Long Island’s Revolutionary War Spies: Inside the Culper Spy Ring

Long Island might be known for its beaches, bagels, and bumper-to-bumper traffic, but did you know it also played a pivotal role in winning the American Revolution? That’s right—the Culper Spy Ring, a covert network of Long Island patriots, helped turn the tide of the war in favor of George Washington and his Continental Army. Here are some crazy facts about these local heroes who risked their lives to outmaneuver the British.

Nathan Hale’s Execution Inspired the Spy Ring

Nathan Hale, a young schoolteacher turned spy, was captured and executed by the British in September 1776.
Before his death, he famously declared, “I only regret that I have but one life to give for my country.”
His tragic fate underscored the need for a more organized and discreet spy network, leading to the formation of the Culper Spy Ring.

Formation and Leadership

The Culper Spy Ring was officially formed in 1778 by Major Benjamin Tallmadge under the direct orders of George Washington.
The name “Culper” was chosen by Washington himself, derived from Culpeper County, Virginia.
Washington recognized the importance of intelligence gathering, leading him to personally oversee aspects of the spy ring’s operations.

Mission: Keep George Washington Informed

The Culper Spy Ring’s primary objective was to relay information about British troop movements and activities in New York City.
The British had strongholds in Setauket and Strong’s Neck on Long Island’s north shore, making the island a crucial battleground for intelligence gathering.
The spies famously uncovered Benedict Arnold’s treasonous plot to hand over West Point to the British, preventing a major loss for the Continental Army.
The ring also discovered a British plan to flood the colonies with counterfeit Continental currency, which could have wrecked the economy.

Espionage Tools of the Trade

The ring used invisible ink to send secret messages—an innovation credited to Sir James Jay, brother of John Jay (the first Chief Justice of the United States).
Messages were written in coded texts and disguised as everyday correspondence to avoid detection.
Many members used aliases, including Abraham Woodhull, who operated under the codename “Samuel Culper” before later becoming “Samuel Culper Sr.”
Some identities of Culper Ring members remained a mystery even after the war, emphasizing the secrecy of their work.
The spy ring was so secretive that even George Washington himself didn’t know the identities of all the members.

Setauket: The Heart of the Spy Ring

Abraham Woodhull was a native of Setauket and was recruited by his friend and neighbor, Major Benjamin Tallmadge.
Tallmadge, an officer in the Continental Army, orchestrated the operations and coordinated with Washington.
Woodhull is buried in the Setauket Presbyterian Church Cemetery, where his epitaph acknowledges his contributions to the Revolution.
British forces regularly occupied Setauket, making espionage a high-risk operation for the ring members.

Agent 355: The Mystery Woman

The Culper Spy Ring may have included a female operative known only by the code number “Agent 355.”
She is believed to have been a high-ranking socialite in British-occupied New York City, possibly feeding intelligence to Robert Townsend.
Her true identity remains one of the great mysteries of Revolutionary War history.

A Raid to Remember: The Tallmadge Trail

Major Benjamin Tallmadge led a daring mission in which he crossed the Long Island Sound from Connecticut to Mount Sinai’s Cedar Beach.
From there, he and his men marched 20 miles to Shirley, where they burned down the British fort known as Manor St. George.
On their return, they destroyed British hay stockpiles in Coram, an essential resource for British forces.
This march is now commemorated by the Tallmadge Trail on Long Island.

Caleb Brewster: Sailor, Spy, and Smuggler

Caleb Brewster, a friend of Woodhull, carried messages between Setauket and Tallmadge in Connecticut via whaleboat.
After the war, Brewster joined the United States Revenue Cutter Service, a precursor to the U.S. Coast Guard.
His cousin, Joseph Brewster, owned a tavern that served British troops while secretly aiding the spy ring.
The Brewster family home, built in 1665, still stands today as one of the oldest structures in Brookhaven.
Joseph Brewster was later involved in the committee that built Route 25A, which is now known as Washington’s Spy Trail.

Robert Townsend: The Secret Merchant Spy

Robert Townsend of Oyster Bay was recruited by Woodhull in 1778 and operated under the codename “Samuel Culper Jr.”
As a merchant and reporter, Townsend had access to vital British intelligence in New York City.
His contributions were so secretive that even Washington himself didn’t know his identity.
Townsend is buried in Fort Hill Cemetery in Oyster Bay.

Enemies and Near Misses

The British commander Major John Simcoe, portrayed as a villain in the AMC series TURN, was indeed a threat to the spy ring.
In 1779, Simcoe traveled to Setauket to hunt down Woodhull after learning he was a spy.
Woodhull later wrote that he wanted to kill Simcoe “for his usage to me.”
Simcoe Street in Oyster Bay leads to Townsend Cemetery, linking his name to the very spy network he tried to destroy.
Ironically, Simcoe is also credited with sending the first-ever recorded American Valentine’s Day letter in 1779.

Anna Strong: The Spy Who Used Laundry Signals

Anna Strong, of Setauket, is believed to be the only female member of the Culper Spy Ring.
After her husband was arrested, she stayed behind and devised a clever way to signal spy activity.
By hanging her laundry in a specific pattern, she indicated when and where Brewster would arrive by boat.
Her actions put her in extreme danger, but she successfully aided the network without being discovered.

Bringing the Culper Ring to Light

For years, the spy ring’s contributions were largely unknown until historian Morton Pennypacker identified Robert Townsend as “Samuel Culper Jr.” in 1939.
Pennypacker’s book, George Washington’s Spies, shed new light on their impact on the war.
Without their efforts, many historians agree that the British might have won—and we’d all be speaking with accents right now.

The Washington Spy Trail: A Modern-Day Tribute

In 2017, a 50-mile stretch of Route 25A from Great Neck to Port Jefferson was officially designated Washington Spy Trail.
Informational signs along the route now highlight key locations tied to the Culper Spy Ring.
Visitors can explore the spy trail on their own or join guided tours to uncover Long Island’s secret Revolutionary past.
A blog called TURN to a Historian fact-checks the television series TURN for those curious about its historical accuracy.

The next time you drive down Route 25A, take a moment to imagine the secret codes, covert meetings, and midnight boat rides that helped shape American history. Long Island didn’t just supply bagels to the world—it helped supply the intelligence that won the Revolution!

Photo: DanTD, CC BY-SA 3.0, via Wikimedia Commons