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Around Town Holidays

From The Blog Holiday Season in Woodstock

Woodstock, Vermont's Favorite Time Of Year

Delve into the festive allure of Woodstock, Vermont. From the vibrant Wassail Weekend to tranquil winter walks, discover the traditions and activities that make the holiday season in Woodstock a timeless experience.

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. Dive with us into what makes Woodstock a holiday wonder for you and your date, significant other, or your whole family.

Village Butcher
Farmers Market
Visit with Santa on the stage!

Thanksgiving in Woodstock

Thanksgiving in Woodstock is more than just a meal; it's a tapestry of traditions woven with gratitude. Historic inns and eateries offer feasts 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. 

Holiday Shopping Couple
Evening Aerial Shot of Village Green
Snow Woodstock Downtown Shops

Holiday Shopping & Supporting Small Businesses

In the heart of Woodstock, local artisans and businesses offer a trove of unique finds. Each shop window tells a story, be it handcrafted jewelry from Ferro Jewelers, bespoke wooden toys from Red Wagon Toy Co, or artisanal Vermont cheeses from Vermont Farmstead. As you wander the snow-kissed streets, the town becomes a live advent calendar, each door opening to reveal treasures within. 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 Parade Dogs

Wassail Weekend & The Festival Atmosphere

When it comes to festive spirit, Woodstock's renowned Wassail Weekend stands apart. 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 all of the timeless beauty of winter celebrations.

Wassail Parade Horse Drawn Carriage
Wassail Cheers
Wassail Parade Horses

Outdoor Activities: For the Adventurous & the Serene Seekers

The winter blanket that covers Woodstock's landscapes caters to both adrenaline seekers and those craving tranquil moments. For the adventurous, 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!

Nordic Skiing
Woodstock Inn & Resort