Winter Weekends You’ll want to leave the house for
Winter in New England can be brutal, but it’s also when some of the region’s most unforgettable experiences come to life. We’re not talking about just skiing and cocoa (though we love both). We’re talking snowmobile festivals, mountaintop rides, 1800s-style lantern-lit villages, and even polo on the beach. Here are five winter weekend trips in New England that feel anything but ordinary, and yes, they’re all worth bundling up for.
These five unique New England Winter Weekend Getaways will help you enjoy the season to the fullest.
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1. Jackson, New Hampshire
Don’t Miss: Great Glen Trails SnowCoach Tours & Jackson Invitational Snow Sculpting
Why Go:
Jackson is already one of New Hampshire’s most picturesque villages; but come winter, it ups the magic. The star experience? Riding in a heated SnowCoach that climbs 4.5 miles up the Mount Washington Auto Road, dropping you into otherworldly, wind-swept alpine terrain. No crampons, no avalanche gear, just views for days.
Time your trip in late January for the Jackson Invitational Snow Sculpting Competition, where professional sculptors transform 8-foot blocks of packed snow into wild, intricate frozen art. The atmosphere is low-key, friendly, and creative; think artists carving dragons or castles while visitors sip cocoa and cheer them on.
Stay at: The Wentworth Inn – classic New England charm with fireplaces and outdoor hot tubs. Be sure to Conclude your day with a lively dinner at the Wildcat Tavern, a beloved Jackson institution. Enjoy classic American cuisine in a cozy and historic setting. It’s a great spot for friends to gather, share stories, and enjoy a delicious meal.
2. Brattleboro, Vermont
Don’t Miss: Brattleboro Winter Carnival (early February)
Why Go:
Brattleboro is Vermont’s indie, artsy town—and its Winter Carnival keeps that quirky energy going even in the dead of winter. The weeklong celebration features snowshoe races, ice skating parties, pancake breakfasts, live music, and more. There’s even a cornhole tournament (because, Vermont).
When you’re not outside enjoying the snow, explore the town’s standout food scene. Grab a craft beer at Whetstone Beer Co. with a view of the icy Connecticut River, then catch a show at Latchis Theatre, a stunning Art Deco cinema.
Outdoor option: Hit the nearby Grafton Trails for cross-country skiing or snow tubing with zero lines and all the views.
3. Mystic, Connecticut
Don’t Miss: Lantern Light Village at Mystic Seaport Museum (select weekends in December)
Why Go:
Think Mystic is just for summer? Think again. Come winter, the Mystic Seaport Museum transforms into a 19th-century village lit by lanterns, with carolers in period dress, historic reenactments, fireside storytelling, and plenty of roasted chestnuts. The Lantern Light Village experience walks you through scenes of Christmases past—complete with dancing, drama, and mulled cider.
Once you’re feeling the nostalgic glow, warm up at Engine Room with craft cocktails and some of the best burgers in the region. Or stroll over to the Mystic Aquarium to visit the belugas and penguins.
Where to stay: The Whaler’s Inn – right in downtown Mystic, walking distance from everything, with cozy coastal decor.
4. Newport, Rhode Island
Don’t Miss: Newport Winter Festival (mid-February)
Why Go:
Most people think of Newport for summer mansions and sailing. But in February, the city throws one of the Northeast’s biggest cold-weather parties: the Newport Winter Festival, packed with live music, food tastings, beach bonfires, and even a hot drink contest where local bars battle it out for best winter cocktail.
But here’s the kicker: they play beach polo—yes, actual horse-mounted polo on the snow-covered beach. The mix of elegance and pure winter weirdness makes it unforgettable. Bonus: the Gilded Age mansions (like The Breakers) are open and far less crowded than in summer.
Stay at: Gurney’s Newport Resort & Marina – stunning harbor views, firepits, and a spa if you need a post-festival warm-up.
5. Rangeley, Maine
Don’t Miss: Snodeo Snowmobile Festival (January)
Why Go:
If you want the full-throttle Northern New England winter experience, Rangeley delivers. This remote mountain town turns into snowmobile central every January for Snodeo, a weekend-long snowmobile festival featuring radar runs, vintage sled shows, fireworks, and gear expos.
Even if you’re not into sleds, you’ll love the scene: bonfires, beer tents, ice fishing shacks, and true Maine hospitality. Between events, strap on some snowshoes or try fat biking along the Rangeley Lakes Trail Center. Keep your eyes peeled for the elusive moose are known to make an appearance.
Fuel up at: Forks in the Air – one of the best spots in town for upscale comfort food and craft cocktails.
Where to stay: The Rangeley Inn – classic lodge vibes with modern updates, and snowmobile trail access right out the back.
Final Thoughts
Discover New England Winter Weekend Getaways
Winter in New England doesn’t have to mean staying in and counting the days until spring. Whether you’re into the romance of lantern-lit villages, the thrill of snowmobiles, or the spectacle of polo on the beach, there’s a weekend destination that’ll make you glad you embraced the cold.
Just don’t forget the mittens.
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