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Surrounded by farmland on one side and the Chester River on the other, Chestertown is a look back in time to the flourishing Colonial port it was in the 1640s, when it harbored vessels bound for Europe, the Caribbean and West Africa. The town's population today is barely larger than during the American Revolution, and the people of Chestertown still go about their lives on quiet cobblestone streets amid restored 18th-century houses and churches. The layout of the town, also the county seat of Kent County, is much the same as it was in Colonial times, encompassing dozens of historic structures, as well as newer antique shops, art galleries, restaurants and bars. During the Revolution, Chestertown merchants led protests against British rule, and each year the citizens of Chestertown commemorate their role in the war with the Chestertown Tea Party Festival, a long weekend of tours, parades, Colonial costumes and more.
Stay here:
Brampton Bed and Breakfast Inn, 25227 Chestertown Road, 866-305-1860 or 410-778-1860;