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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 14, 2025

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Today

Wassail participants approach and interact with a carriage horse

Carriage Rides through the Village

Take a whimsical ride through our quaint Village, while the town is decorated like a hallmark Christmas Card. Wassail Carriage Rides through the VillageFri, 1-3PM, Sat. 9:30AM-12:30PM, Sun 10AM-2PM, $10 personMeet...

Skate

Skate with Santa!

Union Arena 80 Amsden Way, Woodstock

Visit Union Arena during Wassail weekend for a public skate event.... with special guest! Adult (ages 13 & up) $8.00 / Youth (ages 4-12) $6.00  / Seniors (ages 60+ )...

Cupcakes w Santa

Cupcakes with Santa

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

Come meet Santa and his elves for this family celebration! Take a picture with the big guy and share some great scrumptious cupcakes in our lobby, made by Woodstock's own...

Free

King-Farm-Woodstock-Vermont-Fall-2021-aerial_2400x1351px

Swag Making at King Farm

Wreath Making Join Vermont Land Trust and WoodstockUnion High School’s CRAFT Program for a festive afternoon of creativity at King Farm in Woodstock.     Drop in anytime between 1:00...

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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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