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Music on the Hill

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

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

Sign Up for the Pasta Dinner

Woodstock Vermont logo with rainbow
The Woodstock, VT logo was designed by local resident T. Belisle and his creative agency; Haystack in 2015. The Pride Rainbow artwork was added by designer Doug Blanchard, a friend of community members John Curtis and Jimmy Serrano.

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!

Explore Pride of Woodstock

4th of July Festivities at Billings Farm & Museum

4th of July
July 5, 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- Expect Fun!
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 7th & 8th, 2024

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 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.

Get crafty

Wassail Weekend in Woodstock Vermont
Billings Farm & Museum

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. Please view the poster for the flavor of the event for 2024.

Get in the spirit