Neighborhoods

The best things to do in every Boston neighborhood this winter

From Allston to West Roxbury, all neighborhoods are represented on this list of the best things to do in Boston this winter.

Snowport 2023 opens in Boston's Seaport neighborhood November 10. Alexander Pickering

December 8, 2023

When searching for things to do in Boston, it’s easy to fall into the trap of focusing on bustling hubs of activity like Downtown and the Back Bay.

There’s nothing wrong with a visit to Boston Common or a stroll on the Freedom Trail, of course. But the fact is that every single Boston neighborhood has its own vibrant culture, and on any given day you can build a fun-filled itinerary of activities, whether you’re in Beacon Hill or Brighton; the West End or West Roxbury.

With that in mind, here is a list of the best things to do in Boston during the next three months, with at least one pick for every neighborhood. Whether you’re looking for a food festival, live music, family-friendly fun, or free activities, we’ve got you covered.

Events key:

🆓 = Free events

👪 = Family-friendly events

🍲 = Food events

🍺 = Beer events

Allston

🆓 Join a Sip ‘n’ Stitch at the library

Bring your knitting and crocheting projects to the Boston Public Library’s Honan-Allston branch, where you can trade tips and tricks with other guests while sipping tea while you work. (Dec. 13 from 6 to 7:30 p.m.; 300 North Harvard St.; free)

Back Bay-Bay Village

Toast your friends at a holiday pop-up bar

The festive lobby of Mandarin Oriental, Boston turns into the pop-up Holiday Cocktail and Whisky Bar from Nantucket’s Triple Eight Distillery. Guests can listen to live jazz, enjoy craft tasting flights, single pours, and light bites while tasting The Notch whiskey, wines from Nantucket Vineyard, and holiday cocktails. (Thursday-Saturday evenings in December from 4 to 7 p.m.; 776 Boylston Street, Boston; various prices)

🆓 👪 Study the stars at Coit Observatory

Observe the night sky through a telescope and learn about astronomy during the Coit Observatory Open Nights at Boston University, held on Wednesday evenings, weather permitting, throughout the year. Because space is limited, tickets are required. (Wednesdays at 7:30 p.m.; 725 Commonwealth Ave.; free)

Oil on canvas by Patrick Anderson, part of the Holiday Art Show at The Hidden Art Gallery in Boston.

Beacon Hill

🆓Attend a Holiday Art Show

For those strolling Beacon Hill this holiday season, the Hidden Art Gallery is hosting a Holiday Art Show Dec. 2-16. Sip on a cup of hot cocoa while perusing the seasonal artwork for sale. The show takes place on Saturday and Sundays only and the gallery gift shop is stocked with greeting cards, digital prints, matted watercolors, and framed paintings of Boston and Beacon Hill. (Dec. 2-16 from 11 a.m. to 5 p.m. on Saturdays and 1 to 4 p.m. on Sundays; 25 Myrtle St.; free)

Brighton

🆓 Watch a free movie

Settle in for a free movie at the Brighton branch of the Boston Public Library, where “A Man Called Otto,” featuring Tom Hanks and based on the bestselling book by Fredrik Backman, will be shown on Dec. 11. It is rated PG-13. (Dec. 11 from 3 to 5:15 p.m.; 40 Academy Hill Rd.; free)

Charlestown

👪Celebrate Army-Navy Game Week at the USS Constitution Museum

Ahead of the Army-Navy game at Gillette Stadium, the USS Constitution Museum is hosting an Army-Navy Game Week full of fun activities such as a field goal challenges, team spirit crafts, relay races, and more. (Dec. 6-9; 10 a.m. to 5 p.m.; Building 22, Charlestown Navy Yard, Charlestown; donations appreciated)

🆓 Take a gentle yoga class

Strike a pose during this gentle yoga class taught at the Charlestown branch of the Boston Public Library by a community yoga teacher from the Hands to Heart Center. It is a meditative practice geared for students of all ages and students should bring their own mat since equipment is limited. (Dec. 4, 11, 18 from 11 a.m. to noon; 179 Main St., Charlestown; free)

Chinatown / Leather District

🆓 👪Attend a Chinese New Year Parade

Enjoy a parade, food, music, and colorful lion dances during Chinatown’s Chinese New Year Parade. The parade begins at Phillips Square, at the corner of Harrison Avenue. and Beach Street. (Feb. 18 from 10 a.m. to 3 p.m.; free)

Dorchester

👪Rock and roll at Chezo-Vous Roller Skating Rink

Lace up your skates and join the fun with family and friends at this roller skating rink that offers special themed nights, days, and weeks for families, toddlers, adults, holidays, school vacation, and more. (Tuesday from 6 to 9 p.m.; Wednesday from 7 to 10 p.m.; Friday from 6 to 11 p.m.; Saturday from noon to 11 p.m.; Sunday from noon to 12 a.m.; 11 Rhoades St., Boston; $10-$20)

🆓 🍲 👪Make a gingerbread house

Get festive this holiday season by making a gingerbread house at Codman Square branch of the Boston Public Library. The program is for all ages and participants can take home their creations. (Dec. 11 from 5 to 6 p.m.; 690 Washington St., Dorchester; free)

The Boston Common Frog Pond Skating Rink in Boston. – The Skating Club of Boston

Downtown Boston

👪Go ice skating in America’s oldest public park

Skate beneath the twinkling trees on the Boston Common Frog Pond, open daily for ice skating through March. Skate rentals are available for those without equipment, as well as skating aids for children. (Daily from 10 a.m. to 3:45 p.m. Monday, 10 a.m. to 9 p.m. Sunday through Thursday, and 10 a.m. to 10 p.m. Friday and Saturday; 38 Beacon St., Boston; $10-$15)

🍲 Sip wine at the Boston Wine & Food Festival

The 35th Annual Boston Wine & Food Festival brings wine dinners, pop-up tastings, seminars, receptions, brunches, master classes, and more to the Boston Harbor Hotel on the historic Rowes Wharf Harbor. (Jan. 12 through March 29; various dates and times; 70 Rowes Wharf, Boston; various prices)

East Boston

🆓 👪Join a Luminaria Walk

Bring the whole family for hot cocoa and singing along to festive music while strolling down the Mary Ellen Welch Greenway, a rail trail and park in East Boston, during the 3rd Annual Luminaria Walk. The group meets at the Blue Caboose.(Dec. 9 at 4:30 p.m.; Intersection between Marginal Street. and S. Bremen Street; free)

The new MGM Music Hall at Fenway. — The MGM Music Hall at Fenway. – John Tlumacki / The Boston Globe

Fenway-Kenmore

Check out a show at MGM Music Hall

Fenway’s newest concert venue brings musicians, stand-up comedians, video game tournaments, and more to the state-of-the-art 91,500-square foot four-level space beside Fenway Park this winter. Just a few of the acts taking the stage this winter are Boyz II Men, Grace Potter, and Andrew Schulz. (2 Lansdowne St., Boston; dates and prices vary)

Hyde Park

🆓 👪Learn about indigenous traditions in Southern New England

Discover the history, culture, and traditional arts of Southern New England tribal communities. The event takes place at the Hyde Park Branch of the Boston Public Library and is led by Silvermoon LaRose, a member of the Narragansett Tribe and the assistant director of the Tomaquag Museum in Rhode Island. (Jan. 18 from 6:30 to 7:30 p.m.; 35 Harvard Ave.; free)

Jamaica Plain

🆓Go for a winter walk at the Arnold Arboretum of Harvard University

Get outside this winter during the Arnold Arboretum of Harvard University’s Winter Wellness Walk. These brisk, 60-minute walks are led by a trained Arboretum docent and geared toward adults. Space is limited so registration is required. (Saturdays and Sundays Dec. 2-March 31 at 1 p.m.; 125 Arborway; free)

🆓 👪Enjoy a large-scale laser light show

Jamaica Plain’s annual laser light show kicked off Dec. 2 and plays nightly on the hour and half hour between 5 and 8 p.m. through Jan. 6, 2024. Music has been incorporated into the event for the first time this year as the laser show projects high onto the steeple of First Baptist Church. (Dec. 2-Jan. 6 from 5 to 8 p.m.; 633 Centre St.; free)

Mattapan

🆓 👪 Fly over to Mass Audubon’s Pigeon Party

Mass Audubon’s Boston Nature Center and Wildlife Conservancy will get you up close and personal with the misunderstood urban-dwelling birds, teaching visitors of all ages about the bird’s keen intellect in an effort to remove the stigma that surrounds them. (Jan. 7 from 1-2:30 p.m.; Boston Nature Center and Wildlife Conservancy; free)

The courtyard at the Isabella Stewart Gardner Museum.

Mission Hill

🆓 👪Join the Dr. Martin Luther King, Jr. Day of Service at the Isabella Stewart Gardner Museum

This free public program for the whole family honors the legacy of Dr. Martin Luther King, Jr. with activities led by educators, artists, and cultural organizers such as storytelling, art, drum circles, and more. (Jan. 15 from 11 a.m. to 4 p.m.; 25 Evans Way; free)

North End

🆓 Find the perfect gift at Boston Public Market

Each weekend during the holiday season, Boston Public Market hosts local entrepreneurs selling handmade greeting cards, home goods, knitwear, jewelry, and more items ideal for gift-giving. (Now through Dec.24 at various times; Boston Public Market, 100 Hanover St., Boston; free)

Roslindale

🆓 Shop local at Roslindale Winter Farmers Market

This award-winning seasonal fixture is more than just a market, bringing children’s activities, live music, and wellness activities to the ABCD parking lot in Roslindale Village every Saturday through the end of March. (Saturdays starting January 7 from 11 a.m.-2:30 p.m.; 32 Birch St.; free)

Roxbury

Sip holiday cocktails at Bully Boy Distillers

Crack open the right door at Bully Boy’s neighborhood distillery and you’ll find a fully decked-out holiday bar serving up festive cocktails throughout the month of December. (Thursday through Sunday at various times; 44 Cedric St., Boston; 21+)

Seaport

🆓 Enjoy free admission to the ICA

Typically closed on Mondays, the ICA will offer free admission for Martin Luther King Jr. Day, offering visitors one of their final chances to see exhibits from Cicely Carew, Tammy Nguyen, and Barbara Kruger. (Jan. 15 from 10 a.m.-5 p.m.; ICA, Harbor Shore Drive, Boston; free)

🆓 Catch a menorah lighting at Snowport

Nine days after its annual tree lighting, Snowport 2023 will partner with Chabad of Downtown Boston to celebrate Hanukkah with a Menorah Lighting celebration, providing tasty treats for visitors like kosher jelly doughnuts and chocolate gelt. (Dec. 10 from 4-6 p.m.; 60 Seaport Blvd., Boston; free;)

South Boston

Laugh along with Jiaoying Summers at Laugh Boston

If you’re looking for a laugh this winter, the up-and-coming Summers, who grew to prominence thanks in part to TikTok, has three consecutive nights of shows scheduled at Laugh Boston. (Dec. 14-16 at various times; Laugh Boston, 425 Summer St., Boston; $33-$45)

Take a frigid polar plunge with the L Street Brownies

On New Year’s Day morning, hundreds of locals will join the L Street Brownies and plunge into the frigid waters of Boston Harbor, continuing a Southie tradition first established in 1904. (Jan. 1 at 8:30 a.m.; M Street Beach, Boston; free)

Plungers kicked up spray as they jumped into the ocean during the annual L Street Brownies New Year’s Day Polar Plunge on Sunday morning. – Jessica Rinaldi/Globe Staff

South End

Shop local at SoWa Winter Festival

Artisan vendors fill the historic Power Station for the eighth straight year through December 17, letting visitors buy holiday gifts and snacks before heading upstairs for cocktails and live entertainment. (Now through Dec. 17 at various times; 550 Harrison Ave., Boston; $10)

Solve a mystery with ‘Holmes for the Holidays’

The game is afoot as Arthur Conan Doyle’s famed literary sleuth takes the stage in Boston this holiday season, unraveling a yuletide mystery starring the regular cast of the Lyric Stage. (Now through Dec. 17 at various times; Lyric Stage Company of Boston, 140 Clarendon St.; $15-$85)

West End

Celebrate the season with Mariah Carey

Is it actually the holiday season if you haven’t heard Mariah Carey’s “All I Want for Christmas Is You” dozens of times already? The queen of Christmas will have plenty of holiday tunes — including her mega-hit, no doubt — on hand at TD Garden exactly two weeks before Christmas. (Dec. 11 at 7:30 p.m.; TD Garden, Boston; $119 and up)

Let your body move with Madonna

After a visit to the ICU due to a “serious bacterial infection” forced the Queen of Pop to postpone her 2023 concert in Boston, Madonna will return to T.D. Garden for a pair of shows in January. (Jan. 8 and 9 at 8:30 p.m.; TD Garden, Boston; $116.50 and up)

West Roxbury

🆓 👪 Step back in time at Brook Farm National Historic Site

Explore several miles of walking trails and Charles River shoreline at Millennium Park, including a path to the former site of a Utopian community founded by author Nathaniel Hawthorne and other Transcendentalists in the 1840s. (670 Baker St.; free)

Wharf District

🆓 👪 Enjoy holiday celebrations on the Greenway

The Greenway is getting into the holiday spirit on multiple weekends this December, hosting a candlelit labyrinth walk at the Armenian Heritage Park on Dec. 10 and caroling parties on Dec. 14 and 16. (Dec. 10, 14, and 16 at 4:45 p.m.; Armenian Heritage Park, Atlantic and Hermitage St., Boston; free)