Skip to main content
Artist working at Taste of Woodstock

Signature Events

Here in Woodstock, we love to celebrate our Vermont heritage and local traditions. We invite you to join in on some of our favorite events of the year.

Cover Bridge Half Marathon Pasta Dinner

31st Annual Covered Bridges Half Marathon and Pasta Supper June 1, 2024!

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

Sign Up for the Pasta Dinner

4th of July Festivities at Billings Farm & Museum

4th of July
July 4, 2024

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.


Taste of Woodstock event view
Taste of Woodstock looking down Elm Street

14th Annual Taste of Woodstock
August 10, 2024

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.

Participate in the Taste of Woodstock



Fall Jumper Show at GMHA
Green Mountain Horse Association

Hunter Jumper Show
August 2024

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.

Head to the races


the green
Art Festival

Woodstock Art Festival
September 9th & 10th, 2023

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 9 & 10, 2023 on the Green in Woodstock, VT.

Participate in the Art Festival

Craft sale

50th Annual Woodstock Apples and Crafts Fair and food truck festival
October 7 & 8, 2023

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.

Get crafty


Wassail Weekend in Woodstock Vermont
Billings Farm & Museum

39th Annual Wassail Weekend 
December 8-9-10, 2023

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.

Horse Drawn Wagon Rides Suggested donation $10 per person

Friday, December 8th from 1-pm
Saturday, December 9th from 9:30am-12:30pm
Sunday, December 10th from 10am-pm

Get in the spirit