50th Annual Woodstock Apples and Crafts Fair and food truck festival
October 12th & 13, 2024
Leaf season gets its own celebration during the Woodstock Apples and Crafts Artisans Fair. Shop with over 100 vendors and purveyors of Vermont crafts and food.
40th Annual Wassail Weekend
December 13-14-15, 2024
Parade Saturday at 2 PM
Woodstock gets into the holiday season during Wassail Weekend, a celebration of the sights, sounds, and spirit of winter. Take in the magic of twinkling light displays, decorated historic homes, and the sounds Holiday music throughout the Village. Here is everything you need to know about the schedule of events for Wassail Weekend.
32ND Annual Covered Bridges Half Marathon (June 1, 2025) and Pasta Supper (May 31, 2025)!
Please sign up or Walk in at 5, 6 or 7!!
Load up on a community pasta dinner before running (or cheering) through some of Vermont’s most beloved covered bridges during the Covered Bridges Half Marathon. Billed as the best 13.1 miles in New England, the community race has raised more than $2 million for local non-profits since 1994.
Run for fun
Pride of Woodstock, Vermont
June 6-8, 2025
Join us for a celebration of love, diversity, and community set against the picturesque backdrop of this charming New England town. The weekend is full of activities for everyone!
Events Include: "Made with Pride" Arts & Crafts Fair on The Green, High Heel Race on Elm St., Drag Brunch, Trivia Night, Tea Dances, LGBTQ+ Movies, and More!
4th of July
July 4, 2025
As summer heats up, revel in patriotic events throughout Woodstock. From traditional fireworks shows and BBQs to historic activities and games, come see how Woodstock celebrates Independence Day.
14th Annual Taste of Woodstock-Expect Fun!
August 9, 2025
Packed with local flavor, Taste of Woodstock is a sample of everything the Woodstock community is known for. In partnership with Artistree and Purple Crayon Productions, over 50 vendors will fill the center of Woodstock Village with favorite Vermont provisions, wine, beer, spirits, music, entertainment, arts, crafts, and a kids’ activity tent.
Hunter Jumper Show
August 2025
Join the Green Mountain Horse Association for a weekend of hunter jumper competitions set among Vermont’s stunning fall foliage. Watch or compete in one of the most exciting disciplines of horseback riding.
Woodstock Art Festival
September 6 & 7, 2025
The Woodstock Art Festival, sponsored by the Woodstock Area Chamber of Commerce, is a weekend-long event of fine art, music, spirits and food. Over 30 New England artists offer landscapes, portraits, photography and more! Always held on the weekend following Labor Day, Woodstock becomes an art-lovers mecca. September 6 & 7, 2025 on the Green in Woodstock, VT.
