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Chestertown, Maryland
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Website: chestertown.com

Chestertown flourishes with a hearty blend of history, art, music, theater, shopping, and exciting lodging and dining experiences.

Discoveries in galleries and shops include traditional and contemporary galleries, artists' studios, fine ceramics, antiques, furniture, woodcarvings, collectibles, and more. Follow brick sidewalks and alleyways that lead to waterfront dining at the Fish Whistle (the curry chicken salad is superb) and in town establishments such as the Front Room at the Imperial Hotel.