Embrace Winter in Boston: Activities by Neighborhood

Boston boasts a unique blend of diverse neighborhoods, each offering its own local haunts and winter pastimes. From ice skating to cozy cafés, there are plenty of winter activities throughout the city. Explore what each of Boston’s neighborhoods has to offer during the winter months.

Neighborhood Highlights

Allston

In the lively student area of Allston, enjoy a cozy afternoon at Tutuland Studio, where you can design and tuft your own rug. Various other craft activities are also available, making it an ideal spot for indoor fun.

Back Bay

Take in stunning views from 700 feet above at View Boston, located in the Prudential Center. Sip on signature cocktails while enjoying breathtaking sights that spread all the way to New Hampshire.

Bay Village

This serene historic area is home to Jacques Cabaret, Boston’s oldest gay bar, renowned for its fabulous drag shows. Saturdays are particularly lively with performances by Dee Dee DeRay.

Beacon Hill

Visit the Boston Athenaeum, a cultural hub for literature and art lovers. Explore its vast collection, steeped in history with connections to renowned figures like Ralph Waldo Emerson.

Brighton

Stay active this winter at Boston Landing, where you can ice skate at Warrior Arena, play pickleball, or enjoy live music at Roadrunner, all while getting warm indoors.

Charlestown

As the oldest neighborhood in Boston, Charlestown features waterfront bars like Pier Six, where you can enjoy signature cocktails alongside beautiful sunset views.

Chinatown, Theater District & Leather District

This bustling area is perfect for warming up with hot meals. Try steaming soup dumplings at Taiwan Café or indulge in delicious ramen at Shojo. In the Theater District, catch a live performance to brighten your winter evenings.

Dorchester

Head to Chez Vous Roller Rink for a nostalgic skating experience or enjoy some delicious fried chicken. This neighborhood offers a vibrant atmosphere even on chilly days.

Downtown

Explore historic sights via various bus tours. Try an unconventional tour such as the Bliss Bus, featuring a unique cannabis-infused experience led by comedians from Improv Asylum.

East Boston

Don’t miss out on delicious pizza at Santarpio’s. This hidden gem is well worth the detour and has a history of serving satisfied customers, including former President JFK.

Fenway/Kenmore

While Fenway Park is a major draw in the warmer months, during winter, locals flock to Time Out Market to savor the best of Boston’s food and drink offerings.

Hyde Park

Try your hand at candlepin bowling at Ron’s Gourmet Ice Cream & 20th-Century Bowling. Enjoy ice cream treats all year round, even in the winter.

Jamaica Plain

Escape the cold at Samuel Adams Brewery, where you can warm up with a smooth Oaked Vanilla Porter, perfect for winter enjoyment.

Mattapan

Savor the rich flavors of Caribbean cuisine with favorites like jerk chicken from Mello Vibez. National parks also offer scenic areas for winter walks and wildlife watching.

Mission Hill

Gather your friends at Tavern of Tales, where you can play board games or join gaming events like Dungeons & Dragons, all while enjoying cozy, warm drinks.

North End

Indulge in hearty Italian meals at family-owned ristoranti on Hanover Street. Follow up your dinner with comforting desserts at renowned cafés.

Roxbury

Sample soul food delights at Slade’s Bar & Grill, famous for its chicken wings, or head to Maxine’s on St James for classic soul food comfort dishes.

South Boston

Visit the Institute of Contemporary Art (ICA), where a new exhibit titled “Wordplay” promises to engage visitors with innovative art and ideas against a stunning waterfront backdrop.

West Roxbury

When snow blankets the city, grab a sled and head to Millennium Park for some thrilling downhill rides and picturesque winter views.

Wharf District

Enjoy afternoon tea at the elegant Boston Harbor Hotel, where you can savor a selection of sandwiches, sweets, and warm beverages while admiring seaside views.

Bonus – Boston Harbor

The Boston Harbor serves as a stunning centerpiece for the city. Although most boat trips pause during the winter, luxury liners such as Northern Lights and Odyssey offer unique dining experiences, allowing you to enjoy dinner and dancing on the water.