Image of Patriots with one of them with finger pressed to lips
Art by Patrick Faricy

Undercover Patriots

How America’s first spy ring helped George Washington win the Revolutionary War

By Allison Friedman | Art by Patrick Faricy
From the October/November 2023 Issue

Learning Objective: Students will read a historical fiction play about the Culper Spy Ring and identify the main character Sally Townsend’s motivations for risking her life to spy for George Washington.

Other Key Skills: character’s motivations, vocabulary, fluency, setting, key details, interpreting text, cause and effect, compare and contrast, character, plot, text features, author’s craft, narrative writing
Topics: History,
UP CLOSE: Character’s Motivations

As you read, think about what motivates, or causes, Sally to take brave actions. 

Prologue

N1: Two hundred and fifty years ago, the United States was not yet a country. 

N2: There were 13 colonies in America, ruled by England . . .

N3: . . . a country across the Atlantic Ocean.

N1: Many in America believed this situation was unfair. These colonists, known as Patriots, wanted to rule themselves. 

N2: Others, called Loyalists, were loyal to the King of England.

N3: In 1775, a war broke out: the American Revolution.

N1: On one side was the Americans’ Continental Army, led by General George Washington.

N2: On the other was the British Army, one of the most powerful armies in the world.

N3: To have a chance of winning, General Washington needed more than strength—he needed smarts. He had to know what the enemy was planning.

N1: And for that, he needed spies.

N2: This story is based on their adventures.

Scene 1
The Townsend Home
Long Island in New York | April 1780

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N3: Fifteen-year-old Sally Townsend is hanging laundry in her family’s yard when she sees a man walking toward her.

Robert Townsend: Hey there, little sister.

Sally Townsend: Robert! What a nice surprise!

N1: The two hug, but they pull apart when a soldier in a bright red coat appears.

Colonel Simcoe: Miss Townsend, my men and I expect our uniforms to be cleaned by this afternoon.

Sally (annoyed): Yes, Colonel. They’ll be ready.

N2: After capturing New York City, British soldiers are staying in the homes of nearby Loyalists, like the Townsends on Long Island.

N3: After Simcoe leaves, Sally sighs.

Sally: All day long, those soldiers bark orders at us. They’ve taken over our entire house. They even chopped down Father’s apple orchard—did you see? For firewood! 

Robert: It isn’t right.

Sally: No! It’s not. I know our family made a promise to support the king, but . . .

Robert (quietly): Actually, Sally, that’s why I came today. I need to tell you something. 

Sally: What? You’re scaring me.

Robert: I can’t continue to support England. I’ve joined a group of people helping the Patriots. 

Sally: The Patriots! How?

Robert: By gathering information on the British Army in New York.

Sally (shocked): You mean . . . spying? 

N1: Robert nods quietly.

Sally: Robert, you can’t! If you get caught, you’ll be sent to jail . . . or worse.

Robert: Sometimes it’s worth risking everything for a cause you believe in. 

Sally: But this is your life!

Robert: Sally, don’t you want America to be free?

N2: Sally looks worried but says nothing.

Scene 2
The Townsend Home
Long Island | July 1780

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N3: Months later, Sally is scrubbing floors upstairs when she hears voices coming from Colonel Simcoe’s room. 

Major André: My spies say Washington’s troops in Rhode Island are weak. If we strike soon, we can defeat them. 

Simcoe: Capturing Rhode Island would certainly be a blow to the Patriots.

André: More than that. It could end this war.

N1: Sally inches closer to the door, her heart pounding.

N2: But she accidentally knocks over her bucket with a loud clatter.

N3: Major André opens the door.

N1: Sally freezes.

André (relieved): Ah, it’s just the girl. 

Sally (nervously): Sorry for my clumsiness, sir. 

Simcoe: Look at that mess!

Sally: I’ll get a mop. 

N2: Back downstairs, Sally paces back and forth.

Sally (to herself): They’re going to attack Rhode Island! Should I tell Robert?  

N3: She gazes out the window.

Sally: No, it’s too risky.

N1: Then she sees the empty field where her father’s beloved orchard used to be.

Sally: But Robert is right. If the British win this war, we’ll never be free of them.

N2: She lets out a shaky breath.

Sally: I must go to the city to tell him. Tonight.

Illustrations by Patrick Faricy

Scene 3
Townsend’s General Store
New York, New York | That night

N3: Late that night, Sally knocks on the door of Robert’s store in New York City.

N1: In the dark shop, she finds her brother with another man his age.

Robert: Sally! What are you doing here?

N2: Sally glances nervously at the stranger.

Robert: This is Abraham Woodhull. He’s part of the group I was telling you about. 

Sally: Then I have news for both of you.

N3: Sally reports the conversation she heard between Colonel Simcoe and Major André.

N1: When she finishes, Robert and Abraham give each other worried looks.

Abraham Woodhull: We must get a message to General Washington at once.

N2: Robert grabs a blank paper, dips a pen into a pot of ink, and begins writing. 

N3: After a minute, he holds up the paper. But it still appears blank.

Sally: Hmm, Robert, your pen must be broken. 

Robert: No—it’s invisible ink. Only a person using a special liquid can reveal the message. To anyone else . . .

N1: He quickly scribbles on the same paper with a different pen.

Robert: . . . it will just look like a bill for soap. Here you are, Culper Senior.

Abraham: Thanks, Culper Junior. 

Sally: Culper?

Robert: They’re code names. I used one for you too: “355,” which means “lady” in our secret code. That way, if our letters fall into enemy hands, nobody will know who we are.

Sally: I hope you’re right.

Jim McMahon/Mapman ®

The Culper Spies’ Route

  1. Robert Townsend gathered information in New York CIty.
  2. Abraham Woodhull brought the information to Long Island, where he passed it along to Caleb Brewster in a cove off Long Island Sound.
  3. Caleb Brewster rowed across the Sound and delivered the information to Benjamin Tallmadge in Connecticut.
  4. Benjamin Tallmadge brought the information to George Washington’s headquarters.

Scene 4
Long Island | Later that night

N2: On Long Island, Abraham sneaks to the shore of a dark cove.

N3: A big, bearded man in a boat slips out of the shadows.

Abraham (handing over the letter): Caleb, you know where to take this. And be careful—the British ships are everywhere tonight.

Caleb Brewster: Don’t worry, Abe. The Brits are no match for the Culper spies.

N1: Caleb rows across Long Island Sound to Connecticut, where another man waits.

Caleb: Here you go, boss.

Benjamin Tallmadge (taking the letter): Thank you, old friend. I’ll bring this straight to the general.

N2: A few hours later, Benjamin arrives at Washington’s camp.

Benjamin: Sir, my spies say the British are planning to attack Rhode Island this week.

George Washington (frowning): Rhode Island? The British have not been active there. Do you trust this report?

Benjamin: Well, it’s from a new spy . . . a woman they’re calling 355. But Culper Junior swears she’s reliable. 

Washington: Fine. Have orders sent at once: more soldiers to Rhode Island!

Scene 5
The Townsend Home
Long Island | August 1780

N3: A week later, Sally sees Major André arrive and head up to Colonel Simcoe’s room.

N1: When the door closes, she tiptoes near and peers through the keyhole.

André: Simcoe, the Americans in Rhode Island seemed to have known we were coming. We couldn’t even attempt an attack. 

Simcoe: Someone must have told them our plan. But who?

André: It doesn’t matter now. We have a new goal. We’re going to capture West Point.

Simcoe: How? It’s the Americans’ most important fort. And Benedict Arnold, their star commander, is in charge there.

André (laughing): Here’s how.

N2: As Sally watches, André shows Simcoe a letter and says something she cannot hear. 

N3: Simcoe grins and tucks the letter inside a book, hiding it in a desk drawer.

N1: When André turns to leave, Sally hurries downstairs.

N2: But later, after they’re gone, she sneaks into Simcoe’s room.

N3: She finds the book with the letter.

Sally (reading): “Mr. Anderson, I will soon be ready to hand over the prize. As discussed, I expect 20,000 pounds in exchange.” Wow, that’s a lot of money.

N1: Sally copies the note onto a scrap of paper and slips it inside her sleeve.

Sally: I must get this to Robert at once.

Scene 6
Long Island, New York | That night

N2: Later that evening, Sally rides swiftly toward New York City.

N3: Suddenly, she hears a man’s voice.

Soldier 1: Halt! Halt, I say.

N1: Sally pulls her horse to a stop as two British soldiers approach.  

N2: Inside Sally’s sleeve, she can feel the scrap of paper poking her skin.

Soldier 2: Where is a young lady such as yourself going so late? And in such a hurry?

N3: Sally’s heart pounds. What if the soldiers find the letter and realize she’s a spy?

N1: Sally forces herself to laugh. 

Sally: Oh officers, I’m a silly goose. I’m having a party tomorrow, and I forgot to buy the tea! 

Soldier 1: Where will you buy tea at this hour?

Sally: My brother’s shop, in the city. He’s waiting for me.  

N2: The two soldiers look at each other. Sally holds her breath.

Soldier 2 (to Soldier 1): She looks harmless. (to Sally) All right, miss, on your way.

N3: Sally rides away.

Sally (to herself): Phew. That was close. Too close.

Illustrations by Patrick Faricy

Scene 7
Connecticut | A few days later

N1: Benjamin is pacing back and forth, Abraham and Caleb by his side.

Benjamin: I trust 355, but why would the British attack West Point? We have so many soldiers guarding that fort. And this strange letter about the 20,000 pounds—

N2: Just then, an American scout arrives, dragging a man with his hands tied behind his back. The man’s clothes are torn, and his face is caked with dirt.

N3: It’s Major André, but no one recognizes him.

Scout: We found him in the forest near West Point, sir. He had these maps of the fort stuffed in his boot! He refuses to talk. But his name must be John Anderson, because he was carrying this note. 

Abraham (reading): “Please allow this man, John Anderson, to travel safely to West Point to meet me.” It’s signed by Benedict Arnold himself.

Benjamin: Hmm. The letter 355 found was addressed to a Mr. Anderson, offering him a prize. Now we have a John Anderson carrying hidden maps of West Point. And a special note from Benedict Arnold . . .

N1: Benjamin’s eyes light up with understanding, and he claps a hand to his forehead.

Benjamin: I fear Benedict Arnold has betrayed us. Arnold must be the one who wrote the letter to Anderson. The “prize” in the letter is West Point. 

Abraham: He’s planning to help the British capture the fort . . . in exchange for 20,000 pounds!

Benjamin: Yes. And I’ve never heard of a John Anderson. But I do know a Major John André—head of the British spy ring! Major André, I suspect it’s you under all that dirt? 

André (quietly): Clever.

Caleb (grinning): Yeah, I’d say we are.

Abraham: Enough! Washington will deal with him. Let’s take him to the general’s camp now.

Benjamin: And let’s go by West Point and pick up Benedict Arnold. I’m sure General Washington will want to hear how his star commander has been secretly working for the British.

Scene 8
A Tavern on Long Island | April 1783

N2: Though Benedict Arnold managed to escape, the British plan to take West Point was foiled.

N3: The Culper spy ring gave Washington vital information that helped the American army win the war for independence.

N1: Three years later, with the war over, Sally, Robert, Benjamin, Abraham, and Caleb gather at a tavern to celebrate.

N2: As they joke and laugh, General Washington walks in. 

Washington: Ah, the Culper spy ring! Finally, I get to thank you in person.

N3: Washington’s eyes turn to Sally.

Washington: You must be 355. Without you, Rhode Island would have been lost and West Point captured. 

Sally: It took all of us, sir.

Washington (to the group): History may not remember your names . . . but I will. We would not have won this war without you.

Benjamin (raising a glass): To freedom!

Everyone: To freedom!

Write to Win

Pretend you’re Sally. Write a top secret diary entry telling why you decided to become a spy. Use details from the play to explain what you did and why you are good at this job. Send your entry to “Spy Contest” by December 15, 2023. Five winners will each receive copy of Sophia's War by Avi. Visit the Storyworks Contests page for more information.

This play was originally published in the October/November 2023 issue.  


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Step-by-Step Lesson Plan

Table of Contents

1. Preparing to Read

2. Reading and Discussing

SEL Focus, Close Reading, Critical Thinking

3. Skill Building and Writing

4. Differentiate and Customize

Striving Readers, Advanced Readers, Multilingual Learners

5. Can’t-Miss Teaching Extras

6. Literature Connections

1. Preparing to Read

Build Background, Preview Vocabulary, and Set a Purpose for Reading

  • The American Revolution is a broad and important topic that students may or may not have previously studied. To help you teach this play in context, we’ve prepared some special resources to build kids’ knowledge and vocabulary around the Revolution.
  • Start by showing the Vocabulary Slideshow. Note that it presents key words for talking about the American Revolution; not all of them appear in the play.
  • Build background knowledge by showing students the slideshow “Timeline of the American Revolution.” It will introduce students to important events before, during, and after the Revolutionary War.
  • Preview challenging vocabulary from the play with our Vocabulary Skill Builder. Highlighted terms: betrayed, cause, colonies, commander, cove, foiled, loyal, reliable, scout, vital.
  • Call on a volunteer to read the Up Close box on page 22.

2. Reading the Play

Author’s Note From Allison Friedman:

All the characters in this play are based on real people, and the events are based on the real-life adventures of the Culper Spy Ring. Most of the Culper spies were childhood friends who grew up together on Long Island in the town of Setauket, so they knew they could trust one another. The spies really did help thwart an attack on Rhode Island and unmask Benedict Arnold as a traitor. But even 250 years later, many mysteries about the ring remain—including the identity of 355, the group’s lady spy. Some have speculated that she was Sally Townsend, Robert Townsend’s younger sister, and this is the theory that inspired our main character. Maybe your students will want to read more about the spy ring and develop theories of their own!

  • Assign parts and read the play aloud as a class or in small groups. Students can also listen to our Author Read-Aloud of the play as a first read. Note that larger speaking roles are marked with an asterisk in the character box on page 23; the smaller roles can be a good fit for students who feel less comfortable reading aloud in class.
  • After reading, put students in small groups to discuss the close-reading questions. Then talk about the critical-thinking questions as a class. 

Close-Reading Questions

  1. Based on the Prologue, what is happening in the American Colonies during the time this play takes place? (setting) The American Colonies are at war with Britain. They are fighting to free themselves from British rule.
  2. Reread Scene 1. Why are British soldiers staying in the home of the Townsend family? How does Sally Townsend feel about this? (key details) The British captured New York City and are staying in the nearby homes of people who are loyal to Britain, like Sally’s family. Sally is unhappy about the soldiers in her home. They’ve taken over the family’s house, are constantly ordering the Townsends to do things for them, and have chopped down the Townsends’ apple trees. 
  3. Explain what Robert Townsend means when he says, “Sometimes it’s worth risking everything for a cause you believe in.” (interpreting text) Robert means that some beliefs are important enough for people to fight for, even if doing so puts them in danger. Robert feels that America’s freedom is this kind of cause. He’s willing to risk jail, or even death, to spy on the British and help America win the war.
  4. Reread Scene 2. After Sally overhears that the British plan to attack Rhode Island, why does she decide to tell Robert? (character’s motivation) Looking at her father’s destroyed orchard, Sally decides that her brother is right: The colonists will never be free of the British unless America wins the war. Sally decides that she must tell her brother what she overheard to try to help the American army.
  5. In Scene 3, what do we learn about the spy ring that Robert is part of? (key details) We learn that the spy ring uses invisible ink to pass along messages secretly and code names to keep enemies from knowing who they are. Also, we learn that Sally’s code name is 355, the spy ring’s code for lady, and Robert’s is Culper Junior.
  6. How does the information Sally overhears in Scene 2 affect George Washington in Scene 4? (cause and effect) At first, Washington wonders whether the information about the British plan to attack Rhode Island is correct. After all, there weren't many British soldiers active in Rhode Island at the time. But he decides to trust the information when he hears that Culper Junior says it’s reliable. He sends more soldiers to Rhode Island to help defend against any British attack. 
  7. Compare Sally’s actions in Scene 5 with her actions in Scene 2. How is the second time she spies on Colonel Simcoe and Major André different from the first? (compare and contrast) In Scene 5, Sally tries to find out what Simcoe and André are planning, so she listens at the door on purpose and looks through the keyhole to find out. She later bravely sneaks into Simcoe’s room to read and copy the letter André showed to Simcoe. In Scene 2, Sally  happens to be outside the door cleaning and accidentally overhears the two men. She’s not trying to spy on them. At this point, she’s not sure what to do after overhearing the British plans but, finally, decides to tell her brother. In Scene 5, Sally knows immediately that she needs to get the information to her brother as quickly as possible.
  8. In Scene 6, why does Sally call herself “a silly goose”? (character) Sally calls herself this to convince the British soldiers who stop her that she’s not a threat and they don’t need to search her. She wants them to believe that she’s a silly girl who cares only about getting tea for her party. 
  9. Reread Scene 7. Explain who the captured man is and what his plans were. (plot) The captured man is Major André in disguise as John Anderson. André was planning to work with the American traitor Benedict Arnold to capture the fort at West Point. 
  10. In Scene 8, when Washington thanks Sally for saving Rhode Island and West Point, she responds, “It took all of us, sir.” How is Sally’s response supported by the map and caption on page 25? (text features) The map and its caption show how the Culper Spies worked together to pass along messages. 

 

 

Critical-Thinking Questions

 

  • Think about how British soldiers react to Sally throughout the play. How is being a young girl helpful to Sally as she spies? Explain using evidence from the text. (character) Being a young girl is helpful because it leads the British soldiers to assume Sally isn’t a threat. It makes it easier for her to spy without getting caught. In Scene 2, André says, “Ah, it’s just the girl” when he and Simcoe discover her on the other side of the door. And the British soldiers in Scene 6 decide not to search Sally because they think “she looks harmless.”
  • Near the end of the play, Washington says, “We would not have won this war without you.” How does his statement connect to what we learn in the Prologue? (author’s craft) In the Prologue, we learn that the British Army was very powerful and that the Americans were unlikely to beat them through strength alone. Washington would need to know what the British were planning so he could outsmart them. Spies, like those in the Culper Spy Ring, were critical for winning the war. 

 

 

3. Skill Building and Writing

Featured Skill: Character’s Motivations

 

  • Distribute or digitally assign the Character’s Motivations Skill Builder. Have students complete it independently or with a partner. This skill builder will help prepare students to respond to the writing prompt on page 27. Then you can send their work to our writing contest (see page 2 of the magazine for details)!

 

Science Connection: Make Your Own Invisible Ink

 

6. NEW! Literature Connection

Differentiate and Customize
For Striving Readers

Like many spy stories, this one includes secret plans, double crosses, and disguises. To support striving readers in keeping track of the characters and the plot, gather students to read the play in a small group. Assign parts, taking some of the parts for yourself, or play the Author Read-Aloud as students follow along. Pause at the end of each scene and have students turn and talk with a partner about what happened in it. Clarify any parts students are confused about by guiding them to reread and locate where comprehension is breaking down; for example, not knowing a word’s meaning or not making a connection to what happened earlier.

For Advanced Readers

Read the Author’s Note from the Reading the Play section of this lesson plan to students. Have them research the Culper Spy Ring in pairs or small groups and come up with a theory about who 355 was. They should then create a presentation on their theory and what they learned that supports it. 

For Multilingual Learners

Gauge your multilingual learners’ knowledge of the American Revolution and work with them to build on it, as needed. Use the Vocabulary Slideshow and Timeline of the American Revolution for learning about this time in American history.

Can't-Miss Teaching Extras
Explore the Storyworks Archive

Let students discover more about the American Revolution with our thrilling nonfiction article “Blood, Smoke, and Freedom” from our March/April 2018 issue. Be sure to check out the Resources tab to find a “Virtual Field Trip to the Museum of the American Revolution,” hosted by Lauren Tarshis.

Read More About Spying During the Revolution

Spend time at the website of George Washington’s home, Mount Vernon, where you’ll find an online collection of primary and secondary sources (including the Culper Spy Ring Code), interactive tours and games, videos, and information about spying during the Revolution, among many other captivating resources.

Meet the Members of the Culper Spy Ring

Go to the national Intelligence Community’s website, where you’ll meet the members of the Culper Spy Ring and learn more about how they helped Washington win the war.

Practice Spycraft

The Spy Museum’s website has a page dedicated to activities useful for spies, like how to crack a secret code or create your own spy gadget. 

Text-to-Speech