Second House, on the western edge of Montauk, stands as one of the most historic, but overlooked, structures in the Town of East Hampton. Drivers who pass by its low lying, neatly trimmed hedges, and dark, aged shingles en route to the Montauk Lighthouse (or perhaps to one of the notorious night spots) without stopping are missing the oldest standing house in Montauk, and the tales it might tell.
The house, built in 1746 and rebuilt in 1797, dates to the years when cattle and sheep were driven from East Hampton and points west to Montauk, where they were pastured from May 1 to Nov. 1. Although it took most of the men and boys in town to get the herds there, cattle-keepers, and often their families, stayed on.
Second House was, in fact, the second of the only three houses on Montauk that existed in the late 18th and early 19th centuries. First House, to the west at Hither Hills, was not rebuilt after a second fire in 1909. Third House, however, built in 1742 and reconstructed in 1806, has its own unique history. Now in Montauk County Park, it was the headquarters of Col. Theodore Roosevelt’s Rough Riders, who were brought to Montauk to recuperate after the Spanish-American War.
According to Jeannette Edwards Rattray’s 1969 booklet, “The Story of Second House,” the keeper there was tasked with keeping the cows out of the sheep pasture in Hither Hills. Each of the three houses served as inns over the years as intrepid East Hamptoners and some of New York City’s most influential families braved the bad road – and mosquitoes – to cross Napeague and go on Montauk for fishing and gunning. In later years, East Hamptoners made excursions to Montauk for its berries.
Nathaniel Talmage was the first cattle-keeper to live at Second House, and they all had familiar local names – Hedges, Miller, and Osborn, for example. UlyssesTillinghast Payne, whose children were born there, was the last of the lot.
Old guest books, Mrs. Rattray noted, testified that visitors were often ecstatic about Montauk. One couple, Mr. and Mrs. David Kennedy, who were boarders for several years, fell in love with Second House and bought it in 1910.
Driving onto the gravel and grass driveway at Second House, which sits at the intersection of Montauk Highway and Second House Road, visitors today will pass small square-trimmed hedges and a row of hydrangeas that line the front of the property. Well-worn tracks of gravel lead to a field of lush grass, which is used for parking. It is clear that Second House, which is now operated by the Montauk Historical Society, does not get many visitors.
The main entrance is through the back of the house, which is somewhat hidden, but a privet archway guides visitors toward the door. The door may be locked, for the museum is only open when Jean Ruggles, a docent, is there. (During the summer, its hours are 10 a.m. to 4 p.m. every day except Wednesday.)
If no one is around, however, the gardens are worth a good look. Designed and maintained by Catherine Smyth-Keogh of Smyth Fine Gardening, they were created to replicate what East End gardens may have been like generations ago. Amid the winding paths within the two small gardens, including a flower garden with daisies, roses, and poppies, are herbs and edible plants. Chives, mint, sage, dill, and lavender are there, all somehow escaping the wrath of the white-tailed deer. These small gardens, with wooden benches beneath arches of pink roses, bring a visitor back to earlier times.
Walking around the exterior of the house, visitors might notice similarities and differences between the first Montauk houses and the houses of today. Cedar shingles are there, a longstanding architectural tradition on the East End, and there is a small rectangular brick patio from which you can see the ocean. The house also has a traditional saltbox roof, built more than 200 years ago by the hands of a few strong men who, the town records note, were paid with three gallons of rum.
Inside the house, there is a small reception area, which opens to the main room, which was the original kitchen. It has old plank floors and a brick fireplace with a bake oven and the kind of iron kettles and cooking tools that would have been used in the early years. One side of the room has displays and artifacts, including arrowheads and old carpentry and weaving tools. “The kids really love these displays,” Ms. Ruggles said on a recent visit.
A step into the room to the south will take guests back to the time when the Kennedy family made Second House their summer home. The room, decorated as it might have been in the Victorian era, has blue and white checkerboard flooring made by Kentile Floors, the company that gave the Kennedys their wealth. This room was redecorated in 1990 by a magazine called Victoria, which is defunct.
A tiny front hall with a winding staircase leads to the bedrooms upstairs. The curved railing and stairs are said to have been built by a Sag Harbor ship’s carpenter. A second staircase, on the other side of the house, is closed to the public due to its steep and deeply worn steps. But looking at them brings the history of the house to life.
The bedrooms have been redecorated in keeping with the history of the house and have antique rope beds. The wallpaper and paint are new, but they were chosen to invoke what the rooms might have looked like a hundred years ago. A small nursery, in the southeast corner of the second floor, has a child’s bed and a cradle, and windows through which there is an ocean view.
One of the more surprising rooms in the house is in the northwest corner of the first floor. It is a school room, with seating for 12 and a wood stove. It was the only school in Montauk for a number of years.
It’s clear, even from a quick visit, that Second House is a very special place. “It’s a lovely little thing. It’s charming. It’s historical. It’s a part of Montauk’s early life,” Ms. Ruggles said. Looking at its own guest book, only a few people seem to visit every few days. The parking lot was empty on this visit, and the only people around were Ms. Ruggles and the hedge trimmers. U