Charlestown was established by the Maryland General Assembly in 1742 as a port town to facilitate trade within the region. It is situated on the North East River at the head of the Chesapeake Bay and was among the few places where large ships could enter. Named for colonial proprietor Charles Calvert, it was laid out by Deputy Surveyor for Cecil County John Veazey, on an ambitious plan calling for a public wharf and warehouses, town squares, courthouse, market house, church, fairgrounds, and two hundred house lots. An inspection station guaranteed Charlestown a share in the lucrative flour trade and rendered it a key port within the Chesapeake Bay’s trade network and a supply depot for the Continental Army. It was likewise a popular stop along the Post Road between Philadelphia and Annapolis.
The town’s potential attracted an influential citizenry and much speculation. While town managers hoped it might form the county seat, it did so only briefly, from 1782 to 1787. The town faced a setback when Elkton was selected instead. Although the fishing and fish-packing industries helped to sustain it, Charlestown’s slow decline began. In the twentieth century, pleasure boating gave rise to a community of summer cottages. Today, only submerged remnants of the stone and log-cribbed wharf and a cluster of eighteenth-century houses and former taverns along the once-bustling Market Street speak to Charlestown’s early history and the influence of Chesapeake culture on its economy and architecture.
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