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The Culper Spy Ring

    Imagine living in the late 18th century in Setauket, NY. British soldiers were everywhere. They took over the Presbyterian Church and made into a garrison. They even used gravestones to make a wall around the army base. This upset the people of Setauket very much. As a matter of fact, this type of thing was happening in many of the colonies, so it was time for a revolution!

    Even though Setauket was covered with British soldiers, or Redcoats, there were secret things happening that only few people knew about and those people were spies! Setauket was a very important place during the Revolutionary War. George Washington had a secret spy ring on Long Island and much of it took place in Setauket. It was called the Culper Spy Ring because Culper was one of the code names they used. The spies sent secret messages starting in New York City to Setauket and then across the Long Island Sound to Connecticut where it was brought to General Washington in New Jersey or it went from General Washington in reverse order back to New York City. Some of these messages were written in disappearing ink called Sympathetic Stain. Sometimes a message would be on a clothesline!

It started after Nathan Hale died. He was a young Patriot spy from Connecticut who was caught and hanged by the British soldiers because he was caught carrying a secret message in his shoe. George Washington knew he needed someone to get information for him and he had to make sure the spy ring worked better. Major Benjamin Tallmadge, a 24 year old from Setauket, was the man he was looking for. They organized a secret service.
"I only regret that I have but one life to lose for my country."

--Nathan Hale


Robert Townsend whose code-name was Samuel Culper, Jr., was a patriot who pretended he was a loyalist living in New York City. He needed everyone to believe that he wanted the British to win the war. He was a storeowner and his partner didn’t even know he was a patriot! He also wrote for a loyalist newspaper, so people gave him information. He listened to redcoats and other British Officers that knew what was happening in the war. He passed this very important information to Austin Roe.
Austin Roe was a tavern owner in Setauket. He would ride to New York City and exchange information with Robert Townsend. Though Long Island was occupied by the British, Austin Roe was never caught because he would often go to New York City to get supplies for his tavern. The soldiers thought he was just doing his business. He would then bring the information back to Setauket and give it to Abraham Woodhull.


Austin Roe

Austin Roe & Abraham Woodhull

Abraham Woodhull was 27 when the spy ring started. He was considered the leader of the Long Island Spies. Even though he was skinny and small for a spy, he was very good at his job. His code name was Samuel Culper. His job was to decide which information needed to be moved along the spy ring and then exchange that information with Austin Roe and then with Caleb Brewster or vice versa. Abraham Woodhull would know where to find Brewster by Anna Strong’s clothesline.

Anna Strong whose code name was Nancy Smith, lived on Strong’s Neck. Her husband, Selah Strong, was on a British prison ship, so she wanted to help the Long Island Spies. She would help Abraham Woodhull find Caleb Brewster and his crew. She did this by hanging certain clothes on her clothesline. If she hung her black petticoat on the line, that would tell Woodhull that Brewster was in Setauket. There were six possible coves for Brewster in which to bring his whaleboat and each was assigned a number. To tell which cove he was in, she hung one to six handkerchiefs on the line. She did this because Abraham Woodhull couldn’t see Brewster from where he lived but he could see Anna’s clothesline. The British never suspected her to be a spy because she was a woman.

Anna Strong and her clothesline

It looks like Brewster is in Setauket and he is in cove number one!

Caleb Brewster and his crew

Caleb Brewster grew up in Setauket and also had a very important job during the spy ring. He would either give or get information from Major Tallmadge in Fairfield, Connecticut or Abraham Woodhull in Setauket. He and his crew would secretly row whaleboats across the Long Island Sound to and from Connecticut. They had to be cautious because there were British frigates patrolling the Sound and they were in constant danger. When Caleb Brewster pulled into Setauket he had to be sneaky because he was well known in there. He had to hide the whaleboat in the willows in Conscience Bay, which is why Abraham Woodhull needed Anna Strong and her clothesline.
Major Benjamin Tallmadge, code named John Bolton, was second in charge of the spy ring after George Washington. He was based in Fairfield, Connecticut because the British soldiers did not occupy Connecticut. He would either get information from General Washington and give it to Caleb Brewster or vice versa. He had to make sure that everything went smoothly and that the spies didn’t get caught.


Here is a piece from Major Tallmadge’s journal:

"This year 1778 I have started a secret service for George Washington. It was going on during The Revolutionary war."

Major Benjamin Tallmadge

Spy Ring Route

    Men who were spies had to make hard choices. If they were to become spies, they would put their families in danger because if they were caught, they would have been killed. They made the choice to be spies because they believed they should have their freedom, which meant they had to win the war!

Caleg Brewster with his crew!Another picture of Caleb Brewster and his crew crossing the Long Island Sound.

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