The Spy Ring’s Methodology: Tactics and Information Gathered
In the Culper Ring’s early days, Abraham Woodhull frequently travelled to New York City under the cover of his occupation as a farmer delivering produce, or to visit his sister, who lived in the city. While in New York, he gathered information about the units in the city, their dispositions, and any news he overheard from talkative Loyalists and British officers.
It was valuable information, but close questioning by inquisitive British soldiers during one of those visits drove home the dangerousness of what he was doing, and how a single slip, wrong move, or simple bad luck, could send him to the gallows. So to reduce his exposure and the frequency of his travel from Long Island to New York and back, Woodhull began leaning more on recruiting spies in the city, and using their reports instead of his personal observations. An early recruit was his sister’s husband in New York, but his brother in law’s reports were often so vague as to be useless.
Initially, Woodhull would gather the information from New York City, return with it to Setauket, Long Island, then deliver it to Caleb Brewster, who delivered it to Benjamin Tallmadge, who delivered it to George Washington. It was a time consuming process that was eventually shortened by using couriers to collect the information in New York and speedily get it to Setauket, 55 miles away. The process was further shortened by the use of express riders to transmit the intelligence from Tallmadge to Washington.
A neighbor and friend of Woodhull in Setauket, Anna Strong, used her laundry as a code to coordinate between Brewster and Woodhull as to when intelligence was ready to gather, and where it should be collected. When Brewster was in the area, ready to pick up Woodhull’s reports, Anna would hang a black petticoat in her laundry as a signal to Woodhull. Woodhull would then finish compiling a report, and stash it in a prearranged hiding spot in one of six coves near Setauket. Anna would then hang up white handkerchiefs to dry, their number corresponding to the number of the cove where Woodhull had stashed the report. Brewster would then go to the correct cove, pick up the report, and deliver it across the Long Island Sound to Tallmadge in Connecticut.
