Fly into JFK, look toward the setting sun, and you see Manhattan, the city that never sleeps, the Big Apple. Turn the other direction, however, and drive two hours east — past the scenic Southampton Golf Club and Napeague State Park — and you’ll take in a much different vista: a land where time stands still.
By Trey Garrison

Since 1639, Gardiner’s Island and its 3,300 acres have belonged to Lion Gardiner and his descendants. The six-foot scion of this American dynasty bought his domain not from the Crown or some colonizers but from Native Americans. More than 350 years later, his island is valued at $125 million (almost $40,000 per acre). Or at least that’s what it was when it was last formally appraised in 1989. On the island itself, the family manor stands as it has since 1774, nestled among chestnut trees, cherry trees, and willows, overlooking the bay. Behind the manor, a wide commons sprawls out to the edge of a white oak forest, interspersed with orchards and grain fields. Down near the shore, the famous Gardiner’s Island windmill can be found. The sense of legacy is palpable — from the Indian artifacts and the manor house and barns to the carpenter’s shed, the oldest wooden structure still standing in New York, built in 1639.
Not surprisingly, the island has been witness to an enormous sweep of American history; warring Indian tribes, infamous pirates, and British forces during the American Revolution and the War of 1812 all sought refuge there. In 1869, it was a rally point for an American expeditionary force bound for Cuba.
For more than a dozen generations, this Old World estate has remained in the hands of the Gardiner family, beginning with Lion Gardiner in 1639 and continuing to Alexandra Goelet today. Although the island and its properties are not cheap to maintain — property taxes and upkeep reportedly cost nearly $2 million a year — Goelet seems content to continue this tradition.
This indomitable legacy begins with Lion Gardiner. Popular history has it that his ownership was derived from a land grant from King Charles I. This simple, clean, and very formal pedigree is in fact a fiction, one perpetuated by the Gardiners themselves. The reality of how Lion came to own the island is much more interesting.
“Most of what you read about the early days of Gardiner’s Island comes from the Gardiner family themselves, so of course it sounds better and more prestigious to say it was part of a royal grant,” says Richard Barons, executive director of East Hampton Historical Society.
Lion was a decorated military engineer in the English army who served in the Netherlands with great distinction during the war of liberation against Spain. According to Appleton’s Cyclopedia of American Biography, Lion was persuaded by Hugh Peters and other Englishmen to enter the service of a company of lords and gentlemen colonizing an American settlement for the Puritans. In 1635, he arrived in the New World and took command of 300 soldiers and workers, drawing up and executing plans for towns and forts. After Saybrook Fort was completed, the Pequots declared war on their new Connecticut neighbors.
During the two-year war with the Pequot, Lion commanded Saybrook. At the same time, on the eastern half of Long Island, Wyandanch led the Montaukett tribe. According to Barons, Wyandanch watched the war between the English and the Pequot with great interest. Both Lion and Wyandanch were men who could think beyond their own perspectives, Barons says, and this was critical to the relationship that formed between the two. Wyandanch soon recognized the superior firepower of the English. He repudiated his Pequot kin and formed an alliance with the English commander. According to Faren Siminoff’s Crossing the Sound: The Rise of Atlantic American Communities in Seventeenth-Century Eastern Long Island, such a repudiation was fully within the bounds of traditional native culture. Wyandanch made sure to negotiate the terms of the alliance according to Indian standards, and he insisted on a client-patron relationship rather than complete subordination.
In turn, Wyandanch enfolded Lion in traditional Indian forms by offering him land, specifically, the island that now bears his name. The Montauketts called it Manchonake, which loosely translates to “the place where many have died.” The island had been the site of an epidemic. Lion reportedly bought it for a large black dog, some powder and shot, and a few Dutch blankets. Conflicting reports say the purchase price was 10 coats of trading cloth.
“Wyandanch could see that Gardiner had a great deal of empathy for the Native Americans that other [settlers] did not have, and that was critical in this relationship,” Barons says. “Gardiner’s son learned to speak Algonquin. So the first real estate deal on Long Island wasn’t a royal land grant but a purchase between the [English] and the Montaukett.”
In 1639, Lion bought the island for a second time — this time from the Earl of Stirling, who had been granted the property by King Charles I. Later, a manorship was granted that gave Gardiner ownership of the island under English law, Barons says. The holding was originally called the Isle of Wight. Although the Gardiners never declared themselves lords or any such thing, they exercised the privileges of the title. How the island came to be called a manor and then a lordship also had little to do with royal ambitions on Lion Gardiner’s part, Barons says. It had more to do with something each and every landowner can identify with: cutting taxes.
“As the taxes on the property increased, Lion Gardiner finally sought to have the island declared a manor under English law,” Barons says. “You didn’t have to pay as much in taxes on a manor.” Lion, who died in 1663 in East Hampton, was always referred to as the Proprietor of the Isle of Wight as were his descendants until at least the 1790s. He was remembered as a steward of the island, a soldier hero, and a man with great vision.
No descendant ever lived larger than Lion Gardiner, but the centuries that followed have proved eventful. Lion’s youngest daughter, Elizabeth, was born on the island in 1641, the first English child born in New York. Though she died in her teens, she played a key role in colonial witch hunts as the accuser in one of the earliest witch trials, according to Curtiss Gardiner, who wrote a history of the family in 1890. In the 1680s, East Hampton attempted to annex the island into the township. Gardiner heirs convinced the powers that be to affirm the island’s special status, which remained in place until after the American Revolution. The largely symbolic designation “Lordship and Manor of Gardiner’s Island” was bestowed by Governor Dongan in 1686.
In 1699, Captain William Kidd entreated Lion’s grandson, John Gardiner, to allow the privateer to bury a treasure of gold, silver, candlesticks, and gems on the island before he sailed to Boston to answer charges of piracy. For their help, Kidd reportedly gave the Gardiners a piece of gold cloth captured from a Moorish ship off Madagascar, as well as a bag of sugar. Upon his departure, Kidd warned that if the treasure was not there when he returned, he would kill the Gardiners. John Gardiner later cooperated with authorities and turned the treasure over, reportedly keeping a diamond, which he gave his daughter.
During the American Revolution, the Gardiners renounced their loyalty to the Crown and declared their support for the fledgling revolution. Throughout this strife-torn era and then some 40 years later during the War of 1812, the British Navy used the island for supplying and staging. All the while, the manor house, which had been built in 1774, was left untouched.
According to the Encyclopedia of New York State, the family produced a number of important heirs through the years, from local representatives to US senators. Julia Gardiner, born on the island in 1820, became the First Lady of the United States, marrying President John Tyler in 1844.
The great Walt Whitman took note of Gardiner’s Island in the latter part of the 19th century, writing: “Imagination loves to trace (mine does, any how,) the settlement and patriarchal happiness of this fine old English gentleman on his island there all by himself, with his large farm-house, his servants and family, his crops on a great scale, his sheep, horses, and cows. His wife was a Dutch woman–for thus it is written by his own hand in the old family Bible, which the Gardiners yet possess.”
By the 1920s, however, portions of the island were leased for hunting. Debt and taxes mounted, and in 1937, the island was slated to be sold at auction. A Gardiner cousin, Sarah Diodati Gardiner, stepped in at the last minute and bought it, keeping Gardiner’s Island in the family.
Title to the island was hotly disputed between two Gardiner descendants for decades. A regional writer named Mary Cummings summarized as follows: “In one corner was Robert David Lion Gardiner, who invariably referred to himself as ‘the 16th Lord of the Manor.’ An undisputed and indefatigable expert on Gardiner ancestral lore, he could hold forth on his ‘noble’ ancestry for hours at a time and rarely passed up an occasion to do so. In the other corner was … Alexandra Gardiner Creel Goelet … who battled under the green environmentalists’ banner.”
The battle raged in the courts for years. It was finally settled when Robert David Lion Gardiner died in 2004, leaving Goelet as the sole owner of Gardiner’s Island. Survival, it seems, may be the dominant family trait. Robert David Lion Gardiner himself said as much during a rare interview: “We have always married into wealth. We’ve covered all our bets. We were on both sides of the Revolution and both sides of the Civil War. The Gardiner family always came out on top.”