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The perfect blend of outdoor recreation, arts, history, and shopping Chestertown is Eastern Shore living at its best! Get lost in the sights and sounds of a vibrant waterfront downtown with over 300 years of history. Start experiencing Main Street with a visit to the Massoniart Gallery, a cornerstone of Chestertown’s art scene, and discover locally based, nationally renowned artists; stop in to The Listening Room to pick up some vinyl or to MusicLife to learn to play your next musical instrument
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