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Tuesday, November 5, 2024

George Washington and The Long Island Spy Ring

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Wherever you go, history is all around you. Luckily for us Long Islanders, we don’t have to search too far beyond our own homes for local happenings with history class appeal. 

One notable famed event with roots to our parts: Washington’s Spy Trail. 

Being that New York was the colony with the largest number of loyalists during the Revolutionary War era, they produced the most red coat-aligned soldiers as a result. Consequently, it was difficult for the colonists to conduct business as usual. And with the Island’s proximity to New York City, the then-Capital of the colonies, neither side could afford to count it out. 

To navigate this issue, George Washington’s Spy Ring, or the ‘Culper Spy Ring’ – named for the alias given to Abraham Woodhull — was comprised of some of the general’s most trusted allies. Most notably, in addition to Woodhull: Robert Townsend, Caleb Brewster, Austin Roe and Anna Strong, all of whom were led by Major Benjamin Tallmadge. 

In order to protect the integrity of the operation, Washington did not even know what his spies looked like. They would transmit messages in newspapers to hide in plain sight. 

Considering the vitality of the situation, it’s no surprise that many of the structures are still standing today. Across the state, blue and yellow signs mark additional points of significance as well. 

For those who are curious, ‘Discover Long Island’ offers a four-day criteria posted along with suggested public transportation on the Long Island Railroad. Your trail starts out as far as the Execution Rock in Port Washington, and takes you as far east as East Setauket – where many of the spies were known to take residency, claims Chris Matteo, 25, of Hauppauge. 

“The Washington Spy Ring is intertwined into my life on Long Island, with my grandmother having lived for many years on Tallmadge Drive, a street named after Major Tallmadge,” said the local history aficionado and neuroscience master’s candidate at Stony Brook University. 

He added, “Tallmadge was also a native of Setauket, where my girlfriend is from, and where you can find the graves of other members of the spy ring like Woodhull, Strong and so forth. It still blows my mind that they were all childhood friends in Setauket who ended up basically being the reason we won the American Revolution.” 

Enhanced experience-hopefuls should stay at the Harbor Rose Bed & Breakfast. The large, vintage European-accented home will further assist you in your quest to fully immerse yourself into the 1770s mold. 

Interested in American history that transpired in your backyard, but not quite ready to visit the landmarks in-person? No problem at all. There is a series currently streaming that is perfect for you. 

“The history of American espionage and spying is such a crucial asset to this country,” said actor Jamie Bell, when AMC’s Turn: Washington’s Spies (2014-2017), in which he stars as Woodhull. “And this is George Washington trying to figure out how to do it.” 

“What this show gives you is that insight; it’s as close as we could get to what it would have been like. The show isn’t so much a history lesson as it is a glimpse into a different era and time,” Bell added, per Reuters.

Dara Pratt
Dara Pratt
Dara Pratt is a contributor to The Messenger Papers.