Best Things to do in Boston in the Winter: Header

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.

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1. Go Ice Skating on Frog Pond

Boston during Winter: 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

Things to do in Boston during Winter: Beacon Hill

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.

3. Have a Board Game Night at Knight Moves

Places to Visit in Boston during Winter: 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 Around the Holiday Markets

Boston during Winter: 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

Things to do in Boston during Winter: Hockey

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. 

Places to Visit in Boston during Winter: Hockey

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

Things to do in Boston during Winter: 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.

Boston during Winter: A day at the Museums

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

8. Be Dazzled at the Somerville Illuminations Holiday Lights Tour

Places to Visit in Boston during Winter: 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

Boston during Winter: Nutcracker

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

Things to do in Boston during Winter: Orchestra

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

Boston during Winter: 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

Things to do in Boston during Winter: 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

Places to Visit in Boston during Winter: 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? Drop us a note and let us know!

About the Author

  • Jacqueline Gualtieri

    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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