Trending Winchester Events
Sidewalk Prophets
Aug 7 •
7:00PM
Hub City Vineyard
Hagerstown, MD
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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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The Temptations and The Four Tops
Oct 17 •
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Hollywood Casino at Charles Town Races
Charles Town, WV
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Gabby Barrett
Aug 7 •
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Hollywood Casino at Charles Town Races
Charles Town, WV
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Rick Springfield
Jul 18 •
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Hollywood Casino at Charles Town Races
Charles Town, WV
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Crowder
Aug 28 •
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Shenandoah County Fairgrounds
Woodstock, VA
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Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Jul 11 •
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Meritus Park
Hagerstown, MD
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Dean Z - The Ultimate Elvis
Dec 13 •
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Hollywood Casino at Charles Town Races
Charles Town, WV
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Travis Tritt
Aug 29 •
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Shenandoah County Fairgrounds
Woodstock, VA
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All Venues And Events In Winchester, VA
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
2-24-25
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
2-23-25
Jul 15
Wed • 8:00 PM
Wed
Jul 15
8:00 PM
Sarah Gross
Hub City Vinyl
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
3-38-25
Jul 19
Sun • 7:00 PM
Sun
Jul 19
7:00 PM
James and the Giant Peach Jr.
Winchester Little Theatre
Winchester, VA
3-38-25
Jul 21
Tue • 11:00 AM
Tue
Jul 21
11:00 AM
James and the Giant Peach Jr.
Winchester Little Theatre
Winchester, 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
3-38-25
Jul 23
Thu • 7:00 PM
Thu
Jul 23
7:00 PM
James and the Giant Peach Jr.
Winchester Little Theatre
Winchester, VA
3-38-25
Jul 24
Fri • 2:30 PM
Fri
Jul 24
2:30 PM
James and the Giant Peach Jr.
Winchester Little Theatre
Winchester, VA
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
3-38-25
Jul 24
Fri • 7:00 PM
Fri
Jul 24
7:00 PM
James and the Giant Peach Jr.
Winchester Little Theatre
Winchester, VA
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
3-38-25
Jul 25
Sat • 7:00 PM
Sat
Jul 25
7:00 PM
James and the Giant Peach Jr.
Winchester Little Theatre
Winchester, VA
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 • 7:00 PM
Fri
Aug 7
7:00 PM
Sidewalk Prophets
Hub City Vineyard
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
2-62-25
Aug 13
Thu • 8:00 PM
Thu
Aug 13
8:00 PM
Matt Schofield
Hub City Vinyl
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
3-74-25
Aug 21
Fri • 6:00 PM
Fri
Aug 21
6:00 PM
Serial Killer Speakeasy
The Maryland Theatre
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
3-74-25
Aug 21
Fri • 8:00 PM
Fri
Aug 21
8:00 PM
Serial Killer Speakeasy
The Maryland Theatre
Hagerstown, MD
3-74-25
Aug 21
Fri • 10:00 PM
Fri
Aug 21
10:00 PM
Serial Killer Speakeasy
The Maryland Theatre
Hagerstown, MD
3-74-25
Aug 22
Sat • 2:00 PM
Sat
Aug 22
2:00 PM
Serial Killer Speakeasy
The Maryland Theatre
Hagerstown, MD
3-74-25
Aug 22
Sat • 4:00 PM
Sat
Aug 22
4:00 PM
Serial Killer Speakeasy
The Maryland Theatre
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
3-74-25
Aug 22
Sat • 6:00 PM
Sat
Aug 22
6:00 PM
Serial Killer Speakeasy
The Maryland Theatre
Hagerstown, MD
3-74-25
Aug 22
Sat • 8:00 PM
Sat
Aug 22
8:00 PM
Serial Killer Speakeasy
The Maryland Theatre
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
2-36-25
Sep 10
Thu • 8:00 PM
Thu
Sep 10
8:00 PM
Struggle Jennings
Backseat Events
Winchester, VA
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
Aaron Tippin
Backseat Events
Winchester, VA
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
4-93-25
Sep 17
Thu • 6:30 PM
Thu
Sep 17
6:30 PM
Clean Hands - The Hagerstown Premiere
The Maryland Theatre
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
2-37-25
Sep 26
Sat • 7:30 PM
Sat
Sep 26
7:30 PM
Classic Stones Live
The Maryland Theatre
Hagerstown, MD
2-23-25
Sep 29
Tue • 7:30 PM
Tue
Sep 29
7:30 PM
Doo Wah Riders
The Maryland Theatre
Hagerstown, MD
2-22-25
Oct 1
Thu • 8:00 PM
Thu
Oct 1
8:00 PM
Black Flag
Hub City Vinyl
Hagerstown, MD
2-24-25
Oct 2
Fri • 7:30 PM
Fri
Oct 2
7:30 PM
Kat Timpf
The Maryland Theatre
Hagerstown, MD
2-22-25
Oct 2
Fri • 8:00 PM
Fri
Oct 2
8:00 PM
The Amish Outlaws
Hub City Vinyl
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
4-95-25
Oct 4
Sun • 7:30 PM
Sun
Oct 4
7:30 PM
Serial Killers with Dr. Scott Bonn
The Maryland Theatre
Hagerstown, MD
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
3-74-25
Oct 16
Fri • 8:00 PM
Fri
Oct 16
8:00 PM
Golden Girls: The Laughs Continue
Hollywood Casino at Charles Town Races
Charles Town, WV
1-65-17
Oct 17
Sat • 12:00 PM
Sat
Oct 17
12:00 PM
Shepherd Rams vs. Bloomsburg Huskies
Ram Stadium
Shepherdstown, WV
2-22-25
Oct 17
Sat • 7:30 PM
Sat
Oct 17
7:30 PM
Lotus Land - A Tribute to Rush
The Maryland Theatre
Hagerstown, MD
2-45-25
Oct 17
Sat • 8:00 PM
Sat
Oct 17
8:00 PM
The Temptations and The Four Tops
Hollywood Casino at Charles Town Races
Charles Town, 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
2-57-48
Oct 28
Wed • 7:30 PM
Wed
Oct 28
7:30 PM
Yaniv Zarif
The Maryland Theatre
Hagerstown, MD
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
2-23-25
Nov 12
Thu • 8:00 PM
Thu
Nov 12
8:00 PM
Fox N' Vead
Bright Box Theater - VA
Winchester, VA
2-23-25
Nov 13
Fri • 8:00 PM
Fri
Nov 13
8:00 PM
Kameron Marlowe
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
2-61-25
Nov 14
Sat • 8:00 PM
Sat
Nov 14
8:00 PM
Twisted Sister
Hollywood Casino at Charles Town Races
Charles Town, WV
2-23-25
Nov 15
Sun • 7:00 PM
Sun
Nov 15
7:00 PM
Megan Woods
Hub City Vineyard
Hagerstown, MD
2-23-25
Nov 21
Sat • 8:00 PM
Sat
Nov 21
8:00 PM
Wheeler Walker Jr.
Hollywood Casino at Charles Town Races
Charles Town, WV
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
Nov 28
Sat • 8:00 PM
Sat
Nov 28
8:00 PM
Little Ozzy
Backseat Events
Winchester, VA
2-37-25
Dec 5
Sat • 8:00 PM
Sat
Dec 5
8:00 PM
Danger Bird
Hub City Vinyl
Hagerstown, MD
2-57-47
Dec 9
Wed • 7:30 PM
Wed
Dec 9
7:30 PM
Cherish the Ladies
The Maryland Theatre
Hagerstown, MD
2-37-25
Dec 11
Fri • 8:00 PM
Fri
Dec 11
8:00 PM
Dean Z - The Ultimate Elvis
Hollywood Casino at Charles Town Races
Charles Town, WV
2-37-25
Dec 12
Sat • 8:00 PM
Sat
Dec 12
8:00 PM
Dean Z - The Ultimate Elvis
Hollywood Casino at Charles Town Races
Charles Town, WV
2-37-25
Dec 13
Sun • 7:00 PM
Sun
Dec 13
7:00 PM
Dean Z - The Ultimate Elvis
Hollywood Casino at Charles Town Races
Charles Town, WV
2-37-25
Mar 16
Tue • 7:30 PM
Tue
Mar 16
7:30 PM
Cece Teneal
The Maryland Theatre
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 6 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 |
|---|---|---|---|
| Frederick Keys vs. Jersey Shore BlueClaws | Jul 11 | Nymeo Field at Harry Grove Stadium | $26 |
| Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers | Jul 11 | Meritus Park | $36 |
| National Symphony Orchestra: Steven Reineke - Disney's The Little Mermaid In Concert | Jul 11 | Wolf Trap National Park for the Performing Arts | $71 |
| Dusty Slay | Jul 11 | Hollywood Casino at Charles Town Races | $53 |
| Frederick Keys vs. Jersey Shore BlueClaws | Jul 12 | Nymeo Field at Harry Grove Stadium | $32 |
| Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers | Jul 12 | Meritus Park | $36 |
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 |
|---|---|---|---|
| Ne-Yo & Akon | Jul 17 | Jiffy Lube Live | $50 |
| Bob Dylan | Jul 24 | Wolf Trap National Park for the Performing Arts | $126 |
| Lynyrd Skynyrd & Foreigner | Jul 25 | Jiffy Lube Live | $32 |
| Bob Dylan | Jul 25 | Wolf Trap National Park for the Performing Arts | $83 |
| Riley Green, Justin Moore, Zach John King & Hannah McFarland | Aug 8 | Jiffy Lube Live | $96 |
| Kesha | Aug 14 | Jiffy Lube Live | $40 |
| Tim McGraw & 49 Winchester | Aug 15 | Jiffy Lube Live | $40 |
| Yacht Rock Revue | Aug 16 | Wolf Trap National Park for the Performing Arts | $102 |
| Iron Maiden & Megadeth | Sep 11 | Jiffy Lube Live | $58 |
| Erykah Badu | Sep 20 | Wolf Trap National Park for the Performing Arts | $138 |
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 |
|---|---|---|---|
| Frederick Keys vs. Jersey Shore BlueClaws | Jul 11 | Nymeo Field at Harry Grove Stadium | $26 |
| Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers | Jul 11 | Meritus Park | $36 |
| National Symphony Orchestra: Steven Reineke - Disney's The Little Mermaid In Concert | Jul 11 | Wolf Trap National Park for the Performing Arts | $71 |
| Dusty Slay | Jul 11 | Hollywood Casino at Charles Town Races | $53 |
| Frederick Keys vs. Jersey Shore BlueClaws | Jul 12 | Nymeo Field at Harry Grove Stadium | $32 |
| Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers | Jul 12 | Meritus Park | $36 |
Top Venues in Winchester, VA
Wolf Trap National Park for the Performing Arts
Vienna, VA
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Jiffy Lube Live
Bristow, 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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Nymeo Field at Harry Grove Stadium
Frederick, MD
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Meritus Park
Hagerstown, MD
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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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Virginia Credit Union Stadium
Fredericksburg, VA
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All Venues Near Winchester, VA