Deep Hollow Ranch - A Rich History Rooted in Family Tradition

Deep Hollow Ranch By Joan D. Dickinson The following article appeared in the August 1995 issue of American Cowboy. The oldest ranch in the country is located 110 miles outside New York City, of all places. Deep Hollow Ranch, is at the easternost point of Long Island in Montauk, New York. The landscape has changed dramatically over the years, but the spirit of the Ol' West still lives on in this part of the Ol' East.
	The owners of Deep Hollow, Diane and Gardner "Rusty" Leaver, have dedicated their lives to preserving the ranch's heritage. For Diane, ranching in Montauk is a family tradition. She is a fifth generation rancher. Diane and Rusty are raising their two children, Retta and Gardner, to be the sixth generation.
In the 1600s, ranching was a popular way of life in Montauk and the surrounding areas, known as the East End. The land was known for its lush, green pastures and cattle drives to Montauk from as far as 70 miles away were commonplace.
Ranchers would lease the land for grazing cattle from the Montauk Indians through officials at East Hampton, a nearby town. Since the end of Long Island is narrow, there was no need for fences; the Atlantic Ocean on the south and Block Island Sound to the north provided natural boundaries. For more than 250 years--from 1660 to 1914--each family with cattle had its own earmark registered with town clear, to help claim ownership at round-up time. During these golden years, 2000 to 6000 cattle, horses and sheep roamed the land.
	Only three houses existed on the land in the 1700s, each spaced three miles apart. They were called First House, Second House and Third House, simply because that was the order someone would pass them when riding out. During the cattle drives, the cowboys would stay at Third House. Diane's father, Frank Dickinson, known as Shank, was born at Third House in 1924. He and his brother, Jack, were the last two people born there. Today, the house is part of Deep Hollow Ranch.