Caleb Brewster was a member of the Culper Spy Ring who operated as a messenger between Abraham Woodhull and Benjamin Tallmadge.
His connections as a whaler aided him as a courier and allowed him to travel the Long Island Sound between Tallmadge and the other Culpers undetected. This also allowed him to deliver accurate reports to George Washington regarding the activity of the British Navy in the New York harbor.
Family and Early Years
While some sources suggest that Caleb Brewster was a direct descendant of Mayflower passenger William Brewster, this is unlikely.
The Brewster name is a well-known surname in England and among those who emigrated to the New World. There were a few Brewsters that came over with the Pilgrims, but Caleb's ancestors came and settled in New Haven, Connecticut.
His ancestor was Francis Brewster. Caleb's family came over during the Great Puritan Migration and, over the following generations, would move to New York.
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 Tallmadge's younger brother Samuel, and the families were related, so Brewster was a known quantity when Tallmadge began working with the militiamen.
Caleb Brewer and the Culper Spy Ring
Caleb was a member of George Washington's Revolutionary War Culper Spy Ring. 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 American 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 rowboat, known as a whaleboat, or he could avoid detection and attack from other parties.
Recruitment
Brewster, having a connection with Tallmadge's brother, was an obvious choice as a resource while Tallmadge was recruiting men for his spy network.
His primary recruit was Abraham Woodhull, who would serve as the main source of information and would send messages through to George Washington.
Eventually, another mainstay would join the spy ring named Robert Townshend. Townshend would operate in a similar way as Woodhull. Woodhull would go by Samuel Culper St., and Robert would be Samuel Culper Jr.
Once Woodhull or Townshend had written the information down, the next person in the ring would be Anna Strong.
Strong would learn that Woodhull or Townshend had information that needed to be sent, which meant that she would signal Brewster by hanging a black petticoat from her farm that Brewster could see from his location on his boat.
She would add a number of handkerchiefs for one of six coves where Brewster would bring his boat, and Woodhull would meet him.
Brewster would serve as a spy for the duration of the war and would play a part in exposing the American Hero Benedict Arnold as treasonous.
Some of his specific actions are as follows:
- In February 1778, Brewster sent a message of his own through the Culper channel that described flat-bottomed boats being built in New York that could be used to ferry troops and Loyalist privateers being outfitted.
- On another trip, he was waiting for Woodhull in Anna Strong's back garden when he surprised a passing British lieutenant. 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
Later Years
Brewster married Anne Lewis of Fairfield, Connecticut, after the war and moved to Fairfield with her, where he set up a blacksmith business.
The couple had eight surviving children.
In 1793, he joined the United States Revenue Cutter Service, a predecessor of the United States Coast Guard.
He took three years off from the service because he disagreed with the policies of President John Adams.
Brewster died February 13, 1827, aged 79, and is buried in Fairfield Cemetery. The inscription on his headstone reads:
In
memory of
Captain CALEB BREWSTER,
who died
February 13th. 1827;
aged 79 years.
He was a brave and active officer
of the Revolution.
