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Hamptons.com
September 14, 2020

Sixty-Something: Gardiner’s Island – The Mysterious Private Island Of East Hampton

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T.J. Clementeby T.J. Clemente
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I have spent the last 17 years infatuated with all things Gardiner’s Island. I see it every time I sail in Gardiner’s Bay, which is quite often. It is the most unknown part of East Hampton Town. There are lores, mysteries and history all about the island that is 6 miles long, 3 miles wide that has 27 miles of coastline and is owned by one person, Alexandra Creel Goelet. She was awarded sole ownership after the death of Robert David Lion Gardiner.

When I sail close to its shores, I conjure up all sorts of thoughts. Having covered many things Hamptons for the last 17 years – for both printed papers and websites, I have written about this island perhaps 100 times. I believe my first assignment about Gardiner’s Island was back in 2004, when I wrote a very boring article about Ms. Goelet’s offer to place a conservation easement on the island in exchange for a promise from the Town of East Hampton not to rezone the land, change its assessment or attempt to acquire it by condemnation; and how then Ms. Goelet and East Hampton Town agreed upon the easement through 2025. Back then, 2025 seemed a million years away, but that agreement is coming up for renegotiation and now the island is reportedly worth well over $100,000,000.

When I sail along the northwest part of Gardiner’s Island, either towards Montauk, the Gull Island Lighthouse or the Block Island Sound, like everyone else I stare at the landmark now called the ruins, the ruins of Fort Tyler! There is debate whether the Fort, built in 1904, was named for Daniel Tyler or President John Tyler. Army documents state $500,000 was appropriated at the start of the Spanish-American War to secure “East Coast” defenses by building a fort there. Over time, the shifting sands of the point it’s located on caused problems for the fort and it was abandoned in the late 1920s. Then, in 1938, the island (the fort is an island at high tide) was declared a National Bird Refuge by President Franklin D. Roosevelt and transferred to the Agriculture Department. However, during World War II, Fort Tyler was used for target practice and was reduced to its present state where it is popularly called “The Ruins.” I have taken hundreds of photos because I just can’t help but look at it over and over again – as I make sure I sail by as close as is safe, because they say there are very dangerous unspent live munitions left over around it. Fascinating to know between 1854 and 1894 there was a Gardiner’s Island Lighthouse there!

Gardiner’s Island. (Photo: TJ Clemente)


Then there is the pure history of the island. How the founder, in 1639, was awarded the island by the Native Americans after negotiating a peace between warring Native Americans. How the “British Crown” legitimized his ownership. Perhaps the most famous is of the pirate Captain Kidd and of him burying his treasure on the island in June 1699, having stopped there while sailing to Boston to answer to charges of illegal piracy against the crown.

When I sail to Louse Point, I always see the big white windmill, the farmhouse, and the main house, of course not the original historic home, that was lost in a fire. What I remember most when I look at the island is not theories of folks walking and driving trucks across a frozen Gardiner’s Bay from Springs Fireplace to the island, nor the fact that both Prince Phillip and Prince Charles paid a visit to tour the Bostwick’s Oak Forest on the island, then called the undisturbed oak forest in the world. What I remember is the very first year I owned a sailboat, back in 2003 on the Thursday before Labor Day, I tried to sail/motor around the whole island starting by going northwest. I thought I had done it successfully as I was all but through the Cartwright Island Shoals, until boom the boat was stuck and listing badly in less than a foot-deep of water. I was stranded there for eight hours and was rescued by not one, but two sea tow boats. I have never attempted that route ever since. I once swam to the shore on the beach of Bostwick Bay. I was 61-years-old, but felt like Tom Sawyer or Huck Finn for the only ten minutes I stood on Gardiner’s Island. Someday I am going to figure out how to get a tour.

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  • Tucked inside the Sole East hotel, this hidden gem offers one of Montauk’s most relaxing dining experiences. The setting alone is worth the trip: the restaurant sits right beside a giant swimming pool ringed with loungers, where you can grab a drink, stretch out on the lawn, and settle into true Montauk fashion for the afternoon. It’s the kind of scene that makes you forget you have anywhere else to be.

But as cool as the setting is, the food is the real standout. The seafood is the star of the menu, featuring fresh fish sourced directly from the boats at Gosman’s, so what lands on your plate practically came straight off the dock. You can taste the difference immediately. Paired with seasonal vegetables and thoughtfully prepared dishes, every plate feels light, flavorful, and perfect for summer.

The drink menu deserves its own mention. Sole East’s mezcal negroni is one of the best drinks I’ve tasted. It’s smoky, balanced, and a standout on an already impressive drink menu.

From the welcoming, owner-operated atmosphere to the laid-back setting and exceptional food, Sole East is a spot we’ll gladly return to. It’s everything we love about dining in Montauk.
@soleeastmontauk #montauk #soleeast
  • Top Hamptons Events This Weekend✨⁠
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🎤 Ms. Lauryn Hill Live at The Clubhouse⁠
📅 Saturday | 7–9 PM⁠
📍 Clubhouse Hamptons, East Hampton⁠
GRAMMY Award winner Ms. Lauryn Hill performs a special acoustic concert featuring her iconic hits.⁠
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🎨 Guild Hall Clothesline Art Sale⁠
📅 Saturday | 9 AM–2 PM⁠
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Shop original works from local artists with pieces ranging from $75 to $3,500.⁠
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🧘 Elements Barre Class & WATSKIN Trunk Show⁠
📅 Saturday | 9:30 AM⁠
📍 Sag Harbor⁠
Start your morning with a barre class followed by an exclusive WATSKIN trunk show.⁠
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🌸 Marni Blooms Pop-Up⁠
📅 Friday–Sunday | 11 AM–7 PM⁠
📍 il Buco, Amagansett⁠
Browse limited-edition handcrafted fabric flowers made in Italy from archival Marni prints.⁠
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🎭 Shakespeare at the Manor: Twelfth Night⁠
📅 Saturday | 6–8 PM⁠
📍 Shelter Island⁠
Enjoy Shakespeare under the stars at historic Sylvester Manor. Bring a chair or blanket!⁠
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✨ The Watermill Center Summer Festival⁠
📅 Friday & Saturday | 6 PM⁠
📍 Water Mill⁠
Experience “LIMITLESS TIME,” an immersive celebration of Robert Wilson featuring performances, dinner, and more.⁠
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Celebrate the Evelyn Alexander Wildlife Rescue Center’s 26th anniversary.⁠
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Their Helix model doesn’t require a pilot’s license to fly over eligible non-congested areas. According to Pivotal, most people can learn to fly it with just 3-4 days of training.

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  • Looking to shop local in Montauk? Visit the Montauk Farmers Market on the Montauk Village Green every Thursday from 9am - 2pm and explore fresh produce, flowers, baked treats, and more from 40+ local vendors.

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