Events
Horror Film Festival
Woodstock Town Hall Theatre
October 30–November 1, 2026 ·
Three days of horror classics, cult favorites and Halloween films.
Sunday, November 1: 4:00–6:00 PM Saturday, October 31: listings include 7:00–9:00 PM and 10:00–11:30 PM screenings....
Annual Killington Turkey Trot
Pickle Barrel (1741 Killington Road)
Starts: 9:30am
15th Annual Killington Turkey Trot
Kick off Thanksgiving morning with the 15th Annual Killington Turkey Trot, a 5K run/walk starting at 9:30 a.m. on Thursday, November 26, 2026, at the Pickle Barrel (1741 Killington Road). All ages are welcome, and the event goes on rain, snow, or ice—so lace up and get ready to trot! Proceeds benefit the Pico Ski Education Foundation and the Killington World Cup Foundation.
About the Race
Started in 2011 after Tropical Storm Irene, the Killington Turkey Trot has grown into a holiday tradition that mixes fitness, community, and fun. After the race, stick around at the Pickle Barrel for live music, drinks, and raffle prizes.
Frequently Asked Questions: Killington Turkey Trot
Can I register on race day?
Yes. Registration opens at 8:00 a.m. at the Pickle Barrel.
Is the event family-friendly?
Absolutely! Runners and walkers of all ages are welcome.
Will the race be canceled for bad weather?
No. The Turkey Trot is held rain, snow, or ice....
The Stifel Killington Cup
If you're visiting Vermont this winter, don't miss the excitement of the Stifel Killington Cup, taking place Thanksgiving weekend 2026 at Killington Resort. This major event on the Audi FIS Ski World Cup tour features elite women’s giant slalom and slalom races, attracting some of the biggest names in ski racing, including seven-time Killington Cup champion Mikaela Shiffrin. Beyond the races, the weekend is packed with entertainment, including live music, a festival village, a fireworks display, and inspiring discussions focused on women in the ski industry. Stay in the loop, and secure your Killington vacation rental while there's still time!...
Wassail Weekend — Woodstock's major holiday festival
Billings Farm & Museum. Woodstock Village
Wassail Weekend — Woodstock's major holiday festival
Friday–Sunday, December 11–13, 2026 · Woodstock Village
The town's signature holiday celebration includes the horse parade, artisan markets, horse-drawn carriage rides, caroling, holiday lights and winter festivities at Billings Farm & Museum.
Woodstock Wassail Weekend 2026
December 11–13, 2026 | Woodstock Village, Vermont
Experience the magic of the holidays during Woodstock's beloved Wassail Weekend! This three-day celebration transforms the historic village into a festive winter wonderland filled with twinkling lights, holiday markets, carolers, horse-drawn carriage rides, and seasonal traditions.
Wassail Weekend Event Schedule
Date
Time
Event
Friday, Dec. 11
4:30 PM
Candlelit Walk from East End Park to the Village Green
Friday, Dec. 11
To Be Announced
Wassail Welcome Party at Peace Field Farm
Friday–Sunday, Dec. 11–13
Various Times
Winter Celebration at Billings Farm & Museum
Friday–Saturday, Dec. 11–12
Hours To Be Confirmed
Wassail Artisan Market on the Village Green
Saturday, Dec. 12
10:00 AM–3:00 PM
Wassail Café on the Green
Saturday, Dec. 12
2:00 PM
Horse Parade Through Woodstock Village
Saturday, Dec. 12
3:00 PM
Memory Tree Lighting and Yule Log Bonfire
Saturday, Dec. 12
4:00 PM
Lighting of the Luminaries on the Green
Saturday–Sunday, Dec. 12–13
To Be Announced
Wassail Holiday Craft Fair at Masonic Hall
More Holiday Fun
Enjoy Cupcakes with Santa, ice skating, festive crafts, Christmas caroling, live concerts, and charming horse-and-carriage rides throughout the weekend.
Plan Your Visit: Some event times, activities, and ticket details are still being finalized. Check for schedule updates before attending.
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