In this photo from The East Hampton Star’s photo archive, William Cooper (b. 1899), owner and proprietor of Deep Hollow Ranch in Montauk, is seen with one bent knee on a hay-covered truck bed next to several calves. Judging by their apparent height, the calves are likely less than 6 months old. Based on their various hides, there are at least two breeds represented, and the fuzzier calves may even be bison.
Long before European settlers built the first permanent homes in Montauk, the land that makes up Deep Hollow Ranch was used as a cattle pasture as early as 1658. Third House, constructed there in the 18th century and one of the first structures built in European style, has a storied history. During the Camp Wikoff encampment, Theodore Roosevelt and the Rough Riders quartered there. The house was used at different times as a home and as a hotel.
William Bell (b. 1913) and Phineas Dickinson (1864-1964) developed Third House into Deep Hollow Ranch in 1938, adapting it into a modern dude ranch, and events like rodeos and turkey hunts were held there. The building’s capacity as both hotel and ranch drew the interest of William and Mary Cooper, a couple who owned and ran Cooper’s Hotel in Bay Shore. In May of 1946, they bought Deep Hollow.
The Coopers were capable hoteliers who also had experience cattle ranching, or “duding,” in Arizona. The couple renamed the business Cooper’s Deep Hollow Ranch and added a cocktail lounge to the main lodge.
During their time in Montauk, the Coopers were active in the community. Bill became president of the Montauk Historical Society in 1964 and remained in that post until he and Mary moved west to Garden City in 1968.
Third House and Deep Hollow Ranch exist today as separate entities, with the cattle ranch continuing to operate and Third House serving as home to an environmental education nonprofit.
Moriah Moore is a librarian and archivist in the East Hampton Library’s Long Island Collection.