How to Enjoy the Holiday Season in Woodstock

Set against Vermont’s winter landscapes, Woodstock shines brilliantly during the holidays. Often seen as the heart of New England’s yuletide charm, the town blooms in festive glory when the shops dawn their holiday decor. As the season unfolds, visitors are drawn to the village’s winter magic. There are so many things to do during the holiday season in Woodstock, Vermont.

Holiday Shopping

In the heart of Woodstock, local artisans and businesses offer a trove of unique finds. Each shop window tells a story, curated sustainable goods from Echo Market, great gifts from Woody’s Mercantile, bespoke wooden toys from Red Wagon Toy Co, or a plethora of gifts and unique treasures at Gillingham’s. Supporting these small businesses not only brings joy to loved ones but ensures that the town’s community of locally owned shops continues to thrive.

WASSAIL WEEKEND & THE FESTIVAL ATMOSPHERE

Woodstock’s renowned Wassail Weekend stands apart when it comes to the festive spirit. The town immerses itself in the ancient traditions of ‘wassailing’, a heartwarming spectacle that ties together both reverence for the old and the vibrant enthusiasm of the present. Streets come alive with festive décor, carolers dress in 19th-century attire, and the nostalgic sounds of horse-drawn carriages carry through the town. The aroma of mulled cider fills the air, drawing visitors and locals alike to community gatherings, bridging the gap between eras, and reminding us all of the timeless beauty of winter celebrations. See the full Wassail Weekend schedule in Woodstock.

Wassail Artisan Market

Shop for unique and special handmade holiday gifts from a variety of Vermont vendors during the Wassail Artisan Market, located on the Village Green, December 12, 1-6pm and December 13, 10am-4pm.

Winter Celebration at Billings Farm

Discover the charm of Victorian Christmas as you explore the authentically decorated farmhouse parlor at Billings Farm & Museum.  Enjoy the festive holiday tree and decorations that fill the Visitor Center and historic barn.  Dip your own candle to take home.  Warm up by the outdoor fire pits with hot cocoa, hot spiced apple cider, and cider donuts available for purchase in the Museum Gift Shop. Take a horse-drawn sleigh or wagon ride and meet the farm animals including jersey cows, chickens, goats, pigs, sheep, and more. December 6-7 and Daily from December 20, 2025 – January 4, 2026, 10:00AM – 4:00PM.  (Closed December 24 & 25.)

ACTIVITIES DURING THE HOLIDAYS

The winter blanket that covers Woodstock’s landscapes caters to adventure seekers and those craving tranquil moments. The surroundings become a playground: cross-country skiing through meandering trails , downhill skiing, or enjoying tranquil moments curled up by a cozy fire. Opt for a peaceful winter walk, or a spa day while the snow falls, taking in the beauty of frosted trees and the gentle hush that snow brings. Every option is an invitation to enjoy everything Woodstock has to offer.

VISIT LOCAL FARMS

Woodstock offers incredible farm experiences with Sugarbush Maple and Cheese Farm (free samples!) and Billings Farm & Museum, a fully functional farm and one of the finest outdoor history museums. Gather the whole family to say hello to friendly animals, get an inside look at how things are made, and discover hidden gems on hundreds of acres. Just a short drive from Woodstock is Plymouth Cheese Factory Store, open 11am-5pm everyday in Plymouth, Vermont.

Weekly Events

The holiday season is filled with fun events whether you’re looking for a cooking class, outdoor adventure, live music, or theater. Make sure to check our events calendar for everything that’s happening in and around town.