Chestertown 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.
Founded in 1705, 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.
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 eighteenth century homes.