Deep Hollow Ranch - A Rich History Rooted in Family Tradition

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Cattle Day, the first day the cattle went out to graze, was an important event on the East End for over 275 years. The cattle went out the first of May and came back the first of November, more or less, depending on the weather. Traditionally, Thanksgiving Day in Montauk was held the first Thursday after the cattle were driven back.
	When the Long Island Railroad made its way to Montauk in 1885, life out east changed considerably. The new mode of transportation made the East End accessible to the residents of New York City and neighboring towns. Word of the beautiful, rolling hills and excellent fishing brought in droves of tourists and visitors. It also brought and end to Cattle Day celebrations.
In 1898, Teddy Roosevelt and his Rough Riders came to Montauk to recuperate from the war in Cuba. Roosevelt set up his office at Third House and used it as home base. Many ranchers gave up their way of life in the early 1900s for new industries, and the area became better known for its great sport fishing and farming.
New York City real estate developer and entrepreneur, Arthur Benson, brought polo ponies to Montauk in 1926, with plans of developing the town into a resort for the rich. He had purchased most of the area in 1879, but his resort schemes never materialilzed.
	Benson rented part of his land to 15-year-old Phineas Dickinson in 1936. With a helping hand from his father and grandfather, who were cowboys from way back, Dickinson brought in 150 head of cattle to graze. His younger brothers, Shank and Jack, helped out too, espcially on cattle drives. Shank recalls, "We'd ride our horses out to East Hampton the day before to stay at my grandparent's house. Then we'd be out at 5 a.m. to drive the cattle to Montauk.
When World War II came, most of the ranching at Deep Hollow stopped. But when the Dickinson boys returned from the service, in 1947, Phin brought white face cattle in from Texas by railroad. He would buy them thin, put them out to pasture to fatten up, and sell them to New York slaughterhouses. This went on through the '60s. In 1971, Rusty Leaver decided to leave New York City and move to Montauk

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