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About Chestertown, MD

Founded in 1706, Chestertown rose in stature when it was named one of the English colony of Maryland's six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. In the mid-eighteenth century, Chestertown trailed only Annapolis and was considered Maryland's second leading port. A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that sprang up along the waterfront. Another area in which Chestertown is second only to Annapolis is in its number of existing eighteenth century homes.