Winchester, VA

Winchester Comedy Tickets

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Trending Winchester Events

A comedian laughs into a microphone on stage while a crowd watches.
Ben Bankas
Sep 5 • 7:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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A male comedian on stage at a brick wall venue, holding a microphone and addressing an audience.
Gary Owen
Nov 27 • 7:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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A male comedian on stage at a brick wall venue, holding a microphone and addressing an audience.
Gary Owen
Nov 27 • 9:30PM
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
Four men on a comedy stage, three holding microphones, with brick walls and a black curtain behind them.
Killers of Kill Tony: Ari Matti, William Montgomery, David Lucas & Hans Kim
Jun 13 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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A Black woman with braided hair laughs while holding a microphone on a stage with a dark blue curtain background.
Leslie Jones
Oct 23 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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A woman with red hair in a black leather jacket laughs into a microphone on a stage with red curtains.
Kathleen Madigan
Oct 24 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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A short man with a beard and cap tells jokes into a microphone on a stage.
Brad Williams
Oct 10 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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Person on stage with a floral shirt facing a blurry, cheering audience under colorful lights.
Margaret Cho
Oct 3 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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Comedian with long brown hair, glasses, and a red baseball cap holds a microphone in front of a brick wall.
Dusty Slay
Jul 11 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets

Winchester Comedy Schedule

2-24-25
Jun 13
Sat • 8:00 PM
Sat
Jun 13
8:00 PM
Killers of Kill Tony: Ari Matti, William Montgomery, David Lucas & Hans Kim
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
2-24-25
Jul 11
Sat • 8:00 PM
Sat
Jul 11
8:00 PM
Dusty Slay
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
2-24-25
Sep 5
Sat • 7:00 PM
Sat
Sep 5
7:00 PM
Ben Bankas
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
2-24-25
Sep 18
Fri • 8:00 PM
Fri
Sep 18
8:00 PM
D.L. Hughley
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
2-24-25
Sep 25
Fri • 7:00 PM
Fri
Sep 25
7:00 PM
Jay Leno
The Maryland Theatre
Hagerstown, MD
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2-24-25
Oct 3
Sat • 8:00 PM
Sat
Oct 3
8:00 PM
Margaret Cho
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
2-24-25
Oct 10
Sat • 8:00 PM
Sat
Oct 10
8:00 PM
Brad Williams
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
2-24-25
Oct 23
Fri • 8:00 PM
Fri
Oct 23
8:00 PM
Leslie Jones
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
2-24-25
Oct 24
Sat • 8:00 PM
Sat
Oct 24
8:00 PM
Kathleen Madigan
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
2-24-25
Nov 27
Fri • 7:00 PM
Fri
Nov 27
7:00 PM
Gary Owen
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
2-24-25
Nov 27
Fri • 9:30 PM
Fri
Nov 27
9:30 PM
Gary Owen
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets

Find the Best Comedy Shows in Winchester for 2026

Winchester is a hub for exciting live entertainment. We've analyzed our sales data to bring you the most popular comedy shows so you can easily plan your next outing.

Top 2026 Summer Comedy Shows in Winchester

Summer is the perfect time for live events in Winchester! Check out this list of the top comedy shows happening from May through September.

Event Name Date Venue Lowest Price
Todd Barry Jun 4 Jammin Java $107
Killers of Kill Tony: Ari Matti, William Montgomery, David Lucas & Hans Kim Jun 13 Hollywood Casino at Charles Town Races $184
Jim Jefferies Jun 26 Capital One Hall $111
Jim Jefferies Jun 27 Capital One Hall $96
Dusty Slay Jul 11 Hollywood Casino at Charles Town Races $52
Ben Bankas Sep 5 Hollywood Casino at Charles Town Races $66
D.L. Hughley Sep 18 Hollywood Casino at Charles Town Races $81
Jay Leno Sep 25 The Maryland Theatre $167

Top Venues in Winchester, VA

jiffy lube live
Jiffy Lube Live
Bristow, VA
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wolf trap national park for the performing arts
Wolf Trap National Park for the Performing Arts
Vienna, VA
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a hyper-realistic wide-angle aerial photograph of hollywood casino at charles town races in charles town, west virginia, captured at sunset
Hollywood Casino at Charles Town Races
Charles Town, WV
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eaglebank arena
EagleBank Arena
Fairfax, VA
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a photograph of capital one hall in tysons, virginia, captured at sunset.
Capital One Hall
Tysons Corner, VA
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image of the weinberg center for the arts
The Weinberg Center For The Arts
Frederick, MD
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a photograph of the maryland theatre in hagerstown, maryland, captured at sunset with warm, golden light illuminating the venue’s historic brick and stone facade.
The Maryland Theatre
Hagerstown, MD
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nymeo field at harry grove stadium
Nymeo Field at Harry Grove Stadium
Frederick, MD
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an exterior promotional venue picture of luhrs performing arts center with a sunset sky
Luhrs Performing Arts Center
Shippensburg, PA
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Backseat Events
Backseat Events
Winchester, VA
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All Venues Near Winchester, VA