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8 Charming New England Winter Destinations You Must See

Take this season to the next level with these New England winter destinations!

Discovering the magic of winter in New England is an adventure like no other.

With its dramatic landscapes, historical appeal, and a touch of old-world grace, New England offers many delightful winter destinations that appeal to travelers looking for an enchanting and unique getaway.

New England winter destinations are famous for their postcard-worthy settings, where snow-covered roads, colonial architecture, and cozy bed and breakfasts create a winter wonderland straight out of a children’s book.

Whether you enjoy cozy fireside retreats, outdoor adventures, or exploring charming towns decked out in holiday lights, this region of our beautiful country has it all.

From the magnificence of Vermont’s Green Mountains to the coastal gems of Maine, we’ll take you on a trip through the heartwarming New England winter experiences that will leave you with never-ending memories.

So, let’s embark on a memorable winter voyage as we introduce you to these 8 Charming New England winter destinations.

New England Winter Destination
Photo by Prestigious PHotos at Shutterstock

Stowe, Vermont

Foodies will love their drive into Stowe with the Cold Hollow Cider Mill and the Ben and Jerry’s Factory on the drive off the highway. Be sure to leave enough time to visit both on your way into this adorable New England winter destination.

Once you arrive in Stowe, you’ll have several fun activities for families, including those at Stowe Mountain. It’s a lovely, quintessential New England town with boutiques, restaurants, and many beautiful things to see.

Freeport, Maine

Freeport is mainly known for being the worldwide headquarters of LL Bean. But the area also has several outlet stores and smaller shops.

If you’re traveling with kids or grandkids, they’ll love exploring the flagship LL Bean store, where there are many kids’ activities in addition to clothing and other outdoor gear. And for a completely different experience, check out Wolfe’s Neck Farm.

It offers several family programs and has free admission daily. Freeport is also conveniently located around other popular towns in Maine. So you can simply drop by on a day trip if you’d prefer.

And even though we’re talking about a different season today, this charming New England winter destination is also an incredible place to visit to glimpse the beautiful fall foliage.

Stockbridge, Massachusetts

Your next stop on this quest to find the best New England winter getaways is the charming and traditional Christmas town of Stockbridge. It might just be the perfect destination if you’re looking for winter holiday charm.

If you’re a fan of Norman Rockwell, you’ll get a glimpse of his slice of classic Americana because he painted many of his works of art inspired by this New England winter destination.

Cradled among the Berkshires, Stockbridge has lots to offer, and there’s plenty in the towns nearby as well. For instance, in Lenox, you can join one of the holiday tours at Edith Wharton’s The Mount.

And you can also head off to the historic estate of Naumkeag. It puts on the magical Naumkeag Winter Lights for the holidays from December through January.

Westerly, Rhode Island

Another charming New England winter destination, Westerly, is usually visited as a summer vacation hotspot. But those stunning ocean views don’t stop being exquisite when winter rolls around!

You’ll enjoy exploring the downtown area without fighting off the summer crowds, and there’s plenty for you to explore! You can stop in Tapped Apple Cidery and Winery for a tasting, go shopping, and eat at any of Westerly’s top eateries.

But if you decide to book a room at the elegant Ocean House resort, you won’t even have to leave your hotel to have the perfect New England winter getaway! We must mention that it’s on the pricier side when it comes to New England winter destinations.

Yet it delivers a lot of value in exchange for its higher rates, with gourmet dining, an onsite spa, ocean views, and adorable little touches of luxury everywhere you look.

Ask about their charming Gondola Village winter experience and book a suite with an ocean view and a fireplace to maximize the winter coziness!

New England Winter Destination
Photo by Ritu Manoj Jethani at Shutterstock

Jackson, New Hampshire

Another lovely little New England winter destination, Jackson, is home to so much fun in the colder months, making this a great family vacation destination.

You can go skiing at Wildcat Mountain, then head to Nestlenook Farms for quaint, family-friendly winter fun like sleigh riding, ice skating, and, obviously, hot cocoa sipping!

Families with smaller children will love the nearby Story Land amusement park in nearby Glen and Santa’s Village amusement park in Jefferson!

There are several cozy cabins in the White Mountains if you’d like to rent a place for your stay, but if you’d like to stay in Jackson, check out Christmas Farm Inn and Spa!

While not Christmas-themed, it’s cozy and has an onsite spa and indoor pool. So there will be something for everyone in the family to enjoy!

Lincoln, New Hampshire

Lincoln is a serene New England winter destination for those seeking the best getaways for the colder months. A mere 2 hours from Boston, it’s a lovely place for those who like to spend time outdoors in nature, especially in winter.

The charming place has a cozy, small-town vibe but with a few quirky, locally-owned shops and restaurants. It’s home to some of the most popular ski resorts on the Eastern Coast and includes one of the only Ice Castles in our country.

You can spend your day skiing at the Village of Loon Mountain Lodges. The small, family-friendly resort has 370 acres of skiable terrain and 61 runs. And the nearby RiverWalk Resort is also an amazing choice for winter activities in town.

For some delicious grub with an eclectic atmosphere, grab lunch at the Gypsy Cafe in the middle of Lincoln. And at night, go to the Common Man for dinner. Then, visit the Ice Castles in the neighboring community of North Woodstock.

This acre-sized frozen fortress is completely made of ice. With ice caves, slides, tunnels, and fountains, this icy attraction looks like something out of a storybook. The entire experience is illuminated in the evening with color-changing LED lights implanted in the ice.

All in all, it’s a fun New England winter destination for adults and kids alike to spend a few hours exploring.

Rockport, Maine

Located on Cape Ann in Massachusetts, Rockport has a small-town charm and beautiful views…and it’ll probably be your new favorite New England winter destination!

In this artistic town in the middle of Maine, first inhabited in 1769, you can observe seagulls circling the lobster boats in the harbor and take a stroll through the downtown area to find farm-to-table, restaurants and galleries.

And check out the statue that’s been dedicated to Andre the Seal, and doubles as the perfect spot for a cozy nature hike at Beech Hill Preserve.

Just be sure to pack some warm and comfortable shoes for your trip. Here are OUR favorites from Amazon: Columbia Women’s Ice Maiden II Snow Boot

New England Winter Destination
Photo by Carol Ann Mossa at Shutterstock

Mystic, Connecticut

This New England winter destination offers many family activities, including Olde Mistick Village, a shopping center of little buildings designed to look like a village from the 1700s. It’s a fun historical town to explore.

Mystic is also home to the Mystic Aquarium, a wonderful aquarium your children will love. But if your kids are a bit older, they’ll relish seeing Mystic Seaport, a maritime museum with interactive displays and exhibits.

We recommend staying in Mystic for at least a weekend since you’ll want to have a few days to see the Aquarium, Seaport, and Village. And be sure to stop by Mystic Pizza while you’re here!

Be sure to leave us a comment and let us know which of these New England winter destinations you’ll be visiting first. But don’t go away yet!

Must See Places has much more to offer. For instance, we highly recommend you check out: Top 5 Low-Cost Winter Vacations in Our Beautiful Country

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