Woodstock Inn & Resort

Woodstock, VT

The Proposition

Embrace winter in all its sit-by-the-fire-in-a-cozy-sweater glory at The Woodstock Inn & Resort, where you can ski, spa, eat, relax — and bring the kids (pets, too!). Set in a postcard-perfect town in the Green Mountains, the inn offers 142 charming, upscale rooms with furnishings by local artisans.

The lobby’s monstrous stone fireplace beckons immediately, as if you’ve arrived in a classic New England living room. Touches of the inn’s Federalist history (it was first opened in 1793) are visible all around, while the newly renovated lobby (part of a recent multimillion-dollar refresh) showcases books and artwork from the private archives of Laurance and Mary Rockefeller, who reopened the Inn in 1969. 

Cozy nooks abound: Play chess or backgammon behind French doors in the library or grab a hardcover off the bookshelf and park yourself in one of the comfy public seating areas. If you’re traveling with kids, hit the lower-level rec room, complete with arcade favorites, pool, Ping-Pong, Wii, and a giant, wall-sized Scrabble game. (Warning: You will have to drag them away!) Guest rooms are luxurious but not stuffy, with wood-burning fireplaces and ample, white subway-tiled bathrooms.   

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On-property dining includes Richardson’s Tavern (historic-
tavern atmosphere, farm-fresh pub food, local craft brews and spirits) and the Red Rooster, using the ingredients of revered New England purveyors. The 10,000 sq ft, LEED-certified spa (offering a bit of funky, modern décor to break up all the Colonialism) is not to be missed. 

If you’re not up for winter adventures — or you have kids under “snowplowing” age — stroll the quintessentially Vermont Main Street. Quaint shops, eco-friendly boutiques, darling toy stores (plus an impressive children’s library), and country restaurants blend seamlessly. Just outside of town, you can spot covered bridges on your way to Billings Farm & Museum, the oldest registered Jersey dairy farm in the country. 

Must Do 

Experience the Green Mountains in winter. Just minutes away are the Suicide Six ski area (despite the scary name, it’s actually a great mountain for kids and beginners) and Tubbs Snowshoe & Nordic Adventure Center (more than 30 km of groomed trails for cross-country skis, snowshoes, and fat bikes, plus specialized excursions including family-friendly scavenger hunts). 

Average High & Low Temperatures

Dec: 34°F & 14°F
Jan: 29°F & 6°F
Feb: 33°F & 8°F
Mar: 41°F & 19°F

Average Snowfall

Dec: 17 inches
Jan: 23 inches 
Feb: 17 inches
Mar: 18 inches

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Prices start at $280; www.woodstockinn.com


Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

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