There is something undeniably cinematic about Boston when the first dusting of snow hits the cobblestones of Beacon Hill. In 2025, the city has fully embraced its "snow globe" reputation, blending its deep-rooted history with a high-energy social scene that makes even the coldest February night feel like a scene from a holiday rom-com. Whether you are a local looking to spice up your weekend or a traveler chasing that perfect winter aesthetic, Boston’s winter lineup is more vibrant than ever.
The best winter activities in Boston this year range from the nostalgic to the ultra-trendy. You can glide across the historic Frog Pond, browse the sprawling Snowport Holiday Market in the Seaport, or test your aim with curling at the Liberty Hotel. For those who prefer to stay warm, the city’s nightlife has leveled up with glowing igloo bars at the Envoy Hotel and "après-ski" pop-ups at Deck 12. If you’re looking for a cozy indulgence, nothing beats a thick, gourmet drinking chocolate from L.A. Burdick in the Back Bay.
1. Glide Across the Historic Frog Pond
There is no winter activity more quintessential than ice skating at the Boston Common Frog Pond. Nestled within the oldest public park in the United States—established way back in 1634—this rink offers a sense of history that you simply won't find at a modern arena. As the sun sets and the surrounding trees begin to twinkle with thousands of LED lights, the atmosphere becomes purely magical.
We recommend visiting on a weekday evening to avoid the heaviest crowds. The rink attracts thousands of skaters annually between November and March, but there is plenty of room for everyone from wobbly beginners to seasoned pros. After you’ve worked up an appetite on the ice, head over to the Frog Pond Café for a hot cocoa or a quick snack to warm your hands.
Fast Facts: Frog Pond Skating
- Location: 38 Walnut St, Boston (Boston Common)
- Price: Admission is $10 for skaters 58 inches and taller; free for those under 58 inches.
- Rentals: Skates are available for $10–$15.
- Best For: Families, romantic date nights, and history buffs.
2. Shop and Sip at the Snowport Holiday Market
If you’ve seen a festive reel of Boston lately, chances are it was filmed at Snowport. This seasonal takeover in the Seaport District has become one of the largest and most successful holiday markets in New England. It isn't just a place to shop; it's a full-blown winter festival that runs from early November through late February.
The market features a curated selection of over 120 small businesses, offering everything from hand-poured candles to artisanal jewelry. But let’s be real—half the fun is the food. With 17 different dining concepts on-site, you can find everything from Swiss-style Raclette (melted cheese over potatoes) to hearty Tuscan soups. We suggest grabbing a drink at the "Tree Bar" and exploring the various "Instagrammable" photo ops scattered throughout the stalls.
- Pro-Tip: Download the Seaport Insider App before you go. It often features exclusive discounts for market vendors and real-time updates on wait times for the popular food stalls.
- Must-Try: The hot buttered rum from the central bar area is the perfect companion for a brisk walk through the market.
3. Experience 'Après-Curl' at the Liberty Hotel
One of the trendiest ways to spend a Saturday afternoon in 2025 is "Après-Curl" at the Liberty Hotel. For those who aren't familiar with the venue, the Liberty is a stunning architectural marvel—a luxury hotel converted from the historic Charles Street Jail. Every winter, they transform their private outdoor courtyard into a synthetic curling rink.
This isn't your typical Olympic curling match; it’s a high-energy social event for groups of two to six. The hotel offers 45-minute slots where you can try your hand at the sport while enjoying a dedicated "après-curl" menu. Think less "locker room" and more "chic lounge."
The vibe here is unbeatable—expect a crowd of well-dressed professionals and social media influencers enjoying the crisp air under the shadow of the hotel's granite walls. It’s the perfect blend of activity and indulgence.
The Après-Curl Menu Highlights
- Cinnamon-Dusted Churros: Served warm with a chocolate dipping sauce.
- Korean Chili Chicken Sliders: For a spicy kick to combat the cold.
- Spiced Hot Chocolate: Available with or without a "kick" of bourbon or peppermint schnapps.
4. Cozy Up in a Rooftop Igloo or Ice Box
If you want the best view of the Boston skyline without the frostbite, the city’s rooftop igloos are a must-visit. The pioneer of this trend, the Lookout Rooftop at the Envoy Hotel, remains the gold standard. These glowing, heated bubbles allow up to six people to sip craft cocktails while looking out over the Fort Point Channel and the downtown skyline.
For a slightly different vibe, head over to Deck 12 at Yotel. Their winter pop-up leans into the "Ice Box" and "Après-Ski" aesthetic. Instead of just igloos, they often feature themed gondola tables and a menu focused on alpine comfort foods like fondue. It’s the closest you’ll get to a Swiss ski resort while staying in the heart of the city.
Igloo Bar Comparison: Envoy vs. Yotel
| Feature | Lookout Rooftop (Envoy) | Deck 12 (Yotel) |
|---|---|---|
| Max Capacity | 6 People | 6-8 People (Gondolas/Yurts) |
| Time Limit | 2-hour maximum | 90 minutes - 2 hours |
| View Type | Harbor & Financial District | Panoramic Seaport & Cityscape |
| Food Focus | Small plates & shared apps | Fondue & Après-ski comfort food |
| Vibe | Sophisticated & Trendy | Playful & Nostalgic |
5. Master the Art of Candlepin Bowling at Sacco’s
When the wind chill becomes too much to bear, retreat to the suburbs (specifically Somerville) for a round of candlepin bowling at Sacco’s Bowl Haven. If you aren't from New England, candlepin might look strange—the balls are small enough to fit in your hand (no finger holes!), and the pins are thin and tall. You get three rolls per frame, and the fallen pins (the "wood") aren't cleared away between rolls, adding a layer of strategy to the game.
Sacco’s is legendary not just for the bowling, but for the food. It shares a space with American Flatbread, meaning you can enjoy organic, wood-fired pizzas while you play. The atmosphere is loud, retro, and incredibly welcoming.
- Best For: Budget-friendly fun, large groups, and pizza lovers.
- Price: Around $30–$40 per hour per lane (check their site for peak vs. off-peak pricing).
6. Sip the City's Richest Drinking Chocolate at L.A. Burdick
Forget the watery cocoa of your childhood. At L.A. Burdick, hot chocolate is treated like a fine art. Known as "Drinking Chocolate," this beverage is essentially a melted chocolate bar served in a cup. You can choose from milk, white, or dark chocolate, with the dark being a fan favorite for its intense, complex flavor profile.
For the ultimate winter treat, order the "Spicy Dark Chocolate," which includes a hint of chili and spices to warm you from the inside out. Don't leave without picking up one of their signature hand-crafted chocolate mice. These tiny treats take three days to make and are almost too cute to eat (almost).
Insider Tip: The Back Bay location on Clarendon Street is the most iconic, but it’s often crowded. If you’re looking for a slightly quieter experience, head to their Harvard Square or Coolidge Corner locations.
7. Get Crafty: Rug Tufting at Tutuland
Looking for a viral hobby to try this winter? Rug tufting has taken over social media, and Tutuland in Allston is the place to do it in Boston. This activity involves using a pneumatic tufting gun to shoot yarn through a fabric canvas, creating your own custom rug, wall hanging, or mirror frame.
It’s an incredibly satisfying process, though it does require a bit of patience. A standard session lasts anywhere from 2.5 to 4 hours depending on the complexity and size of your design (a small rug is usually about 17x17 inches). It’s the perfect indoor activity for a group of friends who want to create something tangible while staying out of the slush.
- Location: Allston (The "student" hub of Boston, filled with great Korean BBQ and boba spots for post-tufting fuel).
- Level: Beginner-friendly; instructors guide you through the whole process.
8. Embrace the Cold with a Nordic Cycle at Moki
One of the newest and most unique additions to Boston’s wellness scene is Moki. Following the Nordic tradition of "contrast therapy," Moki offers wood-fired saunas and cold plunges. The idea is to spend 15 minutes in the intense heat of the sauna followed by a quick dip in a 40-degree cold plunge.
This cycle is scientifically proven to improve circulation, reduce stress, and provide a massive endorphin rush. Moki has locations in South Boston and Allston, offering both indoor and outdoor setups. There is something incredibly invigorating about sitting in a hot sauna while looking out at the falling snow, only to step out and feel the freezing air on your skin.
9. Catch an Indie Film at the Iconic Coolidge Corner Theater
If you want to escape the winter weather while soaking in some culture, the Coolidge Corner Theater is a Brookline institution. Opened in 1933 as a community playhouse, it maintains its stunning Art Deco design, complete with neon signs and plush velvet drapes.
While they show major blockbusters, the real draw here is their independent, international, and documentary programming. They also host the famous "Sound of Silents" series, where silent films are screened with a live musical score. It’s a sophisticated, cozy way to spend a Saturday night.
- Why it’s great: It feels like stepping back in time. Grab some popcorn, head to the "Big Screen 1," and forget that it's 20 degrees outside.
10. Take the 'Ski Train' to Wachusett Mountain
Did you know you can go skiing without ever touching a car steering wheel? The MBTA Commuter Rail runs a "Ski Train" on the Fitchburg Line that takes you directly to the Wachusett station. These trains are specially equipped with modified ski coaches that have racks to hold your skis and snowboards.
Once you arrive at the station, a complimentary shuttle picks you up and whisks you away to Wachusett Mountain. It’s the ultimate "car-free" winter getaway for city dwellers. Whether you’re a black-diamond expert or just there for the lodge vibes and après-ski drinks, it’s a refreshing break from the urban grind.
Logistics Tip: Check the MBTA website for the "Winter Weekend" schedules, as times can vary. The train ride takes about an hour and a half, giving you plenty of time to enjoy the scenic New England views.
Frequently Asked Questions (FAQ)
What is the best way to get around Boston in the winter? While Boston is a very walkable city, the "T" (the subway system) is your best friend when it’s snowing. The Green Line and Orange Line serve most of the tourist-heavy areas like the Seaport, Back Bay, and Downtown. If you’re heading to the igloo bars, ride-sharing apps like Uber and Lyft are very reliable even in the snow.
How far in advance should I book the igloos or curling? For the Envoy’s Lookout Rooftop and the Liberty Hotel curling, we recommend booking at least 2-3 weeks in advance, especially if you want a weekend slot. These are some of the most popular activities in the city and they sell out fast.
Is the Snowport Market open every day? Yes, the Snowport Holiday Market is typically open daily, though hours are extended on Fridays and Saturdays. Keep in mind that it can get very crowded on weekends, so a weekday visit is preferred if you want a more relaxed shopping experience.
Ready to embrace the chill? Boston in 2025 is a masterclass in making the most of the winter season. From the historic charm of the Common to the high-tech warmth of a rooftop igloo, there is a vibe for everyone. Don't forget to tag us in your "après-curl" photos!
