Events for October 11, 2025 › Windsor County › – Happy Vermont

Vermont Events

Vermont Apple Festival and Craft Show in Springfield

Riverside Middle School 13 Fairground Road, Springfield

Celebrate fall at the annual Vermont Apple Festival and Craft Show in Springfield. The event features craft and food vendors, kids activities, apples and much more.

Recurring

The Woodlife Carving Festival

The WoodLife Carving Festival 1126 VT Route 103N, Chester

Get ready for two unforgettable days of artistry, skill, and the roar of chainsaws at The WoodLife Carving Festival in Chester. About a dozen talented chainsaw carvers will gather to showcase and sell their incredible one-of-a-kind creations. Festival Highlights: -Quick Carve Competitions: Watch carvers transform...

Ludlow Rotary Club Chili Cook Off

Ludlow Chili Cook Off Main and Depot Streets, Ludlow

The 34th annual Ludlow Rotary Club Chili Cook Off is a chance to sample unique and delicious chili recipes submitted by local chefs and at-home cooks. Vote for your favorite! Admission $15 per person; kids under 12 $10. Price includes chili, bread, ice cream and...

Recurring

Harpoon Brewery Fall Festival in Windsor

Harpoon Brewery 336 Ruth Carney Drive, Windsor

Celebrate the season at the Harpoon Brewery Fall Festival in Windsor. This two-day event showcases tasty beer, live music, local vendors and delicious food.

Vermont Food & Music Festival at Mount Ascutney

Ascutney Outdoors 449 Ski Tow Road, Brownsville

Join the Brownsville Butcher & Pantry in partnership with Ascutney Outdoors to celebrate Vermont’s food, music, and community at the Vermont Food & Music Festival. The event features a full day of live music, local flavors, and craft beverages in a beautiful mountain setting. This...

Reggie Harris Performs at Chester Town Hall

Chester Town Hall 556 Elm St., Chester

Upstairs at Town Hall presents a performance by iconic folk singer, historian, educator and civil rights activist Reggie Harris. As a descendant of an enslaved Black woman and a Confederate general, Harris has embraced his unique heritage to create profound and beautiful music about diverse...