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Jackson Gore Inn at Okemo Mountain Resort
Photograph: Courtesy Okemo Mountain Resort

The best things to do this winter in Boston

Make the most out of the colder season with these winter activities in Boston and New England

Olivia Vanni
Written by
Olivia Vanni
Written by
Eric Grossman
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No matter how snowy or cold winter in Boston can be, it's no time to hibernate. There are many things to do—both indoors and outside—during the city's chillier months. Outdoor sports enthusiasts can ski and snowboard their way through the season, while local ice skating rinks and sledding spots can keep even us novices busy outside. For folks who'd rather seek an opportunity to warm up, there's never a fireplace or hot beverage too far away. For other ways to get cozy beyond the confines of your apartment, grab a steaming hot bowl of the best ramen in Boston or snuggle up with a drink at one of the best cocktail bars in town. 

RECOMMENDED: Full guide to the best things to do in Boston

Best things to do outdoors in the winter in Boston

  • Things to do

One of the many delights of living in Boston is that day skiing is always a short drive away. While no one can predict the traffic, many ski options are within two hours from the city. New England's most in-demand slopes might be a little more of a trek—in other words, warranting a full weekend away from Boston—these ski spots offer well-groomed trails for all skill levels, plus terrain parks, lessons and prime base camp facilities.

  • Things to do
  • Ice skating

Glide your way through winter at one of Boston's many ice skating rinks. From outdoor options like the Common's Frog Pond to maintained indoor rinks like the Warrior Ice Arena, there's a place for everyone. Whether it's for a romantic date or a fun family outing, get ready to lace up a pair of skates and hit the ice is at one of these top spots this winter. 

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  • Things to do

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.

  • Bars

When temperatures drop below freezing, we could all use a stiff, hot drink here in Boston. Spiked libations will keep you toasty and tipsy—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.

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  • Attractions
  • Parks and gardens
  • Jamaica Plain

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.

  • Things to do

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. 

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  • Restaurants

When the winter winds are whirling, it’s easy to forgo plans that require donning your down jacket and heading out into the blistering cold. 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.

  • Attractions
  • Parks and gardens

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.

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  • Restaurants

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.

 

  • Hotels

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.

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  • Restaurants

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.

  • Travel

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. 

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  • Travel

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.

Explore the best of the holidays in Boston

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