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.
Thanksgiving in Woodstock
Thanksgiving in Woodstock is more than just a meal; it's filled with traditions and gratitude. Historic inns and eateries offer delicious meals capturing the essence of New England's culinary heritage. The community gathers, whether in the great outdoors, at Billings Farm, or in cozy taverns, to share stories and give thanks.
In town for the holiday? Grab a Turkey from The Village Butcher, and fixings from the Woodstock Farmers Market. Amid the golden hues of autumn transitioning to the silvery sheen of winter, Thanksgiving here is a heartfelt ode to the town's community spirit and the blessings of the season.
The Drop Offs at Pentangle Arts Town Hall Theater
The Drop Off’s return to Town Hall Theater in Woodstock VT, Friday, November 21, for their annual pre-Thanksgiving show, with special guests The Freeze Brothers. Joining them on stage will be members of Lakou Mizik, one of the most well-known Haitian groups in the country. Join us for a special evening of music and community! Get tickets here.
Zack's Place Turkey Trot
The Turkey Trot is Woodstock’s annual family walk/run that supports the local non-profit, Zack’s Place. Zack’s Place is an organization for people with special needs to build friendships and community connections. It’s a wonderful and festive way to support an integral community organization that draws the community together in a special way.
A Family Thanksgiving at Billings Farm
Give thanks, share, and learn at Thanksgiving on the Farm, Friday, November 29 – Sunday, December 1, 10am–5pm. Enjoy an experience for the whole family with 19th-century Thanksgiving traditions, crafts, and food.
Holiday Shopping
In the heart of Woodstock, local artisans and businesses offer a trove of unique finds. Each shop window tells a story, handcrafted jewelry from Ferro Jewelers, 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 rich tapestry of craftsmen and merchants thrives for years to come.
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 or embarking on exhilarating snowshoe expeditions. But if serenity calls, one might simply opt for a peaceful winter walk, or a spa day while the snow falls, taking in the crystalline beauty of frosted trees and the gentle hush that snow brings. Every option is an invitation to enjoy everything Woodstock has to offer.
Vermont Comedy Festival
Get ready to laugh! Pentangle Arts welcomes back Vermont Comedy Festival with headliner Judy Gold. Judy Gold has had stand-up specials on HBO, Comedy Central and LOGO, and was a part of Netflix’s Stand Out: An LGBTQ+ Celebration. She is the author of Yes I Can Say That: When. Get Tickets Here.
Winter Carols by BarnArts
BarnArts original event, Winter Carols, is a free & festive opportunity to join with neighbors and friends and celebrate the season as a community. Winter Carols includes audience sing-alongs as well as instrumental performances by musicians from the community. December 19 at 7pm, First Universalist Church and Society of Barnard.
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.
