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Plan your trip early and stay in Chestertown! Click here for local lodging.

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Chestertown Car Show

Downtown Chestertown - High Street, Chestertown - Downtown Chestertown - High Street, Chestertown

Bring your pride and joy to compete for trophies or just stroll the street to admire the vintage. collectible, sport, custom and other fine automobiles on display.

Chestertown Car Show

Downtown Chestertown - High Street, Chestertown - Downtown Chestertown - High Street, Chestertown

Register your own pride and joy to compete for trophies, or just stroll the street to admire what other auto enthusiasts have brought to display, from custom hotrods to classic and antique beauties. Category prizes and food and beverage offerings contribute to a fun afternoon that welcomes all. Event is free to the public. A… Continue Reading Chestertown Car Show

Dickens of a Christmas

Chestertown Historic District - 200 block High Street

Chestertown's Dickens-inspired holiday festival returns with more street performers, live music, food and drink, carriage rides, and more!

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