Forget Texas: America's Oldest Working Ranch Is A Cowboy Escape In A New York Beach Town

While Texas is home to almost 250,000 farms and ranches, the most of any state, America's oldest working ranch is actually found in an unlikely part of New York. On the tip of Long Island about 120 miles east of New York City lies Montauk's Deep Hollow Ranch, which was founded in 1658. While Montauk is renowned for its surfing today, its grassy inland terrain made it a prime spot for cattle grazing centuries ago. The ranch played an important role after the Spanish-American War in 1898 when American soldiers and their horses returning from Cuba were sent to quarantine in Montauk. Theodore "Teddy" Roosevelt and the Rough Riders, his volunteer cavalry, were housed near the ranch, and their horses grazed on the ranch's pastures.

Today, the family-owned ranch is considered the "birthplace of the American cowboy" and maintains its centuries-old cowboy spirit (per its website). Located between downtown Montauk and the historic Montauk Point Lighthouse, Deep Hollow Ranch covers about 26 acres in the larger Montauk County Park. While this land was originally grazed by cattle, the ranch is now home to 40 horses. Here, both beginner and established riders can experience Montauk's coastal landscape on horseback by heading out on authentic Western-style trail rides on scenic paths.

Deep Hollow Ranch is 120 miles from New York City or a nonstop train ride from Penn Station, followed by a 10-minute drive to the ranch. Deep Hollow Ranch is open year-round, but hours vary depending on the time of year. 

While Montauk is a trendy summertime resort and one of New York's most famed beach towns, a visit to Deep Hollow Ranch provides visitors with a different perspective on this scenic landscape. Though Atlantic Ocean waves crash onto Ditch Plains Beach less than two miles away, driving into Deep Hollow Ranch is like being transported out West. Horses wander in enclosed paddocks near the entrance, while the large timbered barn and stables, marked by Western-style saddles and standalone wheels, lies adjacent. Rising in the hills behind the barn are the pastures where the cattle once grazed and the horses currently feed.

Deep Hollow Ranch offers trail rides for all ages and abilities, supervised by the ranch's cowboy and cowgirl guides. Children under six years old can learn the basics riding on the ranch's ponies, while older children and adults can embark on trail rides through grassland paths that weave through Montauk County Park. For the longest ride, make the journey through the park to Montauk's secluded coastline. Here, you'll come upon Oyster Pond before reaching a long crescent beach lapped by the calm waters of Block Island Sound. "The path leading out to the coast is scenic and peaceful but once you hit the beach, it is just spectacular," raved a reviewer on Google, where the ranch has a 4.6-star rating. "Riding horseback along the shoreline with the ocean views is an unforgettable experience," they said. Trail ride prices range from $20 per person for a pony ride to $190 per person for a trail and beach ride.

After you've trotted back to the barn from your trail ride at Deep Hollow Ranch, head next door to the Third House Nature Center, which was also once part of the ranch's property. The house earned its name as the third house built in Montauk in the mid-1700s for the ranch's cattle keepers. After it burnt down in a fire, it was rebuilt in its current shingled state in 1806, and Teddy Roosevelt later stayed there in 1898 after returning from Cuba. Now, the historic building hosts history lectures and community events. North of the center are the nature trails that lead to Big Reed Pond, which is a National Natural Landmark tucked back from the beach.

For more outdoor adventures, you can take a 10-minute drive east of Deep Hollow Ranch to Camp Hero State Park, home to a once-thriving U.S. military base that now lies eerily abandoned, or a 10-minute drive west to Hither Hills State Park, which offers coastal camping and a beautiful beach. If you've worked up an appetite after horseback riding, just a mile down Montauk Highway from the ranch is Crow's Nest, a scenic hotel and restaurant perched over Lake Montauk. Open only for dinner during the summer, Crow's Nest has a delicious menu with some locally sourced cuisine, such as Montauk tuna tartare, whipped ricotta with local lavender honey, East Coast lobster and halibut, and grass-fed cowboy ribeye, appropriate after a visit to Deep Hollow Ranch.