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.)
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- Tallamadge would then hire British calvary men as carriers to deliver the message to George Washington.