[2][1] The town on the Chester River, became the chief port for tobacco and wheat on the Eastern Shore of Maryland between 1750 and 1790.

In consequence, Chestertown acquired a collection of more than fifty Georgian style town houses.

The 18th-century residential area survived without harm a 1910 fire that destroyed the central business district of Chestertown.

[3] The historic residential area is concentrated along Water Street between the business district and the Chester River.

[3] Denton House and Widehall are also individually listed Registered Historic Places included in the district.