Anna remained alone on the family farm during the American Revolution, where she assisted with General Washington’s Culper Spy Ring.
Continental Army Major Benjamin Tallmadge began working with Abraham Woodhull in the summer of 1778 at the height of the Revolutionary War to provide Washington information on British Army operations in their headquarters in New York City. Members of the Spy Ring gathered and passed information between autumn 1778 and the British evacuation of New York in 1783.
Anna Strong’s role in the ring was to relay signals to a courier named Caleb Brewster, who would row periodically across Long Island Sound to retrieve the information uncovered and take it to Major Tallmadge in Connecticut.
Anna would take her laundry out to the tip of Seaton’s Neck where her clothesline was easily visible from a boat in the Sound, and also visible to Woodhull at his nearby farm. A black petticoat indicated that a message was ready to be picked up, and the number of white handkerchiefs identified the cove on Long Island Sound where Woodhull and Brewster would meet.
The Culper Spy Ring achieved more than any other intelligence network during the war. In 1780, they uncovered British plans to ambush the newly arrived French Army in Rhode Island. They also uncovered information involving the secret negotiations between Benedict Arnold and the British to surrender the American fort at West Point, New York, in return for money and a command in the British Army.