Winchester, VA

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Trending Winchester Events

Man facing away from camera on stage, lit by spotlights with blurred audience in background.
Sidewalk Prophets
Aug 7 • 7:00PM
Hub City Vineyard
Hagerstown, MD
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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 singing group in matching suits performs on stage with colorful lights and a crowd in the foreground.
The Temptations and The Four Tops
Oct 17 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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Singer Gabby Barrett performs on stage, holding a microphone and wearing a denim vest over a t-shirt.
Gabby Barrett
Aug 7 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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rick springfield performing on stage with red electric guitar.
Rick Springfield
Jul 18 • 8:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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A man with a beard and glasses plays a harmonica into a microphone while a drummer plays in the background.
Crowder
Aug 28 • 7:30PM
Shenandoah County Fairgrounds
Woodstock, VA
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Dean Z - The Ultimate Elvis
Dean Z - The Ultimate Elvis
Dec 13 • 7:00PM
Hollywood Casino at Charles Town Races
Charles Town, WV
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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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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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Winchester Concert Schedule

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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2-23-25
Jul 15
Wed • 8:00 PM
Wed
Jul 15
8:00 PM
Sarah Gross
Hub City Vinyl
Hagerstown, MD
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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 • 7:00 PM
Fri
Aug 7
7:00 PM
Sidewalk Prophets
Hub City Vineyard
Hagerstown, MD
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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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2-62-25
Aug 13
Thu • 8:00 PM
Thu
Aug 13
8:00 PM
Matt Schofield
Hub City Vinyl
Hagerstown, MD
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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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2-36-25
Sep 10
Thu • 8:00 PM
Thu
Sep 10
8:00 PM
Struggle Jennings
Backseat Events
Winchester, VA
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2-23-25
Sep 11
Fri • 8:00 PM
Fri
Sep 11
8:00 PM
Aaron Tippin
Backseat Events
Winchester, 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
Sep 26
Sat • 7:30 PM
Sat
Sep 26
7:30 PM
Classic Stones Live
The Maryland Theatre
Hagerstown, MD
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2-23-25
Sep 29
Tue • 7:30 PM
Tue
Sep 29
7:30 PM
Doo Wah Riders
The Maryland Theatre
Hagerstown, MD
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2-22-25
Oct 1
Thu • 8:00 PM
Thu
Oct 1
8:00 PM
Black Flag
Hub City Vinyl
Hagerstown, MD
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2-24-25
Oct 2
Fri • 7:30 PM
Fri
Oct 2
7:30 PM
Kat Timpf
The Maryland Theatre
Hagerstown, MD
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2-22-25
Oct 2
Fri • 8:00 PM
Fri
Oct 2
8:00 PM
The Amish Outlaws
Hub City Vinyl
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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2-22-25
Oct 17
Sat • 7:30 PM
Sat
Oct 17
7:30 PM
Lotus Land - A Tribute to Rush
The Maryland Theatre
Hagerstown, MD
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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
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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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2-57-48
Oct 28
Wed • 7:30 PM
Wed
Oct 28
7:30 PM
Yaniv Zarif
The Maryland Theatre
Hagerstown, MD
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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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2-23-25
Nov 12
Thu • 8:00 PM
Thu
Nov 12
8:00 PM
Fox N' Vead
Bright Box Theater - VA
Winchester, VA
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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
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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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2-61-25
Nov 14
Sat • 8:00 PM
Sat
Nov 14
8:00 PM
Twisted Sister
Hollywood Casino at Charles Town Races
Charles Town, WV
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2-23-25
Nov 15
Sun • 7:00 PM
Sun
Nov 15
7:00 PM
Megan Woods
Hub City Vineyard
Hagerstown, MD
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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
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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
Nov 28
Sat • 8:00 PM
Sat
Nov 28
8:00 PM
Little Ozzy
Backseat Events
Winchester, VA
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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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2-57-47
Dec 9
Wed • 7:30 PM
Wed
Dec 9
7:30 PM
Cherish the Ladies
The Maryland Theatre
Hagerstown, MD
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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
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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
Get Tickets
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
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2-37-25
Mar 16
Tue • 7:30 PM
Tue
Mar 16
7:30 PM
Cece Teneal
The Maryland Theatre
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 2 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
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

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
Ne-Yo & Akon Jul 17 Jiffy Lube Live $45
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 concerts this weekend with tickets under $100.

Event Name Date Venue Lowest Price
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

Top Venues in Winchester, VA

Sunset over a modern, octagonal building on stilts surrounded by a grassy lawn.
Wolf Trap National Park for the Performing Arts
Vienna, VA
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An aerial view of a modern, circular building with a sloped glass roof on a grassy hill at sunset.
Jiffy Lube Live
Bristow, VA
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A large beige building with red-tiled roofs and arched doorways, illuminated at sunset.
Hollywood Casino at Charles Town Races
Charles Town, WV
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Aerial view of a large octagonal building with a tan roof, surrounded by trees and a circular road.
EagleBank Arena
Fairfax, VA
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Modern glass building with tiered facade reflects a vibrant sunset.
Capital One Hall
Tysons Corner, VA
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Baseball stadium at sunset with illuminated field and colorful clouds.
Nymeo Field at Harry Grove Stadium
Frederick, MD
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Meritus Park
Meritus Park
Hagerstown, MD
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Grand concert hall stage with pipe organ, grand piano, and tiered seating.
The Weinberg Center For The Arts
Frederick, MD
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Art deco theater with arched windows and marquee at sunset.
The Maryland Theatre
Hagerstown, MD
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Baseball stadium at sunset, with lights on and a warm glow over the field and stands.
Virginia Credit Union Stadium
Fredericksburg, VA
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All Venues Near Winchester, VA