Cap. Caleb Brewster (Culper Spy Ring) - Grave

3D Model

Brewster was born in Setauket in 1747 and signed on to a whaling boat as a young man. By the time hostilities between colonial revolutionaries and the British Crown escalated in 1775, he was an expert seaman. He was especially familiar with the many intricacies of the northern Long Island coastline, as well as the 18-mile stretch north to Connecticut, particularly Fairfield and what is now Bridgeport.

Among Brewster’s acquaintances when he was a young man were members of the Tallmadge family, also of Setauket. Benjamin Tallmadge was a graduate of Yale who became General George Washington’s chief intelligence officer and rose to the rank of colonel. Tallmadge was a classmate of Nathan Hale in college and, in the early years of the Revolutionary War, helped organize the Culper Spy Ring.

Brewster’s friendship with the Tallmadges and his expertise as a seaman made him a natural for recruitment to the Culper Ring. Culper was the phony name used by Abraham Woodhull, of Setauket, who was one of the ring’s agents.