There’s something truly magical about winter in New England—and Massachusetts stands out as one of the region’s most captivating destinations. From charming small towns draped in snow to vibrant cities buzzing with holiday festivities, the Bay State transforms into a winter wonderland that’s hard to resist.
Not sure where to go or what to see this season? Don’t worry—we’ve rounded up some of the best places across Massachusetts to help you make the most of your winter getaway. Keep reading to discover top spots that are perfect for snowy adventures, cozy retreats, and everything in between.
Lenox: A Cultural and Cozy Winter Retreat
Lenox is another Berkshire gem that shines in the winter months. Known for its cultural richness and Gilded Age mansions, Lenox blends history, arts, and snowy landscapes like few places can.
A visit to The Mount, author Edith Wharton’s grand estate, is especially enchanting with a dusting of snow.
Many local inns and bed-and-breakfasts offer fireside relaxation, gourmet meals, and spa services perfect for warming up after a day outdoors. If you’re into winter sports, nearby ski areas like Bousquet or Jiminy Peak are within easy reach. Or simply stroll the peaceful streets and pop into locally-owned bookstores, boutiques, and bakeries.
Lenox offers the kind of winter calm that makes you want to stay an extra day—or three.
Nashoba Valley Snow Tubing Park
Can’t ski? Try tubing! Head to Nashoba Valley Snow Tubing Park in Littleton this winter and hit the tube slopes. Reserve tubing time slots for up to 2 hours in one of the park’s 18 tubing lanes.
Just be sure to buy your admission ticket in advance – tubing tends to sell out quickly!
Lowell Winterfest
Lowell hosts an annual Winterfest every February, which features a weekend of activities, entertainment and food.
The winter carnival is one of the top highlights of the annual Winterfest. It features an inflatable slide, carnival rides, marshmallow roasting, horse and carriage rides, a chocolate-eating event and more. Make sure to mark your calendars accordingly and get to Lowell this February.
Plymouth: History Meets Winter Tranquility
Plymouth is best known as “America’s Hometown,” and while most visitors flock here in the warmer months to explore its iconic historic sites, winter in Plymouth has a quiet beauty that’s just as worth experiencing. Imagine standing by the harbor where the Mayflower once docked, with snow gently falling and the chilly Atlantic breeze carrying centuries of stories.
The crowds are gone, which means you can explore spots like Plymouth Rock, the National Monument to the Forefathers, and Plimoth Patuxet Museums at your own pace—and often with discounted admission.
Winter brings a special calm to the waterfront, where you can stroll along the jetty, watch the winter waves roll in, and grab a steaming cup of chowder from a local seafood joint. Many of the restaurants and cafes stay open through the season, offering cozy spots to warm up and enjoy local flavors. The town also lights up with seasonal events, from holiday strolls to ice sculptures, giving it a festive vibe through January and beyond.
Jiminy Peak
Wachusett Mountain isn’t the only place in Massachusetts to hit the slopes this winter. Jiminy Peak, located in Hancock, is an outdoor enthusiast’s paradise. Known for its status as the largest ski resort in southern New England, you can hit the slopes while taking in a great view.
Another neat thing about Jiminy Peak is its Mountain Adventure Park, which features thrill rides and scenic chairlift rides to take in the views.
Bash Bish Falls
Bash Bish Falls on Mount Washington isn’t just breathtaking in the summer months. The tallest waterfall in the state is also beautiful in the winter. Located within Bash Bish Falls State Park, you can choose to hike trails anywhere from 0.6 to 12.4 miles to get to the waterfall depending on how much time you have and your hiking skill level.
Boston Frog Pond
Looking to lace up the skates and hit the ice this winter? The Boston Frog Pond in downtown Boston is a perfect destination.
Skating on the Frog Pond opens every December and runs through March. Skate rental is also available. If you’re there in late November, you might even be able to catch The Haydenettes ice skating club as it performs annually to coincide with the annual Boston Common Tree Lighting to usher in the holiday season.
Northampton: Artsy Vibes with a Winter Twist
Northampton is one of those places that feels effortlessly cool, no matter the season. But in winter, this progressive college town takes on a serene and magical feel.
The snow-covered sidewalks are lined with locally owned shops, indie bookstores, and art galleries that beckon you inside for warmth and inspiration. If you’re into music or theater, check out a show at the Academy of Music.
Hungry? The food scene here is unexpectedly amazing, with everything from vegan cafés to cozy pubs. Winter hikes in nearby Mount Tom State Reservation offer stunning views—and fewer crowds. Whether you’re after culture, coffee, or just a unique winter vibe, Northampton is a chill (in the best way) place to be.
