Caleb Brewster (1747-1827)br>
Caleb Brewster was born in Setauket and went to sea as a young man, serving on a whaling ship and making him an expert seaman by the outbreak of the Revolutionary War. Caleb Brewster was friendly with spymaster Benjamin Tallmadge's younger brother Samuel, and the families were related, so Brewster was a known quantity when Tallmadge began working with the militiaman. It is difficult to get specific details about Brewster's life, but most historians believe he was already engaged in some secret operations by the time he started working with the Culper Spy Ring. Brewster's job was to carry the spy ring's dispatches between Setauket and Fairfield, Connecticut, where he personally ensured they would travel to Tallmadge and Washington, usually via courier service.
The spy ring's success was largely dependent on Brewster's skill and knowledge as both a fighter and a captain. Brewster's knowledge of the local waters allowed him to use a variety of well-hidden coves near Strong's Neck and Setauket Harbor, while escaping detection from the British soldiers occupying the town. Long Island Sound was a dangerous place of constant fighting and guerrilla warfare during the Revolution, and Brewster was very much a part of that environment. He could navigate the waters to attack a ship much larger than his small row boat, known as a "whale boat" or he could avoid detection and attack from other parties.
Brewster is usually credited for his involvement in all the major whale boat raids on British-held Long Island, such as Sag Harbor, Lloyd's Neck, and Fort St. George.
After the war, Brewster married Anne Lewis, the daughter of the Fairfield, Connecticut wharf owner where he ran most of his war-time operations from. Brewster briefly worked as a farmer and blacksmith before serving as a captain to a government ship in charge of preventing smuggling. This ship, known as a revenue-cutter, was part of the predecessor to the United States Coast Guard, and Brewster remained with this service from 1793 until 1816, when he retired to his farm in Black Rock, Connecticut. He died there in 1827.