The North Fork is so very rich with history.
Most of it precedes the 1900s. Orient Point, which is the most north point of the North Fork, 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 back in the mid 1600s.
During those days Orient was actually called Oysterponds because of the large shellfish ponds that are still there to this day. The famous five families that received much of their land grant from the British throne were names such as King, Terry, Vail, Latham and Tuthill. Of course they also had to deal with the Poquatucks.
Nearby Marion was named in 1836 to honor local native General Francis Marion, who fought with notation during the American Revolution.
It was during this era that the British Navy set sail with the evacuated British troops from Boston and settled on the South Fork, mostly in Sag Harbor, which was a busy whaling port by then. Today many of the homes that housed British troops still exist intact in Sag Harbor.
During the occupation, many supply and support vessels were parked right off Orient Point. Therefore from Orient Point for years sat many of the great British war frigates on display. The British used Orient as a staging area to launch attacks on many Connecticut coastal towns where some colonist from Long Island had fled.
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 Orient, or Oysterponds as it was known then.
The Village Lane Tavern in Orient was once the home of the founding Vail family served as Benedict Arnold’s headquarters during the revolution. Because of the notoriety of Oyster Bay during the Theodore Roosevelt presidency did the residents of Oysterponds change the 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 stationed in Riverhead, laid down Postal markers from Riverhead to Orient Point, many that still stand today. There is no doubt he marveled at the view from Orient Point. Probably the same way the many visitors who visit the park annually still do to this day.
After the war, that one year the federal government was located way downtown in New York City, Thomas Jefferson, and James Madison shared a coach that stopped in Mattituck at the historic tavern on their way to Orient Point.
During the war of 1812 the British War Fleet returned and tried to blockade the sound. However, when they tried to come ashore they were repelled on the docks of Sag Harbor by men led by a local American officer named Vail.
It was a menacing sight to see the mighty British War frigates off the Long Island shores. Although Sag Harbor was shelled there are no accurate reports of Orient being shelled. It may have been these events that led to the construction of Fort Tyler at the tip of Gardiner’s Bay and Block Island Sound.
By the way, 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.
The legend is that any house built in the town of Orient since World War II is called a new house.
Concerning the ferries, in 1798 the State of New York passed a law giving a 20-year lease to all steam ferries to be operated in the waters of New York to the Livingston and Fulton families. However, cross sound ferry service did not actually start until the 1930s. Now thousands drive out to Orient Point to whisked by ferry to New London Connecticut, saving hours of driving and perhaps tanks of gas.