Traditions & Gatherings
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.
Woodstock, Vermont
Friday, December 11, 2026 – Sunday, December 13, 2026
Celebrate Wassail Weekend in Woodstock with Pentangle Arts! Enjoy three days of holiday music, cherished community traditions, and festive gatherings for the whole family.
From beautiful holiday music to warm community gatherings, there's something for everyone. Explore our Wassail Weekend events below.
Friday, December 11, 2026
7:00 PM
Woodstock Town Hall Theatre
$20 per person
A joyful evening of holiday music featuring the Pentangle Community Band, Pentangle Community Choir, Pentangle After School Performing Arts, and Boston Conservatory @ Berklee Musical Theatre Singers.
Event Details & TicketsSaturday, December 12, 2026
11:00 AM–2:00 PM
Woodstock Town Hall Theatre
FREE — No Tickets Required
Come in from the cold for kids' crafts, complimentary cider, hot chocolate, cookies, and a festive gathering with the Pentangle Arts staff and board.
Explore the Open HouseSaturday, December 12, 2026
7:00 PM
Woodstock Town Hall Theatre
$30 per person
An unforgettable evening of world-class a cappella music with special guests The Blue Streak Quartet.
Event Details & TicketsSunday, December 13, 2026
12:00 PM–2:00 PM
Woodstock Town Hall Theatre
FREE — No Tickets Required
Celebrate the season with cookies, hot chocolate, and a visit with Santa at Woodstock Town Hall Theatre.
Visit with SantaSunday, December 13, 2026
4:00 PM
Our Lady of the Snows Church, Woodstock
FREE — Optional Registration
Join a cherished Woodstock tradition and lend your voice to Handel's Messiah alongside a world-class ensemble and soloists.
Event Details & Free RegistrationAcross the village
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.
Pentangle does not maintain the complete Woodstock-wide schedule. The official weekend information remains the source for current community-wide details.
Explore the full weekend
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)Whether you're joining us for a holiday concert, singing along to Handel, or stopping by for hot chocolate and a little Christmas magic, we can't wait to welcome you to Wassail Weekend in Woodstock.
