Caleb Brewster was a member of the Culper spy ring during the American Revolutionary War, reporting to General George Washington through Major Benjamin Tallmadge.
17 Facts About Caleb Brewster
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Caleb Brewster 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.
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Caleb Brewster made direct reports to Washington concerning naval activities in the New York City area.
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Caleb Brewster was recruited to carry messages between Woodhull and Tallmadge, running regular trips in whaleboats across the Sound on a variety of smuggling and military missions.
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Caleb Brewster agreed to command the boat service only under condition that he be allowed to select his own boat crews.
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Caleb Brewster chose several men from eastern Long island, including half-brothers David and Benjamin Dickerson who were on active duty in another command within the Continental Army.
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At one point, the Dickersons along with several others of Caleb Brewster's crew were suddenly recalled to their original commands.
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Caleb Brewster in navigating from the main to L I have been remanded to their regiments, in consequence of which a service of a particular nature is very much impeded if not entirely stopped.
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Caleb Brewster 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.
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Caleb Brewster would add a number of handkerchiefs for one of six coves where Brewster would bring his boat and Woodhull would meet him.
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Caleb Brewster pulled him off his horse and had the opportunity to capture or kill him, but he refrained from doing either in order to avoid drawing suspicion on Anna as a member of the Ring, and instead pretended that he and his men were thieves.
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Caleb Brewster participated in military actions as a Continental Army officer serving under Tallmadge.
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Caleb Brewster married Anne Lewis of Fairfield, Connecticut, after the war and moved to Fairfield with her, where he set up a blacksmith business.
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Caleb Brewster took three years off from the service because he disagreed with policies of President John Adams, and he commanded the revenue cutter USRC Active from 1812 to 1816.
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Caleb Brewster retired to his farm in Black Rock, Connecticut.
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Caleb Brewster died February 13,1827, aged 79, and is buried in Fairfield Cemetery.
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Caleb Brewster is played by Daniel Henshall in the TV series Turn: Washington's Spies, on AMC.