Festivals & Fairs USA
Woodstock Wassail Weekend

Woodstock Wassail Weekend

Seasonal Cultural Family

About this event

The Woodstock Wassail Weekend is a seasonal festival in Woodstock, Vermont, at The Green. Woodstock's beloved holiday weekend turns the village into a winter wonderland with a horse-drawn parade, craft fair, caroling, wreath-making, visits with Santa, and festive lights across one of Vermont's most picturesque towns.

Annual, mid-December weekend (2026 dates not yet published)

Location & directions

The Green, Woodstock, VT 05091

Frequently asked questions

Where is Woodstock Wassail Weekend held?

Woodstock Wassail Weekend is held in Woodstock, Vermont, at The Green, Woodstock, VT 05091.

What is Woodstock Wassail Weekend?

Woodstock's beloved holiday weekend turns the village into a winter wonderland with a horse-drawn parade, craft fair, caroling, wreath-making, visits with Santa, and festive lights across one of Vermont's most picturesque towns.

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