Royal Port of Entry

In colonial times, Chestertown was designated the primary port of entry for the upper Eastern Shore, with bustling wharves along the waterfront where laborers loaded ships with local crops bound for Europe and the Caribbean, while vessels from across the Atlantic brought trade goods, slaves, and convict laborers. The large brick building traditionally known as the Custom House dates to about 1746, though the actual office of His Majesty's Customs was likely in an adjacent building; the mansion was instead the home of Thomas Ringgold, a merchant, lawyer, and prominent advocate of American liberty who was also a large-scale slave trader whose ships brought hundreds of captive Africans through the Middle Passage to work plantations in the Chesapeake region. By the Revolutionary War era, Chestertown had become the largest and most important town on Maryland's Eastern Shore, with thriving cultural and educational institutions, and in 1782 Washington College, the first college founded in the newly independent United States, was established there. Over time the riverfront wharves disappeared as the economy changed, and most water traffic today comes from recreational boating.

Chestertown, Maryland · United States