The Culper Spy Ring:
How a Group of Long Island Patriots Helped
George Washington Win the Revolution
BENJAMIN TALLMADGE, Organizer and leader of the Revolutionary War Setauket Spies, was born in Setauket on February 25, 1754. He was the son of the minister of the Setauket Presbyterian Church. The home where he was born is still standing in Setauket at the end of Runs Road. Tallmadge grew up in Setauket, attended school here with his close friend Abraham Woodhull and like many residents of Suffolk County he grew to have a healthy distrust for British authorities in New York. Tallmadge, a classmate of Nathan Hale, graduated from Yale in 1773 and, like Hale, taught school for a time in Connecticut.
When the Revolution began, he enlisted in the Continental Army and was soon awarded the rank of Major. Shortly thereafter General Washington appointed him head of his secret service and tasked Tallmadge with establishing an espionage network against the British in New York City. To conduct this vital undercover operation on Long Island, Tallmadge choose his boyhood friend Abraham Woodhull. They also chose other friends and neighbors from Setauket; men and women who could be trusted and who would prove to be so discreet in all their contacts that some of their identites would not be discovered until the 20th century.
Major Tallmadge, referred to by the code name John Bolton, not only led Washington's secret service, but was also in most of the battles involving the Continental Army in the northern states. Among his many exploits was the capture of Fort St. George at Mastic in November 1780.
After the war was over he retired from the Army with the rank of colonel. In 1784 he married Mary, eldest daughter of General William Floyd of Mastic - Long Island's signer of the Declaration of Independence. Tallmadge lived in Litchfield, Connecticut and represented that state in congress for 16 years. He died at Litchfield in 1835 at the age of 81.
ABRAHAM WOODHULL, a direct descendant of Richard Woodhull, one of the most outstanding of Setauket's original settlers, was born on his family's farm in Setauket, overlooking Little Bay, in 1750. He was a farmer by occupation. Probably because of his elder brother Richard's death at the early age of 32, Abraham inherited the family home [circa 1690] and farm. The land had been in the family since Richard Woodhull, immigrant, came to Setauket, sometime between 1655 and 1657.
From the beginning of the Setauket Spies in 1777-78, Woodhull was in charge of day-to-day operations. His code name was Samuel Culper and the spy operation came to be known as the Culper Ring. Woodhull was referred to as Samuel Culper Senior after he recruited Robert Townsend, who became known as Culper Junior. Not only did Woodhull direct field activities, but he also risked his life countless times by personally collecting information in New York and on western Long Island.
Woodhull was responsible for evaluating the reports received from all sources, determining what was to go forward to Washington's headquarters and seeing that the dispatches were carried across the Sound by Caleb Brewster. Woodhull's health was not good and he lived in constant fear of discovery.
After the Revolution, he became the first Judge of Suffolk County. He died January 23, 1826 and his grave in the Setauket Presbyterian Church graveyard was marked by the Mayflower Chapter of the Daughters of the Revolution in 1936. Bricks from the foundation of the Woodhull homestead, which was destroyed by fire in 1931, were used in the memorial.
CALEB BREWSTER was perhaps the most bold and daring of the spies. He was the only one of the group that the British had definitely identified as a spy. When the Revolutionary War broke out, he immediately enlisted in the local militia.
After the Battle of Long Island he joined the Continental Army with the rank of a lieutenant of artillery. He returned to Setauket in August of 1777 as part of the attacking force from Connecticut that fought in the "Battle of Setauket." In November 1780 he was one of the officers under Major Benjamin Tallmadge who captured Fort St. George at Mastic. They returned to Connecticut with the entire complement of the fort captured.
In spite of his service designation, his task throughout the war was to command a fleet of whale boats operating from the Connecticut shore against British and Tory shipping on Long Island Sound [known as the "Devil's Belt"]. This, together with his knowledge of the Long Island shoreline, and his boyhood association with Benjamin Tallmadge, made him an ideal choice to carry intelligence back and forth across the Sound.
Brewster made numerous trips with his Whaleboat Navy; into Long Island Sound to attack British shipping; and across to Setauket to bring messages back for Major Benjamin Tallmadge to deliver to General Washington.
The known spies also included a local woman who was a strong and ardent patriot. ANNA SMITH STRONG, the great grand-daughter of Colonel William [Tangier] Smith devised, according to family folklore, a wash line signal system to identify for Abraham Woodhull the whereabouts of Caleb Brewster's Whaleboat, so that Woodhull could find him and pass along the messages meant for General Washington.
To avoid detection by the British it was necessary for Brewster to hide his boat in six different places, each identified by a number. "Nancy" Strong, as she was known by friends and neighbors, hung her laundry from the line in a code formation to direct Woodhull to the correct location. A black petticoat was the signal that Brewster was nearby, and the number of handkerchiefs scattered among the other garments on the line showed the meeting place. Using the most ordinary of personal items and improvising on the most ordinary of personal tasks, "Nancy" made an extraordinary contribution to the cause of freedom.
Anna Strong was alone on Strong's Neck throughout most of the war. Her husband, Selah Strong, was confined on the British prison ship "Jersey" in 1778 for "Surreptitious correspondence with the enemy." She got permission to bring him food, which evidently saved his life and she obtained his release by appealing to her Tory relatives. He was still in danger and spent the rest of the war in Connecticut, taking their children with him.
While British officers luxuriated in the Manor House [no longer standing - a 19th century Manor replaced it], "Nancy" lived in a small cottage across the Bay from Woodhull's farm, staying there to also protect her family's rights to the estate.
After the war Anna & Selah were reunited and Selah led Washington's carriage and party to the Roe Tavern in April of 1790 when the then President Washington made his tour of Long Island. Nancy died in 1812 and Selah in 1815. They are buried in the Smith-Strong family graveyard along Cemetery Road on Strong's Neck.
The member of the Setauket Spies most visible to the British and Tories in this area was AUSTIN ROE. Roe ran a tavern in East Setauket where food and drink were served and where travelers could stay overnight on their way to or from the south or east end of Long Island. The original location of the tavern [it was moved in 1936] was along what is now Route 25A, just west of the south end of Bayview Avenue. The site is marked by a State road sign which details a few of the most important facts about Austin Roe and the tavern.
Captain Austin Roe used his position as a tavern owner to justify his trips to New York City [Manhattan]. While in New York Roe gathered the supplies he needed for the tavern as well as the intelligence that had to be relayed to General Washington.
The spy network in New York coordinated their efforts through ROBERT TOWNSEND [code name Samuel Culper Junior]. We will probably never know all the spies who contributed information on British movements, but we do know that Townsend was the principal contact in New York for most of the period between 1778 and 1781. During portions of that time Abraham Woodhull [Samuel Culper Senior] took over from Townsend, as he had done before recruiting Townsend.
The Culper Spies organized a route for the secret messages from New York City to Setauket and across the Sound to Connecticut and on to Westchester County. This spy network supplied General Washington with vital information concerning British troop movements, fortifications, and intentions in New York and the surrounding area during the perilous war years from 1778 - 1783.
The sensational intelligence transmitted by the spies led to the capture of Major Andre [he was hung as a spy on orders of General Washington] and the discovery of Benedict Arnold's plot to turn over West Point to the British. In another instance the spy network supplied Washington with information which enabled him to prevent the British from capturing Newport, Rhode Island, and destroying the French fleet.
Austin Roe, born in 1748, was 29 years old when he first agreed to be a part of the Culper Spies. He made the 110-mile round trip to New York City to pick up messages at least once a week. The road was heavily traveled by British & Tory troops and by highwaymen. Captain Roe would receive information [usually directly from Culper Junior] secreted in a bundle of notepaper, written in invisible ink. He would then ride back to Setauket and pass the information to Woodhull. Woodhull would meet Caleb Brewster and the information would go from Brewster to Tallmadge and then to General Washington. Captain Austin Roe made numerous trips to New York and was never discovered. He moved to Patchogue in 1798 where he founded Roe's Hotel. He died there in 1830 at the age of 81.
The present location of the Roe Tavern, where on April 22, 1790, President George Washington enjoyed the hospitality of Austin Roe and spent the night, is off Old Post Road. The house is private and not open to the public. To travel from the state marker to the house continue east on Route 25A and turn right on Old Coach Road [next road to the right]. Follow about three-tenths of a mile to the intersection of Old Post Road. Turn right and go to the top of the hill. The tavern can be seen from the road at the top of the hill on the right. A new road has been cut, leading to new homes constructed on the property surrounding the tavern. The road leads to the left of the tavern which can be seen from any point on the road.
President Washington's room is believed to be the one with the two windows on the left side of the center section of the house. The window over the main entrance is the upstairs hallway leading to the bedroom the president occupied. The one-story section to the right, with the tall peak dormer, is the original 1703 home built by the first Selah Strong. It was sold to the Woodhulls, and they sold it to Austin Roe who converted the home into a tavern.
Beverly Tyler, Historian for the Three Village Historical Society
The Three Village Historical Society