About The Oldest Ranch In America
Deep Hollow Ranch is surrounded by thousands of preserved acres of coastal land
Unlike a farm which grows crops and offers products produced by livestock, a ranch is an agricultural property that is primarily used for raising livestock, such as cattle, sheep, horses, or pigs.
Deep Hollow Ranch is a historic ranch located on the eastern end of Long Island, New York with an estimated 26 acre property. It is the oldest ranch in America. The ranch is recognized as the oldest ranch in the United States by the National Geographic Society. Suffolk County government describes Deep Hollow Ranch as the first and oldest cattle ranch in the United States.
The compound includes several working barns, a 5,000-square-foot antique timber framed farmhouse, and a 2-acre buildable lot. This oldest ranch in the U.S. is also known as the birthplace of the American Cowboy.
With a history that dates all the way back to 1658, Deep Hollow Ranch is considered to be not only New York's oldest, but also America's oldest working ranch. The ranch traces its history back to the cattle punching of Long Island’s earliest settlers.
These settlers took advantage of the region’s lush pastures and the fact that the ocean and sound provided natural boundaries that made the need for fences moot. The ranch is situated right along the oceanfront.
At the peak of the South Fork ranching era – it was serious business for more than 275 years – as many as 6,000 head of cattle and sheep roamed the land between the beginning of May and the start of November. The property has hosted several "Back at the Ranch" charity concerts during the 1990's, which featured acts like Paul Simon and Billy Joel.
Today, Deep Hollow Ranch welcomes visitors all throughout the year. Also known as a horseback riding attraction, actual cowboys and cowgirls will be your tour guides, leading you out to breathtaking views of the ocean.
The ranch provides well-trained horses and experienced wranglers to ensure a safe and enjoyable riding experience. It’s 90 minutes of walking and trotting through the beautiful parkland opening onto the beach at Oyster Pond for a ride along the shore and then back through the trail to the ranch.
Aside from horseback riding, Deep Hollow Ranch hosts various events and activities throughout the year, including cattle roundups, horsemanship clinics, and cowboy-style barbecues. Although its primary draw is horseback riding,
These activities offer visitors a chance to immerse themselves in the authentic cowboy culture and gain a deeper appreciation for the ranching traditions of the area. These days, the 26 acre property continues to care for horses and cattle, and is dedicated to maintaining the local ecosystem.
The ranch has a retail shop on-site where visitors can purchase souvenirs, western apparel, horse tack, and other ranch-themed merchandise. The shop also sells snacks, beverages, and sundries for guests' convenience
Deep Hollow Ranch is a treasured landmark and popular destination for those seeking a genuine ranch experience in a beautiful natural setting. It combines history, horsemanship, and the charm of the American West, making it a unique attraction on Long Island.
Overall, Deep Hollow Ranch offers a rare blend of history and hands-on experience, making it a standout in Montauk. Whether you’re drawn by its cowboy heritage, the promise of a beach side trot, or simply a taste of old America, it’s a place where the past rides alongside the present—just don’t expect a full cattle drive.