#StayHappening

Upcoming Winchester Events

Check out what's happening all around Winchester, KY

25 upcoming events Winchester, United States Updated 2 Nov 2026
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Things to do in Winchester

All 25 events in Winchester

Sea Glass Tree

Fri, 06 Nov at 06:00 pm 36 N Highland St., Winchester, KY

Ladies’ Night

Sat, 14 Nov at 06:30 pm 36 N Highland St., Winchester, KY
ART

Christmas Market

Sat, 05 Dec at 08:00 am 30 Beckner St, Winchester, KY 40391-1810, United States
CHRISTMAS

Shop Small Saturday!

Sat, 28 Nov at 08:00 am Main Street, Winchester, KY, United States, Kentucky 40391