35th Annual Wassail Weekend
December 13-15, 2019
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, breakfast with Santa, and the sounds of sleigh bells during the iconic Wassail Parade.
A celebration of all things maple sugared, come taste your way around Vermont’s sweetest season during Maple Madness. Try Sugar on Snow, Maple Buttered popcorn; visit a live raptor exhibit on the Green. After that stroll through the Village and taste some maple inspired treats or cruise to a local sugar house and watch sap get turned into Maple Syrup!
29th Annual Covered Bridges Half Marathon and Pasta Supper
June 6-7, 2020
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.
4th of July
July 4, 2020
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.
12th Annual Bookstock Literary Festival
Logophiles, bibliophiles, and bookworms of all genres gather during Bookstock Literary Festival to celebrate authors and poets throughout New England. Enjoy three days of public readings, poetry slams, art exhibits, live music, creative workshops, and an enormous book sale.
11th Annual Taste of Woodstock
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.
Fall Hunter Jumper Show
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.
48th Annual Woodstock Apples and Crafts Fair and food truck festival
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.