Brian Glover live at DJ's Steakhouse

DJ's Steakhouse Bar and Grill 8 Nov 2025

Sip n Shop Event

Coldwell Banker McMahan (Winchester, KY) 8 Nov 2025

Welcome Home: A Cabaret Featuring the Leeds Artist Collective

37 N Main St, Winchester, KY, United States, Kentucky 40391 14 Nov 2025

Brews and Ewes

Avalon Farm LLC 8 Nov 2025

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

920 Bypass Rd 8 Nov 2025

Lauren Mink & Dale Adams at Waterfront Grille & Gathering

Waterfront Grille and Gathering 22 Nov 2025

The Barn Market · Christmas Market and Photo Event

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

WCCFM Christmas Market!

Grace Bible Academy - Winchester, KY 6 Dec 2025

Stronger Than Cancer Walk

30 Wheeler Ave, Winchester, KY 40391-1804, United States 7 Nov 2025

Downtown Winchester Holiday Open House

Downtown Winchester, Kentucky 14 Nov 2025

Donuts with Dems

130 Windridge Dr, Winchester, KY 40391-2367, United States 15 Nov 2025

Christmas Vendor Market

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

Needle in a Haystack Pop-Up at Hamilton Brooks Design

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

Celebrating 10 Years in Downtown

38 N Main St, Winchester, KY, United States, Kentucky 40391 8 Nov 2025

WWKY Radio Chamber After Hours

Boone House Grill 12 Nov 2025

Holiday Market at The Well at Cherry Well Farm

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

Christmas Open House

148 Winn Ave., Winchester, KY 8 Nov 2025

Build Your Stack with Bluegrass Silver Co

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

Women's Tea

Salem Presbyterian Church 15 Nov 2025

Small Business Saturday - CHRISTMAS MARKET

Depot Street Winchester Ky 29 Nov 2025