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Lost in Chestertown: What Does An Out-of-Towner See On a Visit to Chestertown?

  Have you ever wondered how Chestertown looks to those who don’t live here? Lost in Chestertown is the first in a series of stories where Main Street Chestertown invites talented artists, photographers and writers from-away to share their visits through their own eyes. By 

CHESTERTOWN AL FRESCO DINING

Enjoy outdoor street dining on select Fridays and Saturdays while the weather lasts.

Photo by Caroline Phillips

Check out the latest one minute (give or take) videos from downtown Chestertown's shops and restaurants.

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MAIN STREET MINUTE