A Trip Back in Time: Nation’s Oldest Working Cattle Ranches

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If you’re looking to take a trip back in time, to the dawn of the cowboy and the rise of working cattle ranches, visit one of the nation’s oldest cattle ranches.

With 8,000 acres of its own and bordered by 22,000 acres of public leased land, Horse Prairie Ranch is one of the oldest cattle ranches in Montana. The ranch’s goal is to preserve the tradition of working ranch life. As a guest, you can choose from a variety of activities including evening sunset rides, cattle drives, branding, chuck wagon breakfast rides or a history tour, among others.

Similarly, one of the old ranches in Utah, Red Rock Ranch, is a real working cattle ranch complete with cattle drives for guests. Homesteaded in the 1850s, the ranch is nestled among the South Fork canyon’s red rock cliffs. The ranch house is a two-story home build in the 1850s with dove-tailed logs.

The nation’s oldest working cattle ranch, Deep Hollow Ranch is located in, of all places, Montauk, NY. Montauk, known as an inspiration for Peter Benchley’s Jaws and just over 100 miles from New York City, would not seem the place for a cattle ranch, but Deep Hollow Ranch has been operating there since the 1800s.

The history of Deep Hollow began in the 1600s, as ranch life was popular in Montauk. Ranchers there would lease land from the Montauk Native Americans to graze their cattle. There was no need for fencing as the Atlantic Ocean was a natural barrier on the south side, and the Block Island Sound a barrier on the north. Around this time, nearly 6,000 livestock grazed the land.

In 1885, the Long Island Railroad reached Montauk, and life began to change as tourists came from New York City to the place known for its fishing and beautiful scenery.

In 1898, former president Teddy Roosevelt and the Rough Riders recuperated at one of the houses in Montauk, but as the era closed and the 1900s began, ranchers began giving up their livelihood in favor of sport fishing and farming.

Polo ponies arrived in Montauk in 1926 with a New York City-based real estate developer who had dreams of developing a luxury resort town. He purchased most of the area but then rented part of it to teenage Phineas Dickinson in 1936.

At the onset of World War II, as the Dickinson boys went off to service, most ranching at Deep Hollow came to a halt. On their return in 1947, Phineas brought white face cattle from Texas and raised them for slaughter in the 1960s.

The early 1970s brought the Leavers as Rusty Leaver, a former summer ranch hand for Phineas, decided to leave New York City for Montauk. When he heard that the ranch was for sale, he purchased it. Within a few years, he married a Dickinson daughter, Diane.

But if you want to visit Deep Hollow Ranch, you had better do it soon. The family has reluctantly put the ranch on the real estate market in the summer of 2006 as the Hamptons area location has made it exceedingly more difficult for the family to continue to raise cattle and horses. The ranch could soon, like the cowboys of yesteryear, be riding on into the sunset.


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