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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 2022

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! For a full schedule, ticket sales, and more information, visit https://mainstreetchestertown.org/dickens/

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