The Three Houses

With roads as bad as they were (it took six hours, within living memory, to drive the twenty miles from East Hampton to Montauk Point, braving the mosquito-and-horse fly infested, sandy stretch of Napeague Beach, behind a team of fat farm horses) Montauk was no place to live, only to visit, most people thought.

But the few who did live there came to love it. Visitors who stayed at the three houses grew ecstatic in the guest books (some still preserved) over the wonderful sport, the bracing air, the beauty of the hills, and the delicious ample country meals served at the keepers’ houses and, on occasion, by the wife of the lighthouse keeper. It was all an adventure.

First House, built in 1798 (an earlier one was built in 1744) stood on land now part of Hither Hills State Park, almost across the old Montauk shore road from the house where the State Park superintendent lives.

Second House, was first built in 1746, and was restructured in 1797, when, according to the East Hampton Town Trustees’ Journals, the Town allotted “three gallons of rum to raise the house at the Fort Pond.”

It is customary here to this day for carpenters to nail a “bush” onto the roof of a new house, as a signal that the roof is raised and they are willing to partake of the owner’s hospitality. In the old days an owner needed help of friends and neighbors to raise the frame.

The expression “raising the roof” doubtless comes from such celebrations. When the second Manor House was built at Gardiner’s Island in 1774 (the one that burned down in 1947) the owner, David Gardiner, mentioned the “raising” in his diary. He said: “Raised frame May 25, 1774, 49 persons present, some of whom were bystanders. Raised it in less than six hours; none much hurt. No notice given until the night before for fear of a herd of grog-bruisers.” Apparently there was no lack of volunteer help on such occasions.

In 1806, the present Third House was built. A wing was added onto it after the Benson purchase in 1879. Unoccupied for some years, (it once flourished as an inn), Deep Hollow Ranch, and its surrounding fields are again dotted with grazing horses and cattle. Usually the visitor can see deer, too, feeding amicably among the domestic animals. Third House, nearest to the Point and Montauk Lighthouse (built 1796) was headquarters in 1898 for Col. “Teddy” Roosevelt and other officers returning from the Spanish-American War, when 29,500 veterans camped on the hills and plains of Montauk to recuperate from wounds and tropical diseases.

The three houses were spaced miles apart. The keeper at each house had his specific duties with regard to the cattle, horses, and sheep driven on for pasture.