22 best things to do in winter in Boston

The great thing about Boston is it is just a short drive from tons of skiing and snowboarding options. Stay close by and head to the White Mountains,  Blue Hills Ski Area or Nashoba Valley Ski Area for some after work skiing. Nashoba also offers tubing! Take a day trip to Mount Sunapee or Crotched Mountain. Or plan a full weekend trip to world renowned ski resorts like Stowe Mountain Resort, Killington, or Sugarloaf. Read our full guide on the best skiing near Boston.

Winter in New England is not for the faint hearted. The cold days, long nights and howling winds take its toll on all of us. But if you ask any local, they will tell you that you just need to lean into it and try to enjoy the season. One of the best ways to do this is to get outdoors and enjoy the natural beauty that our region is blessed with—just be sure to wear a warm jacket! Heading up North for a ski trip is one of the best ways to stay active in the wintertime and these days there are plenty of activities to keep the non-skiers/boarders busy as well! Stowe, Vermont in particular has so much to offer everyone this year.

Where to stay in Stowe 

The best place to stay in Stowe is the Lodge at Spruce Peak. This ski-in/ski-out hotel is located on the Spruce Peak side of Stowe Mountain Resort, where guests can access Mt. Mansfield via the Over Easy Gondola, which links you up to the main Mansfield Gondola. The Lodge at Spruce Peak has a wide range of accommodation options, ranging from studio rooms to 2-, 3- or 4-bedroom apartments for the whole family. There is also a new development that has just been completed called, One Spruce Peak, which are super luxe condos, many of which are available for guests to rent as well! And yes, the resort is dog friendly. 

Dining in Stowe 

There are so many great options on the mountain, in the Lodge and in the town of Stowe when it comes to dining. Here are all the spots you won’t want to miss: 

Tipsy Trout

Tipsy Trout is a cool, casual spot at the Lodge that focuses on cocktails and seafood. Start with some items from the raw bar and perhaps some sushi and then move onto a main course like the indulgent Uni Bucatini. They are open daily for après ski and dinner.

Alpine Hall

Alpine Hall is the fine dining option on property and this farm-to-table spot works to highlight the best of Vermont. Chef Sean Blomgren crafts an elevated, yet comforting menu each season and right now you really can’t go wrong no matter what you choose. Alpine Hall is open for breakfast, lunch and dinner daily. 

Whistlepig Pavilion

This cozy spot feels like something straight out of the Alps. Focusing on Whistlepig and raclette, this is the place to be during après, each afternoon—there is both indoor and outdoor seating.

Doc Ponds

Head into town for the coolest gastro pub around. Doc Ponds has some amazing beers and elevated comfort food on the menu. But it is first come first serve, so be prepared to wait on busy weekends for dinner.

Chef Dinner Series

Spruce Peak has some exciting foodie evenings coming up this season with a special culinary series at Tipsy Trout. “We’re constantly expanding and adding to our culinary program here at Spruce Peak,” says Executive Chef Sean Blomgren, who oversees the program. “Our winter dinner series welcomes back celebrated chefs to Spruce Peak and allows their creativity to flow using the finest seasonal ingredients from our vast collection of small-batch purveyors.” On February 28 Chef Brendan Vesey of Boticana in Portsmouth, NH and on March 28 Chef Will Gilson of Puritan and Co. in Cambridge, MA will be coming to Stowe. Tickets are $175 per person.

A Boston classic! Once the weather gets cold Frog Pond in the Boston Common is frozen over and open for skating. Admission is $6 for anyone over 4’8” and free for anyone under. Adult skate rentals are $12 and kid rentals are $6. They also have a season pass option for people who want to go regularly.

Get all the details here.

Embrace winter in the Seaport at “Snowport.” Every year the Seaport sets up a winter village, last year Snowport included ice skating, iceless curling, large scale versions of classic games like Jenga and more. We can’t wait to see what Snowport features in winter 2023. Stay tuned for the details here.

You can rent a private igloo at the Envoy Hotel’s Lookout Rooftop Bar. Enjoy cocktails and delicious bites in a cozy, heated igloo with your friends. At night the igloos light up and are the perfect spot to view the Boston skyline. Make reservations for Envoy here.

Need to escape the cold? The Isabella Stewart Gardner Museum offers the perfect tropical oasis. Open 6 days a week, admission is $20 for adults. Or plan a visit for the first Thursday or the month. Museum admission is free from 3 pm through 9 pm and interactive programs kick off at 5 pm. Explore art, architecture, and seasonal horticulture displays in the Palace, and visit the studio for hands-on art-making activities that change each month. The Café is open late for dinner and drinks. Reserve your tickets.

There's nothing quite like feeling that biting winter wind against your face as you shred down a slope of fresh powder on your snowboard. Fortunately, Boston offers pretty ready access to a selection of snowboarding spots that are only a couple hours away from downtown. These areas cater to boarders of all skill levels, from beginner to basically pro. You'll find lessons and great facilities, too, so there's no reason not to go for it.

Fight the cold with some hot chocolate this winter. Lots of Boston restaurants are getting creative with fun takes on this classic drink. Whether it’s after a day of shoveling snow or just following the brisk walk from your place to the bar. Round up your friends (for added warmth) and grab these hot drinks to beat the bitter cold and just chill out. Read our full guide on the best hot chocolate in Boston.

Another hidden sanctuary from the cold, the Map Room Tea Lounge at the Boston Public Library is a great spot to warm up when the weather gets frosty. They host parties of up to 5 guests at one of the three 90-minute dining experience times. Book reservations here.

The BSO has a packed winter season, the season kicks off in January when renowned violinist Midori joins Israeli conductor Omer Meir Wellber in his BSO debut for Pyotr Tchaikovsky’s beloved Violin Concerto. See a full 2022-2023 season lineup.

We all love to take a good walk in a winter wonderland, and the Arnold Arboretum is the perfect place for a picturesque stroll this time of year. While this botanical park is open year round, it just looks so much more peaceful and pristine when coated in a blanket of freshly fallen snow. Listen to the crisp powder crunch beneath your feet and breathe in the cold air—all while admiring its assortment of trees, which impress even when they're bare.

No cozy weekend is complete without a crackling fire. A number of hotels throughout New England offer the ultimate winter luxury of ensuite fireplaces. Whether it's for warming up after an afternoon of outdoor sports, setting the mood for a romantic night in or simply staying snuggly on a snowy day, these spots feature in-room fireplaces that not only offer function, but also an ambiance you can’t get with just any weekend away.

Majestic views of Mount Washington, world class skiing, amazing dining and hotels, what’s not to love about winter in New Hampshire’s White Mountains? New Englanders know that in order to survive winter you need to embrace it and one of the best places to do that is just a 2.5-hour drive from Boston. In the White Mountains there is a little something for everyone, from world class skiing and snowboarding to tubing and snowshoeing. Aside from outdoor activities, the White Mountains are packed with so much worth discovering this season.

Perhaps the most nostalgic winter pastime is spending a day whizzing down a hill on a sled again and again and again. Whether you're a parent who wants to let the kids run wild outside or an adult who's looking to indulge your inner child and slide down a hill yourself, there are plenty of places for sledding and tubing near Boston. Grab your sled of preference and head to one of these spots for a carefree outdoor outing. 

When the winter winds are whirling, it’s easy to opt for take-out or delivery. But several restaurants around the Boston area promise to warm you up to the idea, enticing chilly guests with their roaring fireplaces. What could be cozier than dining next to a warm fire? Next to nothing—so check out these spots.

The biggest Broadway show in the last 10 years, Hamilton is coming to Boston. Playing at the Opera House from January 17 – March 12, tickets start at $85. Don’t miss your chance to see this world famous musical. Book tickets here.

Just outside of the city is the 7,000-acre Blue Hills Reservation. While avid skiers won’t be wowed by its modest downhill runs, it's the perfect place for cross-country skiing. More than 100 miles of trails allow plenty of opportunity to have a heart-pumping trek through a snowy forest. There are loops of varying degrees of difficulty, from 1—4 miles, so skiers of all levels can enjoy.

Al fresco dining in winter is possible here in Boston, thanks to heated patios, terraces and rooftop igloos. Local restaurants have introduced a number of warm options that'll let you eat, drink and snuggle outside, even in the dead of winter. Put on those thick layers of clothing and outerwear, and cozy up at one of Boston’s best restaurants with heated outdoor dining.

There’s no better way to warm up after playing in the snow than a steaming cup of hot chocolate. Luckily, our city plenty of spots where you can enjoy this rich treat. Whether it’s classic hot chocolate with a dollop of whipped cream from LA Burdick, a spicy, chili-tinged concoction from Flour, or a French-style drinking chocolate from Thinking Cup, there's a cup of cocoa that'll please everyone's palate. Find a variety of ways to sip this comforting winter drink with our list of the best hot chocolate in Boston.

Coming to Boston for the first time SIX is a two-time Tony Award winning musical following the lives of Henry VIII’s six wives. Playing from November 9  – December 31, tickets start at $45. Reserve here.

When winter descends upon Boston, too many of us commit to confinement within our apartments when we could be cozying up in some of New England's most picturesque cabins available on Airbnb. Check out these cabins near Boston that you can rent and, in no time, you’ll be unwinding in front of a fire and cooking up comfort food—or going for a brisk hike and swishing down slopes, if you’re the active type. 

If you’re looking to get out of the city for the day—whether it’s to embrace the chilly weather with an outside adventure or simply cozy up indoors to admire the snow from afar—there are plenty of places worth a visit. Explore all that New England has to offer, including quaint, historic towns and shoreline stops, as well as gaming destinations and, of course, buzzing hubs for outdoor activities situated in the beautiful mountains.