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 its captivating winter magic. There are so many things to do during the holiday season in Woodstock, Vermont.
FALL IN WOODSTOCK
50th Annual Apples & Crafts Fair and Food Truck Festival
The Apples & Crafts Fair is a favorite annual event in Woodstock, October 12-13, 10am-4pm. Shop with over 100 vendors and purveyors of Vermont crafts, specialty food producers, and food trucks. Tickets are $5/person and kids under 12 are free! Dogs welcome too.
Fall at Billings Farm
Fall at Billings Farm is truly magical! The gorgeous landscape, friendly farm animals, and festive events make it such a fun place to be. Gather and celebrate the change of the season with harvest activities, food, and fun for the whole family on Saturday, October 12 & Sunday, October 13, 10am-5pm at The Harvest Celebration. This lively two-day Harvest Celebration will feature traditional barn dancing, live music, pumpkin bowling, crafts, stories, and harvest activities.
Halloween in Woodstock
Woodstock is everything you dream of and imagine when you think of picturesque small-town New England Halloween. Get into the Halloween spirit with a “Life & Death Tour” of Billings Farm’s 1890 Farm Manager’s House and the mansion at the Marsh-Billings-Rockefeller National Historical Park, October 25-26.
Experience Halloween at VINS, Saturday, October 26, 10-5. Pumpkin carving, guided explorations, and tons of fun activities.
Join the slightly spooky and super sweet Family Halloween on Sunday, October 27, 10-5. At this spooktacular Halloween on the farm, there will be fun for the whole family with hayrides, costume parades, and more.
Enjoy the musical adaptation of Young Frankenstein presented by BarnArts. October 25-November 3, see here for tickets and showtimes.
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.
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 artisanal Vermont cheeses from Vermont Farmstead. 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.
Woodstock's Sip and Shop
On the second Saturday of the month September-December, enjoy special drinks and surprises at participating stores from 5-7 pm. See our event details for participating stores. Sip and Shop Dates: October 12, November 9 & December 14.
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 Weekend at Billings Farm
Learn about the history of Wassail and step back in time to the Victorian Christmas past, Friday, December 13 – Sunday, December 15, 10am – 4pm. Enjoy the festive holiday tree and decorations that fill the Visitor Center and historic barn. Discover the charm of Victorian Christmas as you explore the authentically decorated farmhouse parlor. Don’t miss Wassail Weekend at Billings Farm.
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.
Christmas at the Farm, Billings Farm & Museum
Travel to Victorian Christmas past, December Weekends, and Daily from Saturday, December 21, 2024 – Sunday, January 5, 2025, 10am – 4pm for Christmas at the Farm (closed December 24 & 25.) Discover the charm of Victorian Christmas as you explore the authentically decorated farmhouse parlor. Enjoy the festive holiday tree and decorations. Dip your candle and make mini mince pies to take home. Warm up by the outdoor fire pits with a cup of cocoa and s’mores. Adventure can be found on a snowshoe, hike, or cross-country ski along the Ottauquechee River, weather permitting.
