Long Weekend in Woodstock, Vermont

Beat the winter blues with some time out of town—and outside—in the quaint Vermont village of Woodstock. With outdoor adventures, notable local cuisine, and unique shops, it's easy to see why Woodstock is consistently considered one of the top towns in the Green Mountain State. Here's how you should spend a snowy winter wekeend in this charming small-town getaway. 

Friday

Kick your snowy weekend into gear with some skiing or snowboarding. Guests at the inn can ski for free on weekdays (children ski free every day) at Suicide Six, just a few minutes north of town. While it may not have a huge number of trails, the lack of crowds and steep runs like The Face make up for any shortcomings. For more resort options, consider stopping en route to Woodstock at larger Okemo or massive Killington.

For a local take on the après-ski scene, stop by the Long Trail Brewing Company for a short self-guided tour and a visit to the pub for hearty dishes like smokehouse sausage and onion rings. On tap, choose from the classic Long Trail Ale family, seasonal beers, or even some limited small-batch brews.

Warm up by the massive lobby fireplace at the Woodstock Inn & Resort, which blends top resort amenities with small town charm. Settle into one of the rooms or suites, all of which feature simple, Shaker-style furniture and white-marble bathrooms.

Saturday

For more Vermont flavor, stop by the Woodstock Farmers’ Market, a year-round indoor store, for excellent baked goods and gifts to go. To learn a bit more about the “farm” in the state's popular farm-to-table food, head to the Billings Farm and Museum, where the town’s story of sustainability is also on full display. Take some time to explore the town and its shops, from Pleasant Street Books, to the perfectly retro Woodstock Pharmacy (19 Central St.), to Lucky Elephant, where you'll find global goods.

For lunch with a side of shopping, head to Simon Pearce in nearby Quechee. The setting, a converted mill perched on the edge of the Ottauquechee River waterfall, is spectacular, and the modern American fare does not disappoint. Before or after your meal, explore the lower level’s glassblowing factory, store, and studio.

Spend the afternoon relaxing at the inn’s gorgeous spa, a recent, custom-built, LEED-certified addition to the property. Seasonal treatments vary, but you can’t go wrong with a massage or one of the spectacular signature treatments. Be sure to save time for the eucalyptus steam room, outdoor hot tub, and cedar sauna—all three are accessible with a day pass if you opt not to enjoy a treatment. Enjoy a spot of afternoon tea, not to mention a few homemade cookies, to further rejuvenate you.

For dinner on-site, you can choose between the cozy Richardson’s Tavern or The Red Rooster, which is more refined, but still relaxed. Whichever dining option you choose, don’t skip out on the throwback game goom—it's not just for kids. Enjoy a cocktail with your favorite diversion, whether it’s an arcade classic or the giant, wall-mounted, magnetic Scrabble board.

Sunday

Start your day with the inn’s buffet breakfast, complete with pancakes and the state's trademark maple syrup. Put on some warm layers and take the shuttle just south of town to the Nordic Center and Tubbs Snowshoes Adventure Center (both part of the larger fitness center, which also features a pool, indoor tennis courts, and yoga studio). Choose from cross-country skiing or snowshoeing on 18.5 miles of trails here. The flats along Kedron Brook are perfect for beginners, while more challenging trails wind up to Mt. Peg.

Before you get back on the road, enjoy lunch at the Worthy Kitchen, a “craft beer and farm diner.” Enjoy café-style service where you order at the counter and the comfort food, all with a local touch, is brought to your table. Favorite dishes include fried chicken and any of the burgers. Just don’t forget to save room for their doughnuts. You deserve a sweet end to your trip.

Additional Tips

Winter really kicks off in town with December’s Wassail weekend and the snow usually lasts until at least late March. But every season is stunning, with perfect weather in summer, glorious fall colors, and celebrations of everything maple syrup in “sugaring season” (a.k.a. spring).

Woodstock is a four-and-a-half-hour drive from New York City and less than three hours from Boston. Vermont highways don’t allow billboards so any route is pretty, but if you have extra time, explore back roads and count the covered bridges.

At the Woodstock Inn & Resort, you can choose from fireplace rooms to suites to the luxurious Tavern Wing options. The Inn offers winter packages, like the Tubbs Snowshoes Romance Excursion, with a horse-drawn sleigh ride and a guided snowshoe trek to a chef's dinner at Mt. Tom cabin.

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