Dec. 13 through 15, from 5 p.m. Friday to 6 p.m. Sunday—Woodstock— Beginning at 5 p.m. on Friday afternoon, Woodstock will transform into a festive wonderland for its annual Wassail Weekend, with events planned through Sunday evening. This cherished tradition blends music, history, and holiday cheer in a packed weekend designed to capture the charm of a quintessential Vermont winter. Here’s everything you need to know about this year’s celebration:
Friday, Dec. 13: A festive kickoff
Opening ceremony — 5-6 p.m., East End Park to The Green
Kick off the weekend with a candlelit procession from East End Park to The Green, featuring bells, music, and piping by the star. Warm up with hot cider, courtesy of Pentangle Arts Council.
‘A Classic Christmas’ by Frisson — 7:30-9:30 p.m., Town Hall Theater
Pentangle Arts presents this concert featuring Frisson, an 11-member ensemble of emerging classical music stars. Celebrate with selections from “The Nutcracker,” “Winter” from Vivaldi’s “Four Seasons,” and a Christmas carol sing-along.
Saturday, Dec. 14: Music, magic, and merriment
Cupcakes with Santa — 11 a.m.-noon, Town Hall Theater
Bring the little ones for a sweet morning with Santa, with cupcakes and Christmas wishes.
Ham Gillett reads Dylan Thomas — Noon-1:30 p.m., Norman Williams Public Library
Enjoy this traditional reading of Dylan Thomas’s lyrical holiday reflections.
Wassail parade — 2 p.m., Downtown Woodstock
Watch as decorated horses and riders parade through the village, celebrating the spirit of the season.
Wrensong Presents “Songs of the Season” — 3-3:45 p.m., Norman Williams Public Library
Delight in Renaissance-era a cappella choral music from Vermont’s own Wrensong ensemble.
Holiday cabaret — 6-10 p.m., BarnArts
Celebrate with live music from the Speak Easy Prohibition Band, a farm-to-table dinner, and dancing at this festive fundraiser.
The Empty Pockets concert — 7:30-9:30 p.m., Town Hall Theater
Enjoy this Chicago-based quartet blending Americana, folk, and rock for a high-energy performance.
Sunday, Dec. 15: Family-friendly fun
Revels Kids performance — 2-3 p.m., Town Hall Theater
Revels North presents a joyous children’s show featuring music and storytelling. Tickets are $10 for adults and free for kids.
Messiah Sing — 4-6 p.m., Our Lady of the Snows Church
Join a world-class ensemble and soloists for a moving rendition of Handel’s “Messiah”—a suggested donation of $10.
Billings Farm & Museum events
Throughout the weekend, Billings Farm & Museum visitors can step back into the 1890s with candle dipping, winter story time, and tours of the Farm Manager’s House decked in Victorian holiday decor. Join the age-old tradition of wassailing the orchard on Saturday to ensure a fruitful harvest. Sunday features horse-drawn wagon or sleigh rides.
Wassail Weekend promises something for everyone, from live music and historic traditions to Santa sightings and festive shopping.
For more information, visit: pentanglearts.org.
Woodstock’s Wassail Weekend, from Dec. 13-15, offers a festive blend of holiday traditions, music, and community celebrations, including candlelit processions, concerts, parades, family-friendly performances, and historic activities at Billings Farm & Museum.
