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Second only to Annapolis in its concentration of 18th-century houses, Chestertown was a major international port in Colonial days: a tall, brick customhouse continues to dominate the High Street waterfront. Still the home of families whose local roots go back many generations, the town has its share of newer residents, many of them retirees. Today inns and good restaurants, fine-art galleries, three
independent bookstores, and antiques shops line the brick pavements of High Street, Chestertown's broad, tree-lined main street. To walk along its narrow streets, some of them cobbled, is to commune quietly with some of the country's earliest history. At the northern edge of Chestertown is Washington College, one of the nation's oldest liberal-arts institutions. George Washington helped found the college in 1782 through a gift of 50 guineas.
Berlin—named not for the German city, but evolving from Burleigh Inn, a Colonial-era way station—is a short drive from Ocean City, yet it could...