25 Things To Do In Boston (And Beyond!) During The Winter

Hello from a chilly Boston, MA! I am coming up on one year of living in Boston and my love for this city has grown throughout the seasons. Boston has four very distinct seasons — each one bringing along with it a new list of activities and experiences to enjoy. This list is going to focus on 25 things to do in Boston during the winter season. I already have similar posts live about things to do during the summer and also during the fall. I also just wrote my 4th & final seasonal guide covering Boston during the spring! This guide is broken down by neighborhood. Despite the freezing temperatures, Boston can feel like a real-life snow globe during the winter season. Let’s dive into the list!

Disclaimer: This blog post is written in collaboration with adidas. I have linked a few of my favorite products in this blog post, but as always, all opinions written below are my own.

Downtown Boston

1. Boston Common Tree Lighting

Every year a massive spruce tree makes it way to Boston Common. Boston’s official Christmas tree usually arrives in mid-November from Nova Scotia. There is a little tree arrival celebration that includes candy canes and an appearance from Santa, although the main lighting ceremony is usually the first week of December.

The tree commemorates 100+ years of friendship with Nova Scotia. The tree lighting in 2025 is December 4 from 4-6pm.

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2. Quincy Market Tree Lighting

Similar to the tree lighting ceremony in the center of Boston Common, a huge 50 foot spruce tree also arrives to Quincy Market each year! The tree lighting is a bit earlier here — usually before Thanksgiving (in 2025 it happened on November 22). Each year, you can kick off the holiday season in Faneuil Hall with festive treats, special guests like Santa, face painting, and live entertainment. Attending a tree lighting ceremony is a top thing to do in Boston during the winter!

3. Celebrate NYE At First Night Boston

First Night Boston takes place every year on December 31 and features a full day of family-friendly programming that begins around midday and continues past midnight. You can enjoy live music, cultural performances, illuminated ice sculptures, parades, and special activities scattered throughout downtown Boston.

Celebrations center around City Hall Plaza, but also extend to the Boston Common and the waterfront, where early evening fireworks light up the sky before the grand midnight display over the harbor.

Public transit (the T) is the easiest way to get around, as many streets close for pedestrian access, creating a festive, walkable atmosphere across the city.

4. See The Boston Ballet

Boston Ballet is the city’s premier dance company, best known for its annual production of Mikko Nissinen’s The Nutcracker. Performances take place at the Citizens Bank Opera House in downtown Boston.

The Nutcracker runs each year from late November through December and is one of Boston’s most iconic seasonal traditions. You can grab tickets here!

5. Ice Skating On Frog Pond

The Boston Common Frog Pond is one of Boston’s most popular year-round attractions. Located in the nation’s oldest city park, the Frog Pond is managed by The Skating Club of Boston and offers public skating as well as lessons through The Skating Academy, with hours ranging from morning through evening depending on the day.

The Boston Common Frog Pond Skating Rink opened for the winter season on Monday, November 24 and will operate daily throughout the colder months. Admission to the Frog Pond skating rink is $10 for skaters 58 inches and taller, while children under 58 inches skate for free. Skate rentals cost $15 for adults and $10 for kids.

Be sure to dress warm for outdoor ice skating in Boston. I recommend wearing layers — including a fleece, winter jacket, hat, and gloves.

Seaport

6. Stroll Through Snowport

The Snowport Holiday Market presented by Constant Contact is Boston’s best Christmas market. Head to the Seaport this holiday season to browse a joyful winter village where you can support over 100+ small business makers, most of which are BIPOC & women-run.

Aside from shopping for gifts for loved ones, you can also enjoy festive decor, live music, mocktails and festive cocktails, dozens of food options, a warming tent, crafting corner, and so much more!

The market is free to attend, although I recommend getting these timed-entry tickets to skip the line on the weekends! Also, be sure to download the Seaport Insider App to save 10% at designated booths.

In December, the market will be open Monday – Thursday from 11am – 8pm, Friday & Saturday from 11am – 9pm, and on Sunday from 11am – 8pm.

7. Lookout Rooftop & Bar Igloos

Grabbing drinks and bites in a heated igloo at Envoy’s Lookout Rooftop & Bar is one of the most classic things to do in Boston during the winter months.

Enjoy stunning views of Boston’s skyline and harbor from a heated igloo or ice box. Lookout serves speciality cocktails and small plates during this time of year. Each heated igloo can accommodate up to 6 people and can be reserved for a maximum of 2 hours. Reservations are definitely needed for this popular Boston winter activity!

8. Deck 12 Apres Ski Pop-up Bar

While we’re on the topic of winterized rooftop bars, I have to mention Deck 12 too! Also located in Seaport (at the top of the Yotel!), this rooftop bar gets transformed each November into an aprés ski-themed destination.

Enjoy views of Boston’s skyline, gondola tables, chair lift seating, fondue for two, themed drinks, and so much more through February / March.

9. Movie At Alamo Drafthouse

For the ultimate cozy night out, head to Alamo Drafthouse in Seaport! Alamo is known as Boston’s “boujee” movie theater. In addition to the reclining, plush seats here being as premium as they get for movie theaters, Alamo also serves a full drinks and dinner menu. Grab a craft cocktail and cozy up to your favorite film this winter season.

Pro-tip: For discounted movie tickets, head to Alamo on Tuesday evenings. Tickets are just $7!

10. Night Out At An Experiential Bar

Most of Boston’s best experiential bars are located in the Seaport District. Here you can find themed, indoor bars like the new F1 Arcade, Flight Club for darts lovers, Puttshack for mini golf, SPIN for ping pong, PKL for pickleball players, and more! I think the Seaport is one of the best places to hangout during the winter months in Boston.

Each of these bars offers food and drink options too, so grab a group and make a night out of it!

South End

11. Shop At SoWa Winter Festival

SoWa Winter Festival is another popular holiday market in Boston. This one is indoors and is located in the South End’s historic SoWa Power Station. This festival typically kicks off around Black Friday (in 2025 it opened on 11/28), and runs through late December.

The Winter Festival features 125+ local vendors, handmade art, speciality foods, holiday-themed cocktails, and offers on-site parking for just $10. The festival is closed on Mondays and open Tuesday – Thursday from 4pm – 8pm, on Fridays from 4pm – 9pm, on Saturdays from 10am – 9pm, and on Sundays from 10am – 7pm. Don’t miss it!

12. Sippin’ Santa At Shore Leave

Shore Leave is a popular bar and restaurant in Boston’s South End inspired by travel, adventure, and a spirit of fun. They serve sushi, burgers, colorful tropical drinks, and more year-round. From mid-November until early January, Shore Leave transforms into the Sippin’ Santa pop-up bar! Enjoy festive cocktails in collectible mugs, holiday decor, twinkling lights, and so much more.

Back Bay / Fenway

13. Boston Pops Orchestra

Aside from catching the Boston Ballet’s performance of The Nutcracker, the other seasonal experience I recommend having in Boston during the winter months is an evening at Symphony Hall. Located on the Back Bay / Kenmore line, Symphony Hall is a historic and world‑renowned concert venue known for its superb acoustics and elegant architecture. It’s also home to the annual Boston Pops Holiday Concert.

Each winter, typically running from late November through December, the Boston Pops Orchestra performs a festive program featuring beloved holiday classics, orchestral arrangements, and choral pieces. Tickets are available to the public, with seating ranging from orchestra to balcony, and popular performances often sell out quickly.

14. Hot Chocolate From L.A. Burdick

L.A. Burdick Chocolates is known for having the best hot chocolate in Boston. With numerous locations around Boston, this spot is a city-wide favorite for seasonable handmade chocolates, pastry creations, and rich hot chocolate. They have dark chocolate, milk chocolate, and even white chocolate beverages.

I recommend grabbing a hot cocoa to-go from the Back Bay location Clarendon Street and strolling down Newbury Street during the holiday season. The shop is open Monday – Sunday from 8am – 9pm.

15. Festive Stroll Down Comm Ave

Similarly to the tree lightings, Commonwealth Avenue Mall also has a lighting ceremony of its own each year! Usually taking place the first week of December, the tree lights on Comm Ave are lit in unison, while you can enjoy free cookies and a visit from Santa.

Even if you miss the official lighting ceremony — which takes place after the Boston Common Tree Lighting, you can still enjoy the lights on Comm Ave from Arlington Street to Charlesgate all winter long. Strolling down Comm Ave (especially after a fresh snowfall!) is one of the top things to do in Boston during the winter months.

16. Visit The MFA

There’s no better time to visit some of Boston’s best museums than the cold and dark winter months. The Museum of Fine Arts is Boston’s largest and most impressive art museum. With new exhibits and interactive activities constantly rotating into the museum, visiting the MFA is the perfect thing to do in Boston during the winter.

Pro-tip: The MFA is now offering a discounted $5 entry ticket every third Thursday! This new monthly event includes strolls through all of the museum’s galleries, plus special hands-on art making, live music performances, and more.

Charlestown

17. Cozy Brunch At The Waverly

Charlestown is one of Boston’s most historic neighborhoods and is really a gem to stroll through in the winter months. Located just steps from the Bunker Hill Monument, the Waverly is one of the city’s coziest neighborhood brunch spots. Not only will the hot meals taste like they were made in your grandma’s kitchen, but the ambiance could not be cozier. There’s even a fireplace in here!

You can enjoy brunch from Friday – Sunday 8am – 3pm.

18. Attend Winter Fest In Charlestown

Winter Fest is Boston’s largest winter festival, and for the second year, will transform Hood Park in Charlestown into an enchanting two-acre winter wonderland. This year, enjoy immersive amusements, a carousel, carnival-style arcade games, an artisan village marketplace, Après Ski Veuve Clicquot Gondola Lounge, a life-size ice castle and gingerbread house, and weekend visits with Santa.

Winter Fest runs on December 6-7, 12-14, and 19-30 (closed December 24 & 25).

Pro-tip: Tickets are just $5 per person and Winter Fest 2025 is offering three hours of free parking at the nearby Hood Park Garage.

19. Dine At Prima In Charlestown

Prima Italian Steakhouse in Charlestown is one of Boston’s most decadent and cozy restaurants. Beautifully adorned with eye-catching red curtains, warm table lamps and lighting, and velvet booths designed by Assembly Design Studio, this restaurant is the perfect place to dine during the winter season.

I can’t wait to order a glass of red wine and Bolognese here this winter season!

Beacon Hill

20. Visit The Liberty Hotel

There is no hotel in Boston that captures the Christmas spirit better than The Liberty Hotel in Boston’s charming Beacon Hill neighborhood. Aside from offering yummy espresso martinis and curling in its stunning courtyard, the hotel is most famous for its aerial Christmas tree display during the winter months. Each year, dozens of upside down Christmas trees are suspended from the lobby’s massive chandeliers. Enjoy over 1,000 holiday lights, 700+ ornaments, and soak up the holiday spirit as you sip a glass of Prosecco in this transformed historic jailhouse.

There’s a reason this hotel has been named the best in Boston and one of the best in the world… don’t miss it!

21. Beacon Hill Books & Cafe

Boston’s most beloved bookshop is the place to be during the winter months in Boston! With over 3 floors of books, a charming fireplace, and cozy cafe downstairs, Beacon Hill Books is the perfect place to visit when it’s cold out.

If you happen to be in Boston in December, the bookstore also gets all decked out for the holidays! Enjoy themed hot chocolate, browse dozens of handcrafted ornaments, and pick up a new book this holiday season!

Brookline

22. Sledding & Ice Skating In Larz Anderson Park

There are several places to go sledding and ice skating on a snow day around Boston (including in the Boston Common and at Jamaica Pond), but Larz Anderson Park is my personal favorite. Located in Brookline, about 15 minutes by car from downtown Boston, Larz Anderson has a massive sledding hill overlooking the Boston skyline and open-air ice skating at the historic Jack Kirrane Ice Skating Rink.

Tickets are just $10 for adults and public skating is open every weekend from 12 – 2pm and 2:30 – 4:30pm on Saturdays and Sundays.

Although there is a place to grab hot chocolate and go to the bathroom at the ice skating rink, you’ll want to dress warm in a fleece and winter jacket when ice skating.

Greater Boston

23. Cross-Country Ski & Snowshoeing At Weston Ski Track

This ski track is one of the largest cross-country ski snowmaking systems in New England. Opened at the DCR’s Leo Martin Golf Course in 1974, Weston Ski Track is a man-made 2.5km (1.5 mi) loop perfect for winter recreation in Boston. They offer night skiing, rentals, instruction and snow making along the scenic banks of the Charles River only one mile away from the Riverside T station!

The track typically opens in December or January (temperatures permitting) and will stay open through March. They are open from 9am – 6pm each weekend.

24. Ski Train To Wachusett Mountain

I experienced the ski train for the first time last winter and honestly couldn’t recommend this experience more! Wachusett Mountain is known as New England’s most accessible ski area in the eastern USA, and getting here from Boston could not be easier. The MBTA Commuter Rail has a specific “ski train” on the Fitchburg Line with  modified coaches equipped for ski and snowboard equipment. Once you arrive at the Wachusett station, enjoy a complimentary shuttle to the mountain!

I booked a half-day snowboarding lesson last winter and honestly think this is one of the best things to do in Boston during the winter, especially if you don’t have a car!

Train departures from North Station:

• (1401) 9:22am
• (1403) 11:52am

Trains from Wachusett Station (Leave Ski Area 30 minutes before listed times):

• (1410) 4:25pm
• (1412) 6:25pm
• (1414) 8:55pm

25. Ski Resorts In New England

I have an entire blog post about this topic, but one of the best things to do in Boston (and beyond!) during the winter is to go skiing! New England has dozens of incredible ski resorts located just a few hours from Boston by car. Whether you plan a day trip or a full winter weekend getaway, you need to check out these 10 ski resorts during winter in New England.

That brings us to the end of this blog post all about things to do in Boston during the winter! I hope these ideas help you make the most of the season and avoid the winter blues. Thank you again to adidas for sponsoring this blog post.

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