The Shady Side peninsula has had a long and varied history. Surrounded by the Chesapeake Bay, the peninsula was called "the Great Swamp" and a portion was "Sedgefield," after the sedge grass found in its marshy areas. With the opening of a post office in 1888, the area was renamed Shady Side. The steamboat era of the Chesapeake Bay brought people to the peninsula for summer vacations. Summer "boarding houses" flourished; there were eight at the turn of the century. Permanent residents at this time were watermen who made their living by fishing, crabbing, and oystering in season.
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