October 31, 2025
Condé Nast Traveler
10 Best Winter Activities in Boston, From Curling to Rooftop Happy Hour in Igloos
There’s a lot to love about winter in Boston, especially if you’re not the one tasked with shoveling the storied brick sidewalks. Even if you are, there’s a soul-warming mug of hot chocolate and a wood-fired sauna awaiting you afterward, among other seasonal delights.
You see, New Englanders are a hardy bunch. They’re experts at maximizing their enjoyment of wintertime in the city—not despite Nor’easters and below-freezing temps, but because of them. The only way to truly enjoy the season is to embrace it, which is why Boston consistently has a long list of cold-weather activities on offer. Ahead, find 10 of the best ways to spend your next Boston winter, with options for both outdoors and indoors enthusiasts.
Ever tune in to the Winter Olympics to see athletes furiously sweeping a path on ice for granite stones to slide down? Curling, no doubt, makes for an intriguing spectator experience. Yet it somehow appears approachable enough to make you think, “I could do that.” You can find out for yourself at Boston’s Liberty Hotel, which offers a “curling experience” for groups of two to six people on the weekends.
The Liberty’s curling setup deviates slightly from the ones you see on TV. The rink is synthetic, for one, and there are no brooms involved. Instead, it’s closer to oversize shuffleboard; you kneel at the center of the lane and hurl the disks (technically called “stones,” though these are smaller than regulation ones) toward the target. As you play, you’ll enjoy a box of treats, complete with cinnamon-dusted churros, homemade strawberry Pop-Tarts, Korean chili chicken sliders, crispy pork and ginger dumplings, and a carafe of hot chocolate. Afterward, enjoy “après-curl” in the hotel’s cozy lounge.
Boston’s Beacon Hill neighborhood is graced by cobblestone streets, gas lamps, and stately brick rowhouses. When it snows, the place seems to resemble a real-life snow globe, so it’s worth taking a trip to wander its meandering sidewalks. One of the best ways to spend an afternoon here is by ducking in and out of the neighborhood’s many antique shops. You’ll want to start your treasure hunt on Charles Street, Beacon Hill’s main thoroughfare, where there’s an antique shop in seemingly every other storefront. Among the standouts are Upstairs Downstairs Home, Elegant Findings Antiques, Fabled Antiques, Boston Antiques and Lamp Shades, and Bridge Antiques and Fine Art. After you’ve secured a vintage print or two, browse the stacks at Beacon Hill Books & Cafe, which feels like stepping inside someone’s beautifully appointed home. Then, with shopping bags in tow, sit for afternoon tea in the shop’s stunning lower-level café.
Lacing up your ice skates and gliding around the Frog Pond in Boston Common is the city’s most iconic winter activity, and rosy-cheeked skaters of all skill levels have been happily circling the pond for decades. Established in 1634, the Common is the oldest public park in the US. It retains much of its old-world charm, thanks to mature trees and wide-open spaces that recall its former life as a pasture for cattle grazing. Come wintertime, those same fields are blanketed in snow, so when you’re on the ice, you’re gazing out at a literal winter wonderland—all softly lit by the glow of colorful twinkle lights. You can rent skates at the rink and stash your stuff in a locker if you’d like. The Frog Pond Café, meanwhile, offers hot chocolate, coffee, and other beverages, in addition to snacks like waffles and grilled cheeses.
If you’re not a native New Englander, you may not be familiar with candlepin bowling. For the uninitiated, this version uses thin, candle-shaped pins and a much smaller bowling ball without any holes to grip it. The pins aren’t cleared between rolls, either, and instead of two shots, you take three. The result is a game that’s a bit more challenging than ten-pin bowling—and a lot more fun. Give it a shot at Sacco’s Bowl Haven in Somerville’s Davis Square neighborhood, where you’ll find all the hallmarks of classic candlepin (wooden booths, scuffed-up lanes, goofy shoes for rent) with an elevated twist: a full bar and wood-fired pizza from American Flatbread. Though the place has been updated since it opened in 1939, its history shines through. Rumor has it Sacco’s is a former mob hangout, and the bowling alley was once featured on an episode of Ghost Hunters because of, well, alleged ghost sightings.
Sipping a steaming mug of hot chocolate is a non-negotiable once temperatures drop. The second non-negotiable? Enjoying the absolute best cup in town, which can be found at L.A. Burdick Chocolates. The stuff is actually gourmet drinking chocolate, and you can choose from a variety of flavors, from milk chocolate and white chocolate to dark chocolate and spicy dark chocolate. The vibes in the store are equally as rich; the Back Bay location feels like a cozy cottage nestled in the heart of the city, while the Harvard Square and Coolidge Corner shops are equally charming. Consider ordering a slice of linzer torte or earl gray mousse cake to enjoy with your hot chocolate. And whatever you do, don’t leave without a box of the shop’s famous chocolate mice—each whimsical bonbon is shaped by hand, taking 12 steps over the course of three days to create.
One of the top places to admire Boston’s skyline is from across the Fort Point Channel. Here, the Envoy Hotel is perfectly positioned to frame views of the city, and its rooftop bar, aptly named Rooftop at the Envoy Hotel, is the ideal place to gaze upon them. Come wintertime, bar patrons are invited to cozy up inside a glowing orb, otherwise known as an igloo. Up to six people can reserve a heated igloo for a maximum of two hours. The experience involves a menu of craft cocktails (care for a “Meili Mule” made with Fabrizia Limoncello and ginger beer?) and small plates (including truffle parmesan fries or buffalo cauliflower bites), not to mention those priceless views. And even if you don’t reserve an igloo, you can still enjoy the rooftop bar—if you’re bundled up, that is.
Sometimes cold weather necessitates a craft day. At Tutuland in Boston’s Allston neighborhood, you can try your hand at a variety of crafts, from poured art to phone-case making to beading. But the flagship experience here at the “land of craft lovers” is rug tufting, a process that involves using a tufting gun to punch loops of yarn through stretched fabric. This creates a puffy pile on the front of the fabric, eventually resulting in a rug of your design. Your rug can take on any shape you like, and there are what feels like endless yarn colors to choose from. Some popular rug designs include strawberries and other fruits, flowers, cartoons, pets, and more. Small rugs, which are about 17 inches by 17 inches, take roughly two and a half hours to complete, while larger ones can take four hours or more.
A surefire way to beat the winter blues isn’t by escaping cold weather, it’s by embracing it. Nordic cultures have been doing this for centuries, and now Boston is doing the same. That’s where Moki comes in: The company creates “outdoor wellness villages” featuring wood-fired saunas, cedar barrels for cold plunges, and fireplaces. The idea is to cycle between hot and cold to experience a list of health benefits, including stress relief, mood enhancement, muscle recovery, and improved circulation. This ancient Scandinavian bathing practice is referred to as “Nordic cycles” or “Viking baths,” and it’s grown in popularity over the past few years. You can try it out at Moki’s location in South Boston—an indoor/outdoor warehouse—or in Allston, which is all outdoors. Real sauna heads can even buy a membership.
Every year from early November through late February, Boston’s Seaport neighborhood hosts the wildly popular Snowport. It’s a wintry takeover of the Seaport’s central plaza, filled with events, shopping, food, drinks, and more. And during November and December, revelers flock to the Snowport Holiday Market, which features more than 120 small businesses, 17 dining concepts (Swiss-style Raclette, anyone?), and one very large mistletoe arch. At the Holiday Market, you can browse booths selling European cheeses, pottery and ceramics, glass art and home decor, artisanal soaps, hand-poured candles, textiles, spices, winter flannels, specialty chocolates, and more. Plus, when the holiday season comes to a close, you can still enjoy Snowport’s curling lanes, appearances from “Betty the Yeti,” and other activities.
Try to picture the Platonic ideal of a vintage movie theater in your head. There’s a good chance what you’re envisioning looks pretty similar to the Coolidge Corner Theater, a beloved independent cinema in Brookline. You can’t miss its iconic Art Deco neon sign out front, but it’s what’s inside that keeps cinephiles coming back. The theater, opened in 1933, specializes in international, documentary, animated, and independent film selections in addition to popular series, seminars, and classes. Listings and screenings are updated weekly, as are signature programs like “Hong Kong Cinema Classics” and “The Sound of Silents.” The design, of course, is another draw; more Art Deco flair bedecks the lobby, and its six theaters are dripping in regal touches like rich red velvet drapes, comfy crimson seating, and gilded wall and ceiling designs.
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