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Woodstock’s rich heritage and culture come alive during special events and annual celebrations that are packed with New England flair. From intimate, farm-to-table parties to winter festivals, come discover what makes the Woodstock area such an inspiring place to visit.

Looking for more information on an an event not listed below? Check out our blog for more itineraries and things to do in Woodstock.

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Family and Kids

Events for December 13, 2025

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artistree ornament making

Wassail Weekend: Holiday Ornament Making for Families

2095 Pomfret Road 2095 POMFRET ROAD, South Pomfret

Celebrate the magic of Wassail Weekend with a joyful, hands-on workshop for all ages! ?✨ Create your own collection of whimsical holiday ornaments at a variety of festive art stations—work...

Wassail2022_3117

Wassail Cafe

Wassail Beverages on the Green! Come quench your thirst with our festival holiday drink (adult & non). $$ Card or Cash 

Garland

Victorian Garland Making

31 The Green, Woodstock Town Hall Theatre 31 The Green, Woodstock Town Hall Theatre, Woodstock

Kick off Wassail Weekend with a cozy, hands-on family craft event! Join us at the Woodstock Town Hall Theatre to create your own Victorian-style garlands using popcorn, cranberries, and charming decorative pieces....

Wassail-Little-elf

Wassail Horse Parade

Join us for the 41st Annual Wassail Horse Parade where we will have 40 participates decked out in Victorian gear and Holiday Cheer. Lead by the Brattleboro American Legion Band,...

Wassail Weekend luminaries

Lighting of the Luminaries

Come walk the green, while the sun goes down and admire the luminaries lighting up the pathway. Sponsored by the Woodstock Rotary Club 

holiday music at artistree

Wassail Weekend: Holiday Music in the Hayloft

2095 Pomfret Road 2095 POMFRET ROAD, South Pomfret

Celebrate the season with a joyous evening of music and togetherness at our annual Christmas concert! Celebrate Woodstock’s Wassail Weekend in style with an evening of jazz and festive cheer at...

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Seasonal Feature

There is something for everyone regardless of the season. From fall foliage guides to winter traditions to spring rebirth and summer adventures, explore the latest that celebrates the best of Woodstock right now.

  • Around Town Holidays
    How to Enjoy the Holiday Season in Woodstock
    Woodstock, Vermont, offers a captivating holiday journey, intertwining age-old traditions with modern charm. Revel in the vibrant festivities of a New England Thanksgiving, Wassail Weekend, or explore artisanal treasures in local shops, and bask in winter’s serenity or adventures outdoors.
    Read article

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