29 Fun Things to Do in Boston in Winter, Indoors & Outdoors (2024)

As a Boston local, I know that winters here can get really cold and snowy. But that doesn’t mean it’s time to hibernate at home for the season! 

I actually love exploring Boston in the winter because that’s when there are fewer crowds and you can enjoy many sights more easily. And there’s nothing quite like seeing Boston covered in a fresh blanket of snow.

With the right preparation, you can still enjoy a variety of outdoor activities in Boston. And when the weather outside is frightful, there are many indoor things to do!

Follow along for a list of 29 fun things to do in Boston in the winter.

29 Fun Things to Do in Boston in Winter

I’ve broken down this list by indoor and outdoor activities, as well as special things you can find in Boston during each winter month. 

Indoor Things to Do in Boston in Winter

If the weather is too cold to handle or you just want to take a break from the chill, here are some awesome indoor things to do in Boston during the winter:

1. See the aftermath of a museum heist

One of the most popular museums in Boston is the Isabella Stewart Gardner Museum, which features the personal art collection of Isabella Stewart Gardner that she acquired over many years. 

The museum is a mystery in action, as 13 of Isabella’s paintings were stolen in 1990, more than 60 years after her death. To this day, the museum has been unable to recover the paintings and there is still a call for leads into the investigation on the museum website.

The museum itself is stunning, modeled after traditional Venetian architecture, but you can’t miss a visit to the rooms where the paintings were stolen. The empty frames are still hanging on the wall as a constant reminder of what is no longer there.

Entrance to the museum is $20 for adults (free for ages 17 and under), but if you visit between 3 and 9 p.m. on the first Thursday of the month, admission is free.

💡 FUN FACT: If your name is Isabella, you can also get into the museum for free for life!

2. Browse the stacks at Boston Public Library

Visiting the Boston Public Library is a great thing to do when the weather won’t cooperate. You could easily spend a couple hours or more browsing the vast collection of fiction and non-fiction books spanning multiple floors.

My favorite part of the Boston Public Library is the historic McKim Building, which dates back to 1895. If you enter the library from Dartmouth Street, you’ll be welcomed by the grand lobby and staircase.

Walk up the stairs to see the Abbey Room with its dimly-lit, muraled walls before heading over to the famous Bates Hall, the impressive reading room with a large vaulted ceiling.

The Johnson Building (the newer part of the library) is where you’ll find most of the books. If you’re traveling to Boston with kids, it’s worth checking out the Children’s Library on the second floor. It’s a beautiful space with fun decor and reading areas to attract the youngest readers.

4. Go to a Bruins or Celtics game

Boston is a city for sports lovers, with some of the country’s best sports teams based here. The winter season is the perfect time to see a Bruins ice hockey game or grab tickets to watch the Celtics play.

Even if you’re not a big sports fan (like me), going to a game in Boston is a really fun experience. The energy of everyone around you is contagious, and you might find yourself hollering and cheering by the end, too.

💡 FUN FACTS:
– The Boston Bruins were one of the original six teams in the National Hockey League, and they have won six Stanley Cups.
– The Boston Celtics’ mascot is Lucky the Leprechaun, and the team itself was named in honor of Boston’s rich Irish heritage. To this day, Boston has one of the largest Irish-American populations in the country.

5. Tour one of Boston’s iconic breweries

Boston is home to several highly-rated breweries that make for a cozy and fun atmosphere to enjoy a drink with friends. Some of the best breweries in Boston include Notch, Trillium, Hopothecary, Vitamin Sea, and Tree House.

The Samuel Adams Brewery Tour is another popular activity for beer enthusiasts, where you’ll get to learn about the Boston Lager brewing process and the history of this famed brand, which was founded in Boston in 1985.

💡 FUN FACT:
Jim Koch named his beer after his favorite Boston patriot, Samuel Adams. Adams himself had once attempted (and failed) to start his own brewing business before deciding to pursue politics instead. Thanks to Koch, his name is forever linked to beer anyway.

6. Catch a birds-eye view of Boston at the Prudential Center

The Prudential Center is home to Boston’s largest indoor mall and is the perfect place to browse and shop for several hours on a cold winter’s day. 

While inside the Prudential Center, check out View Boston, a 360-degree observation deck located near the top of the skyscraper that provides some of the best views of the city from way up high.

Another cool feature of View Boston is that you can tap your ticket under one of the viewfinders along the 360 perimeter to find details about the landmarks and attractions in that viewing area. 

Write down a list of the attractions that sound most interesting to you, and you can hand-pick your own Boston itinerary!

Outdoor Things to Do in Boston in Winter

Bundle up and enjoy these outdoor activities during winter in Boston:

11. Go on an Old Town Trolley Tour

The iconic Old Town Trolley Tours operate year-round, and I would argue that winter is one of the best times to take a tour because you’ll likely be in a less-crowded bus while enjoying the exact same experience you would get in the warmer months.

From December 1-30, you can book a special Holiday Sights & Festive Nights tour where you’ll learn about Christmas celebrations during Colonial times and stop by some of Boston’s most festive locations, including Boston Common and Charles Street.

You can also enjoy the traditional hop-on, hop-off trolley tour experience during the winter, which allows you to get off at any attractions you want and hop on the next trolley any time from 9 a.m. to 4 p.m.

12. Take a Winter Wildlife Cruise

Many people think boat cruises are best to do in the summer, but you can actually see quite a bit of wildlife during the winter months, too. 

Hop aboard a Winter Wildlife Cruise, where you can enjoy a three-hour tour around the Boston Harbor and Boston Harbor Islands, in the comfort of a heated, high-speed ferry.

Check out the City Experiences website for updated cruise dates and times.

14. Go ice skating at the Frog Pond

The famous Frog Pond turns into an ice rink in the winter, and this place attracts nearly as many guests who want to spin around on the ice as it does in the summer when it’s a giant splash pad.

The Frog Pond is a delight for all ages. Kids under 58 inches can skate for free ($10 admission for the taller folks), and skate rentals are $15 for adults and $10 for kids.

For kids learning how to skate, you can also rent “Bobby the Seal,” a skating aid to help them balance on the ice.

15. Sled down the hill at Boston Common

Once Boston gets a few inches of snow, the hill at the Boston Common turns into a sledding paradise. 

While you’ll find much larger and steeper hills outside of the city, there’s something special about being able to sled in the heart of the city. This is especially a good choice for younger kids to enjoy a gentler ride. 

Another perk of sledding in Boston Common is you can easily hop over to Tatte or Starbucks to warm up with a drink and treats.

16. Enjoy snow tubing at Nashoba Valley Ski Area

Not far outside of Boston is the largest snow tubing park in New England: Nashoba Valley Ski Area. Here you’ll be able to ride your own tube down one of 18 separate lanes for an awesome winter thrill.

Be sure to reserve your tubing slot in advance as tickets can sell out quickly. Reservations are for two hours of tubing.

17. Take a tour of Fenway Park

Even though you won’t be able to watch the Red Sox play in the winter, Fenway Park tours are available year-round, in rain, snow, or sunshine. 

Come see the Green Monster for yourself and learn about the history of “America’s most beloved ballpark,” which has been welcoming sports fans since 1912.

Guided tours last one hour and cost $25 for adults and $17 for children ages 2-12. 

If you don’t feel like taking the full one-hour tour, there’s also a “Fenway in Fifteen” tour where you can see the Nation’s Archives at the Royal Rooters Club, the Right Field Roof Deck, and a panoramic view of the ballpark and Boston skyline.

18. Spend a day on the slopes

New England is a haven for skiers in the winter, with dozens of ski resorts to choose from. If you don’t want to venture too far outside of Boston to spend a day on the slopes, you’re in luck. 

Blue Hills Ski Area, located in Canton, MA, is only a short drive from the city and is the perfect place for both beginner and experienced skiers.

If you’ve never skied before, Blue Hills offers ski lessons for all ages. And even if there’s no snow during your visit to Boston, the resort has excellent snow-making capabilities, so you’ll likely still be able to ski.

19. Go on a sunset cruise

Seeing the Boston skyline at sunset is a scene to remember. This sunset cruise runs year-round and has an interior deck where you can order drinks and snacks while taking in the views. 

Before the sun sets, the boat will take you past a few of Boston’s key historic sights, including Old North Church, Bunker Hill Bridge, and the USS Constitution.

🌇 BOOK YOUR SUNSET CRUISE HERE!

If you want to take your cruising experience to the next level, check out one of the brunch or dinner cruises available on the Boston Harbor, including special holiday-themed cruises for Christmas, New Year’s, and St. Patrick’s Day.

Special Things to Do in Boston in December

December is the best time to visit Boston if you want to experience the joys of the holiday season. Boston comes alive during this month and has endless activities and decorations to usher in the holiday spirit.

20. Attend the SoWa Winter Festival

This event is technically not during the winter, as it runs from November 24-December 17, 2023, but I’m still including it in this list because it’s happening in December AND it’s still called a “Winter Festival.”

If you’re planning a pre-Christmas trip to Boston, check out the SoWa Winter Festival, located at the SoWa Power Station, where you can browse the items of more than 100 local artists, makers, and food vendors.

On the second floor of SoWa, you can also enjoy live holiday entertainment.

21. Shop the festive streets

There’s something special about shopping in Boston in December when the streets are decorated for the holidays. My favorite street to visit in December is Charles Street in Beacon Hill. 

The brick streets, old street lights, and decorated storefronts make you feel transported back to Colonial Christmas time in Boston. Be sure to walk over to Rouvalis Flowers to check out their holiday plants and gift displays.

I mentioned Newbury Street earlier, but I have to call it out here again because the street comes alive in December for the holidays. 

Whether you’re shopping for Christmas presents, on the hunt for chocolate or a peppermint mocha, or simply wanting to experience the festive atmosphere, Newbury Street is a must-visit part of Boston this time of year.

Beyond these streets, you’ll run into other holiday events and attractions around the city in December. Boston gets decked out for the holidays and will definitely put you in a celebratory mood.

22. Participate in First Night Boston

Boston’s New Year’s Eve celebration, called “First Night Boston,” has been an annual tradition since 1976. 

First Night events kick off at noon on December 31, with artistic performances, live entertainment, ice sculptures, and more at City Hall Plaza, Faneuil Hall Marketplace, and Rose Kennedy Greenway.

The First Night Parade starts at 6 p.m. along the streets of downtown Boston heading toward Boston Common. At 7 p.m., a family fireworks show lights up the sky at the Common.

The party really begins at 8 p.m. with back-to-back musical performances at City Hall Plaza as the clock counts down to midnight and the giant First Night Fireworks show takes place at Boston’s Inner Harbor. It’s an amazing way to celebrate the New Year!

Special Things to Do in Boston in January

23. Boston Celtic Music Festival

The Boston Celtic Music Festival, known as BCMFest, takes place January 11-14, 2024. This annual event showcases Greater Boston’s deep music, song and dance heritage from Irish, Scottish, Cape Breton, Quebecois, and other Celtic communities. 

Book tickets to see a mixture of traditional and contemporary acts featuring both professional tour groups and local musicians.

24. Attend MLK Day events

Martin Luther King, Jr. Day takes place on January 15, 2024, and Boston always hosts several events to commemorate his legacy. Dr. King called Boston his second home, as it was the place where he met his wife, Coretta Scott King, and earned his Ph.D. in Theology at Boston University.

The Institute of Contemporary Art and the Museum of Fine Arts both offer free admission on MLK Day with special exhibits, live performances, activities, and more.

Boston Cares highlights a number of ways to honor Dr. King’s legacy through acts of service, including volunteering for local organizations and buying from BIPOC-owned businesses.

On MLK Day (or any day really), you can also take time to explore permanent fixtures in Boston that celebrate African American history:

• See the Love Story mural in Roxbury highlighting Dr. King and his wife. 
• Visit the Embrace monument in memory of the Kings and other Civil Rights activists in the Boston Common.
• Walk along the Black Heritage Trail in Beacon Hill to see 10 sites that played a key role in pre-Civil War African American life in Boston.

Special Things to Do in Boston in February

25. Ring in the Chinese New Year

Boston’s Chinatown is worth a visit any time of year if you’re craving authentic Chinese food, but this neighborhood especially comes alive for Chinese New Year. 

Boston is hosting a large Chinese New Year Parade on February 18, 2024, starting at 10 a.m. Stop by for colorful floats and displays, live music, kids’ activities, and much more.

And of course, if you’re in Chinatown, you have to eat at one of the many restaurants. A few highly rated options include The Q, Banh Mi Huong Que, and Dumpling King.

26. Go on a Valentine’s Day cruise

If you’re planning a romantic trip to Boston for Valentine’s Day, consider adding a Valentine’s Day Jazz & Champagne Tasting Cruise to your itinerary. Enjoy live jazz tunes played by a house band while sipping on champagne and gliding along the Boston Harbor. 

This special event is available February 9, 10, and 14 in 2024. Note that dinner is not included with this cruise, so you’ll want to plan to eat before or after.

27. Celebrate Black History Month

Celebrate Black History Month in February by learning about Boston’s African American history and supporting Black-owned businesses.

Boston’s official website contains lists of Black-owned and Black-led businesses and cultural programs you can check out during your visit.

The Boston Public Library also hosts special Black History Month events and readings.

Special Things to Do in Boston in March

28. Participate in Dine Out Boston

Dine Out Boston takes place twice a year, once in the summer and once in the winter. The next Dine Out Boston will happen in March 2024 (exact date TBD).

This is the perfect opportunity to sample a bunch of different Boston restaurants at special, fixed prices. The event is hosted by Meet Boston — check out their website for event updates and how to sign up.

29. Experience St. Patrick’s Day events

Boston has a rich Irish history, and to this day, the city has one of the largest Irish-American populations in the U.S. Because of this, Boston is an amazing place to celebrate St. Patrick’s Day. 

You’ll find no shortage of Irish-themed activities to do in the city around St. Patrick’s Day. Here are some of the best options:

• Check out the St. Patrick’s Day Parade in South Boston (“Southie”) on March 17, 2024, and don’t forget to wear green!

• Listen to Dropkick Murphys play at the House of Blues or MGM Music Hall March 14-17.

• Stop by one of the many Irish pubs around the city for great food and drinks, live music, and dancing, including The Black Rose, The Burren, and Ned Davine’s.

• Book tickets for a St. Patrick’s Day Brunch Cruise on March 16 or 17, where you can enjoy delicious food and Irish music while taking in the sights along the Boston Harbor. (Tickets sell out quickly, so reserve yours soon!)

What to know about winter in Boston

Leave your car behind and use public transportation. 

Parking in Boston is always a bit of a pain, but when there’s snow, it becomes a game of survival of the fittest. 

Most parts of Boston have an unwritten rule about street parking after a snow storm, which is that you shovel out your own space and use an object to mark it as taken. 

If you didn’t clean out the space yourself, I wouldn’t dare to take it. (Trust me, people get pretty crazy over their spaces and you don’t know what might happen to your car. Sad, but true.)

Note that some public roads don’t allow for space-saving, but if you’re not familiar with the area, it can be hard to know where the rule applies.

🚗 Want to know more about parking space saving in the winter?
Check out my detailed post on the topic here. 

After over two years of living in the city, I’ve learned all about the do’s and don’ts of winter parking in Boston.

Beyond street parking, there are parking garages throughout the city, but you can expect to pay $30 or more per day.

Personally, I like to avoid driving and parking in the city as much as possible and use the Boston subway, the “T.” Between the T and the many bus lines, you can get pretty much anywhere you need to go.

If there are any transportation delays or shut-downs, you can get an Uber or Lyft, too.

Dress for the weather.

Exploring Boston in the winter can be just as enjoyable as any other time of the year if you’re dressed appropriately. Thermal underwear is your best friend. 

If I plan to be outside for more than a few minutes, I always wear at least two layers on top and bottom in addition to a thick winter coat, snow boots, a hat, a scarf, and gloves. 

I’m one of those people who gets easily cold, so I aim to be overdressed rather than underdressed. It’s better to take layers off than to wish you had worn more.

Be prepared for unexpected weather patterns.

Boston’s location near the ocean makes it subject to rapidly changing weather. The day might start out sunny and end with snow in the afternoon.

Keep an eye on the weather forecast and make sure you’re prepared for snowy conditions. 

Also note that if there’s a big snowstorm, there may be major delays or shutdowns of public transportation. (But if you’re tempted to drive instead, know that traffic can be miserable, too.) 

If there’s a really big storm, some businesses may close as well.

Because of this, I recommend staying in a hotel downtown so that it’s a fairly convenient walk to most major attractions and you don’t have to worry about transportation. And have a backup plan for any activities you may have to adjust based on the weather.

🛌 POPULAR HOTELS WITH CENTRAL LOCATIONS

📍Omni Parker House Hotel:
Historic hotel near Boston Common and the Freedom Trail

📍The Westin Copley Place:
Close to the Prudential Center, Boston Public Library, and Newbury Street

If you do end up experiencing a big snowstorm during your visit to Boston, be sure to go outside at some point to see the city in the freshly fallen snow. It’s magical. ✨

Weather in Boston in winter

Here is a breakdown of Boston’s average high and low temperatures for each month of the year. As you can see, daytime temperatures are generally in the 30s and 40s from December through March.

Boston gets an average snowfall of over 49 inches every year. I’ve only lived in Boston for two winters, but from what I’ve experienced so far, it seems like most of the snow comes from a couple of big snowstorms, with light snowfalls in between.

How to spend one day in Boston in the winter

If you only have one day to spend in Boston during the winter, here’s one example itinerary I’d recommend to make the most of your time:

• 9-11 a.m.: Start your day in Beacon Hill, exploring the shops on Charles Street and stopping at a few sites on the Black Heritage Trail.
  • If you haven’t had breakfast yet, go to Tatte Cafe & Bakery on Charles Street for delicious coffee, pastries, and more.
    
• 11 a.m.-12:30 p.m.: Visit the Boston Common and go ice skating on Frog Pond.
  
• 12:30-2 p.m.: Grab lunch at one of the many restaurants on Newbury Street. Then walk over to the historic McKim Building of the Boston Public Library.
  
• 2-2:30 p.m.: Hop on the Green Line E train at Copley station (right outside of the library) and get off at the Museum of Fine Arts stop.
  
• 2:30-5 p.m.: Tour the Museum of Fine Arts (MFA) and/or the Isabella Stewart Gardner Museum (not far from MFA).
  
• 5 p.m. and later: Have dinner and see a live show at Symphony Hall or the Boch Center.
  • If you still have time and energy to spare, rent an igloo at Lookout Rooftop & Bar to cap off your night with drinks and city views.

Free things to do in Boston in winter

Here are some of the activities mentioned in this post that won’t cost a dime:

• Visit the Boston Public Library
• Stroll through Faneuil Hall Marketplace
• Volunteer with a local organization
• Go sledding at Boston Common
• Attend First Night Boston
• See the Chinese New Year or St. Patrick’s Day parades

FAQs

See answers to other common questions about winter in Boston below:

Is Boston worth visiting in winter?

Yes! If you don’t mind the cold, Boston is still a great time to visit the city. Summer is of course the most popular time to visit Boston because of the great weather and school vacation, but the city gets really crowded during this time.

Most of the attractions you can see in the summer are still open in the winter. You can benefit from fewer crowds and lines by reserving tickets for museums and other popular sights during the winter months.

What should you do in Boston when it’s really cold?

If the weather is miserable during your time in Boston (I’ve definitely been there), I would plan for indoor activities only. The good news is there are still lots of indoor options to choose from, with many of them highlighted in this post. 

Below are a few examples:

• Book tickets to see a live show
• Reserve a heated igloo for evening drinks
• Watch a Bruins or Celtics game
• Visit one of Boston’s many museums

How do you deal with winter in Boston?

The best way to handle winter in Boston is to dress appropriately. A day can quickly go from pleasant to sour if you’re not wearing the right clothes for the weather.

I always wear at least two layers on top and bottom, in addition to my thick winter coat, socks, scarf, hat, and gloves.

When I’m bundled up, I don’t even notice the cold too much, and I can continue to explore the city to my heart’s content — sans crowds.