Deep Hollow Ranch - Montauk

Deep Hollow Ranch is a historic ranch located in Montauk with an estimated 26 acre property. The ranch is recognized as the oldest ranch in the United States by the National Geographic Society. 

The compound includes several working barns, a 5,000-square-foot antique timber framed farmhouse, and a 2-acre buildable lot. 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. it was owned privately and leased out to livestock owners. They would drive the herds of cattle and sheep out for the summer months to grow fat on the Maritime grasses.

At the peak of the South Fork ranching era, as many as 6,000 head of cattle and sheep roamed the land between the beginning of May and the start of November.  In the 1920s, the ranch became a guest ranch for people to come and stay. They built those nine beautiful cabins on the hill above the stables, as well as adding onto third house with other guestrooms and a wonderful restaurant. That ran until 1971 when the county bought third house and Deep Hollow as well as all the land down to the beach. They kept Deep Hollow as a concession to be open for the public to be able to ride and enjoy all the land. Third house became a museum which is no longer open.

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 are tour guides. The ranch provides well-trained horses and experienced wranglers to ensure a safe and enjoyable riding experience. 

Source:

Deep Hollow Ranch . Historic Towns Of America. (n.d.). https://historictownsofamerica.com/oldest-ranch 

Giustino, S. (2021, November 1). Behind the Scenes at Deep Hollow Ranch. Montauk Sun. https://www.montauksun.com/about-our-cover-behind-the-scenes-at-deep-hollow-ranch/