Trending Winchester Events
Hagerstown Flying Boxcars vs. Lexington Legends
Jun 2 •
6:30PM
Meritus Park
Hagerstown, MD
Get Tickets
Little Mania Midget Wrestling
Jul 2 •
6:00PM
Vanish Hall
Boonsboro, MD
Get Tickets
Hagerstown Flying Boxcars vs. Lexington Legends
Jun 6 •
6:00PM
Meritus Park
Hagerstown, MD
Get Tickets
Hagerstown Flying Boxcars vs. Charleston Dirty Birds
Jun 21 •
2:00PM
Meritus Park
Hagerstown, MD
Get Tickets
Extreme Dwarfanators Wrestling
May 30 •
8:00PM
Shenandoah County Fairgrounds
Woodstock, VA
Get Tickets
Hagerstown Flying Boxcars vs. Lexington Legends
Jun 5 •
6:30PM
Meritus Park
Hagerstown, MD
Get Tickets
Hagerstown Flying Boxcars vs. Lexington Legends
Jun 7 •
2:00PM
Meritus Park
Hagerstown, MD
Get Tickets
Hagerstown Flying Boxcars vs. Charleston Dirty Birds
Jun 17 •
6:30PM
Meritus Park
Hagerstown, MD
Get Tickets
Pro Rodeo
Sep 4 •
7:00PM
Shenandoah County Fairgrounds
Woodstock, VA
Get Tickets
Winchester Sports Schedule
1-39-29
May 30
Sat • 8:00 PM
Sat
May 30
8:00 PM
Extreme Dwarfanators Wrestling
Shenandoah County Fairgrounds
Woodstock, VA
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
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
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
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
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
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
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
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
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
1-39-29
Jul 2
Thu • 9:00 PM
Thu
Jul 2
9:00 PM
Little Mania Midget Wrestling
Vanish Hall
Boonsboro, MD
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
1-69-46
Sep 5
Sat • 7:00 PM
Sat
Sep 5
7:00 PM
Monster Trucks
Shenandoah County Fairgrounds
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
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
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
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
1-65-17
Oct 17
Sat • 12:00 PM
Sat
Oct 17
12:00 PM
Shepherd Rams vs. Bloomsburg Huskies
Ram Stadium
Shepherdstown, 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
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
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 3 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 |
|---|---|---|---|
| Extreme Dwarfanators Wrestling | May 29 | Fredericksburg Fairgrounds | $99 |
| Monster Truck Bash | May 30 | Rockingham County Fair | $68 |
| Extreme Dwarfanators Wrestling | May 30 | Shenandoah County Fairgrounds | $80 |
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 |
|---|---|---|---|
| Extreme Dwarfanators Wrestling | May 29 | Fredericksburg Fairgrounds | $99 |
| Hagerstown Flying Boxcars vs. Lexington Legends | Jun 2 | Meritus Park | $39 |
| Frederick Keys vs. Hudson Valley Renegades | Jun 2 | Nymeo Field at Harry Grove Stadium | $23 |
| Renegade Monster Trucks | Jun 5 | The Grandstand At The Great Frederick Fair - Frederick | $68 |
| Frederick Keys vs. Hudson Valley Renegades | Jun 6 | Nymeo Field at Harry Grove Stadium | $27 |
| Frederick Keys vs. Hudson Valley Renegades | Jun 7 | Nymeo Field at Harry Grove Stadium | $35 |
| Little Mania Midget Wrestling | Jul 2 | Vanish Hall | $83 |
| Frederick Keys vs. Brooklyn Cyclones | Jul 5 | Nymeo Field at Harry Grove Stadium | $35 |
| Frederick Keys vs. Jersey Shore BlueClaws | Jul 12 | Nymeo Field at Harry Grove Stadium | $35 |
| WWE Summer Tour | Aug 6 | EagleBank Arena | $99 |
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 |
|---|---|---|---|
| Extreme Dwarfanators Wrestling | May 29 | Fredericksburg Fairgrounds | $99 |
| Monster Truck Bash | May 30 | Rockingham County Fair | $68 |
| Extreme Dwarfanators Wrestling | May 30 | Shenandoah County Fairgrounds | $80 |
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
See More
EagleBank Arena
Fairfax, VA
See More
Capital One Hall
Tysons Corner, VA
See More
The Weinberg Center For The Arts
Frederick, MD
See More
The Maryland Theatre
Hagerstown, MD
See More
Nymeo Field at Harry Grove Stadium
Frederick, MD
See More
Luhrs Performing Arts Center
Shippensburg, PA
See More
Backseat Events
Winchester, VA
See More
All Venues Near Winchester, VA