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

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Street Party and Stage Debut

Downtown Chestertown - 200 block High Street

The street party to debut the Town’s new Mobile Stage, canceled by last weekend’s cold rainy weather, has been rescheduled for this Saturday evening, June 5, from 7 to 9 p.m. The party will take place in the 200 block of High Street between Court and Cross Streets. Wilmington-based band Best Kept Soul will bring… Continue Reading Street Party and Stage Debut

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

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