Winchester, VA

Winchester Comedy Tickets

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Trending Winchester Events

A Black man in a fedora and suit laughs while holding a microphone on stage, with a city skyline backdrop.
Don Lemon & D.L. Hughley
Apr 18 • 7:30PM
Capital One Hall
Tysons Corner, VA
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Woman in a colorful striped jacket and bow tie winks while pointing and holding a microphone.
Paula Poundstone
Apr 17 • 8:00PM
The Weinberg Center For The Arts
Frederick, MD
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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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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 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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A woman with dark hair in a ponytail, wearing a black leather jacket, holds a microphone.
Anjelah Johnson-Reyes
Apr 11 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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A person in a white shirt speaks to an audience from a stage.
Dante Gebel
Nov 4 • 8:00PM
Capital One Hall
Tysons Corner, VA
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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 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
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Winchester Comedy Schedule

2-24-25
Apr 10
Fri • 7:00 PM
Fri
Apr 10
7:00 PM
Evening of Comedy
The Barns At Wolf Trap National Park for the Performing Arts
Vienna, VA
Get Tickets
2-24-25
Apr 10
Fri • 9:30 PM
Fri
Apr 10
9:30 PM
Evening of Comedy
The Barns At Wolf Trap National Park for the Performing Arts
Vienna, VA
Get Tickets
2-24-25
Apr 11
Sat • 8:00 PM
Sat
Apr 11
8:00 PM
Anjelah Johnson-Reyes
Hollywood Casino at Charles Town Races
Charles Town, WV
Get Tickets
2-24-25
Apr 11
Sat • 9:30 PM
Sat
Apr 11
9:30 PM
Evening of Comedy
The Barns At Wolf Trap National Park for the Performing Arts
Vienna, VA
Get Tickets
2-24-25
Apr 17
Fri • 7:00 PM
Fri
Apr 17
7:00 PM
Ron White
Hollywood Casino at Charles Town Races
Charles Town, WV
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2-24-25
Apr 17
Fri • 8:00 PM
Fri
Apr 17
8:00 PM
Paula Poundstone
The Weinberg Center For The Arts
Frederick, MD
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2-24-25
Apr 17
Fri • 9:30 PM
Fri
Apr 17
9:30 PM
Ron White
Hollywood Casino at Charles Town Races
Charles Town, WV
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2-24-25
Apr 18
Sat • 7:30 PM
Sat
Apr 18
7:30 PM
Don Lemon & D.L. Hughley
Capital One Hall
Tysons Corner, VA
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2-24-25
Apr 23
Thu • 2:30 PM
Thu
Apr 23
2:30 PM
Zakir Khan
Capital One Hall
Tysons Corner, VA
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2-24-25
Apr 23
Thu • 7:30 PM
Thu
Apr 23
7:30 PM
Bored Teachers Comedy Tour
The Weinberg Center For The Arts
Frederick, MD
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2-24-25
Apr 24
Fri • 7:30 PM
Fri
Apr 24
7:30 PM
Bored Teachers Comedy Tour
Luhrs Performing Arts Center
Shippensburg, PA
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2-24-25
May 10
Sun • 6:00 PM
Sun
May 10
6:00 PM
Sumukhi Suresh
Richard J. Ernst Theatre
Annandale, VA
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2-24-25
May 23
Sat • 2:30 PM
Sat
May 23
2:30 PM
Zakir Khan
Capital One Hall
Tysons Corner, VA
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2-24-25
May 23
Sat • 7:00 PM
Sat
May 23
7:00 PM
Zakir Khan
Capital One Hall
Tysons Corner, VA
Get Tickets
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
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2-24-25
Jun 26
Fri • 7:00 PM
Fri
Jun 26
7:00 PM
Jim Jefferies
Capital One Hall
Tysons Corner, VA
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2-24-25
Jun 27
Sat • 7:00 PM
Sat
Jun 27
7:00 PM
Jim Jefferies
Capital One Hall
Tysons Corner, VA
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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
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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
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2-24-25
Oct 2
Fri • 7:00 PM
Fri
Oct 2
7:00 PM
Kanan Gill
Capital One Hall
Tysons Corner, VA
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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
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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
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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 4
Wed • 8:00 PM
Wed
Nov 4
8:00 PM
Dante Gebel
Capital One Hall
Tysons Corner, VA
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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
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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 Comedy Shows in Winchester This Weekend

Planning your weekend? There are 4 comedy shows happening around Winchester this weekend! Here are the most popular comedy shows happening in Winchester from Thursday to Sunday. Don't miss out on the action!

Event Name Date Venue Lowest Price
Evening of Comedy Apr 10 The Barns At Wolf Trap National Park for the Performing Arts $198
Evening of Comedy Apr 10 The Barns At Wolf Trap National Park for the Performing Arts $90
Anjelah Johnson-Reyes Apr 11 Hollywood Casino at Charles Town Races $87
Evening of Comedy Apr 11 The Barns At Wolf Trap National Park for the Performing Arts $114

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
Sumukhi Suresh May 10 Richard J. Ernst Theatre $104
Zakir Khan May 23 Capital One Hall $95
Zakir Khan May 23 Capital One Hall $191
Killers of Kill Tony: Ari Matti, William Montgomery, David Lucas & Hans Kim Jun 13 Hollywood Casino at Charles Town Races $197
Jim Jefferies Jun 26 Capital One Hall $142
Jim Jefferies Jun 27 Capital One Hall $101
Dusty Slay Jul 11 Hollywood Casino at Charles Town Races $52
Ben Bankas Sep 5 Hollywood Casino at Charles Town Races $68

Cheap Things to Do in Winchester This Weekend (Under $100)

Looking for fun in Winchester that won't break the bank? You've come to the right place. This list features the best-selling comedy shows this weekend with tickets under $100.

Event Name Date Venue Lowest Price
Evening of Comedy Apr 10 The Barns At Wolf Trap National Park for the Performing Arts $90
Anjelah Johnson-Reyes Apr 11 Hollywood Casino at Charles Town Races $87

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 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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eaglebank arena
EagleBank Arena
Fairfax, VA
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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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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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image of george mason center for the arts concert hall
George Mason Center For The Arts - Concert Hall
Fairfax, VA
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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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image of merchant hall at hylton performing arts center
Merchant Hall At Hylton Performing Arts Center
Manassas, VA
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All Venues Near Winchester, VA