Winchester Holiday Events

Holiday events Happening Next in Winchester, KY

Nov 8th. Join us.Annual Sip N Shop @Coldwell Banker McMahan, Winchester, KY

 920 Bypass Rd 8 Nov 2025
FOOD-DRINKS FREE

The Barn Market · Christmas Market and Photo Event

 1080 Combs Ferry Road, Winchester, KY, United States, Kentucky 40391 15 Nov 2025
CHRISTMAS

Downtown Winchester Holiday Open House

 Downtown Winchester, Kentucky 14 Nov 2025
HOLIDAY

Holiday Market at The Well at Cherry Well Farm

 2990 Colby Road, Winchester, KY, United States, Kentucky 40391 6 Dec 2025
HOLIDAY

Needle in a Haystack Pop-Up at Hamilton Brooks Design

 21 S Main St, Winchester, KY, United States, Kentucky 40391 15 Nov 2025
POP-UPS

Christmas Vendor Market

 7789 Old Boonesboro Road, Winchester, KY, United States, Kentucky 40391 22 Nov 2025
CHRISTMAS

Build Your Stack with Bluegrass Silver Co

 21 S Main St, Winchester, KY, United States, Kentucky 40391 14 Nov 2025
HOLIDAY

Bakery Popup @ Holiday Market at The Well

 The Well at Cherry Well Farm 6 Dec 2025
HOLIDAY

Little Chef Holiday Workshop

Amy's Asian Kitchen 13 Dec 2025
FOOD-DRINKS

CASA Giving Tree Clark County

 The Past Time Social Club and Cigar Lounge 12 Nov 2025
HOLIDAY