Annual Events in Woodstock, Vermont
From Bookstock and Pride of Woodstock to Apples & Crafts and Wassail, here’s everything you need to know about what’s happening throughout the year.
may 15-17, 2026
bookstock
Bookstock is a celebration of books and storytelling featuring award-winning authors and poets for workshops, master classes, and literary discussions. Enjoy the used book sale, children’s tent with activities, craft vendors, music, food and so much more.
june 4-7, 2026
pride of woodstock
A celebration of love, diversity, and community set against the picturesque backdrop of our charming town. This Pride event combines the spirit of Woodstock, Vermont with the vibrant colors of the LGBTQ+ community, creating a unique and welcoming atmosphere for all. Don’t miss the Craft fair on The Green, High Heel Race, Drag Bunch, Tea Dance and more.
June 6-7, 2026
covered bridges half marathon and pasta supper
The Covered Bridges Half Marathon is one of the most iconic races in New England. Cheer on runners as they pass through Woodstock’s Middle Covered Bridge. The night before, join runners, friends, and community members for the annual Pasta Supper with live music and lots of fun at Saskadena Six.
June 3-October 14, 2026
Market on the Green
Held Wednesdays from 3:00PM – 6:00PM, this weekly outdoor market features local vendors and makers, offering farm-fresh produce, handmade crafts, and artisanal goods. Enjoy live music and delicious food on the beautiful Village Green. It’s a fun, family-friendly way to spend a summer or fall afternoon in Woodstock.
July 1-July 5, 2026
250th celebration: july 4 weekend
Celebrate America’s 250th Anniversary with a weekend of community fun in Woodstock! Festivities begin July 1 with a Vermont Symphony Orchestra concert at Saskadena Six and continue July 3–5. Enjoy Music in the Park, a Firecracker 5K Run/Walk, the Kids Bike Parade, a Market and Craft Fair on the Green, and a festive Community Dinner. Bring the whole family to celebrate the 4th on the Farm at Billings Farm & Museum.
The celebration wraps up July 5 with a free pool party at the Woodstock Recreation Center and a fireworks celebration at Woodstock Union High School Middle School featuring food vendors, games, music, and family activities. Bring your friends, family, and community spirit as Woodstock comes together to celebrate 250 years of independence!
July – august 2026
Music by the river
Music by the River is a free summer concert series in Woodstock, held on Friday evenings from early July through late August. Located at East End Park on the banks of the Ottauquechee River, these concerts invite the community to enjoy an evening of live music in a beautiful outdoor setting. Bring a picnic, gather with friends and family, and enjoy dancing on the lawn as musicians take the stage throughout the summer.
SEP 12-13, 2026
Woodstock Art Festival
This two-day fine art event is held annually on the Village Green the weekend following Labor Day. Featuring more than 30 New England artists, the festival showcases a wide range of work from oil paintings and watercolors to photography and sculptures, alongside live music, local food, and spirits.
Contact the Woodstock Chamber of Commerce for more information.
October 10-11, 2026
Apples & Crafts Fair
This annual Craft Fair and Food Truck Festival in Woodstock celebrates fall foliage, local artisans, and great food. Featuring more than 100 juried artisans and food producers, visitors can browse jewelry, pottery, clothing, photography, and other handcrafted goods while enjoying delicious bites from local food trucks. This festive event supports the Woodstock Recreation Center.
November 26, 2026
zack’s place Turkey Trot
The Zack’s Place Turkey Trot is a beloved Thanksgiving morning tradition in Woodstock, bringing together families, runners, and community members for a festive 5K run or walk through the historic village. The race begins at Woodstock Elementary School and winds past local landmarks before finishing on the Village Green.
With live music, warm drinks, and an awards ceremony after the race, the event is both a fun holiday tradition and a major fundraiser supporting the inclusive programs at Zack’s Place.
december 11-13, 2026
Wassail weekend
Wassail Weekend is an annual holiday tradition in Woodstock that celebrates the charm and spirit of a classic New England Christmas. Organized by the Woodstock Chamber of Commerce, Wassail Weekend transforms the village into a festive scene filled with lights, music, and seasonal activities.
Visitors can enjoy horse-drawn wagon rides, holiday markets, and concerts. The celebration features a beloved horse parade, as well as the Winter Celebration at Billings Farm & Museum. Throughout the village, shops, restaurants, and inns are festively decorated, creating a magical setting for residents and visitors alike.
Contact Jim Kelly for information about sponsoring Wassail Weekend.
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