Throwback Thursday – Deep Hollow Ranch

Deep Hollow Guest & Cattle Ranch brochure, circa 1939 | Josephine Rutkowski Collection | Montauk Library Archives
Cooper’s Deep Hollow Ranch, late 1940s | Dave Edwardes Collection | Montauk Library Archives

Hardly a month had passed after the ’38 Hurricane when the East Hampton Star reported that Third House in Montauk, historically an inn, had been sold to William Bell and Frank Dickinson, who planned to start a dude ranch.


“The house will be restored completely … The Montauk Beach Company has made an informal agreement to allow the new owners to use the Polo Field and stables, if they will keep them up; and to pasture cattle in Indian Field as Phineas Dickinson 3d has been doing.”


All told, visitors at Deep Hollow Guest & Cattle Ranch were about to have 5,000 leased acres to romp in – as well as privileges at the Montauk Yacht Club, the Surf Club, the Montauk Downs Golf Club, and the Montauk Manor tennis courts. They could claim their favorite horse for the length of their stay and were encouraged to ride around with hired cowboys and cowgirls, shoot skeet and hunt pheasants, dine at a chuck wagon, and attend rodeos, dances, and singalongs. Unfortunately, the clientele was “restricted to Gentiles,” as more than one advertisement made clear.


Soon after World War II, William Bell sold the ranch to Bill Cooper, who named it Cooper’s Deep Hollow Ranch and added a cocktail lounge. In this black and white photo by Dave Edwardes, Bill Cooper can be seen directly under the sign bearing his name, with Fanny Gardiner (of the Gardiner’s Island family, a devoted Western horsewoman to the end) second from the left.


The ranch continues to operate today, although it no longer lodges visitors. The “Deep Hollow” sign can still be seen north of Montauk Highway and just east of Third House, which – along with what used to be known as Indian Fields – now is also a part of what today is known as Montauk County Park.


  • User Avatar
    Kelly Dickinson Reply

    I remember all this growing up in Montauk.
    My Dad Frank Dickinson was born at the third house in 1923.
    My uncle Jack ran the restaurant and bar.
    I miss those days soooo much.
    Kelly Dickinson
    Franks youngest son.

  • User Avatar
    Jacqueline Beh Reply

    We ALL do. We were lucky to have lived in those times.

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