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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Signature Event
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Chestertown Car Show
The Chestertown Car Show accepts all years, makes & models of cars, trucks in 10 classes. There will be over 10 trophies for specific classes, awarded on a judged basis. Food Trucks will be onsite. Beer and Wine will be sold by Mainstreet Chestertown. There’s more than just cars and trucks in Chestertown, we have a thriving arts district, […]
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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, and some of the most iconic characters of the holiday season enjoying the downtown.
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