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is a town in Kent County, Maryland, United States. The population was 4,746 at the 2000 census. It is the county seat of Kent County. The zipcode is 21620 and the area codes are 410 and 443 (overlay). The local telephone exchanges are 778 and 810 for 410; and 215, 282, and 480 for 443. It is home to WKHS radio.
Founded in 1706, Chestertown rose in stature when it was named one of the colony'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-18th century, Chestertown trailed only Annapolis as Maryland's leading port.
A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprung up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing 18th century homes.
As of the 1790 census, Chestertown was the geographical center of population of the United States.