Holiday Enchantment Comes to Woodstock, Vermont, During Wassail Weekend 2025
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Ready for a winter weekend that captures the magic of the holiday season in Vermont?
Imagine snow-dusted streets, horse-drawn carriages with awe-struck passengers, and beautiful holiday decor throughout a historic, storybook village.
This annual celebration wraps the town in the timeless spirit of the season, complete with a historic parade, Victorian festivities, local artisan markets, and family-friendly events.
Welcome to Wassail Weekend in Woodstock, Vermont, happening December 12 to 14, 2025.
What makes Wassail Weekend so Magical?
This signature event in Woodstock brings a unique blend of history, tradition, and holiday spirit to life.
Visitors are invited to explore every corner of this charming New England town, which comes alive with a full weekend of festive activities, from the beloved Wassail Parade to traditional carol singing.
It’s also a great weekend to get some shopping done!
Here’s an overview of the weekend’s events.
Friday, December 12: A Festive Start to the Weekend
Start your morning with Christmas at the Farm, a Victorian Christmas celebration at Billings Farm & Museum, where you can step back in time and learn how holiday traditions were celebrated in the late 1800s.
Continue your explorations with a stop at the Rare & Vintage Book Sale at the Norman Williams Public Library, ideal for collectors, readers, and anyone who loves the scent of old paper.
In the afternoon, horse-drawn carriages clip-clop their way through the village, offering scenic rides past historic homes, decorated storefronts, and twinkling lights.
Local artisans begin setting up for the weekend as the Artisan Market on the Village Green opens, filling the historic green with handmade goods, textiles, jewelry, and winter treats.
Friday evening begins with a candlelit glow at the Candle Lit Walk, presented by Pentangle Arts at East End Park. It’s a peaceful and atmospheric way to welcome the weekend as lanterns illuminate the snowy path and families gather together under the early winter twilight.
End the evening at Pentangle Arts for a Classical Christmas.
Saturday, December 13: The Heart of Wassail Weekend
The free shuttle begins running in the morning, making it easy to park outside the village and hop into the heart of the action. Horse and carriage rides resume, offering one of the weekend’s most iconic experiences as teams drive visitors along historic streets.
Throughout the day, Billings Farm continues its Christmas at the Farm festivities while the Wassail Holiday Craft Fair at the Masonic Hall and the Artisan Market on the Green invite shoppers to discover the work of more than two dozen Vermont makers.
By midday, the Wassail Pub opens on the Village Green with warm beverages, including traditional Wassail Punch, to keep visitors toasty.
At 2 pm, it’s time for the much-anticipated Wassail Parade. Live music, majestic horses, old-fashioned costumes, and decorated carriages weave twice around the Village Green, creating a scene that feels both nostalgic and impossibly magical. It’s one of the most photographed events in Vermont each winter.
As the sun sinks behind the steeples and rooftops, the community gathers for the Lighting of the Memory Tree, followed by a bonfire and carol sing.
Luminaries glow along the green at dusk, and the warm light reflects off the surrounding snow, bringing the day to a beautiful and heartfelt close.
Sunday, December 14: A Cozy Close to the Celebration
Sunday offers a gentler pace as festivities shift toward family-oriented fun and a final chance to soak in the magic of Wassail Weekend.
Billings Farm’s Victorian Christmas celebration continues, and horse and carriage rides return for one last day. Shoppers can browse the Wassail Holiday Craft Fair for holiday gifts, stocking stuffers, and local treats.
Later in the day, families gather at Union Arena for Skating with Santa, a favorite with younger visitors. The weekend winds down with cookies and cupcakes with Santa, and a joyful performance from Revel Kids at Town Hall.
Tips for Enjoying Wassail Weekend
As you know, Vermont in December can be unpredictable. Dress in warm layers, and be prepared for lots of outdoor time. Many events require advance reservations, so be sure to grab your tickets early.
On Saturday, take advantage of the complimentary shuttle from Woodstock Union High School to avoid village traffic. Pack your patience and prepare yourself for a magical holiday experience that only Woodstock can deliver.
There’s no other place like Woodstock in the winter. The town’s natural beauty, combined with historic architecture, boutique shopping, and great restaurants, makes for an unforgettable holiday escape.
Wassail Weekend 2025 will make you feel like a kid again!
Also Read: 14 Spectacular Events to Celebrate December in Vermont
