Annapolis, MD

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Trending Annapolis Events

A black monster truck jumps over a dirt mound as a large crowd watches in a stadium.
Monster Truck Wars
Oct 17 • 12:00PM
Charles County Fairgrounds and Event Center
La Plata, MD
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preakness stakes race at the pimlico race course 2023.
Preakness Stakes
May 23 • TBD
Pimlico Race Course
Baltimore, MD
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Washington International Horse Show
Washington International Horse Show
Oct 23 • TBD
Show Place Arena
Upper Marlboro, MD
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Washington International Horse Show
Washington International Horse Show
Oct 22 • TBD
Show Place Arena
Upper Marlboro, MD
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Washington International Horse Show
Washington International Horse Show
Oct 24 • TBD
Show Place Arena
Upper Marlboro, MD
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A black monster truck jumps over a dirt mound as a large crowd watches in a stadium.
Monster Truck Wars
Oct 17 • 6:00PM
Charles County Fairgrounds and Event Center
La Plata, MD
Get Tickets
A black monster truck jumps over a dirt mound as a large crowd watches in a stadium.
Monster Truck Wars
Oct 18 • 1:00PM
Charles County Fairgrounds and Event Center
La Plata, MD
Get Tickets

Find the Best Races in Annapolis for 2026

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

Top 2026 Summer Races in Annapolis

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

Event Name Date Venue Lowest Price
Renegade Monster Trucks Aug 18 Montgomery County Agricultural Fair $69
Renegade Monster Trucks Aug 19 Montgomery County Agricultural Fair $69
Renegade Monster Trucks Aug 22 Great Pocomoke Fairgrounds $80
Renegade Monster Trucks Aug 22 Great Pocomoke Fairgrounds $80
Monster Truck Back to School Bash Aug 29 Buck Motorsports Park & Entertainment Complex $59
Championship Pulling Fall Nationals Sep 12 Buck Motorsports Park & Entertainment Complex $59
Monster Truck Wars Sep 19 Prince William County Fairgrounds $72
Monster Truck Wars Sep 19 Prince William County Fairgrounds $72
Monster Truck Wars Sep 20 Prince William County Fairgrounds $72

Top Venues in Annapolis, MD

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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A baseball stadium at night, with bright lights illuminating the field and a packed crowd in the stands.
Nationals Park
Washington, DC
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Aerial view of Oriole Park at Camden Yards, a baseball stadium in Baltimore.
Oriole Park At Camden Yards
Baltimore, MD
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Modern buildings with large windows reflecting the sunset, and a lit marquee entrance.
The Anthem - D.C.
Washington, DC
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Brick building with a modern glass structure behind it at sunset.
9:30 Club
Washington, DC
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A grand, cream-colored building with many windows, under a blue sky with white clouds.
Warner Theatre - DC
Washington, DC
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Modern theater with bright red and blue neon lights at dusk.
The Fillmore Silver Spring
Silver Spring, MD
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A large brick building with a modern addition and a clear blue sky at sunset.
The Lyric Baltimore
Baltimore, MD
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A modern building illuminated with vibrant pink and blue lights under a dramatic sunset sky.
CFG Bank Arena
Baltimore, MD
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Modern stadium with glowing red accents at sunset with a sky full of pink and purple clouds.
Capital One Arena
Washington, DC
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All Venues Near Annapolis, MD