This photograph was taken in the spring of 1900 at Second House in Montauk. It shows Ulysses Tillinghast Payne with his wife, Nellie, and their children, Betsy, Edward, Elias, and Mildred. Built in 1746, Second House is the oldest structure in Montauk, according to the Montauk Historical Society.
Originally, First House (destroyed in 1909) and Second House housed shepherds in charge of the large numbers of livestock sent to Montauk to graze every summer. The shepherd at Second House looked after both sheep and cattle, making sure they remained separated in the neighboring pastures.
Because the keeper or shepherd at Second House served all of East Hampton, it was the East Hampton Town Trustees who funded the renovation of his shelter. In 1797 Second House underwent its first expansion, which cost the town trustees three gallons of rum for the labor and materials.
In 1879, Arthur Benson purchased all of Montauk, including Second House, and a wing was added to it a year later. In 1895, the Long Island Rail Road began transporting more people to Montauk, and Ulysses Payne, the last keeper of Second House, began renovating the building significantly, making it big enough to allow him to board as many as 25 guests in 1900.
While Payne operated Second House as a hotel, he also shared the building with Martha Osborne of Wainscott, who opened Montauk’s first school there in 1896. The students gathered in an area near the kitchen. In 1909, David and Claire O’Donnell Kennedy, who frequently boarded with the Paynes, bought Second House, intending to use it as their private vacation home.
Following Claire’s death in 1965, the house sat vacant for four years before the Town of East Hampton bought the building and arranged for the Montauk Historical Society to run it as a museum. The society continues to do so today, although it is now undergoing a multiyear renovation project.
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Andrea Meyer is the head of the East Hampton Library’s Long Island Collection.
