The map of Boston is a patchwork of oddly shaped and diversely formed districts, a so-called city of neighborhoods. Some were the original pieces of historic Boston, while others were once independent municipalities that were annexed by the larger city. But all have their own local haunts and favorite pastimes and, when the temperatures drop, ways to embrace the season.
From Charlestown in the north to Hyde Park in the south, from West Roxbury to East Boston, here’s what to do in winter in each of Boston’s 23 ‘hoods — and in the city’s centerpiece Boston Harbor.
Allston: In the `student ghetto’ of Allston, Tutuland Studio offers the perfect indoor activity for a winter’s afternoon – design and tuft a cozy rug to sink your feet into. Lots of other craft activities available too.
Back Bay: Admire this elegant neighborhood—and the entire city—from 700 feet above at View Boston, the observation deck at the top of the Prudential Center. Sip signature cocktails and – on a clear day – take in views all the way to New Hampshire.
Bay Village: There’s not a lot of action in this quiet historic neighborhood, with one big exception: Jacques Cabaret is Boston’s oldest gay bar, beloved for its fabulous drag shows. Saturday nights with Dee Dee DeRay are hot, hot, hot!
Beacon Hill: A distinguished private library and art museum, the Boston Athenaeum has been a center of Boston intellectual life since 1807. Browse the books and admire the art with the likes of Ralph Waldo Emerson and Nathaniel Hawthorne.
Brighton: When it’s cold outside, there are indoor activities and entertainment for all ages and interests at Boston Landing — ice skating at Warrior Arena (home of the Bruins!), pickleball at the Track, and live music at Roadrunner.
Charlestown: The oldest neighborhood in Boston, Charlestown is also one of the few places in Boston with a westward vista. Head to the waterfront bar at Pier Six, where sunset views and signature cocktails keep you warm all winter long.
Chinatown, Theater District & Leather District: Three overlapping districts get tied together in one busy neighborhood. In Chinatown, heat up your insides with steaming soup dumplings from the Taiwan Café or luscious ramen from Shojo. Or, follow the marquee lights to the Theater District, where the Cher Show at the Boch Center will add some sparkle to a dark winter night.
Dorchester: The hottest spot in Dorchester is Chez Vous Roller Rink, beloved by Dot natives for its good vibes, soulful music and long history in the ‘hood (since 1933). Also: fried chicken!
Downtown: All kinds of buses and trolleys ply the city streets, showing off historic sights and other curiosities. The most unusual is the Bliss Bus, which offers a `cannabis-infused’ tour of Boston. Your tour guides are the funny folks from Improv Asylum, who keep you laughing with just a little help from the product at Apex Noire Dispensary.
East Boston: Most visitors make a beeline to/from Logan airport, without stopping to explore the surrounding neighborhood. But locals know it’s worth the trip to East Boston for a pizza at Santarpio’s. Even JFK stopped here when he was on the campaign trail.
Fenway/Kenmore: Baseball may be the main attraction in the Fenway/Kenmore neighborhood, but during the offseason, locals and students hang out at Time Out Market. Stop this fantastic food hall to sample the best of Boston food and drink.
Hyde Park: There are not too many places left for candlepin bowling – the unique New England variation on ten-pin. Fortunately, you can still play a string in Hyde Park at Ron’s Gourmet Ice Cream & 20th-Century Bowling. And yes, you can also go there for ice cream, even in winter. Welcome to New England, where we eat ice cream all year round.
Jamaica Plain: This `streetcar suburb’ used to be a place for wealthy Bostonians to escape the summer heat. Nowadays, residents of all income levels come to escape the winter cold at Samuel Adams Brewery. The Oaked Vanilla Porter goes down smooth and warms you from the inside out.
Mattapan: Mattapan’s spicy Caribbean cuisine will whisk you away to warmer climes. Local favorites include jerk chicken from Mello Vibez and rotis from Ali’s Roti Restaurant. Urban Mattapan is also unexpectedly excellent for winter walking and wildlife watching. Visit Mass Audubon’s Boston Nature Center for a maple sugar demonstration, a winter birdwatching expedition or other outdoor exploration.
Mission Hill: The young folks of Mission Hill get their game on at Tavern of Tales. Bring some friends and play one of the (many) board games that are available, or join an organized gaming event (D&D, Magic the Gathering, etc). Keep things cozy with hot drinks like vodka-spiked latte or boozy hot chocolate.
North End: What better way to spend a winter evening than tucking into a plate of pasta in a warm and welcoming Italian restaurant? Take your pick from the family-owned ristoranti that line Hanover Street, such as Bricco or Terramia, followed by hot cappucini and dessert from Caffe Paradiso or Caffe Vittoria.
Roslindale: Arnold Arboretum is an urban oasis that straddles the border between Jamaica Plain and Roslindale. Stop at the Visitor Center to pick up a map of the Winter Tour, which highlights winter-blooming plants and berries, evergreens, and ornamental bark. The Conifer Collection laden with snow is a sight to behold.
Roxbury: In the mid-20th century, when Southern Blacks migrated north to Boston, many settled in Roxbury — and, halleluiah, they brought soul food. Slade’s Bar & Grill is a neighborhood institution (since 1935), famous for its chicken wings and fried okra poppers. Maxine’s on St James is the place for comforting southern classics like chicken and waffles or shrimp and grits.
South Boston: Sunlight streams into the galleries at the ICA Boston, illuminating the artworks and warming the viewers. This winter, a fascinating new exhibit Wordplay showcases the interplay between words and images in contemporary art.
South End: The area south of Washington Street (SoWa) is Boston’s contemporary art hub. Nosh on wine and cheese and mingle with the artists at the SoWa Open Studio event, held the first Friday of every month.
West End: Winter in Boston means cheering on the Celtics on the basketball court and the Bruins on the ice. Both teams play at the TD Garden in the West End; and this year, both teams are on fire! Pre-game at Nightshift Brewery or Hub Hall.
West Roxbury: When the snow starts to fall, get yourself a sled and head straight to Millennium Park in Roxbury for the best sledding in the city. The view from the top is terrific and the descent is a gas.
Wharf District: Afternoon tea is an elegant affair at the Boston Harbor Hotel, the crown jewel of the Wharf District. Enjoy the wintry water view while you stay warm with a pot of tea (or tea-based cocktails) and a selection of sandwiches, scones and irresistible sweets.
Bonus – Boston Harbor: The Boston Harbor is the glorious centerpiece of this city by the sea. While most boat trips suspend operations during the winter, luxury liners such as Northern Lights, Odyssey and Spirit of Boston set sail several times a week — a unique opportunity for dinner and dancing on the water.
