15 best winter day trips from Boston

What is it?  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.

Why go? The state’s largest ski area, offers 434 acres of ski and snowboard terrain, 101 trails and glades, and four terrain parks. Dog sledding, snow tubing and snowmobiling offer equal thrills for those who seek them.

Don’t Miss: Don’t feel like traveling at top speeds? Try Nordic skiing, snowshoeing or ski-joring, a sport involving one dog, a harness, a bungee and a pair of cross-country skis.

What is it?  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.

Why go? It’s the perfect setting for the annual Woodstock Snow Sculpture Festival (known as The Flurry) held every February – this year it’s Feb 13-15. You can also browse Woodstock’s unique shops like FH Gillingham & Sons general store, or the Arts on the Green gallery.

Don’t Miss: 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 at The Kedron Valley Inn.

What is it?  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.

Why go? The dining scene is thriving in Portsmouth, so what better way to escape the chilly temps than with a piping hot plate and a steaming cup (or a body-warming cocktail or two).

Don’t Miss: 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.

What is it?  This seaside town is on most people’s radar for the Julia Robert’s first breakout role in 1988 in Mystic Pizza, but it has so much more to offer once you dig in.

Why go? Scenic, historic Mystic is renowned for stellar attractions such as the Mystic Aquarium and Mystic Seaport Museum. 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.

Don’t Miss: 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.

What is it?  October may be the busiest time of year to visit Salem, but the northshore seaside city is just as fun in the winter. It’s the same gorgeous views of the water, fun shops and bistros, and eclectic residents - just minus all the spook-seeking tourists.

Why go? 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. Translation: no car needed.

Don’t Miss: For libations and tasty meals, check out Ledger Restaurant & Bar, which elevates 19th-century dishes, cocktails, and techniques. If you want a little history, check out the House of Seven Gables – the inspiration for world-renowned American author Nathaniel Hawthorne’s 1851 novel.

What is it? While you may think summer is the time to visit Rhode Island's beloved ocean-front town, don’t underestimate a winter stroll through its center, stopping along the way for seaside snacks and off-season shopping deals.

Why go? The annual Newport Winter Festival is among New England’s largest winter celebrations and takes place each February with 10 days of events (this year it’s held on Feb 13-22. Along with concerts and a children’s fair, there’s a killer Chili Cook-Off featuring chefs from local restaurants.

Don’t Miss: Stop by The Reef for classic seafood with impressive ocean views. Also a trip to a few of the Newport's Gilded Age Mansions, decked out for the season, is a must-do.

What is it?  The Maine coastline is always beautiful, but it’s even more stunning to see those mighty waves crash on a snowy afternoon.

Why go? There are beautiful beaches (Gooch's and Goose Rocks) to stroll, cozy dining with fireside options, historic inns to stay, and scenic drives (Ocean Avenue) to partake in.

Don’t Miss: 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.

What is it?  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.

Why go? 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!

Don’t Miss: Head to the tubing park in nearby Littleton, which is the largest tubing park in New England and home to 18 lanes are serviced by two lifts.

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.

What is it?  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.

Why go? 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.

Don’t Miss: 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. Also of note is the newly opened Love Farms, which features a year-round market, a restaurant and multi-coursed tasting room. There’s live music every Thursday through Sunday, prix-fixed dinners in their Harvest Room, fire pits and farm tours.

What is it?  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.

Why go? 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.

Don’t Miss: For Berkshire farms inspired eats, try the Break Room at Greylock Works for a menu that changes daily.

What is it?  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.

Why go? 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.

Don’t Miss: After a strenuous day outdoors, dig into a charcuterie board and pan roasted farm sirloin at the Thompson House Eatery.

What is it?  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.

Why go? 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.

Don’t Miss: Go vegan at the Superfresh! Organic Cafe, or head to the Chelsea Royal Diner, an original 1939 Worcester Lunch Car.

What is it?  This easy to navigate city in Rhode Island should be on your radar year round for a day trip. Sure the summer's WaterFire isn't for a few more months, but that doesn't mean the city isn't lit up wtih fun things to do during the colder season.

Why go? 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. There's also a vibrant, historic, and contemporary art scene, nicknamed "The Creative Capital," centered around institutions like the Providence Art Club (one of America's oldest) and Rhode Island Schools of Design (RISD).

Don’t Miss: Visit the RISD’s museum, which includes one the country’s finest university art collections, and don’t miss celebrated Syrian bakery Aleppo Sweets.

What is it?  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.

Why go? 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 our days of wine, beer, and spirits tasting, plus celebrity chef demonstrations.

Don’t Miss: All that gaming and entertainment can work up an appetite, so fuel up at a few of the excellent on-site 44 restaurants - we're fans of Pepe Pizzeria (although it can get crowded) and Boston's own Summer Shack.