Chestertown Historic District

Chestertown Historic District is a colonial port neighborhood with brick buildings dating from the 1700s lining the Chester River waterfront. More than 50 structures in Georgian style form a cohesive collection along Water Street and the surrounding streets.

Between 1750 and 1790, the district grew as a major port for tobacco and wheat trade on Maryland's Eastern Shore. This commercial prosperity led to the construction of the brick buildings that define it today.

Washington College, established in 1782, shapes the district's character with its campus buildings and green spaces woven into the historic streets. The college remains central to how locals and visitors experience the area.

The district is easily explored on foot, with parking areas marked between Court Street and Water Street. The main buildings are clustered in a compact area that visitors can walk through in an hour or two.

The Hynson-Ringgold House contains original Georgian wood paneling from 1767, with sections now at the Baltimore Museum of Art. This division reflects how elements of the district have been dispersed to major institutions.