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Chestertown Tea Party Festival
The Chestertown Tea Party festival is a time honored tradition for visitors and residents alike. This weekend long festival has entertainment for all ages. Kick off the Tea Party weekend […]
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Signature Event
National Music Festival
The National Music Festival transforms Kent County into a hub of music. The nationally recognized event will feature music to suit virtually every taste — from symphonies and chamber music […]
“Heroes of the Chesapeake” Juneteenth Celebration
The Black Union of Kent County and the Town of Chestertown host the annual Kent County Juneteenth Celebration offering a series of events to celebrate history, culture, and achievements. Fountain […]
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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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 […]
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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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