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A Capsule History

SECOND HOUSE, built 1797, is the oldest and most historic building still standing on Montauk. Its purchase, in 1968, by the Town of East Hampton and the New York State Historical Trust, to be operated as a museum by the Montauk Historical Society, established the identity of this community as something much more than a developer's dream, or a place to make money from tourism in summertime and to leave for a warmer climate in winter.

Montauk, although very sparsely settled until the 1920's, has a history that goes back to pre-colonial days. It is more varied and exciting, perhaps, than that of any other village in East Hampton Township. It is high time it should become known and appreciated. The opening of Second House to the public as a museum, on June 28, 1969, was a high spot in that history.

Within the memory of the oldest inhabitant, Montauk was East Hampton's and all eastern Long Island's Wild West. A great cattle range and gunner's paradise, with only the three cattlekeepers' houses, the lighthouse, and Life Saving Stations at Hither Plain and Ditch Plain. A few fishermen's shanties were occupied in summertime by men who came over from Long Island's north fork or Connecticut.

In 1879 Arthur W. Benson of Brooklyn bought most of Montauk, but life went on for a while much as it always had done. The Long Island Rail Road extended its line to Montauk in 1895 and in 1899 built the old Montauk Inn which stood where Montauk Manor does now. A small fishing village grew up around Fort Pond Bay. Austin Corbin, then president of the Long Island Rail Road, conceived a project to make Fort Pond Bay a Port of Entry for trans-Atlantic passenger ships, thus shortening the crossing and avoiding overcrowding in New York Harbor. That project was revived in 1900, 1911, 1927, and 1931. In 1933, the railroad inaugurated inexpensive fishing excursions which brought 40,000 sportsmen each year to Montauk. These were discontinued in 1953 when the channel into Lake Montauk was dredged and the fishing boats moved there from Fort Pond Bay.

But few drastic changes had occurred before 1924, when Robert Moses established the State Parks at Hither Hills and Montauk Point, and 1926, when Carl Graham Fisher bought 10,000 acres for what he envisioned as the "Miami Beach of the North."

Montauk owes a great debt to Carl Graham Fisher. He built roads and clubs and houses and brought in new people to appreciate the beauty of the windswept hills and glorious views of ocean and Sound, although he had no idea that any history had ever been made here until he arrived.

Within the past twenty or thirty years, houses have mushroomed all over the Montauk hills. It is no longer just a summer resort. It has gained year-round community status. Suddenly, within the past few years, a strong civic conscience and pride have created organizations for zoning and beautification. Montauk oldtimers and newcomers have also become increasingly aware of their historic heritage.

The Montauk Historical Society was incorporated in January, 1962, organized that November, and on May 18, 1963, elected the late Richard T. Gilmartin as its first president. Clifford Stanley was vice president, Mrs. Samuel Joyce, Jr., and William Cooper, secretary and treasurer. At the official opening date for the museum, in 1969, the officers were: Mrs. Joyce, president; Mrs. Richard T. Gilmartin, vice president; Mrs. Charles Wallace, secretary, and William Burke, treasurer.


Very few people, up to its sale in 1879, had considered the land at Montauk of any value except for pasturing cattle, fishing, gunning, berry-picking, cutting wood or "medder hay." 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. First House burned down in the spring of 1909.

Second House, the first built in 1746, the present one in 1797, remains much as it was 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 is now flourishing 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 or 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.


In 1655, seven years after East Hampton Town was settled, a group of East Hampton men wanted to pasture cattle on Montauk. The Indian chief, Wyandanch, gave them the right of pasturage and an option to buy.

In 1660, Wyandanch's widow and son sold most of the land to the East Hampton men for 100 English pounds, at the rate of ten pounds a year, payable in Indian corn at four shillings a bushel, "or els in good wampum at 6 a penny."

The 1660 deed gave the Indians liberty to "sitt downe againe uppon ye land." Which they did. They lived in Indian Field, north of what is now Deep Hollow Ranch, until after the 1879 sale to Arthur W. Benson, when they were re-settled in East Hampton.

The average reader of East Hampton Town records is somewhat confused as to the actual ownership of Montauk from 1660 to 1879. According to a thesis written by the late William B. Jackson of New Haven, Conn. and Amagansett, titled "The Manorial Common Pasture System at Montauk," the pasturage system there was unique in America.

It was not the whole town, but a group of first settlers, who purchased most of the peninsula from the Indians. They were the "proprietors." From 1660 to 1852, Montauk affairs were, however, managed by the Town Trustees.

They appointed the time for driving on and off the "cattel, horses and sheep." They chose the pound-keepers, cattlekeepers and gin-keepers, and named their compensation. The cattlekeepers' fee included rights of pasturage, a certain amount of firewood they might gather or cut, the use of a house and barn, garden and pightle (old-fashioned word for back yard.)

But "the use of barnyard and pitties adjoining same" must be turned over to any of the Montauk proprietors, when needed for yarding their cattle. Men were named by the Trustees to assist the keepers on the drives; in shifting cattle from one field to another when the grass grew short; and in repairing fences or sheep-shearing.

When, about 1838, dissatisfaction arose with the Town's management, there was legal action. All rights were released by the Town and turned over to the proprietors in 1852.

Down the years, people inherited shares of Montauk, entitling them to a certain amount of pasturage (usually twelve cattle to one share.) Often, these shares were sold. Deeds transferring so many "shares on Montauk" are still preserved. By 1879--after more than two hundred years--Montauk rights were held by a great number of people.

Cattle brands, ear marks for the herds sent to graze at Montauk, used to be registered with the East Hampton Town Clerk. This continued as late as 1914.

When Richard Gilmartin was Town Clerk he was intensely interested in preserving the valuable old records. He found two crumpled, faded sheets torn out of an old account book in the basement of the Town offices. He pressed them flat and studied them, and found them to be a "List for this year 1727 to put Cattle on Montauk," with the names of owners, number of cattle pastured, and what the owners were charged in pounds, shillings and pence for the pasturage. He totaled up the cattle listed, and it came to the amazing number of 3,424 cattle on Montauk in 1727! He said that "as cattle were considered a symbol of wealth in those days, our old timers must have been a pretty rich lot."

Those old account book sheets which Mr. Gilmartin found made no mention of the sheep, which were driven on Montauk by the thousands. In the East Hampton Trustees' Journals, volume 1725-1772, it says that sheep ranged over the hither end of Montauk from the Highlands eastward as far as Fort Pond; and swine also ran west of Fort Pond in 1744. Beyond that was "cornmon pasture," Indian Field, bull and calf pastures, and fatting field.

In 1662 Isaac Hedges was appointed to "keep the dry herd at Montauk." In 1663, twelve East Hampton men were ordered to go to "Meantaquit" to make a yard for cattle and to build a shelter for the keepers. These shelters were described as rude huts built of crotches and boards. John Stratton and Thomas Talmage were assigned to drive and look after the cattle for the first two days and nights. Then they were to be relieved by two other citizens of East Hampton. It sounded like a regular public duty like jury duty, not to be escaped.

John Stratton agreed in 1669 that his son Stephen, evidently a minor, should keep "ye sheep" for the ensuing year.

Ebenezer Jennings was an early shepherd. Nathaniel Talinage (1711-1784) was first to live at Second House, in 1746. Nathan Hand (1747-1811) ancestor of the late eminent judges, Learned and Augustus Noble Hand, lived at Second House after serving in the Revolution. Christopher Hedges was authorized by the Town in 1809 to make a "seller" for his dwelling house at Fort Pond, and to have "a garden pightel and lot adjoining." Uriah Miller lived there during the War of 1812. He was succeeded by Jonathan Miller. Keepers of the cattle anti sheep at the three Montauk houses of old times represented most of East Hampton's early families.

The land between First and Second Houses was sheep pasture. It was the duty of the man at First House to care for the sheep and tend the bars; to see that no sheep or cattle strayed westward. The keeper of Second House must keep the cows out of the sheep pasture and see that the sheep did not stray eastward. The most important place was that of keeper of Third House. He had oversight of all the cattle, including those in Indian and Point Fields, and it was at Third House that the great June roundup was held.

Cattle and sheep went on Montauk the first of May, and came off the first of November. Most were owned in East Hampton village or Amagansett, but some came from a distance. It took at least two days of hard riding for those west of East Hampton to get the cows to Montauk. Animals from out of town were "baited" (fed) on the green at the west end of East Hampton village; the road there is known as Baiting Hollow Road. Sheep were penned in the Sheep Pound, the triangular green in front of East Hampton's Post Office, today. The herd was driven into a pound at Amagansett the first night, while the drivers stayed at local farm houses and continued the journey next day.

Mrs. Elizabeth Cartwright set down in the East Hampton Star, years ago, some of her memories of the 1860's. She told of the general excitement on Cattle Day; "The family was astir long before daylight; East Hampton street was noisy with cattle lowing, men and boys on horseback, one herd after another going slowly by. Hiram Sandford of Sagg had 400 cattle. The farmers would get their dinner at Third House and ride home in the late afternoon. It was a busy time on Montauk the day before, preparing batches of bread, milkpans of pork and beans, dripping pans of roast veal, home-cured ham, pickles, coffee and pie, for sixty or more men."

Mrs. Cartwright also recollected going on in June when the hills were covered with wild strawberries. Parties of young people would gather all they cared to eat, and have grand frolics. They would stop at one or the other of the three houses for midday dinner. In the 1860's Mrs. George Osborn was hostess at First House; Mrs. Samuel Stratton at Second House; Mrs. Patrick Gould at Third House. She told of bluefish caught only a half- hour before it came to the table; of wild goose and duck; of wild strawberry shortcake; blackberry, blueberry, or beachplum pie according to season; and wild grape preserve; all appreciated by young people with appetites sharpened by fresh air.

For nearly three hundred years the twice-a-year Cattle Drive was a feature of Montauk life; from 1660 to the Carl Fisher purchase of 1926. Then, after a break of ten years, Phineas Dickinson hired Indian Field, in back of Third House, for pas- ture and revived the custom. Amateur cowhands made a great day of it, herding some 200 head of cattle. This went on for ten or fifteen years. Today Deep Hollow Ranch still raises cattle and horses.


On April 10, 1655, it was agreed that a good fence should be kept up south of Fort Pond. In 1703, a three-rail fence was built around the fatting field between Great Pond (now Lake Montauk) and Oyster Pond. Many stone walls were built in 1825. Traces of them can still be seen.

On the edge of woodland, mounds were thrown up and lop fences made to keep the cattle out of the woods. For a lop-fence, pliable oaks were cut two-thirds down; the scions growing up from the stump are bent toward those from the next tree. Lopping formed a good strong fence, "horse-high and bull-proof," and an attractive hedgerow, besides costing next to nothing in those far off days when labor was cheap.

Ponds formed part of the cattle boundaries--Fresh Pond, Fort Pond, Oyster and Reed Ponds, Great Pond.

In 1820 a stone wall was built on the narrow beach between Fort Pond and the ocean to prevent the sea coming into the pond. Sometimes a storm would almost cut the eastern end of Montauk off from the mainland.

Swinging gates crossed the old Montauk road near each house, so that travelers and cattle could be watched.


The Fort Pond Bay area, and Second House, have not remained untouched by war.

Before the white settlers came, the Montauk Indians had trouble. Not with other Long Island Indians--Wyandanch of Montauk was also chief of all the Long Island tribes; but with the Narragansetts of Rhode Island.

William Wallace Tooker, an acknowledged authority on Long Island Indians, said in 1895 that Montauk ("Manatacut," or "Meuntacut"--it was variously spelled) meant "the fort country." Before the settlers came, an Indian fort stood on the west side of Nominick Hills, overlooking Napeague Harbor. In 1661, a "new fort" stood on what is still called Fort Hill, overlooking Fort Pond and the bay, in front of Montauk Manor. Its outline was just visible, thirty years ago.

"Massacre Valley," beside Fort Hill, is where Narragansett warriors abducted Chief Wyandanch's daughter on her wedding night, killing her bridegroom and several other Montauks. She was later rescued through Lion Gardiner of Gardiner's Island.

During the Revolution, a company of militia was sent to Montauk to guard the stock. When three British men-of-war and nine transports left Boston with 600 men, bound for Long Island, doubtless to replenish supplies, local authorities were notified. Some 2,000 cattle were taken off Montauk to safety. But over 3,000 sheep remained. Captain John Hulbert of Bridgehampton, with only 69 men, posted a rider to East Hampton for help.

Captain John Dayton of The Creeks offered to go if forty men would volunteer to accompany him. By the time the hundred-odd men had assembled at Shepherd's Neck, the enemy fleet was in Fort Pond Bay, preparing to land.

The colonials marched single file to the top of a hill just west of Fort Pond, then round it to the foot, where they turned their coats wrongside out (the first "turncoats") keeping this up for some time. The British commander, observing through his glasses that there seemed to be more men than sheep, decided to look for an easier landing and sailed away to plunder Fisher's Island instead.

This was in August, 1775. After the disastrous Battle of Long Island on August 27, 1776, all Long Island was within British lines.

During the War of 1812, a British fleet again lay in Gardiner's Bay. Once more the herds and flocks of Montauk were endangered. Uriah Miller, who kept Second House at that time, is the hero of the following story: The English came ashore and killed and carried off cattle. Uriah swore that they should pay him. Alone he would force indemnity. He drove an Indian at the point of a cowhide whip to take him in a canoe out to the English Commodore's ship. Over the vessel's side he clambered with his cowhide. The officer of the deck demanded his business. Uriah replied that he wanted pay for his cattle or he would take it out on somebody, if he had to thrash the whole English fleet. Uriah was taken to the Commodore, Sir Thomas Hardy, but did not, wilt nor abate his demands in the least. He was paid. The Commodore, amused at his audacity, declared him the bravest man in America.

In the summer of 1898, Montauk hills were dotted with tents for 29,500 soldiers returning from Cuba, Porto Rico, and Florida. Many brought back yellow fever and typhoid. Doctors and nurses did heroic work and only 263 men died here. Col. Theodore Roosevelt's : Rough Riders were disbanded at Montauk, and his boom for Governor of New York State began here. After the governorship, he was elected Vice President in 1900, and in 1901 became President, following the assassination of President McKinley. "Ten-gallon" hats have never gone out of style on Montauk, since they were introduced by Col. Roosevelt in 1898.

In World War I, a United States Naval Training Station and a Naval Aviation Base were established on the shore of Fort Pond .... In World War II, the Army and Air Force took over much of the Point, and the Navy took over Fort Pond Bay. The Air Base is deactivated.


A New York visitor in 1892 told of sitting around the great open fireplace at Third House, before a blazing driftwood fire. In the woodbox lay the carved and ornamented post from a ship's cabin. Every year, Samuel Stratton (who was then keeper there) told the guest, about 2,000 loads of wood washed ashore from wrecks, furnishing Montauk people with all the fuel they needed.

Hardly a winter passed, in sailing-ship days, without a wreck at Montauk. The two Montauk Life Saving Stations (afterward to become the United States Coast Guard) established in the 1870's at Hither Plain and Ditch Plain, were manned only in winter. Local farmers and fishermen could tend their crops or flocks or nets in warm weather, and double as life-savers during the cold, stormy months.

In 1876, George A. Osborn, keeper at different times of both First and Second Houses, was also keeper of Hither Plain Station. Samuel T. Stratton of Third House had charge at Ditch Plain.

Courtland Mulford of East Hampton has a ship's figurehead which his grandfather, George A. Osborn, must have picked up on the shore.


For more than two hundred years the three houses for the cattle keepers were the only places on Montauk where a wayfarer might stay. Going on or off Montauk, for people from west of the Hamptons, in a single day was hardly to be undertaken. Men carne for gunning and fishing. The hills and ponds abounded in wild geese, ducks, quail, and other game birds. The ocean teemed with fish.

"First families" of New York, Brooklyn, and Philadelphia were represented, in the 1860's, '70's, and '80's in guest books kept at all three houses. There were the Gardiners of Gardiner's Island; the Bownes from Flushing; the de Forests, de Rhams, Van Rensselaers, Pierreponts, Bensons, Morgans, Remsens, Agnews, Hoyts, Betts, Gallatins, Jefferys, Floyd-Joneses, Wagstaffs, and Nicolls, bringing maids and coachmen and from two to four horses per party. Some arrived by yacht.

Courtland Mulford has his grandmother's litfie leather-covered guest book kept at Second House (or First House, the George A. Osborns lived in both, and it doesn't say which) from Oct. 19, 1863 to Sept. 5, 1871. The sportsmen wrote down whatever they shot, and where. Mrs. Osborn's cooking was praised by one and all. Most entries were ecstatic. Just one disgruntled visitor wrote, on July 25, 1869: "Ticks! Ticks! Ticks!"

Two Montauk wrecks were described in the book. One was of the schooner Mary Milness of Boston, which went ashore in September, 1869, a total loss, with two men drowned. The survivors were cared for by the hospitable Osborns.

The Osborns were still at Second House in 1879, when Arthur W. Benson built on a wing, so that Mrs. Osborn could accommodate more boarders.

George Strong Conklin kept Second House from 1887 to November, 1899; the Conklin family occupied all three houses, at different times and in different generations.

The last keeper of Second House was Ulysses Tillinghast Payne. He had been at First House from the spring of 1886 to the fall of 1899; the Payne children- Betsey (Mrs. Charles Taylor), Edward, Elias, and Mildred (now Mrs. Benjamin Wells of Sag Harbor) were all born there.

Mrs. Payne, born Nellie Dayton of Hardscrabble Farm, East Hampton, was a forceful, jolly, motherly woman; everyone liked her. She was really responsible for the first school on Montauk-- the little red schoolhouse at Hither Plain. There had been eight school districts in the town since 1813- but no school had actually been established at either Gardiner's Island or Montauk. Teachers were employed in both places, but they stayed in private houses and taught only a handful of pupils.

Betsey Payne Taylor tells how her mother started a school at First House for her three oldest children and a few neighbors. Sarah Filer of East Hampton, Martha Osborn of Wainscott, and Clara Young of Sag Harbor were among the teachers.

Then at Second House, school was held in the north end wing off the kitchen, with about a dozen pupils from all over Montauk. Emerson Taber, who attended that school for two years before the one was built at Hither Plain, remembers the old-fashioned desks for two with seats attached, and the wood stove in the corner. Teachers came and went, Mr. Taber says; most of them were men. He remembers one especially, Perry Clark.

Each of the three houses had a four-rail and post fence around the door yard and house. "Father had teams and wagons to carry people all over Montauk," Mrs. Taylor says. "He worked for the Montauk Association that built summer cottages near Ditch Plain in the late 1880's, until 1895 when the first train came in at Fort Pond Bay. Before that, he went every day except Sunday to Amagansett with a team, three-seated "carryall" with a fringe on top, for people, food, express and mail--an all day trip. While the railroad was building, he worked with horses and wagons, and Mother boarded the surveyors and officials. That was a big time for Montauk, with the train really coming. I was the first girl or woman to ride the new track from Napeague to Montauk station .... "

Mrs. Taylor continues: "Mother helped Miss Mary Benson and the Rev. Oscar F. R. Treder of St. Luke's in East Hampton, to get the first Montauk church started in a small building near the railroad station on the north side of the road going up to the old Inn that burned down in 1926.

"Three of us were married at Second House; Edward, Elias, and myself. The Kennedys who bought the house in 1910, had boarded with us in summer for several years. After the house was sold, my parents built themselves a small cottage on Fort Pond near the Bay, and Mildred was married there."

Ulysses and Nellie Payne lived in that cottage for the rest of their lives.


After the death of Mr. and Mrs. David Kennedy, their children David and Carolyn (now Mrs. James Tyson) had long since been summering elsewhere. The house stood unoccupied. It will take time to restore the grounds and to bring back the warmth and welcome that greeted the visitor indoors, in former days. But that work is well begun by willing hands.

The old post-and-rail fence needed repairs. Honeysuckle was smothering the front porch where the keeper's family and the boarders used to rock. The ancient "Osborn pump" over the well had to be refurbished. The pretty little door yard rose garden needed attention.

An authentic antique specimen of what Colonial Williamsburg in Virginia delicately calls a "necessary" was found over in Wainscott, and installed within a privet hedge enclosure near the back door.

Changes have been made, of course, by the last owners, to turn the old farmhouse into a comfortable summer house; and as in all old houses, additions had been built from time to time. But basic features dating back to the 18th century remain.

The curved staircase leading out of the tiny square front hall is unusual. It is said to have been built by a Sag Harbor ship's carpenter. The back stair leading to the living room--once the kitchen, center of family life, shows far more use and age. its narrow, very steep steps are hollowed by constant use. The great fireplace has a bake-oven, and primitive cooking utensils.

Upstairs are five bedrooms equipped with heirloom beds. Another bedroom downstairs, off the kitchen, is gradually being restored to its use in the 1890's, when it was a schoolroom for Montauk's handful of children.

Second House has an attic where the hand-hewn frame, raised with the aid of three gallons of rum in 1797, looks solid enough to last at least another century or two.

Copyright © 1969 Jeannette Edwards Rattray. All Rights Reserved.

© L.I.B.B.A.