Ranch Roots

Before the colonists pushed eastward, the wind swept meadows of the farthest edge of Long Island were the province of the Montauketts. That all changed in 1658 when Chief Wyandanch is said to have entered into an agreement that allowed the people from East Hampton to pasture their cattle there. It’s that date that Deep Hollow Ranch uses as evidence of it being the “oldest cattle ranch in the U.S.”

The grassland in Montauk was very thick and lush from the salt spray so the livestock would get very fat, very quick, making it prime land for grazing. In the late 1700s, buildings went up to house livestock tenders, but those were destroyed, it is said, during the Revolutionary War. Second House and Third House were rebuilt to house cattle keepers. Third House eventually became an inn.

Cattle drives ended in 1925 but were revived in 1936 by Frank Dickinson, until a pause during World War II, and were reintroduced afterward continuing until the 1950s. Rodeo and other horse-exhibition activities continued for many more years.

In 1938, Third House was purchased by William D. Bell and renamed the Deep Hollow Guest and Cattle Ranch. Deep Hollow Ranch also included the surrounding land and buildings (cabins and stables). The Dickinson family ran the ranch for Bell. Diane Dickinson married Rusty Leaver, and after the county purchased the land in 1971, they took over operations of the ranch as the very first concessionaires, essentially leasing the county property to run the horseback riding operation.

It’s well known that Colonel Teddy Roosevelt and his Rough Riders rested at nearby Camp Wickoff. He is quoted in promotional materials for the Deep Hollow Guest and Cattle Ranch as saying of his stay: “We would gallop down to the beach and bathe in the surf, or else go for long rides over the beautiful rolling plains, thickly studded with pools which were white with water lilies. Galloping over the open rolling country through the cool fall evenings made us feel we were out on the great western plains and might at any moment startle deer from the brush or see antelope stand and gaze far away, or rouse a band of mighty elk and hear their horns clatter as they fled away.”

-KC