Winchester Festivals Events

Daniel Boone Pioneer Festival 2025

Winchester KY 30 Aug 2025

Hamilton Brooks at the Daniel Boone Pioneer Festival

21 S Main St, Winchester, KY, United States, Kentucky 40391 30 Aug 2025

Clark County Demolition Derby

4980 Ironworks Road, Winchester, KY 30 Aug 2025

Winchester Pride + Inclusion Festival 2025

Depot Street Winchester Ky 18 Oct 2025

Christmas Tree Event

36 N Highland St., Winchester, KY 30 Aug 2025

Eli Lev at ShenArts Fest

Civil War Museum in Winchester, VA 6 Sep 2025

Drum Circle at Legacy Grove Park!

1107 W. Lexington Ave., Winchester, KY, United States, Kentucky 40391 27 Aug 2025

Harvest Moon Party

5199 Combs Ferry Rd, Winchester, KY, United States, Kentucky 40391 3 Oct 2025

Feast Over Fire: Farm to Table Dinner x Wine Pairing

5199 Combs Ferry Rd, Winchester, KY, United States, Kentucky 40391 5 Oct 2025

10th Annual Rally4Recovery 2025

College Park 26 Sep 2025

7th Annual Pig Pickin’ for the Past BBQ

28 Beckner Street, Winchester, KY 27 Sep 2025

Sound Bath

55 S Main St, Winchester, KY, United States, Kentucky 40391 1 Sep 2025

Lauren Mink & Dale Adams at Daniel Boone Pioneer Festival

Daniel Boone Pioneer Festival 30 Aug 2025

Jon Curtis at the Daniel Boone Pioneer Festival

Daniel Boone Pioneer Festival 31 Aug 2025

Legacy Grove at the Winchester Pride + Inclusion Festival

Depot St, Winchester, KY 40391, United States 18 Oct 2025

Annual Christmas Market

31 E Broadway Street, Suite B , Winchester, KY, United States, Kentucky 40391 29 Nov 2025

1779 Siege of Ft Boonesboro

Fort Boonesborough Museum 19 Sep 2025