The Best Neighborhoods around Boston to Explore in the Snow

Photo by Madeline Bilis

When a nor’easter hits the city, it’s easy to grumble about the woes of commuting delays, snow shoveling, and slush-soaked shoes. But it’s not all doom and gloom when the flakes decide to fall. Discover beautiful neighborhoods, epic sledding hills, and breathtaking holiday lights in the snow with our guide to the best Boston neighborhoods to explore in winter.

Fort Hill

For the outdoors-y contingent… Bundle up in a snow jacket and scarf before wandering the streets of this Roxbury enclave. It’s stuffed with pocket parks and community gardens begging for a wintry expedition. Head to Highland Park for a steep sled ride down from the Fort Hill Tower. Around the corner, drop by Marcella Playground and Cedar Square Park to play. Or stroll through Margaret Wright Memorial Garden and Rockledge Street Urban Wild for lush public gardens heavy with a fresh dusting.

Photo by Leslee_atFlickr via Flickr/Creative Commons

Back Bay

For chocolate lovers… If staying inside is more your speed when the weather outside is frightful, take to Newbury Street on a snow day. Just off Newbury on Clarendon, sequester yourself in the brasserie-style chocolate shop, L.A. Burdick, with a to-die-for cup of drinking chocolate. Or, one block away, reserve a window booth at MET Back Bay and relish in the hot chocolate flight of your childhood dreams. After you’ve had your fill of warm drinks, brave the cold outdoors for a brisk walk under twinkling lights on the Comm. Ave. mall.

Charlestown

For history nerds… Travel back in time on a snowy evening in Charlestown, where historical buildings and gas lamp-lined streets look particularly picturesque under a dusting of snow. Stroll down Main Street to peep clapboard buildings crafted in the 1800s, from the Former Methodist Meetinghouse to the Charlestown Inn. If it gets too cold to wander any longer, slip into Warren Tavern on Pleasant Street. It’s one of the oldest taverns in the country, and a former haunt of George Washington and Paul Revere. Raise a pint (and a warm cup of soup) in the antique pub while you watch powder coat the streets outside.

Jamaica Hills

For the artists… If an untouched lawn of fresh snow gets your creative juices flowing, trek over to JP and swing by Harvard University’s Arnold Arboretum for an endless supply of vistas to craft your magnum opus. Leave your snowman behind and loop your way around Olmsted Park, north of the Arboretum. It’s packed with picturesque pathways and stone bridges that weave through Willow, Ward’s, and Leverett Ponds. Before you head home, make time for a stop at the Jamaica Pond Sugar Bowl, an inverted hill where adventurous sledders aim for high speeds to launch themselves down one side and up the other.

Photo by Owen and Aki via Flickr/Creative Commons

Buttonwood Village

For the whole family… Pack the kids in the car and head to Larz Anderson Park for a day filled with frosty fun for every family member. As the largest park in Brookline (not to mention a listing on the National Register of Historic Places), it boasts huge expanses of lawn and an active children’s playground on even the coldest days. East of the playground, the Jack Kirrane Skating Rink sits on a hill overlooking the city. Climb up the incline to skate for hours—or to sled right back down the steep slope. The best part? Catch an unparalleled view of Boston blanketed in snow from the top.

Davis Square

For marathon trainers… Disciplined runners know that snowy weather is no excuse for a day off from pounding the pavement. Strap on your sturdiest shoes for the slippery spots and sprint to the Somerville Community Path for a gorgeous tree-lined jog in the snow. Wave hello to the dozens of other pedestrians you’ll surely pass. After all, Boston is a marathon city at heart.

Somerville lights photo by D MW on Flickr/Creative Commons

Winter Hill

For holiday light fanatics… Every year, Somervillians scramble for tickets to the coveted Illuminations Tour. On a guided trolley, the lucky ticket-holders wind through the streets of Winter Hill and East Somerville to ooh and ahh at a show-stopping array of neighborhood Christmas lights. This 2019 tour has already passed, but you can still buy a map and take your own tour to experience the holiday magic. There’s something enchanting about twinkling lights against a backdrop of fresh, fallen snow that could make even the Grinch’s heart grow.

South Boston

For those who prefer the après over the ski… After a long day of sledding—or of clearing a parking spot—you deserve some luxurious rest and relaxation. South Boston is home to some of the coziest restaurants for escaping the wintry chill. Designed to look like an après ski destination, The Lodge at Publico boasts furniture made from repurposed skis and a vintage chairlift. If winter sports aren’t your thing, cozy up by the stone-studded, wood-burning fireplace at Italian restaurant Capo, or at the hearth of the modern Local 149.

Photo by Madeline Bilis

Beacon Hill

For amateur photographers… Under a fresh layer of snow, the cobblestoned streets of Beacon Hill transform into a veritable winter wonderland. Explore historic brownstones sprinkled with festive wreathes and garlands, and marvel at elegant Christmas trees making bashful appearances in living room windows. Holiday décor packs the storefronts of the neighborhood’s boutique shops, luring onlookers inside. Don’t forget a pit stop at the iconic Acorn Street to snag a coveted snapshot for the ’Gram.