Upcoming Events in Winchester

Dare to Dream JR the musical

George Rogers Clark High School 14 Feb 2026
LIVE-MUSIC

Valentine's Day Dinner and Dancing.

 3947 Lexington Rd, Winchester, KY, United States, Kentucky 40391 14 Feb 2026
VALENTINES-DAY

SOLD OUT---Cupid's Last Arrow - Mystery Dinner Series

 Whiskey and Wiles Photography 13 Feb 2026
VALENTINES-DAY

10th Annual Alexis Thompson Memorial 5k/10K

 Winchester, Kentucky 6 Jun 2026
SPORTS

WCCPR Jump Start Group Fitness Challenge 2026

 15 Wheeler Ave , Winchester, KY, United States, Kentucky 40391 13 Feb 2026
CONTESTS

Shearer Musical Theatre Presents: Dare To Dream Jr.

George Rogers Clark High School Theater 13 Feb 2026
LIVE-MUSIC

Fat Tuesday Mardi Gras Glitter Bar

 The Past Time 17 Feb 2026

Dare to Dream Jr the musical school show

George Rogers Clark High School 12 Feb 2026
LIVE-MUSIC

Exotics, Oddities and Ink Showcase

 Winchester KY 4 Apr 2026
ART

My Bloody Valentine

 20 Wall St, Winchester, KY, United States, Kentucky 40391 13 Feb 2026
VALENTINES-DAY

Popup @ Crystal Coven Mystic Cottage

 55 South Main Street Winchester Ky 40391 21 Feb 2026
TRIPS-ADVENTURES

3 Men & A Banjo at The Past Time

The Past Time 20 Feb 2026

Mother's Day at The Vineyard

 5199 Combs Ferry Rd, Winchester, KY, United States, Kentucky 40391 10 May 2026
MUSIC

Easy loop/stock ride

 Paris/winchester exit at bp 12 Feb 2026
MEETUPS

Be Our Valentine Dance Fitness Freebie

 15 Wheeler Ave , Winchester, KY, United States, Kentucky 40391 14 Feb 2026
VALENTINES-DAY

Next Stop Comedy at Waterfront Grill & Gathering! - Winchester, KY

 Waterfront Grill and Gathering 13 Feb 2026
COMEDY USD 28

Parents Night Out💕

 Winchester KY 14 Feb 2026
NONPROFIT

WINCHESTER REDEMPTION MUSIC AND CRAFT FESTIVAL

 37 N Main St 14 Mar 2026
HOLIDAY FREE

Intro to Bungee - Puppy Love Night

 7 N Main Street, Winchester, KY, United States, Kentucky 40391 25 Feb 2026
WORKSHOPS

Open Mic at The Past Time

 The Past Time 15 Feb 2026
MUSIC

More things to do in Winchester

Food & Drinks
Festivals
Comedy
Mardi Gras
Galentines Day
Pop-Ups
St. Patrick's Day
Black History Month
Carnivals
Parades