March 23, 2019
A celebration of all things maple sugared, come taste your way around Vermont’s sweetest season during Maple Madness. Bid on hand-painted sap buckets, sample culinary treats at the Maple Taste-a-Round, get crafty with kids activities, or partake in maple-themed fun runs and bike races.
27th Annual Covered Bridges Half Marathon and Pasta Supper
June 1-2, 2019
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, 2019
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.
11th Annual Bookstock Literary Festival
July 26-28, 2019
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.
10th Annual Taste of Woodstock
August 10, 2019
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
September 7-8, 2019
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.
47th Annual Woodstock Apples and Crafts Fair and food truck festival
October 12-13, 2019
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.
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.