Chestertown is a town in Kent County, Maryland, United States. The population was 5,532 as of the 2020 census. It is the county seat of Kent County. Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the na…Chestertown is a town in Kent County, Maryland, United States. The population was 5,532 as of the 2020 census. It is the county seat of Kent County. Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port.
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