Southold or Southampton? Which Town Is the First Settlement? A Surprise Answer!

Lion Gardiner fighting the Pequot Indians, 1637
Lion Gardiner fighting the Pequot Indians, 1637, Credit: East Hampton Historical Society, Courtesy Christie's Auction House

At the entrance to Southampton Village, you encounter a sign that reads “Welcome to the First English Settlement in the State of New York, Founded 1640.” The trouble is that when you drive out on the North Fork to the entrance to Southold, another sign says the same thing.

Which was really first? I looked into it. The answer is a surprise.

Southampton’s claim is based on the day a 40-foot sloop bearing 40 Christian families dropped anchor at a slender beach in what is now Noyac Bay in Southampton. The date is uncertain, but the month and year are not. It was in June 1640.

According to legend, a woman, the first to come ashore from the ship, stated, “For conscience sake we are on dry land once more.” It was supposed to have been a few days’ sail. It turned out to be much longer than that. Early in that month, they had departed from Lynn, Massachusetts with a patent from the King of England to create a new settlement somewhere on Long Island. They had made a landing near Oyster Bay, only to find that Dutch settlers were already there and were not happy to see the English.

The settlers left, went to New Haven, Connecticut, where they got a new patent for land farther east, and a few days later found their spot at Noyac Bay. Here they were met by friendly Shinnecock Indians who ushered them to a place several miles down a path, to a spot that appeared quite pleasant. They built their first homes. They built a meetinghouse. Records begin in 1640. This pleasant spot is today called Old Town, which is near to Southampton Hospital.

The Southold claim is earlier. But it is a bit sketchier. That is because the early records of the Village of Southold were burned in a fire and had to be re-created in later years. There are, however, land sale deeds and other documents, originals, dating from 1639.

A New Haven man named James Farrett sells land in Southold to a Matthew Sinderland on June 18, 1639. Sinderland is a seaman from Boston, and an assumption is made by present-day historians that he likely sailed down to his property by September. In any case, he is paying rent on the land on September 4, 1639. A bit confusing—why pay rent on land you own? And he is mentioned as being physically here and farming in September in the re-created Southold Town records.

The following year, the man who is considered the founder of the Town of Southold, the Reverend John Youngs, gets permission from the Colony of New Haven to form a new colony to be called Southold, and he leaves New Haven in a small ship with his extended family and friends that year— most say October—to make his first settlement on the shores of Hashamomuck Pond, an inlet from what we call Peconic Bay today, about halfway between the current-day villages of Southold and Greenport. Farmer Sinderland’s first neighbor there is Richard Jackson, who gets his land in August 1640.

It’s in 1653 that John Youngs gathers together his friends and neighbors to re-create the early settlement records. The fire, by the way, took place in New Haven. Southold— originally called Yennecott—was, before Youngs charter, just a colony of the New Haven Colony, not an independent place at all. With Youngs’ charter, it becomes Southold.

From all this information, one would say that Southold wins the right to say their settlement was first. But, as it turns out, they were not the first settlers. And neither were the settlers in Southampton.

Down the road from Southampton is East Hampton Town, which declares itself settled in 1648, well out of the running to be able to call itself the first settlement. But there is a settlement on that property that predates 1648, and even predates both Southampton’s claim in 1640 and Southold’s claims in 1639. It predates the Southold 1639 claim by about 45 days. And it is quite real.

Lion Gardiner, an Englishman, was born in England in 1599. As a young man, he was persecuted for his religious beliefs—which did not coincide with those of the Church of England. As a result, he traveled to Holland, where he went into the service of the Prince of Orange and became a military engineer, a builder of forts.

There, in 1635, he was offered a lucrative job by the settlers in New England, to build for them a fort at the mouth of the Connecticut River. His contract would be for four years, and the pay would be 100 pounds a year. At that time, the settlers were being harassed by a very aggressive tribe of Indians, the Pequots, who were also harassing other tribes in the area—the Wampanoags in the north, the Naragansets and Mohegans in the east and west, and even the Montaukett tribe on eastern Long Island. It was not about property rights. It was about hunting rights, specifically fur trading rights—and the other tribes either had to stay away from the Pequot claims or pay tribute, in wampum. All were paying wampum, a kind of shell found on ocean beaches.

Gardiner, sensing adventure, accepted the offer, and before he left aboard a small 25-ton ship called the Batchelor, he married a Dutch girl named Mary. So she went, too. Gardiner was met in Boston and escorted with 30 soldiers and 40 workmen down to Old Saybrook, where land was cleared for a new fort they wanted Gardiner to build. The settlers had also already built a fenced-in house and vegetable garden for them. There were also several servants for them, armed. This was not a safe place.

Nearly 200 years later, a 45-page manuscript of a book was found in the possession of a former governor of Connecticut, written by Lion Gardiner in longhand when he, Lion, was 60 years old and living in East Hampton! The book is entitled Relation of the Pequot Warres, and it is an account of his time building that fort and his subsequent settlement with his family and servants on what he called “The Isle of Wight,” but in later years became known as Gardiners Island—all part of East Hampton Town today.

The first half of the book is a series of bloody battles—the victimized other Indian tribes and white settlers with their guns against the vicious Pequots. It includes the killing of soldiers and Indians in various skirmishes—Gardiner is wounded in the thigh in one of them—and in the end the virtual destruction of the Pequot tribe, with the burning of their villages and the presentation of the head of Sassacus, the Chief of the Pequots, to the English settlers in Boston, brought to them by the Mohegans and some of the other Indians glad to be rid of him.

The battle lasted nearly two years, and at various times Gardiner’s wife and young son were in danger, too, but he’d gotten through it. He writes at the end of the book about why he decided to leave Connecticut and look for peace and quiet somewhere else.

“And although there has been much blood shed here in these parts among us, God and we know it came not by us, but if all must drink of this cup that is threatened then shortly the king of Sheshack shall drink last and tremble and fall when our pain will be past. Oh yes, I fear I shall be in the country again, that in there but twelve years true repairing cities and towns, made strong forts and prepared all things needful against a time of war, like Solomon, I think the soil has almost infected me but what they or our enemies will do hereafter I know not. I hope I shall not live so long here or for it for I am old and out of date else I might be in fear to see and hear what I think before long will come upon us…”

The Pequot War ended about the time that Gardiner’s contract was up. His bosses in Boston found the fort in disrepair—parts burned by the Indians from the war—blamed its disrepair on Gardiner, and would not renew his contract “nor shall we send you a single shilling more.”

Meanwhile, with the Pequots gone, Chief Wyandanch of the Montauks, the great Sachem of all of Long Island, came over to Saybrook to visit and discuss matters with Gardiner. “Were the English mad at all the Indians?” Wyandanch asked. “No,” Gardiner said.

Wyandanch pledged himself to the English, and after the two men declared themselves brothers and feasted and exchanged gifts, he offered Gardiner a place of his choosing on Long Island. With Indian guides, Gardiner came across the Sound in the early spring of 1639 (probably April) and looked over various islands, finally choosing one. He then went back to Saybrook and returned with his wife and two-year-old son. He paid Wyandanch for the land with gifts and cash. Prior to arriving, he’d obtained a grant from the King to set up his own settlement—separate from Connecticut or New Haven colony. So Gardiner was the Governor of Gardiners Island. He could make and enforce laws there.

It was from Gardiners Island that farmers and settlers crossed over to what is now East Hampton in 1648, joining with other settlers from Southampton and Bridgehampton.

Gardiners Island was settled in April of 1639. Two months before Southold and 14 months before Southampton. The first English settlement in the State of New York.

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