Crazy Days
Hosted by the Downtown Chestertown Association, Crazy Days is Chestertown’s annual sidewalk sale with businesses offering crazy deals and restaurants offering crazy specials.
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Annual Event
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Downrigging Weekend
The Sultana Education Foundation's Downrigging Weekend highlights Tall Ships and Bluegrass, along with nautical history and Chesapeake Bay ecology.
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Hometown Holiday
Kick off the Holiday Season with one of Downtown Chestertowns most iconic events, the arrival of Santa and Mrs. Clause on a fire truck! Enjoy the festive holiday music, candy, […]
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Dickens of a Christmas
National Music Festival
The National Music Festival transforms Kent County into a hub of music. Now in its 13th season, the nationally recognized event will feature music to suit virtually every taste — […]