Chestertown’s waterfront was a flashpoint in the American colonists’ struggle for liberty as Kent County, long loyal to England, saw its ancestral ties weaken with each new generation born on American soil. Tensions erupted in 1758 during the French and Indian War, when a riverfront brawl among occupying British redcoats, visiting sailors, and local youths led to musket fire that killed one man. In May 1774, the brig Geddes arrived from London carrying East Indies goods, including taxed tea, and patriots vowed that anyone caught drinking it would be stigmatized as an enemy to American liberties; Chestertown tradition holds that protesters then marched to the waterfront and dumped the tea into the river, though the event was never documented. The large brick Hynson-Ringgold House across the inlet hosted George Washington overnight in 1773, and Thomas Jefferson, James Madison, Patrick Henry, and other Revolutionary leaders also passed through the area while traveling between the Chesapeake region and Philadelphia. During the war, though no Revolutionary battles occurred here, local military companies left to join General Washington’s army, others fought for the Loyalist side, Kent County shipbuilders launched the row galley Chester to intercept British warships on the Chesapeake Bay, and several of the Continental Navy’s earliest commanders were mariners from Chestertown.