Benjamin Tallmadge established a small group of trustworthy men and women from his hometown of Setauket, Long Island. Known as the Culper Spy Ring, Tallmadge’s homegrown network would become the most effective of any intelligence-gathering operation on either side during the Revolutionary War.

Tallmadge recruited his childhood friend, the farmer Abraham Woodhull, and Caleb Brewster, whose main task during the Revolution was commanding a fleet of whaleboats against British and Tory shipping on Long Island Sound. Brewster, one of the most daring of the group, was also the only member whom the British had definitely identified as a spy. Tallmadge went by the code name “John Bolton”, while Woodhull adopted the pseudonym “Samuel Culper.”

Woodhull personally traveled back and forth to New York collecting information and observing naval maneuvers there. He would evaluate reports and determine what information would be taken to Washington. Dispatches would then be given to Brewster, who would carry them across the Sound to Fairfield, Connecticut, and Tallmadge would then pass them on to Washington. Woodhull lived in constant anxiety of being discovered, and by the summer of 1779 he had recruited another man, the well-connected New York merchant Robert Townsend, to serve as the ring’s primary source in the city. Austin Roe, a tavernkeeper in Setauket who acted as a courier for the Culper ring traveled to Manhattan with the excuse of buying supplies for his business. A local Setauket woman and Woodhull’s neighbor, Anna Smith Strong, was also said to have aided in the spy ring’s activities. She reportedly used the laundry on her clothesline to leave signals regarding Brewster’s location for meetings with Woodhull.

The Culper Ring employed several methods of spycraft in its operations. In addition to providing his agents with code names, Tallmadge devised a cypher system for their intelligence reports. Key words and terms were encoded as a three-digit number based upon their position in John Entick’s The New Spelling Dictionary, a popular work of the day. Those reports were also written with invisible ink that required a special chemical compound to be brushed over it to reveal the writing. Moreover, the reports were frequently embedded in letters addressed to notorious Tory sympathizers on Long Island as an additional step to prevent their seizure by British troops inspecting material carried by Culper agents.

Example Culper Coded Message:

F 592 373 TECERGMZ & BSPW 373 48 8 634 536 666 HGIQ IDGMMAR 50 427 ek.  500 637 183 236 282 677 637 736.

“2 ships, Vigilant & Fury may be about to sail up back channel by November 15.  Prepare to evacuate garrison in secret to New Jersey.”

The Culper Ring developed a complex method of gathering and relaying information to General George Washington. Below is the sequence of steps the Ring would take to gather and relay the valuable information. (The process of replaying information has many different variations due to its complexity and secrecy.)

  1. Abraham Woodhull (Samuel Culper) would visit his sister, Mary Woohull, who lived in New York City. There, Woodhull has easy access to information about British ships, supplies, and movement.
  2. Austin Roe would then come to the city to purchase goods for his tavern. Woodhull would then relay the information he had gathered to Roe. 
  3. With the information, Roe would then travel back to Setauket, New York where he would relay the information to Caleb Brewster. Brewster would then get in a row boat and cross the Long Island Sound from Connecticut. Brewster would then wait in one of the many numbered inlets.
  4. ​Woodhull would then return to his farm on Long Island, which was occupied by Robert Townsend (code name: Samuel Culper Jr.). Woodhull would relay the information he learned in New York City to Townsend.
  5. Townsend would then re-inform Roe of the information from Woodhull. Roe would then create a dead drop for Woodhull by burying a coded message of the information in a field near Woodhull’s farm.
  6. Woodhull would then wait till Benjamin Tallamadge’s sister, Anna Strong, would hang a black petticoat from her clothesline. The black petticoat represented that Brewster had crossed the Long Island sound. Next to the black petticoat, Strong would hang a certain number of handkerchiefs that corresponded with which inlet Brewster was waiting in.
  7. ​Once seeing the petticoat and handkerchiefs, Woodhull would then retrieve the dead drop left by Roe in the field and take it to Brewster. Brewster would then row back across the sound to Connecticut where he delivered the information to Benjamin Tallamadge.
  8. ​Tallamadge would then hire British calvary men as carriers to deliver the message to George Washington.
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