In colonial times, Chestertown was designated the primary port of entry for the upper Eastern shore.
Bustling wharves lined the waterfront, where laborers loaded ships with local crops bound for Europe and the Caribbean. Vessels from across the Atlantic brought trade goods, slaves and convict laborers.
The Custom House, circa 1746
The large brick building in front of you is traditionally known as the Custom House, although the actual office of His Majesty's Customs was likely in an adjacent building. This mansion was in fact the home of Thomas Ringgold, a merchant, lawyer, and prominent advocate of American liberty. In a cruel paradox, he was also a large-scale slave trader whose ships brought hundreds of captive Africans through the Middle Passage to work the plantations of the Chesapeake region.
A Changing Community
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. In 1782, Washington College — the first college founded in the newly independent United States — was established here.
The wharves lining this riverfront disappeared over time as the economy changed. The majority of today's water traffic comes from
recreational boating.
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