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Omni Mount Washington Resort
Photograph: Courtesy Omni Mount Washington ResortOmni Mount Washington Resort

The best winter day trips from Boston

Looking for some winter fun and cold weather comfort? These destinations are all a short jaunt from The Hub.

Written by
Eric Grossman
Time Out Boston Staff

When it comes to winter fun, many locals immediately think of the best ice skating spots, coolest snowboarding destinations, or most popular places to ski near Boston, while others build plans around enjoying their favorite winter highlights, including—in normal times—lively festivals and special events. Some head inland towards quaint, historic towns, while others travel to the shoreline, enjoying another side to normally buzzing beach towns. Alternately, you can always stay close to the city and 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, Bretton Woods is a winter wonderland spread across more than 2,000 acres, at the base of the tallest peak in the Northeast, the mighty Mount Washington. There’s superb Nordic and Alpine skiing, a picturesque mountain top restaurant, and the Bretton Woods Canopy Tour zipline. Choose to glide on the slopes or among the snow-covered hemlocks; or choose both with a Zip & Ski ticket. Stop in after for a hot toddy and grand dinner at the nearby historic Omni Mount Washington Hotel, and soak in the old school glamour.

Woodstock, VT
Photograph: Courtesy The Woodstock Inn

2. Woodstock, VT

With its village green coated in deep snow, a winter visit to the picture-perfect town of Woodstock in central Vermont offers a certain romanticism. It’s the perfect setting for the annual Woodstock Snow Sculpture Festival, held every February. Given the village is a major artists colony, the bright, white sculpture display is something else. Browse Woodstock’s unique shops like FH Gillingham & Sons general store, or the Arts on the Green gallery. Dine at the Woodstock Inn’s garden-to-table Red Rooster restaurant, which boasts vegetables from the inn’s organic garden, or relax in the cozy Richardson’s Tavern, which is named after the village’s original 1793 inn. Visit the Billings Farm & Museum, a working dairy farm open to the public, which, along with the inn, is part of the Laurance Rockefeller estate.

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—with plenty of time for enjoying the town's quaint shops and fresh coastal air—and return before dinnertime, but we recommend making it an overnight trip, and there's no better place to stay than The Whaler’s Inn. Nestled just steps from the banks of the Mystic River and the Bascule Drawbridge, the Inn boasts five unique buildings, boasting hospitality and charm. While there, enjoy a meal at The Shipwright's Daughter, where Chef David Standridge celebrates local products and recipes with an inspired menu that changes daily.

No visit to Mystic is complete without a meal at The Oyster Club. One of Connecticut's most exciting and forward-thinking restaurants, this dining destination proudly introduces guests to the people, places, and practices involved in its truly unique menu. Dine on fried chicken with fermented chili mole negro, or seared hen of the woods mushrooms with warm ricotta, sunflower oil and shoots. Just remember to leave room for a couple of the hand-picked lobster buns, served on soft brioche with Koji butter, crispy shallors and lemon.

Newport, RI
Photograph: Courtesy Discover Newport

4. Newport, RI

Although summer is the most popular time to visit Newport, wintertime means fewer crowds and just as much grandeur—from its gorgeous Gilded Age mansions to a snowy Cliff Walk, there is plenty to see and do. 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 childrens fair, there’s the warming 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. Whether you're a guest or not, stop by the hotel's Nomi Park for only-in-R.I. treats like johnny cakes made with Kenyon's corn meal.

Kennebunkport, ME
Photograph: Courtesy Kennebunkport Resort Collection

5. Kennebunkport, ME

There’s a lot to explore, even during a stormy winter’s day, along the Maine coastline. Kennebunkport’s annual Paint the Town Red event stretches Valentine’s Day into a month-long celebration, bringing visitors to this popular summertime retreat. Lovely Dock Square in “downtown” Kennebunkport 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. The event’s signature Red Plate dining specials and Red Tag sales in shops add up to fun, and deals. 

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

6. Westford, MA

Ski, board, tube and soak in the 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!

Old Saybrook, CT
Photograph: Credit Frank Gilroy

7. Old Saybrook, CT

Every January, the waterside Saybrook Point Resort hosts the Fire & Ice Festival, which includes ice sculpting and fire dancing over two days of revelry. There’s live music and wonderful food and cocktails courtesy of the resort’s lauded Fresh Salt restaurant. Explore adjacent Saybrook Point and Fort Saybrook Monument Park, and take in the quiet winter beauty of these protected coastal wetlands. Take a look around Old Saybrook, a delightfully un-touristy town that’s home to the Katharine Hepburn Cultural Arts Center, or The Kate, which is named for the area’s most famous native daughter. Pop in for a performance, or to look at the lovely Hepburn memorabilia.

North Adams, MA
Photograph: Courtesy Yelp/Emily H.

8. North Adams, MA

Dissected by the Mohawk Trail, North Adams is a former blue-collar manufacturing town by the Hoosic River that now attracts serious art and nature lovers from across the country. For arts, immerse yourself in the spectacular, and very large, Massachusetts Museum of Contemporary Art, better known as MASS MoCA. Nature lovers and hikers head to Mount Greylock, Massachusetts’ highest peak, but best bring your snowshoes in winter. Take in the magnificent vistas over a bite at the Golden Eagle restaurant, which sits on Route 2’s truly hair-raising hairpin bend.

Jackson, NH
Photograph: Courtesy Yelp/Jackson Ski Touring Foundation

9. Jackson, NH

The covered wooden bridge (likely coated in snow) that you cross into this quiet valley town is worth the trip north alone. Once there, head to the Jackson Ski Touring Foundation’s nonprofit cross country ski and snowshoe center. There are 150 km of trails—considered some of the finest cross-country ski trails in the Eastern U.S.—threading around this picturesque village in the foothills of the White Mountains. The main lodge facility includes a retail shop, rental shop, and waxing area. There is a trail-warming hut, and ski lessons are available, along with snowshoe tours. Join the popular Friday gliders social ski, or one of the winter events or competitions. Fuel up and stop by the iconic Wentworth Inn or Eagle Mountain House for a bite.

Brattleboro, VT
Photograph: Courtesy Yelp/Marita G.

10. 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

11. Groton, MA

This tiny town beckons with the Groton Inn, a historic boutique property that dates back to 1678. Located just off Route 2 and overlooking snowy Gibbet Hill, the gloriously rebuilt inn impresses with its Forge & Vine restaurant. Nearby, enjoy a brisk stroll around the Rocky Hill Wildlife Sanctuary, home to uninterrupted woodlands and ample solitude. 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. Serious hikers head to Gibbet Hill Farm, whose trails offer sweeping views of the Merrimack Valley.

Uncasville, CT
Photograph: Courtesy Mohegan Sun

12. Uncasville, CT

Located in the tiny Connecticut village of Uncasville, Mohegan Sun offers a giant indoor winter playground packed with restaurants, bars and entertainment venues. The gaming tables and slots are one option, but there is so much more to do. There’s the Comix Roadhouse, a comedy club with live country music, the VIP-ready Avalon Nightclub, and the lively Lansdowne Irish Pub, just to name a few. While the Arena hosts ticketed, big name concerts, the small, cozy Wolf’s Den bar has free shows, sometimes with well-known performers. In January, the annual Sun Wine and Food Fest adds three days of wine, beer, and spirits tasting, plus celebrity chef demonstrations.

Plymouth, MA
Photograph: Courtesy Mirbeau Inn & Spa

13. Plymouth, MA

Held each January just outside of downtown Plymouth at the French chateau-inspired Mirbeau Inn & Spa, Fete D’Hiver is an indoors-outdoors winter fest with live music and dancing, fire performers, hors d'oeuvres, mulled wine, and special spiked hot chocolate. Stay warm in style by hanging at the roaring outdoor fire pit in the gorgeously designed gardens. Fete d’Hiver is one of many excuses to head south to Mirbeau in winter: it is also a day spa, where you can escape the cold weather wrapped in a plush robe, seated by the fireplace in the spa relaxation room, or soaking in the outdoor hot tub, awaiting much needed spa therapy. Every Sunday, there’s a jazz brunch in the Bistro & Wine Bar, which many attend still wearing robes. 

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