Renowned for its academia, athletics, and history, Boston is a place of many well-deserved legacies. When you explore beyond the expected stops like Back Bay or Fenway and branch out into the 23 diverse neighborhoods of this New England hub, you’ll uncover untold stories.
Some of the most fascinating ones are in the Roxbury, Jamaica Plain, and Dorchester neighborhoods—explorations in living history, and thriving destinations that continue to reinvent themselves through the visual and culinary arts. Whether it’s seasonal nature hikes or performances like The Nutcracker, visiting these areas in wintertime is a chance to immerse yourself in distinctive and multifaceted districts where Bostonians live, work, and play. In this easily accessible urban trifecta, you can step into BIPOC-owned galleries and shops, take in a show at one of the theaters that set the stage for the jazz movement, and try new flavors at a mom-and-pop restaurant. To help you plan an afternoon or longer in Roxbury, Jamaica Plain, and Dorchester, sign up to Meet Boston for ongoing updates.
Try African food and go dancing in Dorchester
Boston’s largest neighborhood is also one of its most historic. When the first waves of Irish immigrants sought refuge in the United States, Dorchester became home to many of them. Today, Dorchester’s Presidential Library & Museum honors John F. Kennedy, who was born in Massachusetts. You can also see spectacular views of Boston Harbor and its islands from the grounds.
Fields Corner is a historic commercial district in Dorchester.
Courtesy of Meet Boston
Many other immigrants from around the world have since followed the Irish, resulting in a diverse mix of global influences in Dorchester, including significant Black, Cape Verdean, and Caribbean communities. One of the tastiest ways to enjoy that heritage is at Comfort Kitchen in pedestrian-friendly Upham’s Corner. The restaurant celebrates the flavors of the African diaspora with dukkah (a mixture of nuts, herbs, and spices), curry, and more.
For dinner and a show, the Strand Theatre is around the corner. A restored vaudeville-era performance hall, it hosts some of Boston’s most diverse cultural programming, including an urban Nutcracker and a Chinese interpretation of Romeo and Juliet.
Go for dinner and dancing at Dbar, which hosts entertainment every night of the week. Heaters extend outdoor dining year-round, and Dbar After Dark transforms the gastropub into a thumping, LGBTQ-friendly nightclub. You can also enjoy nightlife and live music at Boston Harbor Distillery; dinner and pairings at the family-owned Boston Winery; and roller-skating at Chez Vous, a rink that’s been a Dorchester hotspot for nearly a century.
For generations, people of all ages have made memories at Franklin Park Zoo. Encompassing 72 expansive acres, the urban oasis transforms into an otherworldly landscape in wintertime. A backdrop of bright-white snow makes it easier to spot year-round residents, including lions, zebras, camels, and red pandas. The tropical forest is also a welcome respite from the frosty outdoors at a balmy 72 degrees indoors, where you can meet gorillas and hippos.
Explore Martin Luther King Jr.’s legacy in Roxbury
Roxbury has some of Boston’s most impressive murals, including this one by neighborhood native Rob “Pro Black” Gibbs.
Courtesy of Meet Boston/Jessica Mading
Roxbury is the destination for learning about Civil Rights leaders, including Dr. Martin Luther King, Jr., who met his wife, Coretta, in Boston. King ministered at Roxbury’s 12th Baptist Church, whose history spans the Abolitionist Movement, the Underground Railroad, the Civil War, and the early struggle for equal rights and education. Roxbury was also the boyhood home of Malcolm X, and his house is open to visitors.
One of the most immersive ways to fill in gaps in U.S. history books is at the Museum of the National Center of Afro-American Artists, which features visual and performing arts. Winter is the best time to experience them for yourself, with Kwanzaa celebrations and sponsorship of Langston Hughes’ Black Nativity stage shows.
Music fans will enjoy Roxbury’s enduring music heritage, which stems from its role as an incubator of jazz musicians immediately after WWI, leading to a broader appreciation for the genre that continues today. Check out free live jazz each Thursday night at Long Live Brewery & Taproom.
It’s an ideal nightcap after a day of discoveries in Nubian Square, where the buildings serve as canvases for some of the city’s most vibrant street art in turquoise, red, green, and other hues. Wall-sized murals by Pro Blak and GoFive depict famous Bostonians, including Dr. King and musician Donna Summer.
Here, you can also wander in and out of BIPOC-owned galleries and shops, supporting commerce and culture at Black Market Nubian. The community gathering spot features pop-up jewelry and clothing designers (perfect for holiday shopping or a new spring look), a gallery, and a community event venue.
Not a night owl? Another way to experience Roxbury’s history and culture is on a mid-day Live Like a Local walking and eating tour with founder and neighborhood native Collin Knight. Many tours also include tastings at Roxbury’s Bully Boy Distillers, the city’s first distillery since Prohibition.
Go birdwatching and hiking in Jamaica Plain
An escape from the city center into nearby nature offers reflection and peace. Harvard University’s 281-acre Arnold Arboretum stretches across an extensive swath of Jamaica Plain (or “JP” as locals call it). Open 365 days a year with complimentary admission, this gem in Boston’s Emerald Necklace park system, designed by iconic landscape architect Frederick Law Olmsted, offers indoor exhibits, guided hikes, and events year-round. In winter, these include mushroom foraging, a drop-in Little Explorers club for kids, and opportunities that are only available when the trees aren’t in full bloom—it’s much easier to spot owls and other non-migratory birds in winter than in any other season.
JP is also home to many of Boston’s mom-and-pop restaurants, where you can travel the globe every night of the week on a plate. At Noodle Barn, warm up with an aromatic bowl of pho, a traditional Vietnamese soup. Find Scottish comfort food galore at the Haven pub, with house-made lamb sausage. Choose your spice level with the colorful, vegetarian-friendly meals at the Ethiopian restaurant, Blue Nile.
Tres Gatos is another local favorite on Centre Street, the main thoroughfare. A Spanish tapas hotspot and wine bar, it’s more than a restaurant, selling books and vinyl from a tiny shop in the back. The warm woods, earth tones, and vintage brick fireplace make this a top pick for wintry date nights or a solo supper at the high-top counter.
Dessert fans will want to leave room after every meal in JP, too. It’s the original location of Boston’s most iconic ice cream shop, J.P. Licks, which is still going strong on Centre Street. (Try the seasonal peppermint stick flavor, available only in winter.)
Those looking for culture should check the schedule at Eliot Hall, also known as the Footlight Club. The green Greek Revival-style building, listed in the National Register of Historic Places, houses America’s oldest community theater, which has been in operation for nearly 150 years. Today, the line-up includes seasonal highlights like A Christmas Carol and up-and-coming playwrights.
Toast to your trip at the flagship location of Sam Adams Brewery, one of the forefathers of the country’s craft beer movement, in Jamaica Plain. Winter Lager, Cold Snap, and the spiced and citrusy Holiday White Ale are all available on tap during the winter, along with entertainment that includes game night on Tuesdays, wing night on Wednesdays, trivia on Thursdays, and live music every Sunday afternoon.
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