tour is a Boston winter tradition that goes back more than two decades. In early December, this tour hops from event to event around the Boston area. 

The mayor’s trolley brings with it tons of holiday fun and signals a time of coming together for the Boston community. In addition to tree lightings happening at stops throughout the tour, there will also be other famous faces alongside the mayor, including Santa and Mrs. Claus.

5. Shop at the Holiday Markets

Need to get some holiday shopping done? Whether you’re looking for gifts or just looking for fun things to do in Boston in the winter, the holiday markets are the place to be.

Several markets pop up in the winter. Over at the Seaport, you’ll find Snowport , which has quickly become one of the biggest markets in the city. Here, you’ll find more than 100 small local merchants, as well as winter-themed games and foods.

Or head to Somerville to experience a litany of events at Bow Market , offering incredible eats and local artisans displaying their wares. Harvard Square also features its own Holiday Fair , which is always bursting with unique finds.

6. Get Tickets to a Hockey Game

Hockey is simply a part of Boston’s culture. Bostonians take great pride in their Boston Bruins , which is why watching a hockey game is one of the best Boston winter activities. 

However, Bruins games can cost a pretty penny. If you want something a little more budget-friendly but just as fun, head to a college game. 

If you want to see something absolutely wild, join the many fans watching the annual Beanpot tournament , which sees the teams from Boston University, Harvard, Boston College, and Northeastern go head to head on two Mondays in the winter, typically the first two Mondays of February. But be warned: These fans fight hard for their school!

7. Spend a Day at the Museums

Boston is filled with many wonderful museums, and spending time exploring them is one of the best things to do in Boston during winter if you want to escape the cold. There’s something for every interest. 

Are you an art lover? The Museum of Fine Arts and the Isabella Stewart Gardner Museum are two top choices.

Meanwhile, science fans will want to find their way over to the Charles River to discover the Museum of Science , which features over 700 interactive exhibits, live presentations, and much more.

If you’re traveling with little ones, you’ll love seeing them expand their imaginations over at the Boston Children’s Museum . 

8. Enjoy the Somerville Illuminations Holiday Lights Tour

If you love when the holiday season starts because of all the beautiful light displays, you’re going to want to head to Somerville for the Illuminations Holiday Lights Tour , one of the best winter activities in Boston. Starting at the beginning of December, this lights tour is actually a month-long show of one of the best and brightest displays around the city.

Although there used to be a trolley tour to help you see all the lights, that is sadly no more due to the cost. But you can still take self-guided tours of the light displays all month long. Plus, there are special events throughout the month, like an evening of city-wide caroling and another night where you can join others to take the tour by bike. 

9. See “The Nutcracker” at the Boston Ballet

From the end of November to the end of December, seeing “ The Nutcracker ” put on by the Boston Ballet at the Citizens Bank Opera House has been one of the best things to do in Boston in the winter for many, many years. 

While the Boston Ballet Orchestra plays Tchaikovsky’s beloved score, the characters are brought to life on stage by the incredible dancers, surrounded by breathtaking sets. It’s a truly enchanting experience, and you’ll want to come back every holiday season to see it.

10. Listen to the Holiday Pops

Speaking of enchanting holiday experiences, the Holiday Pops are another one of the can’t-miss winter activities in Boston. The Holiday Pops are a Boston winter tradition that’s beloved by Bostonians and visitors alike. 

Throughout December, the Boston Symphony Orchestra invites you to Symphony Hall to listen to holiday music favorites and even sing along yourself. Plus, there’s even a visit from Jolly Ol’ Saint Nick himself.

If you have little ones, book a Kids Matinee performance, which includes post-concert pictures with Santa and additional festive treats. There are also special sensory-friendly performances. 

11. Take a Holiday-Themed Harbor Cruise

You might think that a harbor cruise is just a summer activity, but it’s also one of the most fun things to do in Boston in the winter. Come winter, the cruises offer unique options to experience the beautiful Boston harbor in comfort. 

One of the most fun options is the Cocoa and Carols Holiday Cruise , which is put on by Classic Harbor Line Boston. On this cruise, you’ll board a classic yacht that’s all decked out for the holiday season. 

Holiday tunes will play throughout the 1.5-hour-long journey as you enjoy the sights of the Boston skyline. Food and drinks are available to purchase on board, including hot cocoa for the little ones and alcoholic beverages for the grownups. 

12. Head to Harvard for the Midwinter Revels

Each December, Harvard University is home to one of the best things to do in Boston in the winter, the Midwinter Revels . At this unique show, you’ll delight in traditional songs, dances, and stories from cultures all across the world. 

The productions vary from year to year, which is why you should make this show an annual tradition, as you’ll always see something new. 

13. Watch ‘It’s a Wonderful Life’ at The Brattle Theatre

The Brattle Theatre isn’t just any theater. This historic Cambridge institution is known for its movie showcases, which dive into specific movie genres, eras, and directors.

But once the holiday season rolls around, they start up their annual tradition of playing one of the most beloved holiday movies of all time, “ It’s a Wonderful Life .” No matter how many times you’ve seen this film, there’s nothing quite like seeing it in The Brattle’s famous theater. 

14. Go Sledding

Whether you’re a college kid delighted about their classes being canceled or a child who awoke to the joyful sound of the phone ringing to say that school’s off, there’s no better way to celebrate the snowfall than by going sledding. Boston offers plenty of places to enjoy this winter tradition.

The most iconic spot is Flagstaff Hill in the Boston Common. But you’ll also find plenty of fellow sledders at other locations like the Arnold Arboretum and the Sugar Bowl, both in Jamaica Plain.

15. Shop and Eat Around Faneuil Hall

Decorated with beautiful lights and a massive tree for the holiday season, Faneuil Hall is one of the best places to visit in the winter in Boston. This historic area, with its cobblestone streets, is perfectly charming as the weather gets chilly.

Spend some time hopping from shop to shop, from comic book stores to places to get new ornaments for your tree. Then, grab a bowl of clam chowder to warm up and take a seat inside this beloved landmark.  

There you have it! The 15 best things to do in Boston in the winter. What are your favorite winter activities in Boston? Let us know in the comments!

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About the Author:

Jacqueline is a writer and editor pursuing the freelance life to explore the world. Born and raised in New Jersey, she spent her college years in Boston before settling down with her partner and puppy in Monterey, California. When she’s not writing, you can often find her planning her next trip. Road trips are her favorite, whether it’s driving across the country or simply exploring a new city in her own backyard. She loves uncovering the history of every new place she goes. Jacqueline has a restless passion for learning and makes it a goal to pick up a new skill every year. She’s picked up embroidery, crocheting, knitting, and cross-stitching, but she’s hoping to master more languages to help her in her travels. She’s also a published author, with short stories and poetry appearing in several anthologies.

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16 Top Things to Do in Boston in Winter

Written by Shandley McMurray Updated Mar 24, 2023

Winter in Boston is no joke. With lows bottoming out at around 19 degrees in January, and highs averaging in the high 30s to mid-40s from December through February, you'll need to pack layers while visiting Boston in winter. Don't let the cold dissuade you from an early year visit. Boston is at its most majestic (not to mention quietest and cheapest) during the most frigid months.

Fans of the white stuff will rejoice while sightseeing around Boston in the winter, especially if they arrive in January or February, when the average snowfall ranges from 12 to 14 inches. The fresh powder is optimal for sledding through Boston Common or snowshoeing at Gore Place . There are so many fun things to do in Boston in winter that you'll almost forget that it's cold.

Hit the city during the Holidays, and you'll be blessed with pretty illuminations at the Museum of Fine Art's Festival of Lights , fun tree lighting ceremonies throughout town, Hanukkah celebrations at Faneuil Hall , and an impressive First Night celebration on New Year's.

Plan your cold weather visit with our list of the best things to do in Boston in winter.

1. Skate or Sled in Boston Common

2. walk the freedom trail, 3. admire the view from the prudential skywalk observatory, 4. explore the museums, 5. drink hot chocolate, 6. tour the taza chocolate factory, 7. watch a play in the theater district, 8. shiver while frostbite sailing in boston harbor, 9. shop 'til you drop at the prudential center, 10. visit a holiday market, 11. cheer for the home team at a celtics or bruins game, 12. take an old town trolley tour, 13. snowshoe at gore place, 14. go curling at boston seaport, 15. curl up with a good book at boston public library, 16. board the mayor's enchanted trolley, map of things to do in boston in winter, boston, ma - climate chart.

Unleash your inner Michelle Kwan (or perhaps just try to make it around a lap without falling) on the Boston Common Frog Pond . Set in the heart of the oldest public park in the country, this beloved pond is home to a skating school, and offers skate rentals, including seal-shaped aids to help little ones (or wobbly adults) find their balance.

Once you're well and truly chilled, or tired from landing so many triple axels, head to the Frog Pond Café for some warm and hearty comfort food and hot chocolate. The rink is open from November through March, and skating on it is one of the best things to do in Boston in winter.

If you're lucky enough to visit during a snowfall, grab a sled or a cafeteria tray and head to Flagstaff Hill . This is one of the best-known sledding destinations in the city.

While a smattering of snow might make it hard to spot the 2.5-mile-long red-brick line marking the Freedom Trail in winter, it's still one of the best places to visit in Boston. This long, winding path passes 16 of the city's most important historic sites, including the Massachusetts State House , Old South Meeting House , Old State House , and the site of the Boston Massacre .

The path also leads to Faneuil Hall , home of an iconic marketplace worthy of a few hours at least. From shopping to eating to watching a dance show or concert, there are so many fun ways to pass the time at this historic locale. Plus, Quincy Market is just next door.

The most incredible view of Boston can be found at the Prudential Skywalk Observatory. The best time to visit is during the late afternoon, when you can watch the sunset alight the sky with pink and orange hues.

Set on the 50 th floor of the Prudential Building , the Skywalk Observatory is one of the top tourist attractions in Boston . Visiting during the winter rewards travelers with an impeccable, 360-degree view of the snowcapped brownstones, powder-laden streets, frozen Charles River , and whitewashed Boston Common. On a clear day, you can see as far as 80 miles away.

Inside, you'll stay nice and toasty while learning about the city's history through interesting and interactive exhibits.

Good news for those looking for an inside activity. Boston is home to some of the country's oldest (and some would say best) museums. The Boston Tea Party Ships & Museum is unmissable, and easily one of the best places to visit in Boston in winter.

This iconic, floating spot offers visitors an impressive way to step back in time to 1773. Actors roam the recreated tea ships to help educate and entertain visitors who will all get a chance to throw "tea" overboard. Insider's tip: Visit on December 16 th to catch the annual tea party reenactment.

The Museum of Fine Arts Boston is another top attraction in Boston. Here, visitors can gape at masterpieces in every genre, ranging from ancient Egyptian sculptures to intriguing photography to modern street art. Insider's tip: celebrate Diwali at the ancient festival of lights in mid-November.

Treat the kids to a day at the Boston Children's Museum . Explore bubbles in the Science Playground, create something awesome in the Art Lab, or visit a Japanese silk merchant's home.

There's no better drink to warm your chilled bones than a sweet cup of hot chocolate. From sickly sweet to spicy to vegan, winter travelers will be rewarded with a wide variety of hot chocolate options to tickle their taste buds. Here are our favorite spots:

Tucked away on Clarendon Street, L.A. Burdick Chocolates is tiny yet beautiful, and boy does it smell great! Be prepared to meet many others here while sampling the creamy chocolates and the yummiest hot chocolate around. Insider's tip: the vegan dark is just as good as the milk. Grab a bag to bring home.

While Thinking Cup is best known for its coffee, you'd be amiss to avoid sampling its French hot chocolate. Rich and creamy, it's made with 64 percent Tainori Valhorna drinking chocolate. Insider's tip: there are three locations to choose from: Boston Common, the North End, and Back Bay.

1369 Coffee House has two locations: Inman Square and Central Square . That's a good thing since its offerings are both unique and unmissable. Ever had Mexican hot chocolate? Its spicy blend of coriander and cinnamon will awaken your senses, while the Dutch Homemade Hot Chocolate is a sumptuous gift to your mouth. Technically in Cambridge, it's a short, 15-minute (or less) commute.

Face it, there's no such thing as too much chocolate. That's why we had to add a tour of the Taza Chocolate Factory to our list of the best things to do in Boston in winter. You're welcome!

Technically in Sommerville (a 14-minute drive from Boston Common), this top attraction is a must-see (and taste). Famed for their stone-ground chocolate, Taza offers tours every Monday through Sunday to introduce visitors to their intricate treat-making process. It includes samples!

Insider's tips: Kids will love you forever if you take them to Taza Cacao Scout Bingo or Chocolate Story Time on a weekend morning. Be sure to book in advance, as the spots fill up almost as quickly as your belly will.

It's impossible to leave here empty-handed, so expect to be tempted into purchasing anything from the entire Chocolate Mexicano collection to a few bags of the delectable sea salt and almond dark bark.

Boston's main theater district consists of over a dozen venues set in the downtown core. Whether you're looking to attend a Broadway musical, Christmas-themed performance, or dance show, you'll find it all (and so much more) in this glitzy area.

Even if you aren't a fan of opera, you should visit the iconic Boston Opera House . A Washington Street staple, this lovely Baroque building is an example of luxury at its best. During the months of November and December, this is where you'll find The Nutcracker ballet, a holiday season must-see, especially for those traveling with kids.

Don't miss a trip to the Colonial Theatre on Boylston Street. Recently revamped in an extravagant (and very costly) renovation, the building's innards are intriguingly ornate. This is also where many popular shows have premiered before moving on to New York's Broadway.

Only hardcore sailors would be willing to rip through the frigid waters of Boston Harbor between November and April. Apparently, there are a ton of people willing to do just that. If you're one of them, bundle up and head to the Boston Sailing Center in Lewis Warf or Winthrop Frostbite Sailing Club in Winthrop (near Boston's Logan airport).

In addition to the exhilaration you'll feel as the frosty breeze hits your cheeks, you'll be rewarded with an unbeatable view of the city. A sailing newbie? No worries. You can take lessons at the sailing center, but you'll want to bundle up.

Not willing to risk falling in (or getting frostbite)? Check out the sailing centers' websites to find race times, and head to the harbor to watch from the dry shore with a cup of something hot and steamy to warm your hands.

Whether you're looking for holiday gifts or hoping to spend the day in a cozy, indoor spot, Prudential Center (called "The Pru" by locals) won't let you down. They've got all the big names, like Saks Fifth Avenue , Ann Taylor , Canada Goose , Lululemon , L'Occitane , and Sephora . You can even buy a Peloton bike or an armful of books from Barnes and Noble .

When it's time to eat, get your nosh on at one of the many tasty restaurants. Our faves include: Wagamama for noodles (their juices and dumplings are divine) and Sweet Green for a healthy break (the crispy rice bowl is delish). Eataly offers visitors a three-floor Italian dining and shopping experience.

What's the holiday season without a market? Held annually at the City Plaza Government Center , the Boston Winter Holiday Market is one of the most popular events in Boston, attracting close to 100,000 visitors each year. It opens the day before Thanksgiving and runs through New Year's Eve, offering visitors an ideal place to find the most unique holiday gifts.

The market's eclectic shops are housed in adorable European-looking "chalets," and you'll find a ton of tasty treats to fill your belly, as well as a wide range of festive shows and other entertainment to up the fun factor at this top winter attraction in Boston.

Love markets and craft fairs? Old South Church (in Copley Square ) hosts an annual Christmas Fair in early December. It's worth a visit just to ogle at the building's gorgeous architecture.

The South Boston Holiday Market is another one-day wonder held in early December at the Ben Franklin Institute . You'll be hard-pressed to find more innovative food, jewelry, and clothing designs than those on offer at this unique spot.

It's easy to get excited while watching a game at the TD Garden . The official home of basketball legends the Boston Celtics (they've won 17 NBA Finals) and hockey champs the Boston Bruins , this popular sports and entertainment venue is the largest of its kind in New England, and catching a game is one of the best things to do in Boston in winter.

Visited by more than 3.5 million people annually, the venue boasts over 200 events a year, so you might also be able to catch a concert while you're in town. Grab a bite at one of the Garden's three private restaurants or settle in to enjoy the game with Cheetos popcorn, nachos, burgers, or fries at one of the on-site concessions stands.

Walking through slushy streets can get annoying after a while. Take a break while still seeing the sights with a ride on the Old Town Trolley. Prepare to spend at least 100 minutes riding around town, listening to the guide's fantastic stories as he or she narrates your journey through the city's best spots.

Hop off at one of the 19 stops to enjoy the restaurants, shopping, or historic sites up close. Then, hop back on when you're ready to travel to the next destination. No need to futz around with parking or navigate around snowbanks, let the trolley driver do the hard work while you sit back, relax, and soak up the heat.

Technically outside Boston, Gore Place sits a mere nine miles from the downtown core. This country estate, which spans 50 acres, boasts a historic mansion and a farm so close to the city, you'll forget you aren't there. Each winter, Gore Place allows visitors to practice a pastime many of us have yet to experience: snowshoeing.

For a small fee ($20 for adults and $10 for kids aged 6 to 12), adventure seekers can strap on a pair of snowshoes and trek atop the fluffy white stuff as they explore the vast grounds. No snowshoes? No problem! As long as the ground is covered in snow, you can rent them (for adults and kids) from the Carriage House .

Gore Place isn't the only snowshoe-worthy spot. Strap 'em on and head to the Esplanade , Boston Common , or the Weston Ski Track for more outdoor adventures.

Snowport may well be the best thing to come to Boston Seaport, one of the city's hippest neighborhoods. You'll find it sandwiched between the waterfront and the historic Fort Point district , waiting to wow you with its fun (and sometimes free) activities.

In addition to iceless curling, this winter wonderland is jam packed with fun events the whole family will enjoy. Twirl around the 3,000-square-foot ice rink, munch on a baked waffle, or take a yoga class.

Didn't bring skates? No problem. You can rent them on-site, along with skating aids for less confident skaters. Not a fan of waiting your turn? Curling, which is offered for free, is open to reservations, so you can be guaranteed a slot when you arrive.

If you're looking for historic charm coupled with the intoxicating smell of old books, head to the Boston Public Library. Located on Boylston Street, a six-minute walk from Prudential Tower, the Central Library consists of two buildings located in Copley Square .

The historic McKim Building , which opened in 1895, was designed by architect Charles Follen McKim. Inside, you'll find the rich interiors and elegant touches you've read about, and a charm so inviting, you'll want to curl up at one of the desks with a good book.

The Bates Hall Reading Room is unmissable. Its emerald green desk lamps are almost as captivating as the ornate domed ceiling, intricate windows, and stone balcony.

The more contemporary, Boylston Street Building was opened in 1972 and designed by Philip Johnson. In 2016, it underwent a renovation, making this an uber modern space featuring impressive perks like a broadcasting studio.

Each December, the Mayor boards the Enchanted Trolley for a tour of the city. He spends a weekend (including Friday) aboard the festively adorned trolley, visiting the various neighborhoods throughout town and stopping at multiple spots to participate in tree-lighting ceremonies.

Join the fun festive activities, which include carol singing, holiday performances, and a visit (or more) with Santa. You can find out where the trolley will be and when online.

Looking for more bright lights? Check out Boston's First Night celebration , held every New Year's Eve to ring in the new year in style. You'll see fireworks, concerts, and other fun performances.

More Related Articles on PlanetWare.com

Unmissable Destinations in Massachusetts: The state of Massachusetts has so many great things to offer. From adorable small towns with storied pasts to sandy dune-lined beaches along Cape Cod , you will fall in love with these best places to visit .

Other Places to Visit in Winter : In addition to scoring the best deals on hotels, heading to cold locations boasts a bevy of other bonuses (we're looking at you, Christmas markets and ski resorts). Begin with a look at our list of the best winter vacations in the U.S for ideas. In Canada, check out these fun things to do in Vancouver in Winter . Or, for a little more adventure, head to one of these top winter holiday destinations around the world that are packed with snow!

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A local’s guide to surviving (and thriving) in a Boston winter

Feb 14, 2024 • 7 min read

Boston in winter? Totally worth it. Venture out into the icy air or retreat inside to cozy cafes and fireside tables, with food and drink to warm you from the inside out © Kimberly Maroon/Lonely Planet

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Bostonians don’t let the weather stop us, even in the coldest months. This is New England, after all, so we know how to make the most of winter. Join us as we venture out into the icy air or retreat inside to cozy cafes and fireside tables, with food and drink to warm you from the inside out.  

Embrace your inner winter warrior

Sometimes the best way to survive winter is to embrace it – don your warmest coats, hats and gloves, go outside, and play! Boston offers plenty of opportunities to do so, even right downtown at the Boston Common , where there’s sledding on Flagstaff Hill and ice skating on the Frog Pond. But locals know the hills in the outer neighborhoods are even more exciting, such as at the Sugar Bowl in Jamaica Plain, Walsh playground in Dorchester, and Fallon Field in Roslindale. Escape the crowds on the Frog Pond by heading to The Rink at 401 Park, in Fenway, or Skate @ Canal District, in Kendall Square in Cambridge.

You don’t have to venture too far out of the city for more adventurous snowy ski action. West of Boston, Weston Ski Center in Weston and Great Brook Farm in Carlisle both offer picturesque countryside, groomed trails, and equipment rental for cross-country skiing. For downhill, the Blue Hills Ski Area is just 15 miles south, in Canton.

If you prefer your winter sports at slower speeds, head to Harbor Way in the Seaport District to try your hand at curling. Don’t worry, it’s a lot more fun to do it than to watch it on TV! For less action and more relaxation, do winter the Nordic way with a visit to Moki Sauna Village on the Rose Kennedy Greenway. This outdoor wellness center offers wood-fired saunas and refreshing plunge pools for the ultimate winter warmup.

No matter what your winter recreation, you’re fortunately never far from a rich and rewarding cup of hot chocolate. Bostonians go cuckoo for cocoa, especially for the French hot chocolate at the Thinking Cup (in the Back Bay, the North End and Downtown) and for the dark hot chocolate at LA Burdick (in Harvard Square and in the Back Bay). For extra oomph, cozy up inside Caffé Vittoria in the North End for hot chocolate spiked with Kahlúa and brandy.

Escape the winter chill

If all these outdoor activities are making you shiver, never fear. Boston offers an endless array of indoor attractions for those who prefer to escape rather than embrace the cold. Candlepin Bowling is a classic New England pastime – a regional variation on ten-pin that uses cylindrical pins and smaller balls. Try it at Sacco’s Bowl Haven in Somerville, and follow up with fabulous pizza and craft beers from Flatbread Pizza. Missing your favorite summertime activities? Visit PuttShack in the Seaport District to play a round of mini-golf, or PKL in South Boston to battle it out on the pickleball courts. Both have full-service bars serving craft cocktails and draft beers – and you don’t have to go outside to earn them.

All that activity aside, when the temperatures drop, sometimes you just want to snuggle up with a good book. If that’s the case for you, go directly to Beacon Hill Books & Café. Every exquisitely decorated room of this neighborhood bookstore offers a thoughtful selection of titles to peruse – and plenty of nooks and crannies in which to hunker down and enjoy them. The café’s afternoon tea service will warm up your Sunday.

If you’re still longing for the tropics, Boston has a solution for that, too. The New England Aquarium transports you straight to the Amazon rainforest, the Indo-Pacific coral reef, and other warm-weather destinations. Best of all, the centerpiece Giant Ocean Tank showcases the creatures of the Caribbean Sea. (Pay no attention to those penguins you pass on the way there.)

Arts & culture

Boston is a fabulous destination for the arts year-round – but locals know winter is prime time, as the cultural calendar is packed. In 2024, Boston is hosting an exhibit of `Winteractive’ public art (through April), with 16 playful and poignant installations scattered around the streets of Downtown. Download a map – or just wander and discover.

If you prefer your art indoors, any of Boston’s world-class art museums is an inviting destination on a chilly day. The Isabella Stewart Gardner Museum is a particular favorite for locals, who relish the blooms and greenery in the interior courtyard of this Venetian-style palazzo in Fenway. During the winter months, the garden features glorious tropical plants, including many exotic varieties of orchids.

The performing arts calendar is in full swing all winter, with live jazz and blues heating things up at Wally’s Café and at the Beehive, both in the South End. The Boston Symphony Orchestra and the Boston Ballet both prepare special seasonal programs – this year, the BSO will present Music of the Midnight Sun, a celebration of Nordic composers and artists, and the Boston Ballet’s Winter Experience features three sensuous and soulful ballets by Mikko Nissinen and Helen Pickett.

Eat, drink, and be merry

Nothing warms the body and soothes the soul like a hearty meal. A highlight of any trip to Boston is its seafood – in winter, keep it simple with a hot bowl of creamy clam chowder, especially from Sail Loft in the North End or Row 34 in the Seaport.

Another culinary treat is Boston’s globe-spanning international fare. Every weekend from January to March, the Boston Food & Wine Festival plays host to dinners, classes, and exquisite food and wine pairings from around the world. But you don’t need a festival to tuck into a plate of pasta from Arya Trattoria or Carmelina’s in the North End, or to feast on dim sum at Hei La Moon or Empire Garden in Chinatown. Comfort Kitchen in Dorchester is a beloved local option, serving not-so-local fare from the African diaspora all over the world.

Winter is the perfect time to get cozy with your dinner date next to a roaring fire. Book a table downstairs at the South End Buttery or upstairs at Tresca in the North End. Or for Boston’s most romantic and sumptuous setting, request the firelit library at Yvonne’s. For more casual fireside drinks, sample the mead at medieval-themed Grendel’s Den in Harvard Square; or brush up on your history in Charlestown, where folks have been patronizing the Warren Tavern since 1780.

If you appreciate fresh air (really fresh), several venues keep their outside game going all winter. In South Boston, the Lodge at Publico converts the atrium into a seasonal `ski lodge,’ offering all the amenities of après-ski (if not the slopes). Think flannel blankets, fire pits, and artificial snow, as well as special seasonal cocktails. Fire tables keep patrons warm in the year-round beer garden at Charlie’s Kitchen in Harvard Square and in the courtyard at Bow Market in Somerville. And in the Seaport, the Lookout Rooftop Bar features heated igloos for your outdoor drinking pleasure. Wrapped in clear, weather-proof plastic, it’s a perfect (warm) place to sip a cocktail and admire the views of the sparkling city skyline on a crisp winter night.

Still planning when to book your winter visit? Consider coming for an only-in-Boston holiday. For the first time, the Lunar New Year is an official city holiday, observed on February 10; but the Chinese community will welcome the Year of the Dragon with its festive parade and `cultural village’ in Chinatown on February 18. The following month, March 17 is Evacuation Day, an official holiday commemorating the departure of British troops from the city of Boston in 1776. Of course, this date is better known as St Patrick’s Day – marked by the historic (and now inclusive!) dual-purpose parade in South Boston.

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10 Things to Do in Boston in the Winter

Is Boston worth visiting in the winter? While chilly Boston might not inspire the same kind of excitement as warmer destinations, don’t be quick to dismiss Boston from your list of winter vacation contenders. With its illuminated trees set against a backdrop of historic brownstones and cobble-lined sidewalks dusted with snow, Boston from November to February undergoes a winter wonderland transformation that most US cities only dream of recreating . 

Seeing snow for the very first time is enough of a draw alone for some bucket-list travelers. But if you find the frigid temperatures challenging, not to worry: we’ve included a packing list at the end of this article with everything you need to keep yourself warm and comfortable while you’re out exploring. And when you’re ready for a rest, you’re sure to find a cozy spot right in front of the fireplace at HI Boston hostel . 

Still wondering if Boston is worth visiting in the winter? Here are 10 great things to do that will make you love Boston in the winter!

1. Go ice skating on Boston Common’s Frog Pond

Lace up those skates and join the merrymaking with locals and visitors of all ages at Frog Pond. Whether you’re a first-time skater or a seasoned veteran on the ice, gliding around one of the best outdoor rinks in the USA, in the country’s oldest public park, never loses its charm. The rink is open daily from December to March with ice skates and lockers available for rent. Order some hot cocoa to warm you up between laps.

2. Chill out in an illuminated igloo at The Lookout Bar

Thanks to the growing popularity of “pop-up” experiences around the country, Boston’s winter nightlife offerings have never been hotter. Starting in early November, the Lookout Rooftop Lounge on top of The Envoy Hotel in Boston’s Seaport District is outfitted with its famous “Ice Boxes.” These LED-lit plexiglass igloos can hold up to six people and come with their own thermostats and complimentary blankets. Sip on their winter-inspired seasonal cocktails while soaking in a sweeping view of a glittering skyline and Boston Harbor.

3. Tour around the Taza Chocolate Factory

Chocolate enthusiasts will delight in a multisensory tour of Boston’s very own chocolate factory. Taza Chocolate is a social enterprise producing stone-ground Mexican chocolate, a grittier dark chocolate quite unlike the processed sweets found in most grocery stores. This hour-long tour gives you an inside look at the company’s chocolate-making wizardry, highlighting everything from their ethically sourced cacao beans to their iconic disk-shaped bars. And did we mention they don’t skimp on their free samples? Get ready for some toothsome fun that won’t break the bank.

4. Hitch a ride on Boston’s Old Trolley Tour 

Keep the cold at bay while taking in the city’s historic gems on the hop-on, hop-off Old Trolley Tour. The vintage trolley car operates year ‘round, rain or shine, and is fully heated. The full tour showcases 18 of Boston’s top attractions with engaging commentary from the trolley conductors, which is especially helpful if you’re visiting Boston for the first time and want to cover the most ground without having to walk or take the subway. And if you want to get off and take time savoring a particular stop, each ticket allows unlimited re-boarding.

5. Sample a taste of Boston’s best brews

The Boston brewery circuit is synonymous with good times. $5 at Harpoon Brewery and Beer Hall in the Seaport District nabs you unlimited samples of Mass. Bay Brewing Company’s range of libations. At the beer hall, don’t forget to order their pillowy, fresh pretzels, made with the brewery’s leftover beer grains. For those who like things a little more mainstream, visit the Sam Adams Brewery in Jamaica Plain. Named after one of America’s Founding Fathers, it offers visitors a free tour of its factory operations. Just make sure to reserve ahead of time as the free tour is in high demand.

6. Become a whisky connoisseur at Boston Harbor Distillery

Beyond the standard brewery tour awaits a more refined sampling experience at the Boston Harbor Distillery in Dorchester. Situated in a historic warehouse on the waterfront, women-owned Boston Harbor Distillery stocks barrels of whiskey varieties and has even created a whiskey made from aged Sam Adams beer.

7. Root for your favorite team at a TD Garden game

In this world-class sports city, nothing is more Bostonian than catching a Boston sports game. The winter sports calendar is the prime time to score reasonably priced tickets to see the Boston Bruins hockey team and/or the Boston Celtics basketball team in action. The two teams play at TD Garden on an almost daily basis in the winter and every game is fully indoors. Plus, nothing gets the heart pumping as much as being surrounded by a crowd of Boston sports fans, who are in a league of their own thanks to their brazen attitudes and colorful language. 

8. Sip on innovative cups of hot chocolate

Nothing will thaw you faster than a piping hot cup of hot chocolate. Lucky for you, Boston has no shortage of great cafes featuring not-so-average mugs of hot cocoa. Try the famous Drinking Chocolate at L.A. Burdick’s Chocolate Café ordered either dark, milk, white, or spicy. Gâté Comme des Filles counter-only service in Bow Market carefully concocts Parisian-style hot chocolate served with a thick dollop of whipped cream. Get your dark hot cocoa fix at Curio Coffee, utilizing local Taza chocolate that pairs like a dream with their liege-style waffles. And if you like hot cocoa on the bolder side, visit Flour Bakery for their fiery hot chocolate spiked with chile and cayenne pepper for that extra heat.

9. Support small businesses at an indoor market

Of the many things to do in Boston during the winter, nothing provides more respite from the cold than visiting its indoor marketplaces. The most popular with tourists is Faneuil Hall and Quincy Market , but a stone’s throw away is the lesser known Boston Public Market . Located right next to the Haymarket subway stop, this food hall is home to 30 New England culinary small businesses, each offering artisanal goods and a gourmet spread of the region’s best ingredients. In Union Square, the recently opened Bow Market is a haven for independent creative retailers with a vibrant community feel. You can get everything from adorable stationery to Korean bibimbap bowls. If you’re more into eccentric purchases, the five-story Cambridge Antique Market never fails to impress with its vast array of vintage finds.

10. Experience holiday fun Boston-style

Around the holidays, there are some delightful seasonal experiences that add to Boston’s magical winter quality. Year after year, the Boston Ballet enchants with its annual performance of the holiday classic, The Nutcracker .

If you’re a fan of DIY holiday light installations, enjoy the Illuminations Tour around Somerville to support local businesses while admiring the electric frivolity of facades decked with lights, ornaments, and tinsel. Situated northwest of Boston’s Downtown, Somerville is another city part of the Greater Boston area and can easily be reached by subway (or “T”) on the red line. The Illuminations Tour has been traditionally run as a trolley tour but was converted into a walking tour in 2020 in response to the pandemic. A digital map is available online for you to follow.

Now in its sixth year, the 2021 SoWa Winter Festival brings the revelry of Europe’s Christmas market traditions to Boston. From December 3 to 13, scour the 100 vendors on display for the perfect souvenir, holiday gift, or tasty treat.

What To Pack for Your Visit to Boston in the Winter

When in doubt, layer up. Invest in heattech undershirts to hide beneath chunky knit sweaters. Bring a puffer jacket that’s water- and windproof to keep you extra toasty. 

Winter accessories are essential to fighting wind chill: don’t forget gloves, a scarf, and a warm beanie or earmuffs to keep those ears warm. Last but not least, sturdy, waterproof shoes or boots with good grips are the best when combating sidewalks covered in snow, puddles of slush, or even black ice. And make sure your feet are extra insulated with warm socks. If I know I’m going to be walking around for a long time, I’ll wear long john trousers underneath my jeans too. One can never be too prepared for extreme weather in Boston, especially during winter.

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Master guide to winter fun in and around boston, the most fun you can have in the boston winter  here are some links and ideas to winter fun for kids, teens, & families in the boston area: , local winter fun.

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The 13 Best Day Trips from Boston

Boston is a historic city with plenty of things to do and places to see, but there’s also lots more to explore outside the city limits. Whether you’re heading north to the mountains to ski or taking the ferry to Cape Cod’s Provincetown , there are day trips to take in every direction. Read on for our recommendations, all within driving distance and some you can even access by public transportation.

Portsmouth, New Hampshire

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Portsmouth is a historic coastal New Hampshire city that may be small in size but is full of character and popular restaurants. Have drinks along the docks on Bow Street as the sun sets at Pocos , Martingale Wharf or the Old Ferry Landing . For a seafood dinner with a view, try Surf , also on Bow Street. And for a casual yet tasty breakfast, you can’t go wrong with Colby’s .

Those visiting Portsmouth will enjoy walking around Prescott Park and learning about the history of Portsmouth at the Strawbery Banke Museum . Make sure you reserve some time for walking around the downtown area and popping into shops along the way. This city is growing year-by-year, with hotels and condos being built up as it grows in popularity.

Getting There: Portsmouth is about an hour and a half from Boston and the best way to get there is by car. If you don’t have a car, you can also take the C&J Bus Line.

Travel Tip: Pack a beach chair and drive down Route 1A to take in the Seacoast’s beaches. One of the first destinations you’ll come across in Rye is Ordiorne State Park , where you can walk around along the ocean. Eventually, you’ll get to Hampton Beach before you cross back over into Massachusetts.

Boston Area Beaches

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On a hot summer day, or even when the sun is shining in the spring or fall, there are plenty of beaches in the Boston area to spend a day relaxing at.

On your way back from Portsmouth, drive south along the ocean until you reach the beaches in Rye, or continue on to the popular Hampton Beach strip, where there’s a big beach and plenty of restaurants. Just over the Massachusetts border is Salisbury Beach, another day trip spot just over an hour north of Boston. Other beautiful beaches on Boston’s North Shore include Wingaersheek and Good Harbor Beaches in Gloucester , Plum Island Beach in Newburyport, Crane Beach in Ipswich, Singing Beach in Manchester-by-the-Sea and Revere Beach in Revere.

The South Shore’s beaches are equally as beautiful, with one of the closest options being Wollaston Beach in Quincy, and then many others including Duxbury Beach in Duxbury and Nantasket Beach in Hull. Of course, you can continue south to Cape Cod for plenty more beaches to choose from.

Getting There: Most of these beaches are only accessible by car and the furthest options listed are a maximum of 1.5 hours away, depending on traffic and where you are coming from. If you prefer public transportation , you can get to Singing Beach in Manchester-by-the-Sea and Revere Beach in Revere by the Commuter Rail and MBTA Blue Line, respectively.

Travel Tip: If you want to hit the beach but aren’t the type to stay from sunrise to sunset, try one of the beaches on New Hampshire’s Seacoast and then plan to stop explore Portsmouth before or after. The same applies to Plum Island and Newburyport. 

Newburyport, Massachusetts

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Newburyport is another coastal town, which feels similar to downtown Portsmouth, New Hampshire in many ways. It was settled back in 1635 but has of course modernized over the years. Newburyport is most popular during the summer months given its location and nearby beaches, including Plum Island . But Newburyport is an ideal day trip from Boston at any time of year, as there are quite a few shops to stop by, restaurants to eat at and scenery to take in.

Getting There: Most people drive to Newburyport from Boston, as it’s under an hour and right off exit 56 on I-95 North. You can also take the Newburyport/Rockland Commuter Rail line from North Station.

Travel Tip: While you’re in Newburyport, drive over to Plum Island to spend some time at the beach, no matter what time of year. 

Provincetown, Massachusetts

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Located at the very tip of Cape Cod is Provincetown (also known as “P-Town”), best known as a gay resort community, but also a beautiful place to visit for a day, weekend or more. While driving to the end of the Cape may not seem like a day trip, it’s easy to get there via a 90-minute ferry through Bay State Cruise Company.

Provincetown is surrounded by water on three sides with several beaches to enjoy. Both during the day and in the evening, check out the downtown area’s restaurants, art galleries, boutiques and more.

If you're not able to make it to Provincetown, there are plenty of Cape Cod towns within a shorter driving range.

Getting There: Take the 90-minute Bay State Cruise Company ferry from Boston, which is the fastest way to get there. The ferry operates daily from mid-May to mid-October, with trips leaving Boston three times a day. If you prefer to drive through the Cape, it will take you over two hours, but typically longer, as the roads are oftentimes single-lane and traffic can be bad.

Travel Tip: You’ll find fresh lobster rolls all over Provincetown, but be sure to stop by The Canteen , which serves both hot and cold options.

Martha’s Vineyard and Nantucket, Massachusetts

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Martha’s Vineyard and Nantucket are two islands off the coast of Massachusetts, both of which are popular tourist destinations, especially during the summer months. Both are doable for day trips, especially Martha’s Vineyard, as it’s a bit shorter of a ferry ride. Both islands are quiet during the winter months, so plan your visit from Spring through Fall.

Vineyard Haven in Martha’s Vineyard, where the ferry drops you off, is full of shops and restaurants. You can also head to nearby Oak Bluffs, where you’ll find the 318 colorful Gingerbread Cottages at Wesleyan Grove off of Circuit Street. If you bring your bike or car along, you can explore the island’s beaches and other downtown areas as well.

Nantucket has different coastal vibe than Martha’s Vineyard and is also smaller in size. Here you’ll find cobblestone streets downtown and picture-worthy homes covered in hydrangeas all over the island. Of course, there are beautiful beaches around the island, along with food, galleries and boutiques. Stop by Cisco Brewers for a taste of local beer, which has become more and more popular throughout New England. And have a drink made with Nantucket’s Triple Eight Blueberry Vodka at one of the bars downtown.

Getting There: Martha’s Vineyard is a 45-minute ferry ride via the Steamship Authority from Woods Hole, which takes you to Vineyard Haven. The fast ferry to Nantucket is through Hy-Line Cruises , takes an hour and leaves from Hyannis. There are slower ferry options available, but these are the most efficient for a day trip. Keep in mind that Hyannis and Woods Hole are both on Cape Cod, so you’ll need to leave time for traffic if you’re traveling during peak hours. Both islands can also be accessed by plane from Boston’s Logan International Airport .

Travel Tip: You can choose to bring a car onto the ferry, but it’s recommended that you make plans for that in advance. That, coupled with the cost, is the reason many people choose to take a bike or get around Martha’s Vineyard through the Vineyard Transit Authority.

Providence, Rhode Island

About an hour drive south from Boston is the city of Providence, Rhode Island, also known as the “Creative Capital.” This city has become a popular tourist spot over the years, with popular attractions including WaterFire , a series of over 80 bonfires along downtown Providence’s three rivers, or the annual Halloween Jack-O-Lantern Spectacular or the Faces of the Rainforest exhibit at the Roger Williams Park Zoo . From November through March, head to the Providence Rink for Ice Bumper Cars .

Providence also has a foodie scene, with chefs coming from Rhode Island’s Johnson & Wales opening restaurants within the city, such as Oberlin , a seafood-focused small plates and tapas concept. If you’re looking for Italian, head to Federal Hill , the Little Italy of Providence. The Dorrance is another reputable spot, located within a former bank and serving globally-inspired New England cuisine. And while you’re in town, stop by PVDonuts for delicious and unique brioche donuts in fun flavors like fruit pebbles, butterscotch crunch and brown butter brownie.

Popular Providence hotels include The Dean , built around the city’s history and culture, and the Providence Biltmore , a historic property designed by the architects of New York’s Grand Central Terminal, and the Hotel Providence , another centrally located option that’s great for all types of travelers.

Getting There: Providence is an hour drive from Boston. You can also get there by train , including the Amtrak and MBTA Commuter Rail on the Providence-Stoughton line, both leaving from Boston’s South Station.

Travel Tip: For the best pizza in town, try no-frills Caserta Pizza , also known for their “Wimpy Skimpy,” a spinach pie stuffed with black olives, cheese & pepperoni.

Newport, Rhode Island

 Forty 1° North

Newport, Rhode Island is another coastal town within driving distance from Boston. Here you’ll find the makings of a perfect day trip, from the Gilded Age mansions and beaches, to walking along the famous Cliff Walk. Visitors also enjoy exploring the Brick Market Place , a downtown are with more than 25 shops and eateries. If anyone you’re traveling with is into cars, check out the Newport Car Museum , located in nearby Portsmouth.

Favorite Newport restaurants include The White Horse Tavern, America’s oldest tavern, Winner Winner , Scarpetta Newport , The Black Pearl and Mission Burger . If you plan on staying overnight, top-rated hotels and resorts include The Vanderbilt, Forty 1° North , Gurney’s Newport Resort & Marina and The Chanler at Cliff Walk . Many of these hotels

Getting There: Newport is an hour and a half drive from Boston and car is the easiest way to get there.

Travel Tip: Even if you’re not staying overnight, many of the top hotels are also great spots to grab drinks with a view if you’re in town for just the day. Head over to Forty 1° North and order your favorite cocktail as you look out on the water.

Nashoba Valley Winery & Other Vineyards

 Nashoba Valley Winery

New England may not have a full-blown wine country, but there are several family-owned vineyards that make for great day trips, with at least one option nearby no matter where you are staying. From Boston, your best bet is the Nashoba Valley Winery , where you can sample the vineyard’s wines and also pick your own peaches, nectarines and apples when they are in season and enjoy farm-to-table food at J’s Restaurant.

Another Massachusetts option is Furnace Brook Winery in the Berkshires, about 2.5 hours away from Boston. An hour north of the city, there’s South Hampton, New Hampshire’s Jewell Towne Vineyards. In Rhode Island, try Verde Vineyards or Carolyn’s Sakonnet Vineyard . As you head into Connecticut, follow the Connecticut Wine Trail and try the Lost Acres Vineyard in North Granby, Arrigoni Winery in Portland and Sharpe Hill Vineyard in Pomfret.

Getting There: The Nashoba Valley Winery is around an hour drive from Boston in Bolton, Massachusetts.

Travel Tip: If you plan on visiting several vineyards and wineries in one day, make sure you have a designated driver or look for transportation services, such as limos or tours to take you from one spot to another.

Mountains of Massachusetts and New Hampshire

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Speaking of Nashoba Valley, this destination is not only home to one of the best vineyards near Boston, but Nashoba Valley Ski Area is also a great winter destination for skiing and tubing if you’re into these activities but not long drives. Other places to ski in Massachusetts include Wachusett Mountain in Princeton, Blue Hills Ski Area in Canton and Ski Bradford in Haverhill.

As you head into New Hampshire , popular ski resorts and mountains include Waterville Valley Resort , Loon Mountain , Gunstock , Cannon and more. Another option, Bretton Woods , is not only a ski resort, but also home to the beautiful Omni Mount Washington Resort , which has plenty to do for both skiers and those who prefer après skiing activities. 

Getting There: Nashoba Valley Ski Area is less than an hour from Boston by car, and other Massachusetts ski destinations range between 40 minutes to a little over an hour. Most of the drivable New Hampshire mountains are just over two hours away from Boston.

Travel Tip: To make your ski trip even easier, try Liftopia Experiences , a service that will take you on trips from Boston such as skiing at Crotched Mountain or snow tubing at Ski Ward and to a local brewery. Outdoor retailer REI also offers classes and activities, such as a store to slopes shuttle  that takes you to Stratton Mountain.

Lincoln, New Hampshire

New Hampshire’s White Mountains is where you’ll find the town of Lincoln, where Loon Mountain is located. But that’s not all Lincoln has to offer. During the winter months, the Ice Castles are a picturesque destination to visit. You can also go ice skating at The Rink at RiverWalk Resort , which was transformed from a 167,000 gallon swimming pool that’s available for guests in the summer. While you’re at the RiverWalk Resort, take a sleigh ride, go snowmobiling or taste wine at the Seven Birches Winery , which is right on the property.

Getting There: Lincoln is about two hours from Boston without traffic and your best bet for getting there is by car.

Travel Tip: Beware of traveling north from Boston during the winter months on Friday afternoons and evenings, as it’s likely you’ll run into traffic leaving the city as locals get out of work and head to the mountains. 

Plymouth, Massachusetts

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One of the best spas in the Boston area is located south of the city in Plymouth at the Mirbeau Inn & Spa . There’s more than just great massages and facials here – there’s a heated foot pool surrounded by lounge chairs to relax in, as well as an outdoor jacuzzi to enjoy while you sip champagne from the bar.

While you’re in Plymouth, take a walk along the water and check out the iconic Plymouth Rock and Pilgrim Hall Museum , America’s oldest, continuously operated, public museum filled with artifacts that came to our country with the Pilgrims. Then head 3 miles down the road to the Plimouth Plantation museum.

Nearby in Carver, the kids will enjoy the Edaville Family Theme Park , which is particularly fun around the holidays with their Christmas Festival of Lights. 

With Plymouth being on the water, there’s plenty of fresh seafood and outdoor dining, with restaurant favorites including Woods Seafood , Rye Tavern , East Bay Grille and Cabby Shack .

Getting There: The easiest way to get to Plymouth is via car, which will take about an hour. There is also a Commuter Rail stop in Plymouth if you prefer public transportation.

Travel Tip: While the Plymouth Rock is certainly a Massachusetts landmark, don’t be surprised when it’s nothing substantial when you see the remains in person. There is still plenty to see and do in Plymouth though!

Portland, Maine

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Portland, Maine may sound far away from Boston, but at two and a half hours away, it’s still doable for a day or weekend trip. This coastal downtown area has developed quite the foodie scene and it’s also a great spot to take in New England’s fall foliage season . Top restaurants include Fore Street , Central Provisions , Duckfat , Eventide Oyster Co. and Holy Donut . If you’re into beer, go for a tasting at Shipyard Brewing Company .

You can spend an entire weekend walking around downtown Portland and popping into shops, restaurants and bars. But another fun activity when the weather is nice to take the short ferry over to Peaks Island , where you can rent bikes or golf carts to cruise around the island and take in the coastal views.

Getting There: Portland is about two and a half hours away from Boston by car. Another option is to take Amtrak’s Downeaster from North Station in Boston to Portland, which takes about the same amount of time.

Travel Tip: Fore Street won a 2018 TripSavvy Editors’ Choice Award as one of the Best Iconic Restaurants & Fine Dining . This restaurant books up far in advance, but they reserve spots for walk-ins. The trick is to put your name in right when they open at 5:30 p.m.

Wrentham, Massachusetts

Wrentham Village Premium Outlets

Just south of the city are the  Wrentham Village Premium Outlets , a shopping plaza where both locals and tourists go to get lots of shopping done at once, especially around the holidays. As New England’s largest outdoor shopping center, you’ll find everything from Off Saks and Tory Burch, to Vineyard Vines and the Nike Factory Store.

Getting There: The Wrentham Village Premium Outlets are located just 35 miles south of Boston, right off exit 15 on I-495. The best way to get there is by car.

Travel Tip: Bring your AAA card if you have one. When you get there, show it at the visitor center to get a coupon book that will give you even more discounts than you get at the outlets. 

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35+ Amazing Day Trips From Boston Massachusetts

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

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

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

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

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

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

Best Day Trips From Boston

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

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

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

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

1. Bristol Rhode Island (1:10 Drive)

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

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

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

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

2. Cambridge Massachusetts (5 minute drive)

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

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

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

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

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

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

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

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

3. Cape Elizabeth Maine (2 Hour Drive)

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

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

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

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

3. Charlestown Massachusetts (5 minute drive)

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

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

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

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

4. Chatham Massachusetts

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

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

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

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

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

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

5. Concord Massachusetts (35 Minute Drive)

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

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

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

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

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

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

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

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

6. Concord New Hampshire (1:10 Drive)

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

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

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

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

7. Essex Connecticut (2 Hour Drive)

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

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

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

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

8. Exeter New Hampshire (1 Hour Drive)

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

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

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

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

9. Hanover New Hampshire (2 Hour Drive)

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

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

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

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

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

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

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

10. Hartford Connecticut (1:35 Drive)

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

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

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

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

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

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

11. Keene New Hampshire

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

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

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

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

12. Kennebunkport Maine (1.5 Hour Drive)

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

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

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

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

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

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

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

13. Kittery Maine (1 Hour Drive)

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

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

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

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

14. Lenox Massachusetts (2 Hour Drive)

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

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

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

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

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

15. Lexington (30 Minute Drive)

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

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

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

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

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

16. Madison Connecticut (2 Hour Drive)

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

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

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

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

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

17. Manchester New Hampshire (1 Hour Drive)

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

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

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

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

18. Mystic Connecticut (2 Hour Drive)

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

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

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

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

19. Newburyport Massachusetts (1 Hour Drive)

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

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

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

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

20. Newport Rhode Island (1.5 Hour Drive)

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

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

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

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

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

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

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

21. Old Sturbridge Village Massachusetts (1 Hour Drive)

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

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

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

22. Ogunquit Maine (1:30 Hour Drive)

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

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

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

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

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

23. Northampton (2 Hour Drive)

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

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

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

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

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

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

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

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

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

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

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

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

25. Plymouth (45 minutes)

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

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

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

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

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

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

26. Portland Maine (1:45 Hour Drive)

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

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

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

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

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

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

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

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

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

27. Portsmouth New Hampshire (1 Hour + Drive)

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

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

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

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

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

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

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

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

28. Providence Rhode Island (1 Hour Drive)

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

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

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

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

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

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

READ: 1 Day Itinerary For Providence

29. Provincetown Massachusetts (2 Hour Drive Or Ferry)

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

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

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

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

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

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

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

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

30. Rockport Massachusetts (55 Minute Drive)

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

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

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

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

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

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

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

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

32. Salem Massachusetts (45 Minute Drive)

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

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

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

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

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

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

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

Click here to buy ferry tickets to Salem.

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

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

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

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

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

34. Stockbridge Massachusetts (2 Hour Drive)

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

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

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

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

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

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

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

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

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

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

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

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

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

There a few pullouts for trailheads, providing great photo and hiking opportunities. Continue east until you hit the Rocky Gorge Parking Lot. Here, you can take a walk along the Swift River and get views of the beautiful Falls Pond.

 In Crawford Notch State Park , you can explore the backroads and revel in the beautiful fall colors. If you’d like to do some hiking, there are 35 hiking trails of varying difficulty.

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

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

36. Worcester (1 Hour Drive)

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

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

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

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

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

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

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

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

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

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

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

I would love a lobster roll right now!

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Last Updated on July 4, 2023 by Leslie Livingston

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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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Adventures in New England

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

19 Fabulous Day Trips from Boston

If you are planning a road trip from southern New England, Boston can be a perfect base as it is centrally located. You can get a hotel and then take many great day trips from Boston to experience the best that this area has to offer.

You will want to start by taking a few days to experience New England’s largest city’s feel. You can read my guide for One Day in Boston with Kids (still a good overview even for adults). Also, be sure to check out my list of hikes right around Boston .

Table of Contents

Short Day Trips from Boston

These day trips from Boston are around an hour’s drive from Boston.

Salem, Massachusetts

Witch City, USA, also has a fantastic art museum and Hawthorne’s House of the Seven Gables. Read on for how to spend a day in Salem. 

Fall River and New Bedford, Massachusetts

This center of fishing life in colonial New England is now predominately Portuguese. You can visit the New Bedford Whaling Museum, the church that was part of Herman Melville’s Moby-Dick inspiration, and the Lizzie Bordon House.  Read more about the area in Haunted New England.

Rockport, Massachusetts

Spend a day exploring this picture-perfect fishing village on the coast north of Boston.

Cape Cod, Massachusetts

There is a lot to explore on this peninsula south of Boston, but you can explore the upper Cape in one day from Boston. Most of my exploration of the Cape has been by bicycle.

Portland, Maine

This foodie town also has lighthouses and parks to explore. Check out 47 Cool Things to Do in Portland, Maine.

Providence, Rhode Island

The capital of Rhode Island has canals to stroll along, great restaurants, and art museums. Read on for The Best Things to Do in Providence.

Newport, Rhode Island

This colonial town on Aquidneck Island has excellent beaches, hiking, dining, and a lot of history. Explore A Local’s Guide to Newport.

Sutton, Massachusetts

Hike this trail along the base of the 75-foot rock Purgatory Chasm and get ice cream at the farm next door. Read more about a day at Purgatory Chasm.

Concord, Massachusetts

Concord was not only an important location in the American Revolution but also in American Literature. Walden Pond sits in Concord, as well as Louisa May Walcott’s home. Read my itinerary for one day in Concord, Massachusetts.

Plymouth, Massachusetts

Visit the recreation of the Native American and pilgrim colony following the landing at Plymouth Rock.

New Bedford, Massachusetts

Explore the colonial whaling capital of the world, located on the southern coast of Massachusetts. This area also has a large Portuguese population, a fort, and was a stop on the Underground Railroad.

Read about how to spend a day in New Bedford. 

Whole Day Trips from Boston

It will take about 2 hours to get to these full-day trips from Boston.

Martha’s Vineyard

Sand dunes, farms, Kennedy history, and gingerbread cottages, this island off the coast of Massachusetts will introduce you to the best New England has to offer. Read on for Things to Do in Martha’s Vineyard .

Woodstock, Vermont

Woodstock is sometimes known as the quintessential New England town. It is nestled in Vermont’s Green Mountains and alive with the state’s art culture. Plan your day with Things to Do in Woodstock, Vermont.

Northampton, Massachusetts

This arty town in northwest Massachusetts is the home of Smith College. Read on for how to spend a day in Northampton.

The Berkshires, Massachusetts

One of the most transcendent concerts you can experience will take place at Tanglewood in the rural mountains of western Massachusett. The Berkshires give ample opportunities for hiking, leaf-peeping, and exploring small New England towns.

New Hampshire’s White Mountains

Take a foliage drive or go waterfall hunting through the White Mountains.

Mystic, Connecticut

Explore the seaport at this colonial town on the Mystic River. Investigate more things to do in Mystic.

Mount Major, New Hampshire

The views from the peak of this half-day hike are incredible. You will see New Hampshire’s lakes and highest peak, Mount Washington, in the distance. Learn more about climbing Mount Major.

Shelburne Falls, Massachusetts

This village nestled in the Berkshire Mountains has the Bridge of Flowers, a waterfall, glacial potholes and an art-filled downtown. Read about how to spend a full day in Shelburne Falls.

Which day trips around Boston have you taken? Which are the highest on your list? Please let me know if you have any questions in the comments.

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12 thoughts on “19 Fabulous Day Trips from Boston”

I love this list! Boston is such a cool city and I love the idea of spending more time there and venturing out so this list is so helpful!

So many great day trip options from this city! Nice when there is that option, for travellers, it means you can extend your holiday. Make Boston your home base and see some of those smaller towns you have listed. I would love to see more of the nature, in New Hampshire, like Mount Major or Massachusetts with Martha’s Vineyard.

Such great day trip plans even a month of stay there will not suffice to experience it all! The short day trips really sound good and doable. I have not been to Boston yet, but hopefully I will some day with this helpful post! Great pic to go with the post.

Wow! So many things to do. It would really be worthwhile to make Boston a base for a week and do these trips to immerse yourself in the region.

Visiting the east coast has always been something i’ve wanted to do. I’ve seen Boston & DC but that’s about it! Rhode Island, Connecticut, Vermont, Main, I want to see them all!

Funny enough I’ve heard most of these day trips destinations from Boston although I don’t know their locations to Boston. I would like to visit most of them, but I think Fall be the best time?

Some of the locations are close enough for a day trip but would plan an early start in the day because even though they are close enough for a day trip, traffic can play a big factor especially during rush hours… planning a trip to the South Shore or Cape Cod offers only 2 travel lanes for most of the trip once you are on Route 3 which starts in Braintree which is about 9 miles south of Boston and the from Braintree to the beginning of the cape it’s about 45 miles or so… I mention this trip because I am very familiar with this section of MA and I live in Plymouth which is about 10 miles from Cape Cod… The Fall or Spring would be best as far as traffic to the cape but many places close down from Oct to Apr because many businesses depend on tourists during the Summer.

You are right about Boston traffic being a bugger. It is always best to consult Google traffic before leaving, start early or consider public transport. I love travelling in shoulder season.

While there’s still so much to see and do on my actual Boston list, I *did* take a day trip from Boston during one of my visits. We followed your recommendation to visit Providence, RI, and had a lovely day!

I just love the northeast and you’ve given me even more places to explore up there! Perfect fall long weekends!!!

Cape Cod, Massachusetts would be my #1 choice. Haven’t been since I was little and have such fond memories!

I have been to Boston several times now and even took a trip up to Maine & Connecticut once but I have been quite lax on visiting the other areas. For me, I really want to see more of the New England Coastal areas like Providence and I know Darcee would love to see Martha’s Vineyard!

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What’s up with spring? Weather this time of year is chaotic — for a reason.

Spring in new england typically marches toward summer but often ‘looks back’ just for a little while.

Several times over the past couple of weeks I’ve gotten asked the question “When is spring arriving?”

The calendar says spring has begun but these drastic shifts in temps lately — from warmups to cold snaps and back — and a recent nor’easter that dumped cold, drenching rain in the Boston area and feet of snow up north , it’s hard to make sense of the weather as we head into mid-April.

I know what people mean when they ask that question, but the expectation of what spring is like here in New England is so often far loftier than it should be.

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We got quite lucky on Monday with crystal-clear skies across Maine and other parts of Northern New England and just a few high clouds farther south and west. This led to a phenomenal eclipse experience for many that was unforgettable. And Tuesday delivered another great day.

Temperatures on both days were above average by much more than a degree for the first time in the entire month and were probably what a spring expectation is all about, even if unrealistic.

In reality, March, April, and May are transitional months — between the cold of winter and the heat of summer. The atmosphere lies somewhere between the two and can waffle dramatically. There are days where it can be 70 degrees with sunshine followed quickly by wet snow and cold .

Spring in New England marches toward summer but often looks back just for a little while. If you’re waiting for the perfect spring pattern, you’re missing a lot of the good stuff. Our sunlight is now as strong as it would be in the final week of August and a good sunscreen is a necessity. Much of the daylight to be gained in any year has already occurred, with about an hour more to add on either side of the day.

The ground has not been frozen for a while, the birds are nesting and the activity of spring is approaching a crescendo. The deeper into April we go, the odds of colder weather occurring continue to diminish. However, damp chilly days can be part of the forecast right into May and even June.

Spring weather is chaotic as the atmosphere is trying to balance itself out before moving into hotter months.

You can thank the cold Atlantic for a lot of our weather this time of the year. Anytime a wind comes in off the water from the east, it’s going to drop temperatures back several degrees and can even lead to too chilly conditions. In the right situation, with all that Atlantic moisture, it doesn’t take much to get some fog and drizzle moving inland and bring comments of “Where is spring?” — but that is spring, too!

The upcoming pattern has a renewed chance of showers for Wednesday and Thursday, and although it won’t rain all the time, sunshine will be limited. Temperatures will be fairly mild during the cloudy weather, with both days mostly in the 50s.

On Friday, a stronger cold front approaches ahead of gusty southerly winds that will move milder air across, bringing northward showers and even downpours during the morning commute. The good news is that this frontal system exits into the Atlantic for the weekend, leaving us with partly to mostly sunny skies and seasonably mild air for mid-April.

Further ahead into next week, there’s a lack of cold air and it’s highly likely much of the area east of Route 128 and even perhaps Interstate 495 have seen their last hard freeze of the season.

At least this weekend will afford us the opportunity to plant some pansies and appreciate the greening of the landscape and the kinder side of spring.

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Heading to the Revs’ big match in Foxboro? Here’s how you can get there by train

New England Revolution Unveil Boston Tea Party Kit (David Silverman Photo/New England Revolution)

FOXBORO, Mass. — The MBTA Commuter Rail and Keolis will provide round-trip, special event train service from Boston and Providence for the New England Revolution’s Major League Soccer home match vs. Inter Miami CF on Saturday, April 27.

The interconference game is expected to be the highest-attended match in club history , surpassing the 2002 MLS Cup match against the LA Galaxy which saw 61,316 fans pack the stadium, according to Revolution team officials.

Fans can beat the traffic and get to the April 27 match by train for only $10 per round-trip ticket.

Round-trip tickets are available for purchase exclusively on the mTicket app. Tickets for each special event train are sold separately and need to be purchased for the correct corresponding station of origin (Boston or Providence).

No refunds or exchanges will be available. Tickets must be purchased prior to boarding the event train. All passengers, including children 11 and under, must have a ticket to board the train.

Train service from Boston will depart from South Station with stops at Back Bay and Dedham Corporate Center before arriving at Foxboro Station.

The Providence train service will make stops at Pawtucket/Central Falls, Attleboro, and Mansfield before arriving in Foxboro.

Special event train ticket sales will be stopped once the maximum capacity is reached. Regular Commuter Rail tickets and passes are not valid for special event trains.

The Special Event Train Service Schedule for Saturday, April 27 can be found below:

• Depart  South Station : 5:25 PM
• Depart  Back Bay : 5:30 PM
• Depart  Dedham Corporate Center : 5:50 PM
• Arrive at  Foxboro Station : 6:25 PM

PROVIDENCE:

• Depart  Providence Station : 5:20 PM
• Depart  Pawtucket/Central Falls : 5:26 PM
• Depart  Attleboro : 5:40 PM
• Depart  Mansfield : 5:50 PM
• Arrive at  Foxboro Station : 6:30 PM

Trains will depart Foxboro Station 30 minutes after the match ends.

While there is no weekend train service to Foxboro, regularly scheduled weekday MBTA Commuter Rail trains are available to bring fans to and from Boston for every Revolution weekday match during the season, in addition to the special event service for the Inter Miami match. The full Foxboro Station schedule can be found  here .

This season, New England has two remaining midweek matches on the home schedule: Wednesday, July 3 vs. Atlanta United, and Wednesday, Sept. 18 vs. CF Montreal.

The Revolution also play a midweek match on Tuesday, Aug. 6 vs. Nashville SC in the group stage of Leagues Cup 2024, a 47-team tournament featuring every club in MLS and the top-tier Mexican league, LIGA MX. Tickets for all New England Revolution matches are available at Ticketmaster.com ,  Revolutionsoccer.net/tickets , or by calling 1-877-GET-REVS.

Regular Commuter Rail tickets and passes are not valid for special event trains.

Riders are also reminded that any prohibited items that do not comply with the stadium’s Clear Bag Policy will not be permitted on the train and no personal items may be left on the train during the match. For more information, visit  www.mbta.com/destinations/gillette-stadium .

The April 27 contest could become only the third soccer match in Gillette Stadium’s 23-year history to surpass 64,000 fans in attendance, the last time coming in 2011 when the United States played Spain in an international friendly.

The current record for highest attendance at a Revolution regular season match is 57,407, set on April 20, 1997.

Since Gillette Stadium opened in 2002, the best attendance for a Revolution regular season match was 42,947 on Oct. 17, 2015.

This is a developing story. Check back for updates as more information becomes available.

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