If you’re looking to take a trip back in time, to the dawn of the cowboy and cattle ranching boom, visit one of the oldest cattle ranches in the country.

With 8,000 owned acres and bordered by 22,000 acres of leased public 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, a history tour, and more.

Similarly, one of Utah’s old ranches, Red Rock Ranch, is a true working cattle ranch complete with cattle drives for guests. Established in the 1850s, the ranch is nestled among the red rock cliffs of South Fork Canyon. The ranch house is a two-story home built in the 1850’s out of dovetail logs.

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

Deep Hollow’s history began in the 1600s, when ranch living 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 cattle took over the land.

In 1885, the Long Island Railroad came to Montauk, and life began to change as tourists poured in 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 in one of Montauk’s homes, but as the era ended and the 20th century began, ranchers began giving up their livelihoods 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 rented part of it to the teenager Phineas Dickinson in 1936.

At the start of World War II, when Dickinson’s boys left for the service, most of the ranching at Deep Hollow stopped. Upon his return in 1947, Phineas brought white-faced cattle from Texas and raised them for slaughter in the 1960s.

The early 1970s brought the Leavers when Rusty Leaver, a former hand at Phineas’s summer ranch, decided to leave New York City for Montauk. When he found out that 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 real estate market 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 could soon, like the cowboys of old, ride off into the sunset.