Things to do winter activities winter US > Eastern Massachusetts > Boston

Things To Do In Winter In Boston, Massachusetts, USA

Melanie
Published Nov 21, 2018

When it’s winter in Boston, it can be tempting to just curl up in a blanket and stay indoors, even if you’ve already made the effort to travel there. Certainly, there are some activities that you won’t be able to do during this season that you would otherwise have been able to try out during the other parts of the year. For example, you won’t be able to enjoy riding one of the iconic swan boats on Boston Common, and whale-watching may not be a great idea during this period. However, there are also certain attractions and activities that you can still enjoy even as the city transforms into a winter wonderland. Take a look at this list for things to do in winter in Boston, Massachusetts, USA.

1. Enjoy winter sports (from USD 50)

Winter provides you with the opportunity to enjoy a number of activities that you wouldn’t be able to try in other seasons. Visit Boston Common to experience ice skating at Frog Pond. You can get lessons and rent skates right on the site. Other winter options include skiing and snowboarding at Sunday River, where you can take your pick from 135 slopes.

Sunday River Ski Bus from Boston

Duration 13 hours (Approx.)

Rating 0/5

Number of Reviews 0

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2. Brave the Freedom Trail

If the snow isn’t too deep, you can be brave and explore the brick path to see attractions in the city that allow you to learn more about Boston’s — and the country’s — history. You can explore the 4 km (2.5 mi) trail on your own, but if you want someone to provide you more interesting facts and stories about key events and people, you can get a guide — complete with a costume — to help you immerse yourself into the stories from the past. The tour takes roughly 90 minutes long. Make sure to dress warmly and wear comfortable shoes!

Tour of The Freedom Trail

Duration 90 minutes (Approx.)

Rating 0/5

Number of Reviews 0

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3. Indulge in a chocolate tour (from USD 61)

Be sure to book this tour if you’ve got a sweet tooth. Running for approximately 2.5 hours, this guided tour brings guests to six stops to enjoy the best chocolates that Boston has to offer. Make sure to specify any food allergies or dietary preferences beforehand so you can enjoy this tour to the max. Admission to two historic sites in Boston is also included here. Since this is a walking tour, make sure to wear comfortable shoes.

Boston Chocolate Tours

Duration 2 to 3 hrs (Approx.)

Rating 0/5

Number of Reviews 0

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4. Visit the Cambridge Antique Market


If you love antiques or searching for quirky finds, be sure to drop by the Cambridge Antique Market. Over 150 retailers of furniture, clothes, toys, and artwork occupy five floors, so make sure to dedicate time here if you want to explore the different wares sold here.

Cambridge Antique Market

Address: 201 Monsignor O'Brien Highway, Cambridge, MA 02141, USA

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5. Head to a local brewery (from USD 70)

If you want to warm yourself up with a few drinks, head over to a local brewery to enjoy tasting a local beer. If you want to learn more about Boston’s brewing history while you enjoy a few beers, you can join a 3.5-hour long tour to three breweries, where you can learn more about the city’s beer scene and how some of the award-winning drinks are brewed. The rates are inclusive of the beer tastings and some snacks, as well as transportation to the breweries.

Sip of Boston Brewery Tour

Duration 3 hours 30 minutes (Approx.)

Rating 0/5

Number of Reviews 0

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6. Grab the season's tickets for a Bruins game

If you prefer watching instead of playing a winter sport, why not catch a Boston Bruins game, held at TD Garden? Games are held nearly every day during winter, so if you’re an ice hockey fan, you can save a lot of money by getting season passes instead of buying tickets per match. You may also catch a game of the Boston Celtics are watch a concert at TD Garden.

TD Garden

Address: 100 Legends Way, Boston, MA 02114, USA

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7. Go sailing with Frostbite Sailing


If you are the adventurous type who wants to try out novel activities, consider going sailing during winter in Boston. Frostbite Sailing, as the name suggests, takes adventurers sailing at the Boston Harbor. Make sure to bundle yourself in winter clothes, because the weather is colder when you’re floating on the water.

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8. Huddle up for a movie at the Brattle Theatre

Source: Wikimedia

Watching a film in Brattle Theatre gives you an experience that you won’t be able to enjoy in any other cinema. Considered as an institution in Boston, Brattle Theatre showcases all sorts of films, ranging from first-run movies to classic films, as well as indie and foreign flicks. Make sure to check the schedule before you head to the theatre so you can see what movies are showing during your visit. Brattle Theatre usually follows repertory programming, wherein they showcase the works of a certain director or films from a certain genre within a set period.

Brattle Theatre

Address: 40 Brattle St, Cambridge, MA 02138, USA

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9. Get a bird's-eye city view from Skywalk Observatory (from USD 58)

If you’ve ever wondered what the aerial view of Boston is like when coated in snow, head on over to Skywalk Observatory, located on the 50th floor of the Prudential Center, to enjoy a 360-degree panoramic view of the surroundings. Going to the observatory may also allow you to get access to the Dreams of Freedom Museum, where you can learn more about the city’s culture and history. While there, you may also want to consider dining at the Top of the Hub, the restaurant on the 52nd floor. Just make sure to call ahead to check if the observatory, since they close it for special occasions and when the weather gets rough.

Boston CityPASS

Duration Flexible

Rating 4.5/5

Number of Reviews 43

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10. Head to the Prudential Center for a shopping spree

Source: Wikimedia

Before or after you head to the SkyWalk Observatory, you may also want to drop by the shops below. Dubbed as “Pru” by locals, the Prudential Center features a number of stores, which makes for a great destination for those who want to shop ‘til they drop, or if you want to seek refuge from the cold. There are a number of restaurants there as well, so you don’t have to venture far to grab a bite to eat.

Prudential Center Boston

Address: 800 Boylston St, Boston, MA 02199, USA

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Winter fun in Boston

Who says you have to be cooped up indoors during winter? This list proves that there are plenty of things to do in the city for adventurous souls who can brave the cold. Run through these activities if you’re looking for activities you can enjoy even during the cooler months in Boston.

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Melanie Sison was bitten by the travel bug when she was younger. She was able to go around her home country as a development worker. She considers freelancing for Trip 101 to be a combination of...Read more

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