Maps and Routing
In order to pass information from New York City to George Washington in up-state New York without being caught, the Culpers created an elaborate scheme. It was so elaborate that at times it acted to their detriment. The way it worked is this: as Townsend gathered information about the British soldiers in New York City, Austin Roe would drop by the store every once in a while to buy goods for people on Long Island. At the store, Roe would put in a request in writing from a John Bolton. Bolton was the code name for Tallmadge. Townsend would give Roe the requested goods and Roe would leave. Then Townsend would sneak out back when no one was looking, and run up to his small room, close to the shop. There he would read what Tallmadge had written and answer the letter. Roe would show up again at Townsend's room and take the letter back with the answers. Hiding the letter within the package, Roe, a courageous man, not afraid of riding great distances, would ride as fast as he could the 110 miles to Setauket, New York where he would hand off the letter at its first stop.
Once in Setauket, Roe dropped the letter off in a field that he had rented to tend his cattle. He would tend the cattle and place the letter in a pre-arranged drop box. After Roe had gone, Aaron Woodhull, code name Culper Senior, would enter the field, which was right next to his house and pick up the letter. Woodhull would add his own information to it, and then look across the bay to see where Anna Strong had place her black petticoat on the line. This petticoat would let Woodhull know that Caleb Brewster had arrived in his whaleboat to take the letter across the bay. The number of handkerchiefs on the clothesline would tell Woodhull where exactly Brewster was hiding, or which cove he was in along the shore. Under cover of darkness, Woodhull would sneak to the cove and give Brewster the message. Brewster would row back across Devil's Belt to Fairfield, Connecticut and give Benjamin Tallmadge, who would be waiting on his horse on the other side, the letter. Finally, in a series of mounted dragoons, posted every fifteen miles the letter would be passed all the way to Washington in New Windsor, New York. (source) |