Double Trifecta: A Challenge to Visit All Six of the Windmill Antilles

The Windmill Antilles cartoon by Dan Rattiner
The Windmill Antilles, Cartoon by Dan Rattiner

I have a friend who says he has visited every continent on the planet. I have another friend who says he has visited every state except North Dakota. Well, okay, you are here in the Hamptons, and you should make it your business to visit all of the Windmill Antilles. They are the six islands that are just offshore of this place: Robin’s Island, Gardiner’s Island, Fisher’s Island, Shelter Island, Plum Island and Block Island.

The Windmill Antilles is called that because almost all of them have a windmill. Visiting all six, which is not easy to do, is considered by locals in these parts to be the “double trifecta” (3 x 2). It’s not easily do-able and only a few have done it, and that’s because two of the islands are private, one is exclusive, one is off-limits and only two invite people to come. Nevertheless, it’s possible to do if you know the right people. Here is a bit about each of the Windmill Antilles, from west to east.

Incidentally, the Windmill Antilles does not include Martha’s Vineyard, Nantucket or Cutty Hunk, which also have windmills on them. Those islands comprise the Shetland Antilles and are in another jurisdiction.


Status: Private
Square Miles: 0.7
Miles Offshore: 3
Population: Mr. Louis Bacon and whoever he invites
Windmills: 0
Lighthouses: 0

How to Get There: Best is by boat from Riverhead or Shinnecock. No airstrip. Call Mr. Bacon for further details. He decides. It’s his island.

Ecology: Low hills, dunes and bay beaches. Indigenous birds and wildlife. Largest number of American Mud Turtles in the state. Undisturbed. Three buildings.

History: No known indigenous peoples. Granted by King George I to William Alexander, Earl of Sterling in 1615, but the Earl never set foot there. In private hands since then, sold or handed down from father to son until the 1970s, when first one and then another real estate man tried to put housing developments on it and failed. Taken over by Suffolk County for a time, but then bought at bankruptcy auction in 1993 by Louis Bacon, who has pledged to keep it undeveloped. Most famous owner was Benjamin Tallmadge, a member of the Culpepper Spy Ring during the American Revolution.

Attractions: The attraction is that there is nothing there.


Status: An Incorporated Township
Square Miles: 27.1
Miles Offshore: About 1
Population: 2,392
Windmills: 1

How to Get There: Fly to small private airstrip. Private boat. Take ferry from Greenport or North Haven.

Ecology: Low hills, woods, pastures and bay beaches, wetlands and marshes. One-third of island is a nature preserve. Ospreys.

History: Manhanset Indians indigenous to this island. Nathanial Sterling, a Barbados sugar merchant from Holland, was the first white settler, in 1652, buying the island from Pogatticut, the Sachem of the Manhanset. Sterling and his brother built historic Sylvester Manor, where, with slaves from the Caribbean, they built a plantation, factory and warehouse to serve their sugar interests in Barbados. Visit the Manor, which is now open to the public, and walk through the slave burial ground.

Attractions: Charming Shelter Island Heights, Crescent Beach, Sylvester Manor


Status: Owned by the Gardiner Family
Square Miles: 5.2
Miles Offshore: About 3
Population: The Gardiner/Goulet family
Windmills: 1

How to Get There: Call the Goulet Family to get permission to come. Private airstrip. Small harbor.

Ecology: Old growth forest, hills, largest colony of Ospreys in New York,

History: Montauketts were the indigenous population. Settled by Lion Gardiner and his wife, family and servants when he was granted this island (then known as the Isle of Wight) by King George I in 1639. Gardiner, a fort builder, was first English settler in New York State. Largest privately owned island in the United States. Most famous person to visit there was the pirate Captain Kidd, who buried treasure there in 1688.

Attractions: The limb of a tree where one of the owners of the island caused a criminal to be hung.


Status: Currently owned by the Federal Government
Square Miles: 3
Miles Offshore: 3
Population: 0
Windmills: 0

How to Get There: Contact the Department for Homeland Security for information. A daily ferry runs from Orient.

Ecology: Grasses, dunes, rocky shores and beaches. Ospreys. Island is off-limits except to those approved by the island facility there, the Plum Island Animal Disease Center.

History: No known indigenous people. Originally spotted by explorer Adrian Block, sailing along around 1614—he noted its existence but didn’t stop. Purchased from Wyandanch, the Montaukett Sachem, in 1639 for fishhooks, a coat and a barrel of biscuits. Privately owned by local families until 1899, when it was purchased by the U.S. Government, which built Fort Terry, a fortress to guard the coast during the Spanish-American war; the fort is now in ruins. Site of the historic and now-unused Plum Island Lighthouse, since replaced by a steel tower. Most famous person to visit is American General David Wooster, who in 1775 led 120 colonial soldiers to the island, who advanced, were fired upon by British Man-o-War ships, retreated and fled.

Attractions: Three hundred employees come from the mainland to work at the off-limits Plum Island Animal Disease Center, founded in 1954 and scheduled to close in 2022. Government intends to auction the island soon and hopes to get $150 million to pay for a new Animal Disease Laboratory they’d like to build in Kansas.


Status: Part of Southold Town
Square Miles: 4.1
Miles Offshore: 11 from Orient Point, 18 from Sag Harbor, 2 miles from the Connecticut Shore
Population: 236
Windmills: 1

How to Get There: Private airstrip, otherwise by boat. Helps if you’ve been invited, as there are no hotels or inns. You need to be a guest of the wealthy owners of the many large mansions, or a guest of the local population that largely services the rich from a small town on the west side of the island.

Ecology: Hilly, lawns, fields, woods, ospreys.

History: Indigenous Indians—Pequots. Deeded to John Winthrop the Younger by the Massachusetts Bay Colony in 1640. He lived there one winter, then went on to become Governor of Connecticut. Island subsequently settled by farmers and fishermen. British troops raided and burned the settlement in 1777 and the residents fled. Brick-making factory there for a while. Wealthy tycoons established summer homes and built the Fisher’s Island Yacht Club in 1890—they’re still there, but it’s pretty hard to get into this place. Well known residents have included violinist Efram Zimbalist and filmmaker Albert Maysles. A small town has developed for locals on the western side of the island, where there is a harbor, a café, two boutiques, a restaurant, post office, school and fire department.

Attractions: The whole island


Status: Incorporated Township
Square Miles: 9.7
Miles Offshore: 15 miles off Montauk
Population: 1,051
Windmills: 1
Lighthouses: 2

How to Get There: Public airport, by ferry from Montauk (summer only), New London and Newport.

Ecology: Rolling hills, wind, stone walls, high cliffs and beaches, shorebirds.

History: Indigenous Indians: Nyantic. An expedition to wipe out that tribe was sent by the Massachusetts colony. Its leader, John Endecott, claimed title to Block Island in 1661. Settlers lived shoulder-to-shoulder with Indians on the island until the last Indians died around 1800. Block Island was occupied by the British navy briefly during the War of 1812. Today the island is occupied by as charming a little New England village as you can imagine.

Attractions: The two lighthouses and Mohegan Bluffs. Dan’s Papers will provide an artfully drawn certificate suitable for framing to any person in the Hamptons or on the North Fork who can prove they have done the “Double Trifecta” before the end of 2016.

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