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Hidden gems in Vermont to visit this winter from Boston

Cozy cabins, chic boutiques and tasty eats await.

JQ Louise
Katie McAleer
Edited by
JQ Louise
Written by:
Katie McAleer
stowe mountain
Photograph: Courtesy J.Q. Louise
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Throughout the long winter months many Bostonians escape to Vermont for the world-class skiing and boarding that can be found throughout the Green Mountain State. But Vermont’s allure extends far beyond the mountains, sprinkled throughout the state are charming small towns, award-worthy farm-to-table dining experiences, outdoor adventures and much much more. Put these Vermont hidden gems on your winter bucket list this season.  

The Weston, Weston VT

weston vermont
Photograph: Courtesy Katie McAleer

Formerly The Inn at Weston, this hotel was recently renovated and rebranded to create a bespoke hospitality experience in the heart of the Green Mountains. Every detail at The Weston has been thoughtfully designed, even down to the scent, we went home and immediately ordered the scent diffuser they had in the common areas because the whole place smelled incredible! The design of each room is unique, but they all provide a luxurious but cozy and welcoming atmosphere. The Weston has an impeccable onsite restaurant, The Left Bank. Guests will be drawn in on chilly winter days by the scent of the real wood burning stove but they will stay for the inspired menu serving French country bistro. The onsite spa is the perfect place to relax and enjoy a rejuvenating treatment this winter. The team at The Weston truly goes above and beyond to assure their guests have a wonderful time, oh and did we mention The Weston is dog friendly?!

The Oyster Bar at Pete’s Haven, Brattleboro VT

oyster bar vermont
Photograph: Courtesy Katie McAleer

Bostonian’s have their pick of some of the arguably best raw bars in the world at home, so it’s not always easy to wow a Bostonian with oysters and raw bar when they travel. But The Oyster Bar at Pete’s Haven wows! With a focus on small plates and apps made with fresh seafood, a daily-rotating raw bar, signature cocktails and an expertly curated wines this is the type of place to attract local regulars and visiting travelers alike. The space is small and cozy with a slight nautical vibe. They only serve small plates and apps and seating is first come first serve, for those looking for dinner reservations they can check out The Oyster Bar’s sister restaurant Pete Havens.

The Guilford Country Store and Cafe, Guilford VT

No visit to Vermont is complete without a visit to a classic country store and the Guildford Country Store and Café is an excellent choice. A gourmet deli and grocery store, visitors can grab something to go or order in and eat at the café. They have a delicious selection of specialty sandwiches or you can make your own. Visitors will also find an abundant selection of fresh pastries and baked goods and every day essentials. 

The Brattleboro Ski Hill, Brattleboro VT

Yes, everyone knows you can ski in Vermont, but did you know you can ski for just $5? The Brattleboro Ski Hill is a completely volunteer run hill with a single T-bar lift and 2 runs, and you can spend all day zipping down for just $5. A community gathering spot, this is a great hill for those just learning who aren’t ready to shell out $100+ a day for a lift ticket at one of the bigger mountains. For a small operation, Brattleboro Ski Hill is quite impressive, they have installed small jumps and boxes for those looking to get park practice, they’re open for night skiing for those who can’t make it during the day and they have recruited instructors from local mountains to teach lessons to local kids. They are completely volunteer run and rely on donations to operate, their largest costs come from snow making and grooming. The volunteer board is committed to their mission of keeping skiing accessible to everyone, learn more about the Brattleboro Ski Hill here.

The Mad Taco, Waitsfield VT

Skiing Mad River Glen is a flex for a reason, after a long day on challenging terrain you deserve some tacos! Head to The Mad Taco, just a short drive from Mad River Glen ski area. A local favorite, The Mad Taco serves incredible tacos, house-smoked meats and local craft beer. Chef-Owner Joey Nagy and his partner Georgia Von Trapp run Marble Hill Farm in Fayston, Vermont. The farm directly supplies The Mad Taco with much of the tomatoes, tomatillos, peppers, greens, cilantro, herbs, and a number of other vegetables used in house. Check out the menu here.

Vermont Icelandic Horse Farm, Fayston VT

Tour the mountains, meadows and forests on one of the oldest horse breeds in the world at the Vermont Icelandic Horse Farm. Experience the winter wonderland on horseback, ride Icelandic horses through the scenic trails and enjoy the beautiful Vermont landscape. They offer daily rides of varying lengths as well as 2-5 day riding packages. Must make reservations in advanced, get all the details here.

Dog Mountain, Saint Johnsbury VT

Dog lovers will appreciate a visit to Dog Mountain, it is set on 150 acres on a mountain top location in St. Johnsbury, Vermont. The grounds are always open to people and their dogs. This unspoiled haven is covered with hiking trails and dog ponds. Dogs are not just welcome here, they are cherished! Artist Stephen Huneck and his wife bought the property in the 1990’s and in 2000 opened the Dog Chapel. Today you can visit the Dog Chapel and Stephen’s art gallery on the weekends and the grounds and parks are open 7 days a week. Get more information and plan your visit here.

Hen of the Wood, Waterbury VT

Fine dining, but make it Vermont. Hen of the Wood is a true hidden gem if you’re a foodie, this restaurant offers farm-to-table dining focused on local and seasonal ingredients. Located in Waterbury’s historic downtown, the rustic and cozy atmosphere and innovative menu make it a delightful winter dining experience. Make a reservation, if you have a larger group you can also book their private dining room for the chef’s-choice experience.

The Calm Company Wellness Studio, Stowe VT

wellness studio
Photograph: Courtesy Katie McAleer

Cold plunging and saunas are all the rage in the health and wellness space right now! The Calm Company Wellness Studio in Stowe offers everything one needs for a relaxing and rejuvenating afternoon, including an outdoor barrel sauna! When you book a session in the outdoor barrel sauna it includes a cold plunge. The outdoor barrel sauna is located in their fire pit lounge and the experience can accommodate up to 6 people so you can make a day out of it with your friends. The Calm Company also has massage, cupping and energy healing services available, see the full service menu here.

Vermont Reindeer Farm, Orleans VT

reinndeer
Photograph: Courtesy Katie McAleer

Home of the only real live reindeer in Vermont! January through March visit the Vermont Reindeer Farm in Orleans to learn about the famed animals who pull Santa’s sleigh. After your time with the reindeer, you can opt in for a guided snowshoeing tour. By appointment only, get all the details and set up your booking here.

Want to explore more of New England this winter? Check out our guide to The White Mountains.

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