The original Islesboro Inn, built in 1889-90, burned to the ground on September 30, 1915. The Inn had been built by the Islesboro Land and Improvement Company, with the purpose of drawing wealthy people to Dark Harbor (located in the southern section of the island) and selling them large, expensive lots on which to built summer cottages. The Islesboro Inn was rebuilt in 1916, in the Colonial Revival style.