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The Woodstock Inn
Photograph: Courtesy The Woodstock InnThe Woodstock Inn

The best winter day trips from Boston

From cozy getaways to glittery jaunts, we found the most fun destinations to hit outside The Hub this winter

Written by
Tanya Edwards
Written by
Eric Grossman
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In New England, we take winter fun seriously—it’s how we thrive during this notoriously gloomy, cold season. 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. Rather stay closer to home? Check out some of the best attractions, best free things to do or best museums in Boston.

RECOMMENDED: Full guide to thebest things to do in Boston

Best winter day trips from Boston

Bretton Woods, NH
Photograph: Courtesy Omni Mount Washington Resort

1. Bretton Woods, NH

Located in the White Mountains National Forest, New Hampshire’s stunning Bretton Woods is a winter wonderland spread across more than 2,000 acres, at the base of the tallest peak in the Northeast, Mount Washington. You can take a canopy tour zipline, dine at the mountain top and, of course, glide down the slopes.

Woodstock, VT
Photograph: Courtesy The Woodstock Inn

2. Woodstock, VT

Most New Englanders know this bucolic village from summer and fall visits, but they’re missing the beauty of the green covered in a deep snow. It’s the perfect setting for the annual Woodstock Snow Sculpture Festival, held every February. You can also browse Woodstock’s unique shops like FH Gillingham & Sons general store, or the Arts on the Green gallery. Enjoy farm to table dining at the Prince and the Pauper, or grab a pizza and a nice glass of wine at the Ransom Tavern.

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Mystic, CT
Photograph: Courtesy The Whaler's Inn, Mystic CT

3. Mystic, CT

Scenic, historic Mystic is renowned for stellar attractions such as the Mystic Aquarium and Mystic Seaport Museum. Once you make the 90-minute journey from Boston, you can make a day of it—but if you choose to stay over, try The Whaler’s Inn. Nestled just steps from the banks of the Mystic River and the Bascule Drawbridge, the Inn offers inspired dining at The Shipwright's Daughter. Of course, no visit to Mystic is complete without a meal at The Oyster Club, and a trip to try the award winning pizza at Nana’s Bakery is a must.

Newport, RI
Photograph: Courtesy Discover Newport

4. Newport, RI

While you may think summer is the time to visit Newport’s glorious Gilded Age mansions, the annual Newport Winter Festival is among New England’s largest winter celebrations and takes place each February with ten days of events. Along with concerts and a children’s fair, there’s a killer Chili Cook-Off featuring chefs from local restaurants. Treat yourself to a fun, funky stay at one of the area's buzziest boutique properties, the Wayfinder, or stop by The Reef for classic seafood with impressive ocean views.

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Kennebunkport, ME
Photograph: Courtesy Kennebunkport Resort Collection

5. Kennebunkport, ME

The Maine coastline is always beautiful, but it’s even more stunning to see those mighty waves crash on a snowy afternoon. There’s lots to do too, like Kennebunkport’s annual Paint the Town Red event that stretches Valentine’s Day into a month-long celebration. Dock Square—the town’s unofficial center—is decked out in red twinkly lights, capped with an eight-foot glowing red heart created from lobster traps. Throughout the month, there are special pop-up dinners, mixology classes and wine tastings, many of them offering specials and deals.

Westford, MA
Photograph: Courtesy Nashoba Valley Ski Area and Snow Tubing Park

6. Westford, MA

Ski, board, tube and soak in the wintery scene at the Nashoba Valley Ski Area, just 25 miles west of Boston in quiet Westford. This family-owned resort has 18 beautifully groomed trails on 55 acres of terrain. The adjacent, separate tubing park has 18 lanes, making it New England’s largest such facility. Winter events include the annual Grease the Rail Jam and legendary freestyler Wayne Wong’s annual ski clinics with resort co-owner, Olympian Pam Fletcher. It all comes to a splashy end in March with the Meltdown Pond Skim: ski into slush!

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7. Dennis Port, MA

Is Cape Cod worth the visit in the winter? If you like uncrowded beaches, hiking and getting creative with activities—plus, not sitting in summer traffic—then the answer is yes. Take the under two-hour drive to Dennis Port and head outside to cross-country ski, snowshoe or, if the ground is bare, just walk the Cape Cod Rail Trail for a breathtaking view of the seascape during the winter. Stop by the Pelham House Resort for brunch with an ocean view (without the crowds!) and reserve a private beach bonfire for the whole group with s’more kits and spiked, salted hot caramel cocoa to end your perfect day.

Old Saybrook, CT
Photograph: Credit Frank Gilroy

8. Old Saybrook, CT

Old Saybrook, a very un-touristy town on the coast, is eminently walkable and is  home to the Katharine Hepburn Cultural Arts Center, or The Kate, which is named for the area’s most famous native. You can also explore Saybrook Point and Fort Saybrook Monument Park, and take in the quiet winter beauty of these protected coastal wetlands. Dine at the newly reopened The Essex, a local favorite that’s a Wine Spectator and Yankee Magazine award winner, or pop by the historic Monkey Farm for a more casual experience.

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9. North Adams, MA

North Adams is an old mill town by the Hoosic River that now attracts serious art- and nature-lovers from across the country, primarily due to the spectacular Massachusetts Museum of Contemporary Art, better known as MASS MoCA. Hikers and folks looking for some fresh air head to Mount Greylock, Massachusetts’ highest peak, but bring your snowshoes or a sturdy vehicle in the winter. For Berkshire farms inspired eats, try the Break Room at Greylock Works for a menu that changes daily.

10. Jackson, NH

If covered bridges iced with snow are your thing, you’ll get a treat heading into this quiet valley town. Once there, head to the Jackson Ski Touring Foundation’s nonprofit cross country ski and snowshoe center. Considered some of the finest cross-country ski trails in the Eastern U.S., at the main lodge facility you’ll find a retail shop, rental shop and waxing area. There is a trail-warming hut, and ski lessons are available, along with snowshoe tours. After a strenuous day outdoors, dig into a charcuterie board and pan roasted farm sirloin at the Thompson House Eatery.

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11. Brattleboro, VT

Brattleboro—a funky, artsy destination in the foothills of southern Vermont’s Green Mountains—is surrounded by wonderful hiking terrain, but you might also want to explore the town’s bohemian shops and farm-to-table eateries. Go vegan at the Superfresh! Organic Cafe, or head to the Chelsea Royal Diner, an original 1939 Worcester Lunch Car. In February, the annual Winter Carnival brings together the arts and entertainment communities for a weeklong jamboree. Visit the Vermont Jazz Center or one of the many artisan breweries. To learn about local history, stop into the Brattleboro Historical Society, which has a wonderful collection of memorabilia.

Groton, MA
Photograph: Courtesy Unsplash

12. Groton, MA

Head to this classic New England town and enjoy a brisk stroll around the Rocky Hill Wildlife Sanctuary, home to uninterrupted woodlands and ample solitude, and enjoy more than three miles of hiking trails while keeping an eye out for moose, beavers and porcupines, as well as nearly 100 species of birds. Other options include hiking Gibbet Hill Farm and exploring historic Bancroft Castle. If you’re visiting on a weekend, check to see if Puritan & Co.’s Will Gilson is cooking up dinner at his family farm, the Herb Lyceum.

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Uncasville, CT
Photograph: Courtesy Mohegan Sun

13. Uncasville, CT

If you’re not feeling outdoorsy, plug into the nightlife at Mohegan Sun. The casino is essentially a giant indoor winter playground packed with restaurants, bars and entertainment venues. The gaming tables and slots are one option, but you can also catch a comedy or music act. In January, the annual Sun Wine and Food Fest adds three days of wine, beer, and spirits tasting, plus celebrity chef demonstrations.

Everett, MA
Photograph: Courtesy Encore Boston Harbor

14. Everett, MA

There’s one major reason to head to Everett, and that’s the relatively new Encore Boston Harbor Casino. Stay warm and cozy 24 hours a day while you hit the tables, or enjoy a relaxing massage in the resort's luxurious spa (which is offering winter skin saving treatments, like the Skin Replenishing Ritual, all season long). Sample new flavors at Cheese Meet Wine or bet on the Pats at Wynn BET Sports Bar.

More foodie fun

  • Travel

It doesn't get much better than food and travel—why not combine the two and take a food-focused road trip? Here's a go-to itinerary for anyone looking to take in the area's best treats and culinary experiences. Given New England's relatively small footprint, you can mix and match these stops based on your liking.

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