Caleb Brewster was perhaps the most bold and daring of the Culper Spy Ring spies. He was the only one of the group that the British had definitely identified as a spy.
When the Revolutionary War broke out, he immediately enlisted in the local militia. After the Battle of Long Island he joined the Continental Army with the rank of a lieutenant of artillery. He returned to Setauket in August of 1777 as part of the attacking force from Connecticut that fought in the Battle of Setauket. In November 1780 he was one of the officers under Major Benjamin Tallmadge who captured Fort St. George at Mastic. They returned to Connecticut with the entire complement of the fort captured. In spite of his service designation, his task throughout the war was to command a fleet of whale boats operating from the Connecticut shore against British and Tory shipping on Long Island Sound [known as the “Devil’s Belt”].
This, together with his knowledge of the Long Island shoreline, and his boyhood association with Benjamin Tallmadge, made him an ideal choice to carry intelligence back and forth across the Sound. Brewster made numerous trips with his Whaleboat Navy; into Long Island Sound to attack British shipping; and across to Setauket to bring messages back for Major Benjamin Tallmadge to deliver to General Washington.
Written by and permission granted by historian Beverly Tyler, Education Chair of the Three Village Historical Society. Setauket, New York, Long Island.