Caleb Brewster Crosses the Devil’s Belt for the Culper Spy Ring

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Caleb Brewster relied on a woman’s underwear and his own seamanship to bring vital intelligence to George Washington during the American Revolution. He belonged to the Culper Spy Ring, which operated from 1778 to 1783.

After the British evacuated Boston, New York City became their base of operations. And intelligence about their movements became critical.

The American Continental Army had, in fact, lost New York in part because of a lack of information. George Washington underestimated the strength of the British troops, which handily drove the Americans out of the city.

With Benjamin Tallmadge in charge, the Americans launched a spy ring to infiltrate New York and bring information back to Washington.

Benjamin Tallmadge, Master Spy

Benjamin Tallmadge, a former classmate of Nathan Hale, reported directly to Washington as head of the army’s intelligence gathering operation starting in 1778.  Previous efforts had not gone well — in once case, resulting in Hale’s death.

From his base in Connecticut, Tallmadge moved away from a system of single spies on specific missions. Instead, he used a network system that passed on what information it gathered through a single source – Tallmadge.

But Tallmadge had to get the intelligence out of New York to Connecticut. And that’s where Caleb Brewster, Anna Strong and her petticoats come into the picture.

The British had imprisoned Anna’s husband Selah for spying for the Americans. Anna negotiated his release through her Tory relatives, and he moved from the family’s Setauket, N.Y., home to Connecticut. He left Anna behind.

Caleb Brewster

Caleb Brewster had worked on whaleboats since childhood. He was intimately familiar with the Long Island Sound – known in colonial times as the Devil’s Belt.

Caleb Brewster knew both the Long Island side where he grew up as a child and the Connecticut coast around Fairfield and Bridgeport.

Anna’s clothesline was conveniently visible both to Brewster and the coordinator of the New York spies. Her role was to hang her washing as a signal to the spies who visited New York for information.

The black petticoat meant Brewster would soon make a trip from New York to Connecticut. White handkerchiefs signaled to the the spies which cove he waited in with his boat.

The work was dangerous. At one point, Caleb Brewster encountered a British army lieutenant. He attacked the soldier. Rather than take him prisoner, however, Brewster robbed the man to make him think he had happened upon a robber, not a rebel operative.

Washington’s Spies

Secrecy was so important not even Washington knew the identities of all the men in the spy ring. Tallmadge named it for Samuel Culper, the phony name of one of the key spies who slipped in and out of New York City with information.

The Culper Ring provided essential information to Washington, including specific counts of troops and weapons, details of boats being built, information about British plans to use privateers to augment its Navy and names of Loyalists covertly supporting Britain.

As the focus of the war shifted south, the Culper Ring wound down its operation. Caleb Brewster would eventually make Connecticut his home.  He became a blacksmith after the war and joined the forerunner of today’s Coast Guard.

Caleb Brewster died in 1827 at the age of 79 in Bridgeport. Near his home in Bridgeport a street bears his name.

This story was updated in 2024. Image of whaleboat By The original uploader was Leonard G. at English Wikipedia. – Transferred from en.wikipedia to Commons by IngerAlHaosului using CommonsHelper., CC SA 1.0, https://commons.wikimedia.org/w/index.php?curid=9015484