The Village Washington Trusted With His Secrets
The Village Washington Trusted With His Secrets
How Setauket and Stony Brook, two quiet communities on Long Island's North Shore, became the working heart of America's first spy network.
This is the next stop on "Washington's Spy Trail," a series that looks at the real, ordinary places where George Washington's intelligence network actually operated during the Revolutionary War. Today we're looking at Setauket and Stony Brook, New York, two neighboring communities on Long Island's North Shore that quietly did more to help win American independence than almost any patch of ground its size.
No battles were fought here. There's no monument marking a famous charge. What happened instead was slower, and in its own way more dangerous: neighbors risking their lives to move information — a count of British ships, a note about troop movements — across open water, past patrols, into the hands of a general who could actually use it.
Why a Farming Village on Long Island Sound
Setauket spent most of the war under British occupation, one of thousands of small port towns dotting the coast. What made it valuable to Washington came down to geography and trust.
Long Island Sound narrows to a fairly short crossing near Setauket, short enough that a rower with a fast whaleboat could reach the Connecticut shore in a single dark night. New York City, the headquarters for British forces and a place full of the kind of intelligence Washington needed, sat less than sixty miles away by road. Someone traveling there under an ordinary excuse — buying supplies, visiting family — could gather information and be home within days without drawing much notice.
Just as important, Setauket was full of people Major Benjamin Tallmadge had known his entire life. He'd grown up there and could tell, better than any outsider, which neighbors could be trusted with dangerous, secret work. When Washington asked him in 1778 to build a reliable network for gathering intelligence, Tallmadge didn't start from nothing. He started from home.
The People Who Carried the Risk
Historians know this network by the code name Washington and Tallmadge gave it: the Culper Ring, borrowed from the alias "Samuel Culper" used by its lead operatives. Each member played a distinct part, and almost none of them had any formal military training. They were a tavern keeper, a farmer, a homemaker, a whaleboat captain. Their ordinary lives were the disguise.
| Name | Role in the ring | Setauket connection |
|---|---|---|
| Abraham Woodhull | Lead courier and organizer, known as "Samuel Culper Sr." | Farmed land along the harbor; used his own property as a drop point for messages |
| Anna Smith Strong | Signal relay | Lived on a farm near Woodhull's; reportedly used laundry on her clothesline to indicate when and where a courier's boat would land |
| Austin Roe | Courier to and from Manhattan | Ran the local tavern; made a roughly fifty-five mile round trip to New York City under the cover of business errands |
| Caleb Brewster | Cross-Sound transport | Rowed a whaleboat across Long Island Sound to deliver messages to Tallmadge in Connecticut |
| Robert Townsend | New York City source, known as "Samuel Culper Jr." | Gathered intelligence in occupied Manhattan, then passed it to Roe for the trip back to Setauket |
| Benjamin Tallmadge | Network organizer | Grew up in Setauket; recruited and managed the ring on Washington's behalf |
The clothesline signal attributed to Anna Strong is one of the more memorable details of the story, and it's worth being honest about it: the specific arrangement of petticoats and handkerchiefs comes down mostly through family tradition rather than a written record, so historians treat the particulars carefully. What's well documented is that Strong lived at the right spot, at the right time, with a husband held on a British prison ship and every reason to want the war over. Her broader role in the ring is not seriously disputed.
The Route the Information Traveled
Strip away the code names and the story is really a relay, with each person handling one leg and knowing as little as possible about the rest.
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Robert Townsend gathers intelligence while living and working in British-occupied New York City.
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Austin Roe rides to Setauket carrying the notes, often hidden among ordinary goods.
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The message is left at a prearranged spot on Abraham Woodhull's property.
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Anna Strong's clothesline, according to tradition, signals Caleb Brewster where his boat should land.
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Brewster rows across Long Island Sound to Major Tallmadge in Connecticut, who forwards the report on to Washington.
Matters of business to his friend at Satuket.
George Washington, in a letter to Benjamin Tallmadge, September 24, 1779
Why Stony Brook Holds Two of Washington's Own Letters
Stony Brook University's Special Collections owns two original letters written by George Washington himself, dated 1779 and 1780, that document this same intelligence work in what's known locally as the Three Village area, covering Stony Brook, Setauket, and Old Field together.
One of the letters made a memorable trip off campus: it traveled to Setauket Elementary School, where more than five hundred children and parents came to see it, and it has been featured in exhibitions with the Three Village Historical Society. The university treats the letters as teaching tools as much as artifacts, working alongside the Historical Society and the Ward Melville Heritage Organization on tours, lectures, and a K-12 curriculum built around the ring's history.
Retracing the Trail Today
Unlike a battlefield, most of what made Setauket important is still standing, or close to it: the harbor, the church, the roads a courier would have used without a second thought.
Planning a visit to Setauket's spy trail
- Start at the Three Village Historical Society for exhibits and self-guided tour maps of the ring's local sites
- Visit the Caroline Church of Brookhaven and its historic cemetery, resting place of several ring members
- Look for the Vance Locke murals at Setauket Elementary School, which depict local Revolutionary War history
- Check the calendar for Culper Spy Day each fall, with tours, reenactments, and an invisible ink demonstration
- Stop by Stony Brook University's Special Collections to see how the Washington letters are preserved and studied
The short version
Setauket wasn't chosen for spy work because it was dramatic. It was chosen because it was close to Connecticut, close to New York City, and full of people Benjamin Tallmadge already trusted. A tavern keeper, a farmer, a homemaker, and a whaleboat captain turned those ordinary facts into one of the most effective intelligence operations of the war, and two of Washington's own letters describing it still sit a few miles away at Stony Brook University, available to anyone who wants to see them.
Frequently asked questions
What was the Culper Spy Ring? +
An intelligence network organized in 1778 by Major Benjamin Tallmadge at George Washington's request. Based largely in Setauket and in British-occupied New York City, it gathered information on troop movements, fortifications, and British plans throughout the Revolutionary War.
Why was Setauket chosen for spy operations? +
It sat close to a narrow stretch of Long Island Sound, making a night crossing to Connecticut possible, and it was Benjamin Tallmadge's hometown, so he already knew which neighbors could be trusted.
Who was Agent 355? +
A numeric code referenced in Culper Ring correspondence, believed to refer to a woman who assisted the network. Her identity has never been confirmed with certainty, and while some researchers connect the code to Anna Smith Strong, historians continue to debate it.
Can you visit Culper Spy Ring sites today? +
Yes. The Three Village Historical Society offers exhibits and tour information, the Caroline Church of Brookhaven cemetery holds several ring members, and the annual Culper Spy Day includes tours, reenactments, and demonstrations.
Where can I see original Washington letters connected to the ring? +
Stony Brook University's Special Collections holds two original letters written by George Washington in 1779 and 1780 that document Culper Ring intelligence activity in the Three Village area.
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Douglass Gillespie
Douglass helps buyers, sellers, and downsizers move confidently through Bloomfield, Montclair, Glen Ridge, Nutley, Verona, Cedar Grove, and the rest of Essex County. Before real estate, he spent more than twenty-five years teaching high school English, and that same habit of explaining things clearly, without pressure, still shapes how he works with every client. When he's not writing about local history or helping with a move, he runs The 100th Monkey Foundation, a nonprofit supporting mindfulness, music, and the arts.
This article is provided for educational purposes only and should not be considered financial, legal, tax, or mortgage advice. Historical details are drawn from published research, including materials from Stony Brook University Libraries and George Washington's Mount Vernon; where family tradition and documented record diverge, this article notes the distinction. Consult the appropriate licensed professionals regarding your specific circumstances.
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