Arts Events and Things to do in Winchester, KY

Search for something you love or check out popular events in your area.

Stumbling Stones: The John Rosenberg Story April 19th & 26th
Sun, Apr 19, 2:00 PM + 1 more
Lexington · The Spot: Lex
Stumbling Stones: The John Rosenberg Story April 19th & 26th
Sun, Apr 19, 2:00 PM + 1 more
Lexington · The Spot: Lex
"MAGIC MIKE" Night Lexington, KY (4/7/2026)
Tue, Apr 7, 7:00 PM
Lexington · Neon Moon Bar & Lounge
"MAGIC MIKE" Night Lexington, KY (4/7/2026)
Tue, Apr 7, 7:00 PM
Lexington · Neon Moon Bar & Lounge
Line Dancing Class ft. Boots & Beats Co. at Chenault Vineyards
Thu, Apr 23, 7:00 PM
Richmond · Chenault Vineyards
Line Dancing Class ft. Boots & Beats Co. at Chenault Vineyards
Thu, Apr 23, 7:00 PM
Richmond · Chenault Vineyards
Drag Queen Sip and Paint Lexington The Drag Queen Paint experience
Sat, Mar 14, 4:00 PM + 183 more
Lexington · 267 W Main St
Drag Queen Sip and Paint Lexington The Drag Queen Paint experience
Sat, Mar 14, 4:00 PM + 183 more
Lexington · 267 W Main St
Illusions The Drag Queen Show Lexington - Drag Queen Dinner Show
Friday at 7:00 PM + 189 more
Lexington · Illusions The Drag Queen Show Lexington
Illusions The Drag Queen Show Lexington - Drag Queen Dinner Show
Friday at 7:00 PM + 189 more
Lexington · Illusions The Drag Queen Show Lexington
Stage 152 Comedy Night
Friday at 8:00 PM
Georgetown · Georgetown Underground
Stage 152 Comedy Night
Friday at 8:00 PM
Georgetown · Georgetown Underground
YTOB Audition Workshop 2026
Sat, May 9, 12:00 PM
Georgetown · First Christian Church
YTOB Audition Workshop 2026
Sat, May 9, 12:00 PM
Georgetown · First Christian Church
Just added!
Laugh Now, Thank Starks Later.
Fri, Apr 17, 8:00 PM
Lexington · The Spot: Lex
Just added!
Laugh Now, Thank Starks Later.
Fri, Apr 17, 8:00 PM
Lexington · The Spot: Lex
YTOB's Spring Break Music Theatre Clinic
Fri, Apr 10, 12:00 PM + 1 more
Georgetown · First Christian Church
YTOB's Spring Break Music Theatre Clinic
Fri, Apr 10, 12:00 PM + 1 more
Georgetown · First Christian Church
Standup Comedy at Country Boy Brewing (Georgetown, KY)
Fri, May 1, 8:00 PM
Georgetown · Country Boy Brewing
Standup Comedy at Country Boy Brewing (Georgetown, KY)
Fri, May 1, 8:00 PM
Georgetown · Country Boy Brewing
Legends of Country Drag Show!
Sat, Mar 28, 8:30 PM
Frankfort · Bibb's Pub
Legends of Country Drag Show!
Sat, Mar 28, 8:30 PM
Frankfort · Bibb's Pub
Paint Night at the Kentucky Ice Box
Friday at 7:00 PM
Williamstown · Kentucky Y’all Icebox
Paint Night at the Kentucky Ice Box
Friday at 7:00 PM
Williamstown · Kentucky Y’all Icebox
Art Opening
Sat, Mar 14, 7:30 PM
Lexington · 833 National Ave
Art Opening
Sat, Mar 14, 7:30 PM
Lexington · 833 National Ave
No Menthol Poetry Contest Kentucky
Sat, Apr 4, 6:00 PM
Lexington · 1375 S Broadway
No Menthol Poetry Contest Kentucky
Sat, Apr 4, 6:00 PM
Lexington · 1375 S Broadway
Sales end soon
Performing Arts Team Meeting
Wednesday at 6:00 PM + 14 more
Lexington · artfarm
Sales end soon
Performing Arts Team Meeting
Wednesday at 6:00 PM + 14 more
Lexington · artfarm
Phil Wickham - World Vision Volunteers - Lexington, KY
Sat, May 16, 4:45 PM
Lexington · Rupp Arena
Phil Wickham - World Vision Volunteers - Lexington, KY
Sat, May 16, 4:45 PM
Lexington · Rupp Arena
The Troubadours - World Vision Volunteers - Lexington, KY
Mon, Apr 20, 5:15 PM
Lexington · Lexington Opera House
The Troubadours - World Vision Volunteers - Lexington, KY
Mon, Apr 20, 5:15 PM
Lexington · Lexington Opera House
Sales end soon
Paint w/ Lu
Friday at 5:30 PM
Somerset · The Shine House
Sales end soon
Paint w/ Lu
Friday at 5:30 PM
Somerset · The Shine House
Lake Cumberland Children's Theatre Presents: The Outsiders
Fri, Mar 27, 7:00 PM + 2 more
Somerset · The Virginia
Lake Cumberland Children's Theatre Presents: The Outsiders
Fri, Mar 27, 7:00 PM + 2 more
Somerset · The Virginia
Sam Miller and friends
Fri, Apr 24, 8:00 AM
Warsaw · Sunset Grill
Sam Miller and friends
Fri, Apr 24, 8:00 AM
Warsaw · Sunset Grill

Trends in Winchester

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Frequently asked questions about Winchester

What are the best events to attend?

According to Eventbrite, the best events are:

Stumbling Stones: The John Rosenberg Story April 19th & 26th

"MAGIC MIKE" Night Lexington, KY (4/7/2026)

Line Dancing Class ft. Boots & Beats Co. at Chenault Vineyards

Drag Queen Sip and Paint Lexington The Drag Queen Paint experience

Which events are currently trending in Winchester?

The trending searches this month in Winchester are:

valentines

free kids events

events happening today near me

murder mystery dinner

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Performing Arts Team Meeting

Paint w/ Lu

Illusions The Drag Queen Show Lexington - Drag Queen Dinner Show

Paint Night at the Kentucky Ice Box

Stumbling Stones: The John Rosenberg Story April 19th & 26th

Stumbling Stones: The John Rosenberg Story April 19th & 26th

"MAGIC MIKE" Night Lexington, KY (4/7/2026)

"MAGIC MIKE" Night Lexington, KY (4/7/2026)

Line Dancing Class ft. Boots & Beats Co. at Chenault Vineyards

Line Dancing Class ft. Boots & Beats Co. at Chenault Vineyards

Drag Queen Sip and Paint Lexington The Drag Queen Paint experience

Drag Queen Sip and Paint Lexington The Drag Queen Paint experience

Illusions The Drag Queen Show Lexington - Drag Queen Dinner Show

Illusions The Drag Queen Show Lexington - Drag Queen Dinner Show

Stage 152 Comedy Night

Stage 152 Comedy Night

YTOB Audition Workshop 2026

YTOB Audition Workshop 2026

Laugh Now, Thank Starks Later.

Laugh Now, Thank Starks Later.

YTOB's Spring Break Music Theatre Clinic

YTOB's Spring Break Music Theatre Clinic

Standup Comedy at Country Boy Brewing (Georgetown, KY)

Standup Comedy at Country Boy Brewing (Georgetown, KY)

Legends of Country Drag Show!

Legends of Country Drag Show!

Paint Night at the Kentucky Ice Box

Paint Night at the Kentucky Ice Box

Art Opening

Art Opening

No Menthol Poetry Contest Kentucky

No Menthol Poetry Contest Kentucky

Performing Arts Team Meeting

Performing Arts Team Meeting

Phil Wickham - World Vision Volunteers - Lexington, KY

Phil Wickham - World Vision Volunteers - Lexington, KY

The Troubadours - World Vision Volunteers - Lexington, KY

The Troubadours - World Vision Volunteers - Lexington, KY

Paint w/ Lu

Paint w/ Lu

Lake Cumberland Children's Theatre Presents: The Outsiders

Lake Cumberland Children's Theatre Presents: The Outsiders

Sam Miller and friends

Sam Miller and friends

Things to do around Winchester

Trends in Winchester

1. Valentines

2. Free kids events

3. Events happening today near me

4. Murder mystery dinner

5. Valley dale

6. Trampoline

7. Taylor swift

8. Louisville ky

9. Vendors needed

10. Valentine

11. Thanksgiving eve block party

12. St patrick

What are the best events to attend?

Which events are currently trending in Winchester?

Which events are coming up?