16 best winter day trips from Boston

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.

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.

One of our favorite destinations in New England, Portsmouth has a thriving food scene, offers one-of-a-kind shopping, historic walking trails and a beautiful waterfront. Pick a dry day to walk around the shops, then hit Vida Cantina, owned by James Beard nominee David Vargas; or Toscana Italian Chophouse & Wine Bar for a warming bite. Earth Eagle Brewing’s taproom is a more casual option, with gourmet burgers and dogs that are worth the trip.

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.

October may be the busiest time of year to visit Salem, but the city is just as fun in the winter. With the Peabody Essex Museum, lots of great restaurants and so many other cultural things to do, Salem is a great day trip from Boston--especially because it is accessible via the commuter rail. So you don't even need a car!

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, stay at Castle Hill Inn, or stop by The Reef for classic seafood with impressive ocean views.

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.

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!

Enjoy an off-season stroll through history in this seaport town, on a cool winter day. Start by visiting the Newburyport Historic District, which encompasses most of downtown, and is listed in the National Register of Historic Places and includes the Cushing House Museum & Garden and the Custom House Maritime Museum. After taking in the local lore, dine on classic seafood at Michael’s Harborside or head to the Newburyport Brewing Company, both open year round.

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.

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.

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.

While visiting nearby Watch Hill, or as a stand-alone trip, sweet little Westerly is a decidedly non-touristy town with lots for visitors to do. Take a chilly stroll (or maybe not that chilly, based on the past few winters) on a stretch of Misquamicut State Beach, then head to downtown Westerly for fresh baked doughnuts at Knead, cocktails and oysters at High Hope Tavern and a modern Peruvian meal at Bar Pisco.

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.

This easy to navigate city should be on your radar year round for a day trip. Put on your warmest winter coat and treat yourself to a dine-around through Federal Hill, the city’s impressive Italian neighborhood, loaded with Italian eateries and shops. Visit the Rhode Island School of Design’s museum, which includes one the country’s finest university art collections, and don’t miss celebrated Syrian bakery Aleppo Sweets.

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.