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Hamptons.com
May 29, 2013

Orient Point: George Washington, Benedict Arnold, And The British Fleet In The Hamptons

T.J. Clementeby T.J. Clemente
in Entertainment
Home Entertainment

Sailing the east end waters one can’t help but think about all the history. Most of it precedes the 1900’s. Starting off, Orient Point, which is the most north point of the North Fork (that other Fork for you Hamptons’ newbies) was a landing place for Indians commuting between Connecticut and Long Island.

The Indians that dwelled on that outer-most section of the North Fork were called the Poquatuck. It was with this tribe that deals were made to buy many of the hamlets of the Town of Southold, mostly back in the mid 1600’s. Then Orient was actually called Oysterponds because of the large shellfish ponds that are still there to this day. Five now-famous families received land grants from the British throne. The names King, Terry, Vail, Latham, and Tuthill are still everywhere. Of course they also had to deal with the Poquatucks.

The Town of Marion was founded in 1836, to honor local native General Francis Marion, who fought with notation during the American Revolution. During the American Revolution the British Navy sailed some of the evacuated British troops from Boston to the South Fork mostly in Sag Harbor and East Hampton Village. Sag Harbor was already a busy whaling port by then. Many of the homes that housed British troops still exist in Sag Harbor. During the Revolutionary War the British supply and support vessels were parked right off Orient point.

Fort Tyler is now referred to by sailors as the “ruins.” (Photo: Capt. Dave Brennan)


The British used Orient as a staging area to launch attacks on many Connecticut coastal towns knowing many patriots from Long Island were hiding there. One of the first official battles of the American Revolution pitched a raiding party sent by General George Washington to where the Plum Island lighthouse now stands to intercept British cattle raiding parties; of course the colonial troops were routed and fled via Orient Point.

In fact, after Benedict Arnold escaped the West Point fiasco and a traitor’s hanging, he served as a British general operating out of Oysterponds (Orient). The Village Lane Tavern in Orient, the home of the founding Vail family, served as Benedict Arnold’s headquarters during the revolution.

Because of the notoriety of the Long Island Town of Oyster Bay during the Theodore Roosevelt Presidency, the residents of Oysterponds decided to change the town name to Orient, associating itself with the notoriety of Orient Point. Twenty-six years before the revolution Benjamin Franklin himself on a commission from the British governor of New York, who in the 1750’s was sometimes stationed in Riverhead, laid down stone “Postal Markers” from Riverhead to Orient Point. Many still stand today. There is no doubt Benjamin Franklin marveled at the view from Orient Point.

The first U.S. Federal Government, with George Washington as President was located downtown in New York City in Federal Hall for one year. That year, Thomas Jefferson and James Madison reportedly shared a coach that stopped in Mattituck at the Historic Mattituck Tavern on their way to view Orient Point. There are reports that George Washington himself visited Mattituck and stayed at the inn, back in 1751.

During the war of 1812 the British War Fleet returned to blockade the Long Island Sound and Gardiner’s Bay. However when they tried to come ashore at Sag Harbor, they were repelled on the docks by men led by a local American officer named Captain David P. Vail. However it was a menacing sight to see the mighty British War frigates off the Hampton’s shores as they lobbed cannon shells into Sag Harbor. Although Sag Harbor was shelled there are no reports of Orient being shelled. It may have been the shelling of Sag Harbor that led to the construction of Fort Tyler in 1898 at the western tip of Gardiner’s Island a point separating Gardiner’s Bay from Block Island Sound. The old fort is now referred to by sailors as the “ruins.” Closed after World War I in 1921, the fort became a target for live practice bombing runs during World War II. Live ordinance is reportedly still there, or so a “danger” sign warns.

The Plum Island Lighthouse stands on land purchased by the United States government from Richard Jerome for $90 in 1826. The rough stoned lighthouse was completed in 1827. When I sail around the Plum Gut I love to look at it.

My boat goes in the water this week, hope to see you out on the Gardiner’s Bay!

Purchased in 1826 for a mere $90, Plum Island (shown here) is a focal point for anyone on the ferry or boaters in Plum Gut. (Photo: T.J. Clemente)

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STIRRING THE POT: FLORENCE FABRICANT & PETE WELLS

August 31 @ 11:00 AM - August 31 @ 01:00 PM
158 Main Street East Hampton, NY 11937 United States
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The Power of Poetry: Verse 4 – Go Forth and Multiply

August 31 @ 02:00 PM - August 31 @ 03:30 PM
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LongHouse Talks: Tony Bechara Annotations on Color Schemes

August 31 @ 03:00 PM - August 31 @ 05:00 PM
LongHouse Reserve, 133 Hands Creek Road, East Hampton, NY, 11937
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ANOTR at Surf Lodge

August 31 @ 04:00 PM - August 31 @ 10:00 PM
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Joe Delia & Friends at The Clubhouse

August 31 @ 06:00 PM - August 31 @ 09:00 PM
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Hamptons Hotspot Pink Elephant Is Back

Hamptons Hotspot Pink Elephant Is Back

  • An inside look on the Hampton Classic
#hamptonclasic #horseshow
  • Check out the Top Hamptons Events This Weekend!⁠
⁠
⁠
📍 The Montauk General X Lands’ End⁠
🗓 Thurs, Aug 28 – Sun, Aug 31 | 10am–3pm⁠
📌 Montauk General Store at The Brunch Playhouse, 14 Amagansett Square⁠
🎁 Free limited-edition tote with orders over $100 (while supplies last)⁠
⁠
🐎 50th Annual Hampton Classic Horse Show⁠
🗓 Thurs, Aug 28 – Sun, Aug 31 | 8am–5pm⁠
📌 240 Snake Hollow Rd, Bridgehampton⁠
⁠
🍇 Wölffer Estate Vineyard PPL All-Star 2025⁠
🗓 Sat, Aug 30⁠
📌 Wölffer Estate Vineyard, Sagaponack⁠
🎾 World-class padel at the Hamptons’ most iconic vineyard⁠
⁠
😂 Zarna Garg at WHBPAC⁠
🗓 Sun, Aug 31 | 8pm–9:30pm⁠
📌 76 Main St, Westhampton Beach⁠
⁠
🎶 Joe Delia & Friends at The Clubhouse Hamptons⁠
🗓 Sun, Aug 31 | 6pm⁠
📌 174 Daniels Hole Rd, East Hampton⁠
⁠
🎧 Silent Disco Dance Party in the Garden⁠
🗓 Sun, Aug 31 | 8pm⁠
📌 Guild Hall, East Hampton⁠
⁠
👗 Marfa & Friends Trunk Show⁠
🗓 Thurs, Aug 28 – Sat, Aug 30⁠
📌 Sag Harbor⁠
⁠
🎬 Jaws’ 50th Anniversary Screening at Sunset Theater⁠
🗓 Fri, Aug 29 – Mon, Sept 1⁠
📌 Water Mill⁠
⁠
👠 Hamptons Fashion Week⁠
🗓 Sat, Aug 30 | 2pm⁠
📌 Location TBA⁠
⁠
🎸 Dogpark at The Stephen Talkhouse⁠
🗓 Sat, Aug 30 | 8pm⁠
📌 Amagansett⁠
⁠
🍴 Stirring The Pot: Florence Fabricant & Pete Wells⁠
🗓 Sun, Aug 31 | 11am–1pm⁠
📌 Guild Hall, East Hampton⁠
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🌊 ANOTR at Surf Lodge⁠
🗓 Sun, Aug 31 | 4pm⁠
📌 Montauk⁠
⁠
🎷 Garden Concert ft. Freddy DeBoe⁠
🗓 Sun, Aug 31 | 6pm⁠
📌 Canoe Place Inn, Hampton Bays⁠
⁠
🔗 Link in Bio⁠
⁠
#hamptons #wolffer #padel #landsend #montauk #fashion
  • Earlier this month, Shelter Island’s Rams Head Inn hosted a riveting Gilded Age Finale screening featuring lead actress Cynthia Nixon, award-winning costume designer Kasia Walicka Maimone, and executive producer/director Michael Engler.⁠
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📸:Rob Rich/SocietyAllure.com⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#ramsheadinn #gildedage #shelterisland #cynthianixon #shelterislandny
  • Culinary and lifestyle icon Ina Garten will host an intimate tea and garden tour at her famed East Hampton residence on Wednesday, August 27th from 4:00 – 6:00 p.m. A limited number of guests will be invited to share tea with Ina and walk with her through her celebrated gardens and grounds.⁠
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Known for her signature warmth and effortless approach to cooking and entertaining, Ina has earned a devoted following across generations. With her calm presence, foolproof recipes, and signature phrases like “store-bought is fine,” she takes the pressure off hosting, making room for only joy at the table.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptons #inagarten #community #easthampton
  • The magic of The Soho Sessions returns to the Hamptons this summer, bringing a rare and intimate live performance to Stephen Talkhouse in Amagansett on Monday, August 25, 2025. This one-night-only event features Grammy Award-winning artist Maren Morris (with introduction by the actor Jason Biggs) and the genre-defying powerhouse Yola in a night of music with purpose and soul.⁠
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It’s also a night for change. The event supports Music Will, the largest nonprofit music education program for schools in the U.S., which aims to reach 10 million students annually by 2030. It’s a cause that hits home for Morris: “I loved my choir and theatre classes in high school; they really shaped my theory and love for being creative in every medium,” she recalls. “It also teaches you how to be a team player and work together.”⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#stephentalkhouse #talkhouse #amagansett #marenmorris #yola #concert #hamptons
  • @wagsandwalks @themontaukbeachhouse 

Puppies + Pilates + @montaukila = The Perfect Day

Check out our Events Calendar for more events! (link in bio)

#wagsandwalks #animaladoption #adoptdontshop❤️ #dog #montauk #montaukbeachhouse #montaukila #pilates
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