The Culper Ring’s Real Problem Was Carrying Paper
A letter has one job: to arrive as the thing it was when it was sealed. Not its folds, not its place among the other sheets, not the question of which sheet is the real one can be left to chance. For the Culper Ring, the Revolutionary War spy network built around Setauket, that job came with a risk few paper-carriers ever face.
A Chain Built Around One Village
According to the Culper Ring entry on Wikipedia, the ring was established in 1778 by George Washington and Major Benjamin Tallmadge while the British occupied New York City. Messages passed along a chain: Robert Townsend in New York, Austin Roe as courier, a drop in a field, Abraham Woodhull in Setauket, Caleb Brewster by whaleboat across Long Island Sound, Tallmadge in Connecticut, and then Washington’s headquarters. Every link was a handoff, and every handoff was a moment when the paper could be lost, read or swapped.
Setauket sat under occupation. A TBR News Media account of local history notes that British soldiers held the area after the 1776 Battle of Long Island, and that in December 1776 some 801 residents signed a loyalty pledge to the Crown on the Setauket Village Green, Woodhull among them. The article reads the signature as a likely cover for his spying. That is its interpretation, and the same piece cautions that “spying is very risky, and every person involved knew it.”
The TBR piece also describes Woodhull as a Setauket farmer and businessman born in 1754, who gathered intelligence under the alias Samuel Culper. It credits Anna Smith Strong, a local resident, with using her clothesline to signal Brewster, a detail the article attributes to family oral history passed down by a descendant, Kate W. Strong. The Wikipedia entry also hedges, saying she “allegedly” signaled his arrivals. It is a good story that rests on family memory, and it is told here as that.
The stakes were not abstract. By the same entry, the ring’s most significant success was discovering Benedict Arnold’s plot to surrender West Point in 1780.
The Man Who Knew the Water
Brewster’s job was the Sound. Connecticut History records that he was born in Setauket in 1747, had worked a whaling boat, and “was an expert seaman,” familiar with the crossing north to Connecticut. He “sailed to Connecticut and delivered the information to Tallmadge,” then came back with reports. On one occasion, the same account says, a British officer found him waiting for information from another member of the ring, and Brewster “knocked the officer from his horse” to get away.
Short crossing. Open water, a wartime coast, and a document that had to arrive intact.
A Letter That Never Arrived
The best surviving evidence of how the ring thought about its paper is a single sheet. In August 2020, the Long Island Museum found an uncatalogued letter in its own collection, acquired in December 1951. It is dated November 8, 1779, from Tallmadge, writing under the name John Bolton, to Townsend, who worked as Samuel Culper Jr. The museum describes it as the only surviving Culper correspondence from Tallmadge to Townsend, and notes that it was never delivered and never read by its recipient.
The contents are operational. Tallmadge asks Townsend to rely on their numerical codes for personal correspondence rather than invisible ink. He asks whether Townsend can move “silks, gauzes, and such costly articles from New York to Setauket without danger.” And he asks for a safeguard against a very specific mistake: “give some distinguishing mark to the Sheet which is the true Letter to 711 [Washington].” In the ring’s code, 711 was Washington, and the request is about not sending the wrong sheet to the general.
Tradecraft Was Also Paper Management
By July 1779, as the Wikipedia entry has it, Tallmadge had created pocket dictionaries with numbered codes for verbs, nouns, people and places. The ring also used coded messages in newspapers and invisible ink.
Each technique made a sheet of paper look like something other than what it was, or made its meaning unreadable to anyone but the recipient. A distinguishing mark on the true letter is the same idea turned around: among several sheets that look alike, one has to be identifiable to the right person and to no one else.
What the Sources Do Not Say
None of the sources consulted for this piece describes what the couriers carried their papers in. A satchel, a saddlebag, a boot, a hollowed-out something: any of those would be invention, and this account leaves it out. What the record does support is the problem itself. Paper had to travel through occupied ground and across open water, stay in the order its sender intended, and not give itself away.
A briefcase is a gentler answer to the same question. Marcellino NY makes its briefcases from English bridle leather, made to order, and the long history of the object is laid out in The Evolution of the Leather Briefcase. The job has not changed. Papers go in one place, come out in the same order, and stay dry and flat in between. The longer view of what that object looks like after decades is in How a Marcellino Leather Briefcase Will Look in 100 Years.
Setauket in October
The Three Village Historical Society keeps the story in public view. Its Culper Spy Day is listed as the 12th annual event, on Saturday, October 3, 2026, with activities running into Sunday, October 4. The society’s invitation: “Come learn about the Culper Spy Ring from costumed docents at the Three Village Historical Society.” The listed program includes tours of its SPIES! exhibit, a trolley tour of historic sites, and invisible ink demonstrations. Admission to the event is described as free for the community, with charges for select attractions.
Tallmadge’s letter did not do its job. It never reached Townsend’s hands. It sat in a collection for decades, uncatalogued, until the museum found it in 2020, and by the museum’s account it remains the only one of its kind.
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