Traditions & Gatherings
Wassail Weekend
December 11–13, 2026
Each December, Woodstock gathers for Wassail Weekend, a village-wide celebration of winter traditions, music, light, and community. In 2026, the tradition returns for its 42nd year. Pentangle participates in the weekend by bringing arts and performance programming into the celebration.
Across the village
A tradition shared throughout Woodstock.
Woodstock Wassail Weekend extends across the village, with winter celebrations hosted by community organizations, local businesses, and cultural places. The full weekend is larger than any one organization’s program.
- Candle-lit walks, luminaries, and seasonal light
- Village markets, craft traditions, and gatherings on the Green
- The Horse Parade, caroling, music, skating, and winter activities
Pentangle does not maintain the complete Woodstock-wide schedule. The official weekend information remains the source for current community-wide details.
Pentangle at Wassail
Adding performance to the tradition.
Pentangle’s role is to contribute arts and performance experiences as part of the wider Woodstock weekend. That may include music, film, community performance, or other holiday programming connected to the Town Hall Theatre.
Confirmed Pentangle-specific Wassail programming for 2026 will be shared here when those details are ready. Education programming remains listed with Pentangle Education unless its Wassail relationship is separately confirmed.
Explore the full weekend
Wassail extends throughout Woodstock.
Events and traditions are hosted by organizations and businesses across the village. The official Woodstock Wassail Weekend page carries the complete current schedule and community-wide visitor information.
Explore Woodstock Wassail Weekend(opens the official Woodstock Wassail Weekend website in a new tab)