
Caleb Brewster
BIRTH
Sep 12, 1747
Setauket, New York
DEATH
February 13, 1827
Black Rock, Connecticut
FAMILY
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Brewster, Caleb
(1747-1827)
Caleb Brewster was a member of the Culper spy ring during the American Revolutionary War, reporting to General George Washington through Major Benjamin Tallmadge. He carried messages across Long Island Sound between Major Tallmadge and the ring's main spies on Long Island, New York, and in New York City. He also made direct reports to Washington concerning naval activities in the New York City area.
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Places | Image | Address | GPS | Site |
|---|---|---|---|---|
Setauket Village Green | Caroline Avenue, Town of Brookhaven, New York, 11733, USA | MARKER |
DIED:
Black Rock, Connecticut
Feb 13, 1827
Brewster was born in Setauket, New York, a hamlet of Brookhaven. After the Revolutionary War, he was a blacksmith, an officer in the United States Revenue Cutter Service for 20 years, and a farmer.
Major Benjamin Tallmadge convinced General George Washington on August 25, 1778, that Abraham Woodhull of Setauket, Long Island, would make a good agent to gather intelligence in New York City, the British Army's headquarters and base of operations during the American Revolutionary War. Brewster served as a courier in what became the Culper spy ring, carrying messages between Woodhull and Tallmadge, and he ran regular trips in whaleboats across the Sound on a variety of smuggling and military missions.
Anna Strong's role in the Ring was to signal Brewster that a message was ready, according to widely accepted local and family tradition. She did this by hanging a black petticoat on her clothesline at Strong Point in Setauket, which Brewster could see from a boat in the Sound and Woodhull could see from his nearby farm.













