Beer cheese Trail

June 12, 20267:00 pm-9:00 pm

Free Concert – Courthouse Square NIGHTFLYER – Eagles Tribute Band

June 13, 2026 - June 20, 2026

Experience one of Winchester’s favorite summertime traditions at the Clark County Fair, ...

June 13, 202610:00 am-5:00 pm

Every summer, Winchester comes alive with one of Kentucky’s most unique and beloved trad...

June 20, 2026

Celebrate freedom, culture, and community at Winchester’s Juneteenth Celebration, an ins...

June 20, 20269:30 am-10:30 am

Looking for a one-of-a-kind experience that combines relaxation, laughter, and a little fa...

July 10, 20267:00 pm-9:00 pm

Free Concert – Courthouse Square The RANAHANS Country / Western / Swing

August 1, 20265:00 pm-9:00 pm

Cenenni-Ale Celebration Join Downtown Winchester for a “Centenni-Ale” celebration and ...

August 14, 20267:00 pm-9:00 pm

Free Concert – Courthouse Square The PERFECT STRANGERS Rock, Pop, Funk

September 5, 2026 - September 6, 20268:00 am - 5:00 pm

Celebrate Winchester’s most beloved tradition at the Daniel Boone Pioneer Festival, a tw...