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

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.

caleb brewster

Early map of the Devil's Belt

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.

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 2019.



  1. Patti Pryor Boose

    August 7, 2016 at 8:53 am

    The television show ‘Turn’ showed a similar situation with the clothesline. Smart thinking.

  2. Patti Pryor Boose

    August 7, 2016 at 8:53 am

    The television show ‘Turn’ showed a similar situation with the clothesline. Smart thinking.

  3. Patti Pryor Boose

    August 7, 2016 at 8:53 am

    The television show ‘Turn’ showed a similar situation with the clothesline. Smart thinking.

  4. Sylvia Stanley Woolworth

    August 7, 2016 at 9:20 am

    Thanks for sharing. Grandma used to hang teabags on her line because she had a nosy neighbor. Gave the neighbor something to think about.

  5. Christine Rapoza Souza

    August 7, 2016 at 9:47 am

    Do you watch Turn on TV? It’s about the Culper ring. Love it!

  6. Valerie Chames

    August 7, 2016 at 5:18 pm

    You’ll have to watch “Turn”…

  7. Steve Magill

    August 7, 2016 at 11:40 pm

    It is my understanding the British held NYC until long after Yorktown…but but that was not the end of the “cold war”?

  8. Bob Conner

    August 11, 2016 at 11:09 pm

    How accurate is Turner? I have been watching it on Netflix but am leary of Hollywood.

  9. Anne Garrett

    November 22, 2017 at 11:49 am

    I believe the reference to bloomers is an error. They were invented in the 19th c. and the rest of the article refers to petticoats, which is more accurate. I hope this helps!
    (Not intended for publication on web page, but for correction to article.)

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