Woodstock, Vermont, has once again proven that nobody does the holidays quite like New England. Named the second-best Christmas village in the world by Country Living, this Green Mountain gem feels straight out of a storybook—complete with snow-dusted covered bridges, candlelit streets, and the soft jingle of sleigh bells drifting through crisp mountain air.
Every December, Woodstock transforms into a living postcard of holiday magic. The town’s beloved Wassail Weekend, held from December 12-14 this year, ushers in the season with Victorian flair—think horse-drawn carriages, carolers in period costume, and historic homes glowing with candlelight. The event, which dates back to the early 1980s, captures the essence of old-fashioned New England hospitality while celebrating the spirit of the season.
Visitors can bundle up for sleigh rides through Billings Farm & Museum, cross-country ski along scenic trails, or simply wander through Woodstock Village, where wreath-adorned lampposts and boutique storefronts glow warmly. Light snowfall only adds to the magic, blanketing the iconic Middle Covered Bridge in glittering white. Explore the day-by-day itinerary of upcoming events in Woodstock, Vermont to guide your trip itinerary!
Charming inns such as The Woodstock Inn & Resort deck their halls with classic greenery and boast roaring fireplaces, offering the perfect retreat after a day of exploring. Cozy cafés invite travelers to linger over mulled cider or hot chocolate while holiday lights twinkle across the green.
With its timeless beauty and festive spirit, Woodstock captures everything travelers hope for in the quintessential New England winter getaway. Ranked among the best holiday destinations in the world, sharing the spotlight with Kennebunkport, Maine, this quaint Vermont village reminds us that sometimes, the most unforgettable adventures are the ones that feel just like coming home.