Trending Winchester Events
Ben Bankas
Sep 5 •
7:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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Christopher Cross
Jun 26 •
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Hollywood Casino at Charles Town Races
Charles Town, WV
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The Price Is Right - Live Stage Show
Nov 7 •
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Hollywood Casino at Charles Town Races
Charles Town, WV
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Richard Marx
Aug 8 •
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Hollywood Casino at Charles Town Races
Charles Town, WV
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The Price Is Right - Live Stage Show
Nov 7 •
3:30PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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Travis Tritt
Aug 29 •
7:30PM
Shenandoah County Fairgrounds
Woodstock, VA
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Buddy Guy
Aug 1 •
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Hollywood Casino at Charles Town Races
Charles Town, WV
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Jamey Johnson
Oct 9 •
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Hollywood Casino at Charles Town Races
Charles Town, WV
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Gary Owen
Nov 27 •
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Hollywood Casino at Charles Town Races
Charles Town, WV
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All Venues And Events In Winchester, VA
2-23-25
May 28
Thu • 8:00 PM
Thu
May 28
8:00 PM
Bryan Martin
Backseat Events
Winchester, VA
2-23-25
May 29
Fri • 8:00 PM
Fri
May 29
8:00 PM
Chris Cagle
Backseat Events
Winchester, VA
2-37-25
May 30
Sat • 7:00 PM
Sat
May 30
7:00 PM
MSGBR 80'S Prom Unleashed
Backseat Events
Winchester, VA
1-39-29
May 30
Sat • 8:00 PM
Sat
May 30
8:00 PM
Extreme Dwarfanators Wrestling
Shenandoah County Fairgrounds
Woodstock, VA
2-62-25
May 30
Sat • 8:00 PM
Sat
May 30
8:00 PM
Lounge Fly - Stone Temple Pilots Tribute
Hub City Vinyl
Hagerstown, MD
1-63-29
Jun 2
Tue • 6:30 PM
Tue
Jun 2
6:30 PM
Hagerstown Flying Boxcars vs. Lexington Legends
Meritus Park
Hagerstown, MD
1-63-29
Jun 3
Wed • 11:00 AM
Wed
Jun 3
11:00 AM
Hagerstown Flying Boxcars vs. Lexington Legends
Meritus Park
Hagerstown, MD
1-63-29
Jun 4
Thu • 6:30 PM
Thu
Jun 4
6:30 PM
Hagerstown Flying Boxcars vs. Lexington Legends
Meritus Park
Hagerstown, MD
2-23-25
Jun 4
Thu • 8:00 PM
Thu
Jun 4
8:00 PM
Creed Fisher
Backseat Events
Winchester, VA
1-63-29
Jun 5
Fri • 6:30 PM
Fri
Jun 5
6:30 PM
Hagerstown Flying Boxcars vs. Lexington Legends
Meritus Park
Hagerstown, MD
2-62-25
Jun 5
Fri • 8:00 PM
Fri
Jun 5
8:00 PM
Vicki Peterson & John Cowsill
Hub City Vinyl
Hagerstown, MD
1-63-29
Jun 6
Sat • 6:00 PM
Sat
Jun 6
6:00 PM
Hagerstown Flying Boxcars vs. Lexington Legends
Meritus Park
Hagerstown, MD
2-62-25
Jun 6
Sat • 7:30 PM
Sat
Jun 6
7:30 PM
Jimmy Failla
The Maryland Theatre
Hagerstown, MD
2-37-25
Jun 6
Sat • 8:00 PM
Sat
Jun 6
8:00 PM
High Voltage
Hub City Vinyl
Hagerstown, MD
2-37-25
Jun 6
Sat • 8:00 PM
Sat
Jun 6
8:00 PM
Jason Bonham's Led Zeppelin Evening
Hollywood Casino at Charles Town Races
Charles Town, WV
1-63-29
Jun 7
Sun • 2:00 PM
Sun
Jun 7
2:00 PM
Hagerstown Flying Boxcars vs. Lexington Legends
Meritus Park
Hagerstown, MD
2-62-25
Jun 11
Thu • 7:00 PM
Thu
Jun 11
7:00 PM
Hawthorne Heights
Hollywood Casino at Charles Town Races
Charles Town, WV
2-37-25
Jun 12
Fri • 8:00 PM
Fri
Jun 12
8:00 PM
Tell Me Lies - Tribute To Fleetwood Mac
Hub City Vinyl
Hagerstown, MD
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
2-23-25
Jun 13
Sat • 8:00 PM
Sat
Jun 13
8:00 PM
Leroy Burks and The Voodoo Whiskey Band
Hub City Vinyl
Hagerstown, MD
1-63-29
Jun 16
Tue • 6:30 PM
Tue
Jun 16
6:30 PM
Hagerstown Flying Boxcars vs. Charleston Dirty Birds
Meritus Park
Hagerstown, MD
1-63-29
Jun 17
Wed • 6:30 PM
Wed
Jun 17
6:30 PM
Hagerstown Flying Boxcars vs. Charleston Dirty Birds
Meritus Park
Hagerstown, MD
2-22-25
Jun 17
Wed • 8:00 PM
Wed
Jun 17
8:00 PM
Blacktop Mojo
Hub City Vinyl
Hagerstown, MD
1-63-29
Jun 18
Thu • 6:30 PM
Thu
Jun 18
6:30 PM
Hagerstown Flying Boxcars vs. Charleston Dirty Birds
Meritus Park
Hagerstown, MD
1-63-29
Jun 19
Fri • 6:30 PM
Fri
Jun 19
6:30 PM
Hagerstown Flying Boxcars vs. Charleston Dirty Birds
Meritus Park
Hagerstown, MD
2-37-25
Jun 19
Fri • 8:00 PM
Fri
Jun 19
8:00 PM
Bearly Dead - Grateful Dead Tribute
Hub City Vinyl
Hagerstown, MD
2-100-25
Jun 20
Sat • 12:00 PM
Sat
Jun 20
12:00 PM
Quad State Wine & Music Fest
Washington County Agricultural Education Center
Boonsboro, MD
1-63-29
Jun 20
Sat • 6:00 PM
Sat
Jun 20
6:00 PM
Hagerstown Flying Boxcars vs. Charleston Dirty Birds
Meritus Park
Hagerstown, MD
2-37-25
Jun 20
Sat • 6:30 PM
Sat
Jun 20
6:30 PM
Candlelight: Vivaldi's Four Seasons And More
Franklin Park Arts Center
Purcellville, VA
2-23-25
Jun 20
Sat • 8:00 PM
Sat
Jun 20
8:00 PM
Charley Crockett
Hollywood Casino at Charles Town Races
Charles Town, WV
2-37-25
Jun 20
Sat • 8:00 PM
Sat
Jun 20
8:00 PM
The Bell Bottom Blues
Hub City Vinyl
Hagerstown, MD
1-63-29
Jun 21
Sun • 2:00 PM
Sun
Jun 21
2:00 PM
Hagerstown Flying Boxcars vs. Charleston Dirty Birds
Meritus Park
Hagerstown, MD
2-23-25
Jun 24
Wed • 8:00 PM
Wed
Jun 24
8:00 PM
Jim Lauderdale and The Game Changers
Hub City Vinyl
Hagerstown, MD
2-62-25
Jun 26
Fri • 8:00 PM
Fri
Jun 26
8:00 PM
Christopher Cross
Hollywood Casino at Charles Town Races
Charles Town, WV
1-63-29
Jun 30
Tue • 6:30 PM
Tue
Jun 30
6:30 PM
Hagerstown Flying Boxcars vs. Lancaster Stormers
Meritus Park
Hagerstown, MD
1-63-29
Jul 1
Wed • 6:30 PM
Wed
Jul 1
6:30 PM
Hagerstown Flying Boxcars vs. Lancaster Stormers
Meritus Park
Hagerstown, MD
1-39-29
Jul 2
Thu • 6:00 PM
Thu
Jul 2
6:00 PM
Little Mania Midget Wrestling
Vanish Hall
Boonsboro, MD
1-63-29
Jul 2
Thu • 6:30 PM
Thu
Jul 2
6:30 PM
Hagerstown Flying Boxcars vs. Lancaster Stormers
Meritus Park
Hagerstown, MD
2-45-25
Jul 2
Thu • 8:00 PM
Thu
Jul 2
8:00 PM
Brandon Combs
Hub City Vinyl
Hagerstown, MD
1-39-29
Jul 2
Thu • 9:00 PM
Thu
Jul 2
9:00 PM
Little Mania Midget Wrestling
Vanish Hall
Boonsboro, MD
2-23-25
Jul 3
Fri • 6:00 PM
Fri
Jul 3
6:00 PM
Shenandoah
Hollywood Casino at Charles Town Races
Charles Town, WV
2-23-25
Jul 4
Sat • 7:00 PM
Sat
Jul 4
7:00 PM
The Oak Ridge Boys
Hollywood Casino at Charles Town Races
Charles Town, WV
1-63-29
Jul 7
Tue • 6:30 PM
Tue
Jul 7
6:30 PM
Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Meritus Park
Hagerstown, MD
1-63-29
Jul 8
Wed • 6:30 PM
Wed
Jul 8
6:30 PM
Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Meritus Park
Hagerstown, MD
1-63-29
Jul 9
Thu • 6:30 PM
Thu
Jul 9
6:30 PM
Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Meritus Park
Hagerstown, MD
2-62-25
Jul 9
Thu • 8:00 PM
Thu
Jul 9
8:00 PM
Eliot Lewis
Hub City Vinyl
Hagerstown, MD
1-63-29
Jul 10
Fri • 6:30 PM
Fri
Jul 10
6:30 PM
Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Meritus Park
Hagerstown, MD
2-37-25
Jul 10
Fri • 8:00 PM
Fri
Jul 10
8:00 PM
The Warped Tour Band
Hub City Vinyl
Hagerstown, MD
1-63-29
Jul 11
Sat • 6:00 PM
Sat
Jul 11
6:00 PM
Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Meritus Park
Hagerstown, MD
2-37-25
Jul 11
Sat • 8:00 PM
Sat
Jul 11
8:00 PM
Bostyx - Tribute To Boston And Styx
Hub City Vinyl
Hagerstown, MD
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
1-63-29
Jul 12
Sun • 2:00 PM
Sun
Jul 12
2:00 PM
Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Meritus Park
Hagerstown, MD
2-37-25
Jul 17
Fri • 8:00 PM
Fri
Jul 17
8:00 PM
Given to Fly - A Tribute to Pearl Jam
Hub City Vinyl
Hagerstown, MD
2-62-25
Jul 17
Fri • 8:00 PM
Fri
Jul 17
8:00 PM
Little River Band
Shenandoah Valley Music Festival
Woodstock, VA
2-62-25
Jul 18
Sat • 8:00 PM
Sat
Jul 18
8:00 PM
Rick Springfield
Hollywood Casino at Charles Town Races
Charles Town, WV
2-45-25
Jul 18
Sat • 8:00 PM
Sat
Jul 18
8:00 PM
The Four Tops
Shenandoah Valley Music Festival
Woodstock, VA
1-63-29
Jul 21
Tue • 6:30 PM
Tue
Jul 21
6:30 PM
Hagerstown Flying Boxcars vs. Long Island Ducks
Meritus Park
Hagerstown, MD
1-63-29
Jul 22
Wed • 6:30 PM
Wed
Jul 22
6:30 PM
Hagerstown Flying Boxcars vs. Long Island Ducks
Meritus Park
Hagerstown, MD
1-63-29
Jul 23
Thu • 6:30 PM
Thu
Jul 23
6:30 PM
Hagerstown Flying Boxcars vs. Long Island Ducks
Meritus Park
Hagerstown, MD
1-63-29
Jul 24
Fri • 6:30 PM
Fri
Jul 24
6:30 PM
Hagerstown Flying Boxcars vs. Long Island Ducks
Meritus Park
Hagerstown, MD
2-100-25
Jul 24
Fri • 8:00 PM
Fri
Jul 24
8:00 PM
Shenandoah Valley Music Festival: Diamond Rio
Shenandoah Valley Music Festival
Woodstock, VA
1-63-29
Jul 25
Sat • 6:00 PM
Sat
Jul 25
6:00 PM
Hagerstown Flying Boxcars vs. Long Island Ducks
Meritus Park
Hagerstown, MD
2-49-25
Jul 25
Sat • 8:00 PM
Sat
Jul 25
8:00 PM
Lynchburg Symphony Orchestra: A Big Band Birthday
Shenandoah Valley Music Festival
Woodstock, VA
1-63-29
Jul 26
Sun • 2:00 PM
Sun
Jul 26
2:00 PM
Hagerstown Flying Boxcars vs. Long Island Ducks
Meritus Park
Hagerstown, MD
2-21-25
Aug 1
Sat • 8:00 PM
Sat
Aug 1
8:00 PM
Buddy Guy
Hollywood Casino at Charles Town Races
Charles Town, WV
2-37-25
Aug 1
Sat • 8:30 PM
Sat
Aug 1
8:30 PM
Candlelight: Vivaldi's Four Seasons And More
Franklin Park Arts Center
Purcellville, VA
1-63-29
Aug 4
Tue • 6:30 PM
Tue
Aug 4
6:30 PM
Hagerstown Flying Boxcars vs. High Point Rockers
Meritus Park
Hagerstown, MD
1-63-29
Aug 5
Wed • 6:30 PM
Wed
Aug 5
6:30 PM
Hagerstown Flying Boxcars vs. High Point Rockers
Meritus Park
Hagerstown, MD
1-63-29
Aug 6
Thu • 6:30 PM
Thu
Aug 6
6:30 PM
Hagerstown Flying Boxcars vs. High Point Rockers
Meritus Park
Hagerstown, MD
1-63-29
Aug 7
Fri • 6:30 PM
Fri
Aug 7
6:30 PM
Hagerstown Flying Boxcars vs. York Revolution
Meritus Park
Hagerstown, MD
2-62-25
Aug 7
Fri • 8:00 PM
Fri
Aug 7
8:00 PM
Al Jardine and The Pet Sounds Band
Shenandoah Valley Music Festival
Woodstock, VA
2-37-25
Aug 7
Fri • 8:00 PM
Fri
Aug 7
8:00 PM
Disciple of The Garden - The Legacy of Chris Cornell
Hub City Vinyl
Hagerstown, MD
2-23-25
Aug 7
Fri • 8:00 PM
Fri
Aug 7
8:00 PM
Gabby Barrett
Hollywood Casino at Charles Town Races
Charles Town, WV
1-63-29
Aug 8
Sat • 6:00 PM
Sat
Aug 8
6:00 PM
Hagerstown Flying Boxcars vs. York Revolution
Meritus Park
Hagerstown, MD
2-23-25
Aug 8
Sat • 7:00 PM
Sat
Aug 8
7:00 PM
The Bacon Brothers
Shenandoah Valley Music Festival
Woodstock, VA
2-62-25
Aug 8
Sat • 8:00 PM
Sat
Aug 8
8:00 PM
Richard Marx
Hollywood Casino at Charles Town Races
Charles Town, WV
1-63-29
Aug 9
Sun • 2:00 PM
Sun
Aug 9
2:00 PM
Hagerstown Flying Boxcars vs. York Revolution
Meritus Park
Hagerstown, MD
2-46-25
Aug 14
Fri • 8:00 PM
Fri
Aug 14
8:00 PM
The Travelin' McCourys
Backseat Events
Winchester, VA
2-37-25
Aug 15
Sat • 8:00 PM
Sat
Aug 15
8:00 PM
Don't Back Down - A Tom Petty Tribute
Hub City Vinyl
Hagerstown, MD
1-63-29
Aug 18
Tue • 6:30 PM
Tue
Aug 18
6:30 PM
Hagerstown Flying Boxcars vs. Southern Maryland Blue Crabs
Meritus Park
Hagerstown, MD
1-63-29
Aug 19
Wed • 6:30 PM
Wed
Aug 19
6:30 PM
Hagerstown Flying Boxcars vs. Southern Maryland Blue Crabs
Meritus Park
Hagerstown, MD
1-63-29
Aug 20
Thu • 6:30 PM
Thu
Aug 20
6:30 PM
Hagerstown Flying Boxcars vs. Southern Maryland Blue Crabs
Meritus Park
Hagerstown, MD
1-63-29
Aug 21
Fri • 6:30 PM
Fri
Aug 21
6:30 PM
Hagerstown Flying Boxcars vs. Southern Maryland Blue Crabs
Meritus Park
Hagerstown, MD
2-21-25
Aug 21
Fri • 8:00 PM
Fri
Aug 21
8:00 PM
Hustle Souls with Naptown Brass Band
Hub City Vinyl
Hagerstown, MD
1-63-29
Aug 22
Sat • 6:00 PM
Sat
Aug 22
6:00 PM
Hagerstown Flying Boxcars vs. Southern Maryland Blue Crabs
Meritus Park
Hagerstown, MD
1-63-29
Aug 23
Sun • 2:00 PM
Sun
Aug 23
2:00 PM
Hagerstown Flying Boxcars vs. Southern Maryland Blue Crabs
Meritus Park
Hagerstown, MD
2-22-25
Aug 28
Fri • 7:30 PM
Fri
Aug 28
7:30 PM
Crowder
Shenandoah County Fairgrounds
Woodstock, VA
2-23-25
Aug 29
Sat • 7:30 PM
Sat
Aug 29
7:30 PM
Travis Tritt
Shenandoah County Fairgrounds
Woodstock, VA
4-33-25
Aug 30
Sun • 6:30 PM
Sun
Aug 30
6:30 PM
Modified Truck and Tractor Pull
Shenandoah County Fairgrounds
Woodstock, VA
4-33-25
Aug 31
Mon • 7:00 PM
Mon
Aug 31
7:00 PM
Demolition Derby
Shenandoah County Fairgrounds
Woodstock, VA
1-63-29
Sep 1
Tue • 6:30 PM
Tue
Sep 1
6:30 PM
Hagerstown Flying Boxcars vs. Staten Island FerryHawks
Meritus Park
Hagerstown, MD
4-33-25
Sep 1
Tue • 7:00 PM
Tue
Sep 1
7:00 PM
Demolition Derby
Shenandoah County Fairgrounds
Woodstock, VA
1-63-29
Sep 2
Wed • 6:30 PM
Wed
Sep 2
6:30 PM
Hagerstown Flying Boxcars vs. Staten Island FerryHawks
Meritus Park
Hagerstown, MD
1-63-29
Sep 3
Thu • 6:30 PM
Thu
Sep 3
6:30 PM
Hagerstown Flying Boxcars vs. Staten Island FerryHawks
Meritus Park
Hagerstown, MD
1-69-46
Sep 3
Thu • 7:00 PM
Thu
Sep 3
7:00 PM
Truck Drags
Shenandoah County Fairgrounds
Woodstock, VA
2-23-25
Sep 3
Thu • 8:00 PM
Thu
Sep 3
8:00 PM
The Special Consensus
Hub City Vinyl
Hagerstown, MD
1-63-29
Sep 4
Fri • 6:30 PM
Fri
Sep 4
6:30 PM
Hagerstown Flying Boxcars vs. Staten Island FerryHawks
Meritus Park
Hagerstown, MD
1-53-25
Sep 4
Fri • 7:00 PM
Fri
Sep 4
7:00 PM
Pro Rodeo
Shenandoah County Fairgrounds
Woodstock, VA
2-45-25
Sep 4
Fri • 8:00 PM
Fri
Sep 4
8:00 PM
Soul Project NOLA
Hub City Vinyl
Hagerstown, MD
1-65-17
Sep 5
Sat • 12:00 PM
Sat
Sep 5
12:00 PM
Shepherd Rams vs. Frostburg State Bobcats
Ram Stadium
Shepherdstown, WV
1-63-29
Sep 5
Sat • 6:00 PM
Sat
Sep 5
6:00 PM
Hagerstown Flying Boxcars vs. Staten Island FerryHawks
Meritus Park
Hagerstown, MD
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
1-69-46
Sep 5
Sat • 7:00 PM
Sat
Sep 5
7:00 PM
Monster Trucks
Shenandoah County Fairgrounds
Woodstock, VA
2-37-25
Sep 5
Sat • 8:00 PM
Sat
Sep 5
8:00 PM
Hotel California - The Original Eagles Tribute
Shenandoah Valley Music Festival
Woodstock, VA
1-63-29
Sep 6
Sun • 2:00 PM
Sun
Sep 6
2:00 PM
Hagerstown Flying Boxcars vs. Staten Island FerryHawks
Meritus Park
Hagerstown, MD
1-63-29
Sep 11
Fri • 6:30 PM
Fri
Sep 11
6:30 PM
Hagerstown Flying Boxcars vs. Lancaster Stormers
Meritus Park
Hagerstown, MD
2-23-25
Sep 11
Fri • 8:00 PM
Fri
Sep 11
8:00 PM
Martina McBride
Hollywood Casino at Charles Town Races
Charles Town, WV
1-65-17
Sep 12
Sat • 12:00 PM
Sat
Sep 12
12:00 PM
Shepherd Rams vs. Gannon Golden Knights
Ram Stadium
Shepherdstown, WV
1-63-29
Sep 12
Sat • 6:00 PM
Sat
Sep 12
6:00 PM
Hagerstown Flying Boxcars vs. Lancaster Stormers
Meritus Park
Hagerstown, MD
1-63-29
Sep 13
Sun • 2:00 PM
Sun
Sep 13
2:00 PM
Hagerstown Flying Boxcars vs. Lancaster Stormers
Meritus Park
Hagerstown, MD
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
2-62-25
Sep 18
Fri • 8:00 PM
Fri
Sep 18
8:00 PM
Doc Marten and the Flannels
Hub City Vinyl
Hagerstown, MD
1-65-17
Sep 19
Sat • 12:00 PM
Sat
Sep 19
12:00 PM
Shepherd Rams vs. California (PA) Vulcans
Ram Stadium
Shepherdstown, WV
2-37-25
Sep 19
Sat • 7:00 PM
Sat
Sep 19
7:00 PM
High School Musical Sing-Along
The Maryland Theatre
Hagerstown, MD
2-61-25
Sep 19
Sat • 8:00 PM
Sat
Sep 19
8:00 PM
Nicholas Pare and The Jags
Hub City Vinyl
Hagerstown, MD
2-23-25
Sep 19
Sat • 8:00 PM
Sat
Sep 19
8:00 PM
Trace Adkins
Hollywood Casino at Charles Town Races
Charles Town, WV
2-62-25
Sep 20
Sun • 7:00 PM
Sun
Sep 20
7:00 PM
Ted Nugent
Hollywood Casino at Charles Town Races
Charles Town, WV
2-24-25
Sep 25
Fri • 7:00 PM
Fri
Sep 25
7:00 PM
Jay Leno
The Maryland Theatre
Hagerstown, MD
1-65-17
Oct 3
Sat • 12:00 PM
Sat
Oct 3
12:00 PM
Shepherd Rams vs. Millersville University Marauders
Ram Stadium
Shepherdstown, WV
2-37-25
Oct 3
Sat • 8:00 PM
Sat
Oct 3
8:00 PM
Magical Mystery Girls - Beatles Tribute Band
Hub City Vinyl
Hagerstown, MD
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
2-23-25
Oct 9
Fri • 8:00 PM
Fri
Oct 9
8:00 PM
Jamey Johnson
Hollywood Casino at Charles Town Races
Charles Town, WV
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
2-37-25
Oct 10
Sat • 8:00 PM
Sat
Oct 10
8:00 PM
Nirvani - Nirvana Tribute Band
Hub City Vinyl
Hagerstown, MD
1-65-17
Oct 17
Sat • 12:00 PM
Sat
Oct 17
12:00 PM
Shepherd Rams vs. Bloomsburg Huskies
Ram Stadium
Shepherdstown, WV
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
1-69-20
Oct 24
Sat • TBD
Sat
Oct 24
TBD
24 Hours of Lemons: Capitol Offense - Weekend Pass
Summit Point Motorsports Park
Summit Point, WV
4-92-25
Oct 24
Sat • 7:00 PM
Sat
Oct 24
7:00 PM
Dr. Temple Grandin
The Maryland Theatre
Hagerstown, MD
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
2-37-25
Nov 6
Fri • 7:30 PM
Fri
Nov 6
7:30 PM
Turn To Stone - ELO Tribute
The Maryland Theatre
Hagerstown, MD
3-74-25
Nov 6
Fri • 8:00 PM
Fri
Nov 6
8:00 PM
The Price Is Right - Live Stage Show
Hollywood Casino at Charles Town Races
Charles Town, WV
1-65-17
Nov 7
Sat • 12:00 PM
Sat
Nov 7
12:00 PM
Shepherd Rams vs. Lackawanna College Falcons
Ram Stadium
Shepherdstown, WV
3-74-25
Nov 7
Sat • 3:30 PM
Sat
Nov 7
3:30 PM
The Price Is Right - Live Stage Show
Hollywood Casino at Charles Town Races
Charles Town, WV
3-74-25
Nov 7
Sat • 8:00 PM
Sat
Nov 7
8:00 PM
The Price Is Right - Live Stage Show
Hollywood Casino at Charles Town Races
Charles Town, WV
3-74-25
Nov 8
Sun • 6:30 PM
Sun
Nov 8
6:30 PM
The Price Is Right - Live Stage Show
Hollywood Casino at Charles Town Races
Charles Town, WV
2-37-25
Nov 13
Fri • 8:00 PM
Fri
Nov 13
8:00 PM
Several Species - The Pink Floyd Experience
Hub City Vinyl
Hagerstown, MD
2-37-25
Nov 14
Sat • 8:00 PM
Sat
Nov 14
8:00 PM
Several Species - The Pink Floyd Experience
Hub City Vinyl
Hagerstown, MD
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
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
2-37-25
Dec 5
Sat • 8:00 PM
Sat
Dec 5
8:00 PM
Danger Bird
Hub City Vinyl
Hagerstown, MD
Find the Best Events in Winchester for 2026
Winchester is a hub for exciting live entertainment. We've analyzed our sales data to bring you the most popular events so you can easily plan your next outing. Whether you're searching for the top concerts, must-see sporting events, or unique things to do in Winchester, you'll find it all right here.
Top Events in Winchester This Weekend
Planning your weekend? There are 31 events happening around Winchester this weekend! Here are the most popular events happening in Winchester from Thursday to Sunday. Don't miss out on the action!
| Event Name | Date | Venue | Lowest Price |
|---|---|---|---|
| Kid Cudi | May 29 | Jiffy Lube Live | $51 |
| Extreme Dwarfanators Wrestling | May 29 | Fredericksburg Fairgrounds | $99 |
| The Music Man | May 29 | Capital One Hall | $142 |
| The Music Man | May 30 | Capital One Hall | $99 |
| Monster Truck Bash | May 30 | Rockingham County Fair | $68 |
| Virginia National Ballet Spring Recital | May 30 | Merchant Hall At Hylton Performing Arts Center | $92 |
| Yacht Rock Gold Experience | May 30 | Luhrs Performing Arts Center | $89 |
| SatchVai Band: Joe Satriani & Steve Vai & Animals As Leaders | May 30 | Wolf Trap National Park for the Performing Arts | $70 |
| The Music Man | May 31 | Capital One Hall | $128 |
| The Music Man | May 31 | Capital One Hall | $132 |
Top 2026 Summer Events in Winchester
Summer is the perfect time for live events in Winchester! Check out this list of the top events happening from May through September.
| Event Name | Date | Venue | Lowest Price |
|---|---|---|---|
| Kid Cudi | May 29 | Jiffy Lube Live | $51 |
| Machine Gun Kelly & Wiz Khalifa | Jun 3 | Jiffy Lube Live | $38 |
| Evanescence, Spiritbox & Nova Twins | Jun 27 | Jiffy Lube Live | $42 |
| National Symphony Orchestra: Lizzo | Jul 7 | Wolf Trap National Park for the Performing Arts | $126 |
| Buju Banton & Stephen Marley | Jul 15 | Jiffy Lube Live | $68 |
| Ne-Yo & Akon | Jul 17 | Jiffy Lube Live | $46 |
| Kesha | Aug 14 | Jiffy Lube Live | $39 |
| Tim McGraw & 49 Winchester | Aug 15 | Jiffy Lube Live | $52 |
| Pitbull & Lil Jon | Aug 19 | Jiffy Lube Live | $83 |
| Iron Maiden & Megadeth | Sep 11 | Jiffy Lube Live | $64 |
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 events this weekend with tickets under $100.
| Event Name | Date | Venue | Lowest Price |
|---|---|---|---|
| Bryan Martin | May 28 | Backseat Events | $32 |
| Kid Cudi | May 29 | Jiffy Lube Live | $51 |
| Extreme Dwarfanators Wrestling | May 29 | Fredericksburg Fairgrounds | $99 |
| The Music Man | May 30 | Capital One Hall | $99 |
| Monster Truck Bash | May 30 | Rockingham County Fair | $68 |
| Virginia National Ballet Spring Recital | May 30 | Merchant Hall At Hylton Performing Arts Center | $92 |
| Yacht Rock Gold Experience | May 30 | Luhrs Performing Arts Center | $89 |
| SatchVai Band: Joe Satriani & Steve Vai & Animals As Leaders | May 30 | Wolf Trap National Park for the Performing Arts | $70 |
| Extreme Dwarfanators Wrestling | May 30 | Shenandoah County Fairgrounds | $80 |
| Dan Bern | May 31 | Jammin Java | $95 |
Most Popular Family-Friendly Events in Winchester This Weekend
Looking for something fun for the whole family? Check out this list of top family events happening this weekend in Winchester. From children's concerts and theater to magic and circus shows, there's something for everyone!
| Event Name | Date | Venue | Lowest Price |
|---|---|---|---|
| Every Brilliant Thing | May 29 | Maryland Ensemble Theatre | $87 |
| Every Brilliant Thing | May 30 | Maryland Ensemble Theatre | $28 |
Top Venues in Winchester, VA
Jiffy Lube Live
Bristow, VA
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Wolf Trap National Park for the Performing Arts
Vienna, VA
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Hollywood Casino at Charles Town Races
Charles Town, WV
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EagleBank Arena
Fairfax, VA
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Capital One Hall
Tysons Corner, VA
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The Weinberg Center For The Arts
Frederick, MD
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The Maryland Theatre
Hagerstown, MD
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Nymeo Field at Harry Grove Stadium
Frederick, MD
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Luhrs Performing Arts Center
Shippensburg, PA
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Backseat Events
Winchester, VA
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All Venues Near Winchester, VA