What is it about spies and secret messages that fascinates us all? We can probably all imagine ourselves tasked with carrying an important message that might change the world, and the thrill and the danger involved. And what better mission than American independence?
In recent years, there has been renewed interest in the Culper Spy Ring, created by George Washington himself, tasked with gathering intelligence about the movement of British troops during the American Revolution. Several books and a TV series have created an entire following (and thankfully, even more interest in the Revolution!).
As you know, I strive to make history come alive for my children in our homeschool, so I couldn’t resist adding the exciting story of the Culper Spy Ring to our study of the American Revolution. And I’m sharing our resources with you today!
About the Culper Ring
In 1778, George Washington appointed Samuel Tallmadge, a major in the Continental Army, as the head of a new spy network on Long Island, New York. Tallmadge recruited a couple of his childhood friends from Setauket, as fellow trustworthy spies. They worked together with a few key characters to uncover the plans of the British, including troop movements, planned attacks, and even the treason of Benedict Arnold!
This article from History.com is a great starting place to begin a study of the Culper Spy Ring.
Read a little bit here about the life of Samuel Tallmadge.
Tallmadge’s main contact on Setauket was Abraham Woodhull, otherwise known as SAMUEL CULPER (and later, Culper, Sr.).
Woodhull was to be a new type of American spy. For the first few years of the Revolution, Continental Army leaders preferred to sneak operatives into British territory where they skulked around for a few days, acquired information, and then slipped back out through the lines to report to American commanders. The tactic was sometimes effective but the information often lacked the detail, accuracy and timeliness that Washington needed. Nor had the Americans uniformly mastered the techniques of successfully moving in and out of enemy territory. To overcome these problems Washington and Tallmadge envisioned a permanent network of spies that lived behind British lines and communicated their information through coded messages. Tallmadge’s recruitment of Woodhull enabled them to put their plans into action.
Caleb Brewster was another friend of both Tallmadge and Woodhull. He was a sailor, and carried many messages between Woodhull and General Washington.
In Brewster’s case, the British knew his name, they knew he lived and operated in and around Setauket, and some accounts indicate they knew he was the primary courier between Long Island and Connecticut. The British never captured him, though. Brewster had a reputation for being extremely brave and some accounts indicate several occasions where he effectively battled British ships far larger than his whaling boat. Of equal importance were his resourcefulness, his seamanship, and his familiarity with every cove and eddy on both sides of the sound. In combination, these enabled him to carry out his work aiding the revolutionary cause.
Anna Smith Strong was also a childhood friend and fellow Setauket resident.
Anna Smith Strong’s assignment in the Culper Ring was to signal Brewster’s arrival to Abraham Woodhull. She did this by hanging laundry on her clothesline in pre-arranged configurations, a system that fooled all by the wisdom of its simplicity. If she hung up a black petticoat, it meant that Brewster was in town. By counting the number of white handkerchiefs scattered through her wash, Woodhull knew in which of six coves Brewster hid his boat. Under cover of darkness, Woodhull then rendezvoused with Brewster and passed along the secret messages. Brewster and his men then crossed Long Island Sound to Connecticut and passed the information to Tallmadge who passed it on to Washington’s headquarters in Westchester County, New York.
Robert Townsend is remembered as perhaps the most important spy of the Culper Ring. He lived in New York, and collected the information that was passed between the other members of the ring. Townsend was known as Culper, Jr.
…he did his most historically significant reporting for George Washington, writing his reports in invisible ink on pages concealed within half-reams of blank paper that were packaged and addressed to the coded name of an American officer. A writer carried the packages 55 miles east to Setauket, where they were retrieved by Culper Sr. from a pickup point in a cow pasture.
“The identity [of] Robert Townsend (Culper Jr.) was discovered in 1939, when a trunk of old letters was discovered in the Townsend family home. Historian Morton Pennypacker noticed the resemblance in the handwriting in these letters and letters written by Robert Townsend in George Washington’s letter collection. Pennypacker then discovered the identity of the other spies in Setauket and New York City and published his findings in a book, General Washington’s Spies on Long Island and in New York, in 1939.” (Source)
Austin Roe owned a tavern in Setauket, and used his position as a means to carry messages back and forth to New York.
Austin Roe rode from Setauket, Long Island, to New York City, where he entered Townsend’s establishment. There Roe placed an order from Tallmadge who signed under his code name John Bolton. Contained in this message were prearranged code words from Washington to Tallmadge to which Tallmadge responded in code. The messages were then hidden in goods that Roe took back to Setauket, and hid on a farm belonging to Abraham Woodhull who would later retrieve the messages.
The Culper Spy Book was developed by Tallmadge and consisted of 763 numbers that represented names, places, and other vital information that could be used to protect the real meaning of letters.
My Favorite Book
The best discovery I made during this study was a series written especially for kids by Robert J. Skead. You could do a “school-type” study of the spy ring (and possibly squelch every last spark of interest in your kids), but I prefer a great story that draws them in and keeps them asking for “one more chapter!” A story like this brings a few historical facts to life for kids in a way no lesson plan can possibly do. And they will remember the history in the story far longer than a textbook paragraph and a quiz.
So skip the boring lessons and get yourself these books:
When Revolutionary War Patriot Lamberton Clark is shot by British soldiers while on a mission for the Continental Army, he has only two hopes of getting the secret message he’s carrying to General George Washington: his 14-year-old twin boys John and Ambrose. Upon discovering that their father is a spy in the Culper Spy Ring, the boys accept their mission without a clue about what they may be up against. They set off from Connecticut to New Jersey to find General Washington, but the road to the commander-in-chief of the Continental Army is full of obstacles; including the man who shot their father who is hot on their trail.
I have been reading these to my sons and nephew, ages 9-11. They love it! The stories include a lot of exciting fiction woven with the facts of the Ring. These books are available on Amazon and at Barnes and Noble. (Book 3 is in the works as we speak!).
Fun Stuff To Do
Explore the history of the Turtle, the primitive submarine used in the Revolution to deliver explosives beneath British ships. (We did this when reading Book 2 of Robert Skead’s series.)
Learn about the Cardan Grille, a device used to write a secret message within a larger harmless letter. “[A] Cardano Grille [was] a sheet of stiff material with irregularly spaced rectangular holes which was placed over the writing paper. The secret message was then written in the holes, the grille or mask removed from the writing paper, and a harmless message was filled in around the secret message to camouflage its being there. To read the message, an identical grille or mask was placed over the writing.”
Follow these directions to let the kids make one of their own!
While there is some debate about the actual use of boiled eggs with the Culper Spy Ring, the trick is used in the series TURN, and is an interesting twist on secret codes. See how to do your own here.
Using a mixture of alum (a common household spice) and vinegar, the sender writes a message on the shell of a hard-boiled egg. On the outside, the egg looks unaltered; however, when the shell is peeled away, the message is exposed on the egg white. della Porta’s invention vaulted the humble egg from breakfast centerpiece to spycraft superfood. (Source)
Invisible ink was used by both the Americans and the British in the Revolutionary War, and it’s still fun to do today. Read about The History of Invisible Ink at The Art of Manliness. There are several methods (and hundreds of websites with ideas), so try a couple and see what works.
Books for Teens (and Grownups)
This is the first book I read on the subject. It it excellent, and a fast read. I highly suggest this one for the teenagers in your life, for an addition to their high school study of the American Revolution. My 16-year-old is currently reading it. If you prefer (or your teen does), get the Audible version. It’s narrated by the author, which I always find to be preferable.
This book is what the popular AMC series “TURN” is based on. I haven’t read this one myself, but it its a New York Times best-seller, and has rave reviews on Amazon.
THIS memoir by Benjamin Tallmadge is on my list to read next. I love to read history as written by those who were there.
Only 21 at the start of the America’s Revolutionary War, Benjamin Tallmadge was an enthusiastic patriot. Appointed by George Washington to organize intelligence in British-occupied New York, Tallmadge formed the famous Culper Spy Ring, whom he mentions in this volume without giving names. Scenes of battle, the discovery of Benedict Arnold’s betrayal, the execution of his classmate, Nathan Hale, were all part of Tallmadge’s experiences in the war. This memoir is nevertheless an important document by one of America’s great heroes. His description of Washington’s parting in New York from his officers after the victory is especially moving and shows a more human side of the great leader. From inside the book: THE following Memoir of Colonel BENJAMIN TALLMADGE was prepared by himself, at the request of his children, and for their gratification. It is confined, principally, to those incidents of the Revolutionary War with which he was more immediately connected, and therefore becomes the more interesting to his descendants and family friends.
And another piece of history by the man who was there: Major John Andre. John André (1750 – 1780) was a British Army officer hanged as a spy by the Continental Army during the American Revolutionary War for assisting Benedict Arnold’s attempted surrender of the fort at West Point, New York to the British. This book is his journal from 1777-1778.
- Abraham Woodhull’s homesite and grave
- Four Fearless Friends
- 9 Rules of Spying that Nathan Hale Failed to Follow
- Spy Techniques of the American Revolution
Follow my Pinterest Board: Washington’s Spies for updates!
Well, that’s a wrap! I hope you dive in and explore this exciting part of the American Revolution!
Nicki Truesdell is a 2nd-generation homeschooler and mother to 5. She loves books, freedom, history, and quilts, and blogs about all of these at nickitruesdell.com. She believes that homeschooling can be relaxed and that history is fun, and both can be done with minimal cost or stress, no matter your family’s circumstances. Nicki is a member of the Texas Home Educators Advisory Board and The Old Schoolhouse Homeschool Review Crew. You can also find her on Instagram, Facebook, Twitter, and Pinterest.