Tri-Spy Tours – The True Story of the Culper Spy Ring

For over 150 years the story of the Culper Spy Ring, also known as the Setauket Spy Ring, remained a well-kept secret. In the late 1930’s a historian by the name of Morton Pennypacker stumbled upon the Spy Ring story during his research, and he wrote a book about it entitled George Washington’s Spies on Long Island and in New York published in 1939. 

The spy ring was a group of loyal Patriots who worked with General George Washington in obtaining information about the British, who were known as Redcoats. The Redcoats had set up camp in Strong’s Neck and Setauket, as well as in various other towns on Long Island. Washington needed information on their plans and whereabouts, so he asked Colonel Benjamin Tallmadge, a Setauket native based in Connecticut, to form a network of spies on Long Island. 

A young man by the name of Abraham Woodhull, had a farm between Conscience Bay and Little Bay, which became the base of spy ring operations. Woodhull, whose alias was “Samuel Culper, Sr.” would travel back and forth to New York City carrying messages. During his travels, he took note of British troop movement, what they were doing, and the size of their forces. Since the British occupied his farm as well, when it became too dangerous Woodhull would enlist the help of his friend, Austin Roe, a young tavern keeper from Setauket, to help deliver the messages to Tallmadge. Woodhull allowed Roe to bring his cows to pasture on his property so it would not look suspicious when Roe would come by the farm. Roe was able to hide messages in the hollow of a tree. 

Another man, an ex-whaler by the name of Caleb Brewster, became a huge asset to the spy ring because he knew how to navigate the waters off Long Island. Brewster, who was also a lieutenant in Washington’s army, would deliver messages with a small group of men by rowing across Long Island Sound to Fairfield, Connecticut. Along the way he would often attack British ships, steal their supplies, and burn everything else. 

Anna Smith Strong of Strong’s Neck, known in the Spy Ring as “Nancy,” was very instrumental in providing secret information. She lived in a cottage on Setauket’s Little Bay, which just happened to be across from Abraham Woodhull’s house and farm. She and Woodhull devised a secret code by way of a clothesline. Depending on what color petticoat or how many handkerchiefs Anna hung, would determine what information was coming through. If a black petticoat was hung on the line, it meant that Caleb Brewster was in town. The number of handkerchiefs would indicate which of the six landing places Brewster was at. Woodhull would use his spyglass and look at the clothesline across the way. He would then know how to get his information to Brewster. 

Another one of Washington’s spies, Robert Townsend from Oyster Bay, assisted the Setauket spies, and became known as “Culper, Jr.” Anna’s husband, Judge Selah Strong, was not officially listed as a “spy” but he must have had something to do with it because he was captured and thrown onto a British prison ship. 

These famous men and women of the Culper Spy Ring helped change the course of the American Revolutionary War through their bravery and their unending dedication to our country.