{"id":312985,"date":"2026-08-03T23:58:13","date_gmt":"2026-08-03T23:58:13","guid":{"rendered":"https:\/\/www.newsbeep.com\/us-ny\/312985\/"},"modified":"2026-08-03T23:58:13","modified_gmt":"2026-08-03T23:58:13","slug":"forget-texas-americas-oldest-working-ranch-is-a-cowboy-escape-in-a-new-york-beach-town","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/us-ny\/312985\/","title":{"rendered":"Forget Texas: America’s Oldest Working Ranch Is A Cowboy Escape In A New York Beach Town"},"content":{"rendered":"


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Michael Rega\/Shutterstock<\/p>\n

While Texas is home to almost\u00a0250,000 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<\/a>, which was founded in 1658.\u00a0While 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\u00a0Spanish-American War in 1898 when American soldiers and their horses returning from Cuba were sent to quarantine\u00a0in Montauk. Theodore “Teddy” Roosevelt and the Rough Riders,\u00a0his volunteer cavalry,\u00a0were\u00a0housed near the ranch, and their horses grazed on the ranch’s pastures.<\/p>\n

Today, the\u00a0family-owned ranch\u00a0is considered the “birthplace of the American cowboy”\u00a0and maintains its centuries-old cowboy spirit (per its website<\/a>). Located between downtown Montauk and the historic Montauk Point Lighthouse, Deep Hollow Ranch covers about 26 acres in the larger Montauk County Park<\/a>. While this land was originally grazed by cattle,\u00a0the ranch is now home to 40 horses. Here,\u00a0both beginner and established riders can experience Montauk’s coastal landscape on horseback by heading out on authentic\u00a0Western-style trail rides on scenic paths.<\/p>\n

Deep Hollow Ranch is\u00a0120 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.\u00a0<\/p>\n

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Trail rides at Deep Hollow Ranch<\/p>\n


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James Kirkikis\/Shutterstock<\/p>\n

While Montauk is a trendy summertime resort and one of New York’s most famed beach towns<\/a>, 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,\u00a0marked 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.<\/p>\n

Deep Hollow Ranch offers trail rides for all ages and abilities, supervised by the ranch’s cowboy and cowgirl guides.\u00a0Children 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\u00a0grassland paths\u00a0that weave through Montauk\u00a0County Park. For the longest ride, make the journey through the park to Montauk’s secluded coastline.\u00a0Here, you’ll come upon\u00a0Oyster Pond\u00a0before reaching a long\u00a0crescent beach\u00a0lapped by the calm waters of Block Island Sound.\u00a0“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<\/a>, 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.<\/p>\n

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What to see and do near Deep Hollow Ranch<\/p>\n

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<\/a>, 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\u00a0for\u00a0the ranch’s cattle keepers.\u00a0After it burnt down in a fire, it was rebuilt in its current shingled state in 1806, and\u00a0Teddy Roosevelt later stayed there in 1898 after returning from Cuba. Now, the historic building hosts history lectures and community events.\u00a0North of the center are the nature trails that lead to Big Reed Pond,<\/a> which is a National Natural Landmark tucked back from the beach.<\/p>\n

For more outdoor adventures, you can take a 10-minute drive east of Deep Hollow Ranch to Camp Hero State Park<\/a>, home to a once-thriving U.S. military base that now lies eerily abandoned<\/a>, or a 10-minute drive west to Hither Hills State Park,<\/a> which offers coastal camping and a beautiful beach<\/a>. If you’ve worked up an appetite after horseback riding, just a mile down Montauk Highway from the ranch is Crow’s Nest<\/a>, a scenic hotel and restaurant perched over Lake Montauk. Open only for dinner during the summer, Crow’s Nest has a delicious menu\u00a0with some locally sourced cuisine, such as Montauk tuna tartare, whipped ricotta with local lavender honey,\u00a0East Coast lobster and halibut,\u00a0and grass-fed cowboy ribeye, appropriate\u00a0after a visit to Deep Hollow Ranch.<\/p>\n


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