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Disturbance histories are important factors in determining the composition and structure of today’s forests, and not least among these disturbances is the human use of the land. Land clearing in Maine peaked in 1880 at six and a half million acres, beginning on the coast and lower river valleys and spreading northward and eastward. The forests of Maine’s coastal islands have endured a longer period of clearing than any other in the state. Long Island, located in Blue Hill Bay, was first settled in 1779, primarily by farmers. Sheep-herding, lumbering, fishing, and granite quarrying provided supplemental livelihoods. By 1920 all of the island’s year-round residents had moved to the mainland, leaving only a few summer camps scattered along the coast. This article looks at Long Island from a historical perspective, then compares this land-use history to modern vegetation data and tree core samples. Kristen Hoffmann earned her M.S. in Forest Management from the University of Maine in 2007. She is currently working as a forestland steward for the Forest Society of Maine in Bangor.