Surveyor in Cherry Grove

Cherry Grove dates its modern history to the 1868 purchase by Archer and Elizabeth Perkinson. They bought the land between Lone Hill (now Fire Island Pines) and the Cherry Grove Hotel from the ocean to the bay for 25 cents per acre and named the area for the black-cherry trees in the area. The Perkinsons opened a hotel in 1880. According to local legend Oscar Wilde stayed at the Perkinson Hotel.

In 1921, the Perkinson family sold all the land east of Duryea Walk to Lone Hill, and then divided what was left into 109 building lots. A lot 50 × 80 feet (24 m) could be purchased for $250 or less, and ocean-front lots cost no more than a dollar a front foot. Buildings from the newly deactivated Camp Upton in Yaphank, were ported over to form the core of the new colony. A post office was established in 1922 at the site of where “Tides” (formerly “The Monster”) is today; the first boardwalks were built in 1929. In 1930, Duffy’s Hotel replaced the original hotel and was the only place with electricity and a phone.

The 1938 Long Island Express Hurricane destroyed much of Cherry Grove and discouraged mainlanders from coming. In their stead, the gay community that already frequented the island settled there moving from Ocean Beach, with figures such as Antoine de Paris and W. H. Auden leading the way.