A trip back in time: the oldest working cattle ranches in the country
If you’re looking to take a trip back in time to the dawn of the cowboy and the boom in cattle ranching, visit one of the oldest cattle ranches in the country.
With 8,000 acres owned and bordered by 22,000 acres of public leased land, Horse Prairie Ranch is one of the oldest cattle ranches in Montana. The goal of the ranch is to preserve the tradition of working life on the ranch. As a guest, you can choose from a variety of activities including sunset rides, cattle drives, branding, breakfast wagon rides, or a history tour, among others.
Likewise, one of Utah’s oldest ranches, Red Rock Ranch, is a real working cattle ranch complete with cattle drives for guests. Established in the 1850s, the ranch is nestled among the red rock cliffs of the South Fork canyon. The ranch house is a two-story home built in the 1850s from dovetail logs.
The oldest working cattle ranch in the country, Deep Hollow Ranch is located, of all places, in Montauk, New York. Known as an inspiration for Peter Benchley’s Jaws and just over 100 miles from New York City, Montauk might not seem like the place for a cattle ranch, but Deep Hollow Ranch has been operating there since the 19th century.
Deep Hollow’s history began in the 1600s, when ranch life was popular in Montauk. Ranchers would lease land from 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 Block Island Sound a barrier on the north. Around this time, nearly 6,000 head of cattle took over the land.
In 1885, the Long Island Railroad reached Montauk, and life began to change as tourists flocked from New York City to the place known for its fishing and beautiful scenery.
In 1898, former President Teddy Roosevelt and the Rough Riders recovered in one of Montauk’s homes, but as the era ended and the 20th century began, ranchers began giving up their livelihood in favor of sport fishing and farming. .
Polo ponies came to Montauk in 1926 with a New York City real estate developer who dreamed of developing a luxury resort town. He bought most of the area, but later leased part of it to teenager Phineas Dickinson in 1936.
At the start of World War II, when the Dickinson boys left for the service, most of the ranching in Deep Hollow stopped. Upon his return in 1947, Phineas brought in white-faced Texas cattle and raised them for slaughter in the 1960s.
The beginning of the 1970s brought the Leavers when Rusty Leaver, a former farmhand at Phineas’s summer ranch, decided to leave New York City for Montauk. When he found out the ranch was for sale, he bought it. Within a few years, he married a Dickinson daughter, Diane.
But if you want to visit Deep Hollow Ranch, you better do it soon. The family reluctantly put the ranch on the market for real estate in the summer of 2006, as the location in the Hamptons area has made it much more difficult for the family to continue raising cattle and horses. The ranch might soon, like the cowboys of old, ride off into the sunset.