Winchester, VA

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Trending Winchester Events

Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Jul 11 • 6:00PM
Meritus Park
Hagerstown, MD
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image of pro rodeo
Pro Rodeo
Sep 4 • 7:00PM
Shenandoah County Fairgrounds
Woodstock, VA
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monster trucks
Monster Trucks
Sep 5 • 7:00PM
Shenandoah County Fairgrounds
Woodstock, VA
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Hagerstown Flying Boxcars vs. Long Island Ducks
Hagerstown Flying Boxcars vs. Long Island Ducks
Jul 23 • 6:30PM
Meritus Park
Hagerstown, MD
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Hagerstown Flying Boxcars vs. York Revolution
Hagerstown Flying Boxcars vs. York Revolution
Aug 8 • 6:00PM
Meritus Park
Hagerstown, MD
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Hagerstown Flying Boxcars vs. Long Island Ducks
Hagerstown Flying Boxcars vs. Long Island Ducks
Jul 22 • 6:30PM
Meritus Park
Hagerstown, MD
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Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Hagerstown Flying Boxcars vs. Gastonia Ghost Peppers
Jul 12 • 2:00PM
Meritus Park
Hagerstown, MD
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Hagerstown Flying Boxcars vs. York Revolution
Hagerstown Flying Boxcars vs. York Revolution
Aug 7 • 6:30PM
Meritus Park
Hagerstown, MD
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Hagerstown Flying Boxcars vs. Long Island Ducks
Hagerstown Flying Boxcars vs. Long Island Ducks
Jul 24 • 6:30PM
Meritus Park
Hagerstown, MD
Get Tickets

Winchester Sports Schedule

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
Get Tickets
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
Get Tickets
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
Get Tickets
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
Get Tickets
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
Get Tickets
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
Get Tickets
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
Get Tickets
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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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1-69-46
Sep 3
Thu • 7:00 PM
Thu
Sep 3
7:00 PM
Truck Drags
Shenandoah County Fairgrounds
Woodstock, VA
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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
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1-53-25
Sep 4
Fri • 7:00 PM
Fri
Sep 4
7:00 PM
Pro Rodeo
Shenandoah County Fairgrounds
Woodstock, VA
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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
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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
Get Tickets
1-69-46
Sep 5
Sat • 7:00 PM
Sat
Sep 5
7:00 PM
Monster Trucks
Shenandoah County Fairgrounds
Woodstock, VA
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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
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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
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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
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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
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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
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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
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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
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1-65-17
Oct 17
Sat • 12:00 PM
Sat
Oct 17
12:00 PM
Shepherd Rams vs. Bloomsburg Huskies
Ram Stadium
Shepherdstown, WV
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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
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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
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Find the Best Sporting 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 sporting events so you can easily plan your next outing.

Top Sporting Events in Winchester This Weekend

Planning your weekend? There are 4 sporting events happening around Winchester this weekend! Here are the most popular sporting 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
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 Sporting Events in Winchester

Summer is the perfect time for live events in Winchester! Check out this list of the top sporting events happening from May through September.

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
Frederick Keys vs. Jersey Shore BlueClaws Jul 12 Nymeo Field at Harry Grove Stadium $32
Loudoun United Fc vs. Tampa Bay Rowdies Jul 18 Segra Field $34
Loudoun United FC vs. Hartford Athletic FC Aug 1 Segra Field $34
WWE Summer Tour Aug 6 EagleBank Arena $81
Loudoun United FC vs. Charleston Battery Aug 8 Segra Field $34
Frederick Keys vs. Bowling Green Hot Rods Aug 15 Nymeo Field at Harry Grove Stadium $35
Pro Rodeo Sep 4 Shenandoah County Fairgrounds $51
Monster Trucks Sep 5 Shenandoah County Fairgrounds $52

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 sporting 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
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

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