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.
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.
As of the 1790 census, Chestertown was the geographical center of population of the United States.
Chestertown was incorporated in 1805, and was named for the Chester River.
Airy Hill, the Bernice J., Brampton, Carvill Hall, Chester Hall, the Chestertown Armory, the Chestertown Historic District, Chestertown Railroad Station, Denton House, Gobbler Hill, Godlington Manor, the Island Image, Lauretum, Radcliffe Mill, Reward-Tilden's Farm, Rose Hill, the Silver Heel, the Charles Sumner Post No. 25, Grand Army of the Republic, Thornton, Washington College: Middle, East and West Halls, and White House Farm (Chestertown, Maryland) are listed on the National Register of Historic Places.