Winchester, VA

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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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Musician in a hat and suit plays a blue guitar on stage with a flamingo logo backdrop.
Christopher Cross
Jun 26 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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Musicians perform on a stage with a large screen displaying a singer and drummer.
Richard Marx
Aug 8 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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A man plays an acoustic guitar and sings into a microphone on a stage.
Travis Tritt
Aug 29 • 7:30PM
Shenandoah County Fairgrounds
Woodstock, VA
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A man with long hair and a beard plays an acoustic guitar while singing into a microphone.
Jamey Johnson
Oct 9 • 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 • 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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buddy guy live at the grand center arts district in st louis missouri
Buddy Guy
Aug 1 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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crowder singing at texas trust cu theatre in grand prairie texas
Crowder
Aug 28 • 7:30PM
Shenandoah County Fairgrounds
Woodstock, VA
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Winchester Concert Schedule

2-23-25
May 28
Thu • 8:00 PM
Thu
May 28
8:00 PM
Bryan Martin
Backseat Events
Winchester, VA
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2-23-25
May 29
Fri • 8:00 PM
Fri
May 29
8:00 PM
Chris Cagle
Backseat Events
Winchester, VA
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2-37-25
May 30
Sat • 7:00 PM
Sat
May 30
7:00 PM
MSGBR 80'S Prom Unleashed
Backseat Events
Winchester, VA
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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
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2-23-25
Jun 4
Thu • 8:00 PM
Thu
Jun 4
8:00 PM
Creed Fisher
Backseat Events
Winchester, VA
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2-62-25
Jun 5
Fri • 8:00 PM
Fri
Jun 5
8:00 PM
Vicki Peterson & John Cowsill
Hub City Vinyl
Hagerstown, MD
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2-62-25
Jun 6
Sat • 7:30 PM
Sat
Jun 6
7:30 PM
Jimmy Failla
The Maryland Theatre
Hagerstown, MD
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2-37-25
Jun 6
Sat • 8:00 PM
Sat
Jun 6
8:00 PM
High Voltage
Hub City Vinyl
Hagerstown, MD
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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
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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
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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
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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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2-23-25
Jun 13
Sat • 8:00 PM
Sat
Jun 13
8:00 PM
Leroy Burks and The Voodoo Whiskey Band
Hub City Vinyl
Hagerstown, MD
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2-22-25
Jun 17
Wed • 8:00 PM
Wed
Jun 17
8:00 PM
Blacktop Mojo
Hub City Vinyl
Hagerstown, MD
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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
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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
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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
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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
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2-37-25
Jun 20
Sat • 8:00 PM
Sat
Jun 20
8:00 PM
The Bell Bottom Blues
Hub City Vinyl
Hagerstown, MD
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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
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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
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2-45-25
Jul 2
Thu • 8:00 PM
Thu
Jul 2
8:00 PM
Brandon Combs
Hub City Vinyl
Hagerstown, MD
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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
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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
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2-62-25
Jul 9
Thu • 8:00 PM
Thu
Jul 9
8:00 PM
Eliot Lewis
Hub City Vinyl
Hagerstown, MD
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2-37-25
Jul 10
Fri • 8:00 PM
Fri
Jul 10
8:00 PM
The Warped Tour Band
Hub City Vinyl
Hagerstown, MD
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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
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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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2-37-25
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
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2-62-25
Jul 17
Fri • 8:00 PM
Fri
Jul 17
8:00 PM
Little River Band
Shenandoah Valley Music Festival
Woodstock, VA
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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
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2-45-25
Jul 18
Sat • 8:00 PM
Sat
Jul 18
8:00 PM
The Four Tops
Shenandoah Valley Music Festival
Woodstock, VA
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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
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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
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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
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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
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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
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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
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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
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2-23-25
Aug 8
Sat • 7:00 PM
Sat
Aug 8
7:00 PM
The Bacon Brothers
Shenandoah Valley Music Festival
Woodstock, VA
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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
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2-46-25
Aug 14
Fri • 8:00 PM
Fri
Aug 14
8:00 PM
The Travelin' McCourys
Backseat Events
Winchester, VA
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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
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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
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2-22-25
Aug 28
Fri • 7:30 PM
Fri
Aug 28
7:30 PM
Crowder
Shenandoah County Fairgrounds
Woodstock, VA
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2-23-25
Aug 29
Sat • 7:30 PM
Sat
Aug 29
7:30 PM
Travis Tritt
Shenandoah County Fairgrounds
Woodstock, VA
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2-23-25
Sep 3
Thu • 8:00 PM
Thu
Sep 3
8:00 PM
The Special Consensus
Hub City Vinyl
Hagerstown, MD
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2-45-25
Sep 4
Fri • 8:00 PM
Fri
Sep 4
8:00 PM
Soul Project NOLA
Hub City Vinyl
Hagerstown, MD
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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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2-37-25
Sep 5
Sat • 8:00 PM
Sat
Sep 5
8:00 PM
Hotel California - The Original Eagles Tribute
Shenandoah Valley Music Festival
Woodstock, VA
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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
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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
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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
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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
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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
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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
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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
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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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2-37-25
Oct 3
Sat • 8:00 PM
Sat
Oct 3
8:00 PM
Magical Mystery Girls - Beatles Tribute Band
Hub City Vinyl
Hagerstown, MD
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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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2-23-25
Oct 9
Fri • 8:00 PM
Fri
Oct 9
8:00 PM
Jamey Johnson
Hollywood Casino at Charles Town Races
Charles Town, WV
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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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2-37-25
Oct 10
Sat • 8:00 PM
Sat
Oct 10
8:00 PM
Nirvani - Nirvana Tribute Band
Hub City Vinyl
Hagerstown, MD
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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
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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
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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
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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
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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
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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
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2-37-25
Dec 5
Sat • 8:00 PM
Sat
Dec 5
8:00 PM
Danger Bird
Hub City Vinyl
Hagerstown, MD
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Find the Best Concerts in Winchester for 2026

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

Top Concerts in Winchester This Weekend

Planning your weekend? There are 13 concerts happening around Winchester this weekend! Here are the most popular concerts happening in Winchester from Thursday to Sunday. Don't miss out on the action!

Event Name Date Venue Lowest Price
Bryan Martin May 28 Backseat Events $32
Kid Cudi May 29 Jiffy Lube Live $51
Loveletters - Band May 29 Jammin Java $70
Manassas Chorale: Lights, Camera, Music! May 29 Merchant Hall At Hylton Performing Arts Center $57
Chris Cagle May 29 Backseat Events $105
Eyes of The Nile - Iron Maiden Tribute May 29 State Theatre - VA $87
Ten: A Tribute to Pearl Jam May 30 Tally Ho Theater $52
MSGBR 80'S Prom Unleashed May 30 Backseat Events $14
SatchVai Band: Joe Satriani & Steve Vai & Animals As Leaders May 30 Wolf Trap National Park for the Performing Arts $70
Dan Bern May 31 Jammin Java $95

Top 2026 Summer Concerts in Winchester

Summer is the perfect time for live events in Winchester! Check out this list of the top concerts 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 $58
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 $86
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 concerts 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
Loveletters - Band May 29 Jammin Java $70
Manassas Chorale: Lights, Camera, Music! May 29 Merchant Hall At Hylton Performing Arts Center $57
Eyes of The Nile - Iron Maiden Tribute May 29 State Theatre - VA $87
Ten: A Tribute to Pearl Jam May 30 Tally Ho Theater $52
MSGBR 80'S Prom Unleashed May 30 Backseat Events $14
SatchVai Band: Joe Satriani & Steve Vai & Animals As Leaders May 30 Wolf Trap National Park for the Performing Arts $70
Lounge Fly - Stone Temple Pilots Tribute May 30 Hub City Vinyl $81
Dan Bern May 31 Jammin Java $95

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