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    Chestertown, which was established in 1706, gained notoriety when it was selected as one of the six Royal Ports of Entry for the English colony of Maryland. The settlement at the navigable head of the Chester River became prosperous as a result of the shipping boom that came after this designation. Chestertown was regarded as Maryland’s second-largest port in the middle of the eighteenth century, just after Annapolis.

    The residents of Chestertown drafted a set of resolutions that forbade the buying, selling, or consumption of tea in May 1774, five months after the British closed the port of Boston following the Boston Tea Party. The citizens allegedly organized their own “tea party” on the Chester River as a show of colonial defiance based on these resolutions.

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