America’s Oldest Cattle Ranch

Iconic Communities, On the Road, Traditions
on December 31, 2000

Mention the oldest cattle ranch in the United States, and most of us mentally head west, the wrong direction. The distinction goes to a spread in a state seldom associated with cowboysNew Yorkin a town best known for its lighthouseMontauk.

Few who head to Montauk (pop. 3,001) think of it as a historic destination; surfers come to brave the waves at Ditch Plains Beach, sport fishermen entertain notions of adding to its 30 world records, and work-weary weekenders seek rejuvenation while watching sunsets on Fort Pond Bay. But as far back as the 1650s, herds of cattle went to Montauk the first of May and pastured until the first of November. They came from Long Island’s eastern-end towns. One document from the 1700s listed 3,400 head summering in the town of Montauk.

The annual cattle drives continued for nearly 300 years, until people realized Montaukwhich juts into the Atlantic Oceanwas good for more than grazing. But a reminder of the tradition still exists: At Deep Hollow Ranch, the country’s oldest cattle ranch, cows still graze.

“We keep about 80 head,” says Rusty Leaver, who with his wife, Diane, owns the ranch. Situated on rolling hills, it’s about three miles from the heart of town, a plaza with shops, restaurants, and a post office where locals pick up mail, meet friends, and catch up on the news. Leaver has been involved with Deep Hollow since he worked there as a kid in 1963; Diane’s family goes back further. Their children will be the sixth generation associated with the 3,000-acre ranchpart of which is owned by the state but used by the Leavers.

They maintain the herd for two reasons: “We like the historical significance of keeping cattle, but we also train cutting horses and need the cattle for that,” says Leaver.

“A cutting horse is one trained to keep a cow from getting back to the herd,” explains Diane, “for doctoring reasons or to separate it from a calf.” The activity has evolved into a sport, creating a demand for cutting horses. Leaver shows and sells his own in Texas, where he and his wife have friends. The Leavers also operate horseback riding concessions in Montauk, and Diane runs much of the day-to-day operations: “I’m doing what I want to do, and I’m where I want to be,” she says.

A cowboy at heart, Leaver admits to romanticizing about what it must have been like in the old days, and, to a degree, wishes he could have been around. “But I’m pretty happy now the way things are.”

His wistfulness about the drives is understandable; cattle day was an exciting event. Townspeople along the way turned out to watch the men and boys on horseback driving herds to their destination. It took at least two days to get the cows from East Hampton (about 20 miles west) to Montauk. In the 1700s, three houses were built on Montauk for the cattle keepers, and each keeper had duties, such as keeping the cows out of the sheep pasture and preventing them from straying. In later years, the days before the drives were busy as bread, beans, roasts, and pies for all the drovers were prepared.

Cattle brands were registered with the East Hampton town clerk as late as 1914, but by the 1920s the drives had ended. The custom was revived for about 10 years, and amateur cowhands tried their skill at being cowpokes, but that, too, ceased. Now the cattle stay put and vacationers arrive in spring and stay until fall. “They’re welcome at the ranch,” says Leaver, where they can take a wagon tour or go riding.

Those unfamiliar with Deep Hollow’s history are amazed, he adds: “People in general are taken aback that the oldest cattle ranch exists within 120 miles of New York City.”

In keeping with the western atmosphere, during summer Deep Hollow Ranch hosts an evening barbecue dinner theater with a performance that’s historically based. The way to the site is via horse drawn wagon, which is greeted by a Buffalo Bill impersonator who presents a one-man wild west show. The entertainment includes a cowboy who teaches kids to rope.

Who knows: one of those youngsters might someday fill Leaver’s bootsand continue the cowpoke tradition that began on Montauk more than three centuries ago.