Chestertown Town Extension

Founded in 1706, Chestertown rose when it was named one of the colony's six Royal Ports of Entry. The shipping boom that followed made this town at the navigable head of the Chester River wealthy, and by the mid-18th century only Annapolis outranked it among Maryland's ports. Washington College was founded here in 1756. Cut off from the growing Baltimore and Washington, DC corridor, the region saw little growth for the next two centuries, and the town's historic character stayed almost perfectly preserved until the mid-20th century.

Red brick walls, steep roofs and paired chimneys appear on houses in the drawings for the extension, and on a building with dormers above its shopfronts. Two buildings with towers and a low street of attached fronts round out the set.