15 Ways to Spend the Perfect Winter Day in Woodstock, Vermont
In the heart of the Green Mountains, a Christmas card–worthy village and its surrounding hamlets shine with New England charm.
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Nestled in Vermont's Green Mountains, Woodstock is bound to charm visitors in any season thanks to its pretty historic homes, well-curated shops, and quaint, small town details: there are zero stoplights in town and local events are announced on a bulletin board on the town green known as the Woodstock Town Crier.
Winter is especially picturesque though, thanks to an annual average snowfall of 82 inches, which means a winter wonderland is practically guaranteed. Spend the day exploring the snowy trails of the state's only National Park or swooshing down the slopes of the nearby Suicide Six Ski Area— or just unwinding with a visit to Woodstock Inn & Resort's Spa. In December, Woodstock hosts its annual Wassail Weekend, which includes an equine parade through town, sleigh rides across snow-dusted fields at the historic Billings Farm & Museum, and strolls to take in the Christmas lights along the town's streets, festooned in holiday decorations, followed by free hot wassail and cookies at the First Congregational Church.
A visit to Woodstock is easy to combine with trips to other nearby, beloved Vermont towns like Stowe or Shelburne, and is a 1.5 hour drive from the airport in Burlington (BTV). For other travel ideas, be sure to checkout our guide to New England's most charming small towns.
Ready to start planning your winter getaway to the small town of Woodstock? Read on for the ideal itinerary, which includes our favorite restaurants, shops, sights, and ways to celebrate the season.
Rise & Dine
Start the morning at Mon Vert Cafe, which serves Vermont Coffee Company brews and breakfast specialties like the Monte Vert Cristo: ham and Cabot Swiss cheese on challah French toast with a side of local maple syrup.
Read All About It
Get the latest local news and info on upcoming events via the community bulletin board, the Woodstock Town Crier. Then pop by the ongoing used-book sale in the lobby of the Norman Williams Public Library (housed in a ca.-1884 pink sandstone building on the Green), or browse new titles on the shelves of Central Street’s Yankee Bookshop, Vermont’s oldest bookseller.
Hit the Trails
Cross-country ski or snowshoe the groomed grounds of Marsh-Billings-Rockefeller National Historic Park with equipment from the Woodstock Nordic Center. Trek to the top of Mount Tom for a pretty bird’s-eye view of town.
Stroll & Shop
Load up on stocking stuffers like maple syrup samplers, penny candy, and the shop's famous St. Emilion macaroons at the 135-year-old F.H. Gillingham & Sons general store. Cross the street for cozy, handcrafted clothing and blankets from town mainstay Vermont Flannel Company, then take a short drive to South Woodstock Country Store, which sells festive essentials like fresh wreaths and candles alongside lunch fare, local craft beers, and old-fashioned doughnuts.
Book a Clay Date
Make your own souvenir—and shop seriously beautiful handmade ceramics like these Christmas ornaments—during a workshop at Farmhouse Pottery's flagship studio.
Cross the Covered Bridges
Four historic covered bridges span the Ottauquechee River, including Middle Bridge on Mountain Avenue, just off the village green.
Celebrate the Season
Woodstock’s annual Wassail Weekend takes place December 10th through 12th. The celebration includes an equestrian parade, as well as holiday stories, gingerbread ornament- and candle-making, and warm cups of wassail served with cider donuts at the dairy barn of the 150-year-old Billings Farm & Museum. Bundle up the family for a horse-drawn sleigh ride through snow-covered pastures.
Settle In for the Evening
Picturesque Woodstock Inn & Resort supplies plenty of holiday cheer with festive decor and treats like tea and cookies. For a cozy evening at the inn, visit Richardson’s Tavern for fondue followed by games in the library.
Nominate Your Favorite Small Town!
Where should we mosey to next? Tell us at countryliving@hearst.com, or start planning your next getaway with more of our small town guides:
• The 50 Best Small Towns for Antiques
• 20 Small Towns That Leave a Big Impression
• 18 Photos That Capture the Charm of Small Town Living
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