Log In   ·   Become A Member

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

T.J. Clemente

  |   1 Comment · Print Article

Orient Lighthouse, also called the "Coffee Pot", with Orient Point in the background was a landing place for Indians commuting between Connecticut and Long Island. (Photo: T.J. Clemente)

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)

Related Articles:

Guest (Sue Morin) from USA says::
Sag Harbor: Captain David P. (Porter) Vail was born in 1817. He was a "Captain" on Whalers. He was Master of the ship Sabina on whaling voyages, and sailed the Henry Lee around the horn abt. 1849 to deliver Argonauts to SF. His father, Abraham Vail, of Sag Harbor served in the War of 1812, as did his maternal grandfather, Capt. David Hand. It was Capt. David P. Vail who retained some of their relicts and passed on the history associated with them.
Aug 16, 2013 12:55 pm


Submit Your Comment

Please note, you are not currently logged in. Your comment will be submitted as a guest.
To submit your comment as a member, please click here.
Your Name:
* Comments will be reviewed and posted in a timely fashion
* All fields are required
What color is the sky?
(For spam prevention, thanks)
Gary R. DePersia, Corcoran Real Estate
With over $2 billion in transactions on the East End and since 1995, Gary DePersia is consistently ranked among the top producers in the Hamptons. A year-on-year member of The Corcoran Group President’s Council, he has qualified as a national list maker since 2007. In 2008 he was Corcoran's top broker on the East End by sales volume and rental units; and ranked as the nation’s 4th top broker. In the 2017 REAL Trends & The Wall Street Journal list of America’s top real estate professionals, he was designated #26 nationally, #4 in the Hamptons and #3 at Corcoran overall by volume with nearly $200 million of transactions for the past year. His office operates with four licensed assistants allowing him to build a business stretching from Southampton to Montauk and Sagaponack to Shelter Island. gdp@corcoran.com

East End Tick Control
The East End's only New York State licensed dedicated tick and mosquito control specialists!

Advertise on Hamptons.com - Have your business be seen by over 2 million viewers including NEW searches
Hamptons.com- Our exclusive online magazine has 2.6 million Page Views YTD for 2015. Contact us to join our elite group of clients that benefit from having a presence on the Hamptons award winning publication www.Hamptons.com

Hamptons Carpet One Floor & Home
We pay less,and so do you.With over 1,000 stores in our buying group, we can get the lowest prices from the best flooring manufacturers — and pass the savings on to you.Visit our other locations: Hamptons Carpet One Floor & Home, 675 North Sea Road,Southampton, NY 11968

Southampton Masonry-Visiting the Southampton or the Wainscott locations is an exciting experience.
Southampton Masonry has been serving Long Island's masonry and tile needs since 1975. Delivering quality products from Manhattan to Montauk for over three decades. The company's continued success is due primarily to their number one priority: customer satisfaction, with a promise of prompt and courteous service from the professional, knowledgeable staff. Southampton Masonry has the largest inventory on the east end. As direct importers they can offer a large variety of the finest quality products at the most competitive pricing for both your interior and exterior projects.

RJD Gallery specializes in contemporary art with a focus on Magical, Figurative Realism, Narrative Portraiture and Urban Landscape.
We exhibit representational artists from around the world, who produce fine art of exceptional quality that challenge collectors to contemplate concepts about the artist, themselves, and our human experience. Utilizing timeless techniques in creating their drawings, paintings and sculptures, our artists have developed unique, signature styles that present a current vision of our world.

CP Complete- Landscape Design & Construction
Paul Guillo And Chris Hall Two Of The Most Respected Names In The Community Together, they are partners in CP Complete. They bring their years of experience and integrity to creating and renovating luxury backyards.

CP Complete- Landscape Design & Construction
Paul Guillo And Chris Hall Two Of The Most Respected Names In The Community Together, they are partners in CP Complete. They bring their years of experience and integrity to creating and renovating luxury backyards.