After European discovery by Dutch fur trader Adriaen Block in 1614, Fishers Island was first settled in the 1640s by John Winthrop, Jr., the son of the founder of the Massachusetts Bay Colony. The younger Winthrop saw the Island’s promise as an offshore livestock plantation and sanctuary. For six more generations the land was passed down within the Winthrop family and utilized primarily for raising cattle and sheep for stock and dairy farming purposes. In 1863, the last of the Winthrop owners fell on hard times and sold the undivided property to Robert R. Fox, a successful manufacturer and merchant of cotton duck based in New York City. His goal was to retire to the island and restore the largely abandoned farms to their former grandeur.
After the unexpected death of Mr. Fox in 1871, his widow and the executors of his estate began the process of turning the island into a seaside resort. The first land lots were sold to individuals beginning in 1876. By the early 1880s, a small town center had formed, a fishing community was thriving, and a tourist hotel had been built at the western end of the island. Soon large steamers were bringing hundreds of excursionists to Fishers Island for a day filled with clambakes, sports activity, dancing and drinking. This brief tourist period came to a halt in 1889 when Edmund & Walton Ferguson, two successful businessmen and bankers, purchased 9/10ths of Fishers Island from the Fox heirs for the sum of $250,000. They received the entire island in return excepting 101 small lots that had already been sold to individuals. The two brothers bought out and shut down the tourist hotel and proceeded to develop the island as a family-based resort with new cottages and new hotels that catered to seasonal visitors. The Ferguson brothers financed a navigation company, a water works, and an electric power plant as part of an overall infrastructure worthy of a first class resort.
In the mid-1920s, Henry L. and Alfred L. Ferguson, representing the second generation of Ferguson owners, turned their attention to the eastern two-thirds of the island, land that had been utilized almost exclusively for farming and sporting purposes before that date. They hired Frederic Law Olmsted, Jr., the son of the legendary designer of Central Park, to draw up a plan for a private residential development (“the park”) covering the eastern-most 1,800 acres. They also hired golf course architect Seth Raynor to design an 18-hole golf course on the Island’s eastern tip. The new Fishers Island Corporation opened its grand clubhouse and its golf course on July 1, 1926. However, the Crash of 1929 slowed down development and today there are still only approximately 245 metered residences and living units within the private “park” and 404 on the more fully developed western end.