Annapolis Boat Shows
Annapolis Powerboat Show: October 2-5, 2025. Annapolis Sailboat Show: October 9-12, 2025. Tens of thousands of boaters and enthusiasts descend on Annapolis to see the latest and greatest boat models, maritime tech, and boating products. Come...
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Great Annapolis Pumpkins
October 2025. You never know when these 1,000-pound pumpkins will pop up in downtown Annapolis, but they are hard to miss once they do! Sponsored by Visit Annapolis & Anne Arundel County and coordinated through the Downtown Annapolis...
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Annapolis Coffee Crawl: Café Diem
September 28th - October 5th. Get ready to seize the day, support local businesses, and sip your way through delicious coffee, lattes, and espresso martinis. Café Diem: The Annapolis Coffee Crawl runs from September 28 to October 5, featuring...
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Maryland Corn Maze
September - November 1, 2025. People have been getting lost in 8 acres since 2006. If you are new to 'corn mazing'... The object is to negotiate your way (on foot) through the design we've cut into the corn. The corn is taller than you... so...
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USNA Football
August - December 2025. Anyone who’s been to Annapolis during the fall knows about the spirited atmosphere that engulfs the city during football season. Every Naval Academy home game, the city swells to capacity with fans from all around...
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Maryland Million Day
October 11, 2025. Bring the whole family to enjoy thrilling horse races, interactive games, and local food favorites, all set in the heart of beautiful Maryland.
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Bay Bridge Run
The Bay Bridge Run is a 10K race that provides the perfect opportunity for runners, walkers, and spectators alike to race across the Cheasapeake Bay Bridge’s eastbound span from Anne Arundel County to Kent Island to Queen Anne’s County.
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USNA Football
August - December 2025. Anyone who’s been to Annapolis during the fall knows about the spirited atmosphere that engulfs the city during football season. Every Naval Academy home game, the city swells to capacity with fans from all around...
Learn More
Maryland Corn Maze
September - November 1, 2025. People have been getting lost in 8 acres since 2006. If you are new to 'corn mazing'... The object is to negotiate your way (on foot) through the design we've cut into the corn. The corn is taller than you... so...
Learn More
