Chestertown is a historically important port town on the Chester River in Maryland.
Originally one of the English colony of Maryland’s six Royal Ports of Entry, Chestertown is home to historical buildings, nautical artifacts, and other points of interest.
Each fall, Chestertown hosts the annual Downrigging Weekend along the Chester River waterfront.
Within walking distance of the waterfront are numerous historic homes, buildings, and other places of interest. The business district is home to an array of restaurants, cafes, specialty shops, and other resources.
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