A horseman without a head riding through the woods
Gary Hanna

The Legend of Sleepy Hollow

Ichabod Crane, Brom Bones, and the Headless Horseman come to life in this fun adaptation of the classic American tale. It’s paired with a text about life in 1790, the year the legend takes place.

By Washington Irving
From the Issue

Learning Objective: Students will make inferences about characters’ actions and motivations.

Guided Reading Level: U
DRA Level: 50

Scene 1

Knickerbocker: I was never one for ghost stories—not until I happened upon a village called Sleepy Hollow. It’s a dreamy place—a place of superstitions. It was here I heard about a man named Ichabod Crane.

N1: A lanky fellow enters, absentmindedly whistling. His long nose is buried in a book.

Knickerbocker: Ichabod was very tall, with long arms and hands that dangled a mile out of his sleeves. His head was small, with huge ears and big green eyes.

N2: Two old women shuffle by.

Martha: Good day, Schoolmaster.

Ichabod (startled): Why, good day, ladies.

Ida: You seem quite interested in your book.

Ichabod: Yes, A History of Witchcraft. It’s fascinating.

Martha: We’ve no witches here, only ghosts.

Ida: Did you hear the Wailing Widow last night?

Ichabod: No, but I did hear the wind in the trees.

Martha: That wasn’t the wind. That was the widow’s ghost. She always shrieks when a terrible storm is coming.

N3: The women walk on. Ichabod looks up at the darkening sky and shivers.

STEVE STANKIEWICZ

Washington Irving may have gotten his idea for “The Legend of Sleepy Hollow” when he was just 15 years old. Yellow fever, a deadly disease, was spreading through cities. So his parents sent him from their home in New York City to a friend’s house in Tarry Town, a small village on the Hudson River. Irving fell in love with the region, including its Dutch-American people and their many ghost stories.

Scene 2

N1: At the Van Tassels’ mansion, Ichabod has just given a singing lesson to Katrina.

Katrina: Would you like to stay for tea?

Ichabod: I would be delighted.

N2: While Katrina pours tea, Ichabod devours a big slice of honey cake.

Katrina: So . . . are you enjoying Sleepy Hollow?

Ichabod (with his mouth full): Yes, quite.

Katrina: And where are you staying this week?

Ichabod: With the Van Rippers.

Katrina: You don’t mind going from place to place, carrying all your belongings?

Ichabod (blushing)Alas, that is the life of a schoolmaster. My wages are so low that I must rely on the kindness of my students’ parents to house and feed me.

N3: Ichabod is interrupted by the thundering of hooves. Katrina leaps up.

Katrina: That must be Brom Bones, come to take me riding. His black horse, Daredevil, is the finest in the valley!

N1: Ichabod looks at Katrina adoringly as she dashes off.

Scene 3

N2: Ichabod eats dinner with his host, Mr. Van Ripper.

Ichabod: Katrina and her father are having a party tonight. Should I attend?

Van Ripper: Of course. Why wouldn’t you?

Ichabod: Well, Brom Bones will be there. He said if he caught me near Katrina, he’d flatten me like a pancake.

Van Ripper (laughing): Brom may be rough, but he’s just a joker. Still, once he began courting Katrina, no other fellow dared come near.

Ichabod: Well, I’m merely giving Katrina singing lessons. But I can’t help noticing her many charms.

Van Ripper: And that her family has quite a fortune.

Ichabod: I suppose Brom should have some competition, don’t you think?

Van Ripper: Sure. You’re a worthy lad. Take my old horse, Gunpowder, and go to the party.

GARY HANNA

GHOSTS OF THE WAR

In 1790, when this tale takes place, America was a brand new country. It had just won independence from Great Britain in the American Revolution. Many ghost stories of the time had to do with losses suffered during the war.

Scene 4

N3: Ichabod arrives at the party.

N1: Wide-eyed, he stares at the table laden with ginger cakes and pumpkin pies.

N2: Ichabod sinks his teeth into an apple pastry. Sugar falls down the front of his suit.

N3: Just then, a broad-shouldered man struts into the room.

N1: He and Ichabod lock eyes.

Ichabod (coldly): Good evening, Brom Bones.

Brom (coldly): Ichabod.

Martha: That Brom Bones looks ready for a fight.

Ida: Come, now. Brom is more mischievous than mean.

N2: Brom walks up to Katrina.

Brom: What is that overgrown grasshopper doing here?

Katrina: The schoolmaster? He’s an honored guest.

Brom: Ha! Honored guest? He’s got dinner plates where his ears should be and shovels for feet.

Katrina: Oh Brom, you’re just jealous.

Scene 5

N3: The guests dance merrily to the lively sounds of a fiddle.

Ichabod: Dear Katrina, may I have this dance?

N1: Katrina glances slyly at Brom.

Katrina: Why certainly, Mr. Crane.

N2: As Ichabod dances, his long limbs fly around the room like an octopus in a tornado.

N3: Katrina laughs with delight. As she spins, she sees Brom Bones brooding in the corner.

Scene 6

N1: Later that night, Ichabod joins a group of guests by the fire.

Martha: In these parts, Mr. Crane, you must take care to be a decent person. Those who don’t are carried away by ghouls in the night.

Jansen: Oh yes, many ghosts haunt Sleepy Hollow. There’s the old Dutchman who walks the docks—

Hans: —and the woman in white. You can hear her crying on cold nights.

Jansen: But no ghost compares to the Headless Horseman.

Ichabod (trembling): W-w-who?

Jansen: The Headless Horseman. He is said to be the ghost of a soldier whose head was blown clean off by a cannonball during the Revolutionary War.

Martha: His body is buried in the churchyard. Every night he rides in search of his head.

Ida: He cannot rest until he finds it, so take care not to be on the roadway at the witching hour!

Brouwer: I once met him on the road. I called to him: “Show me your face, good man.”

N2: The room is silent. All are listening.

Brouwer: When he turned, there was nothing there—only the stump of a neck.

Ichabod: Heavens!

Brouwer: He pulled me up onto his horse.

N3: Brouwer takes a bite out of his apple and chews it slowly.

Ichabod (gulping): What happened next?

Brouwer: We galloped over hill and swamp. We reached the old church bridge. That’s when the Horseman . . .

Ichabod: What? When the Horseman what?!

Brouwer: He turned into a skeleton, threw me into the brook, and with a clap of thunder, sprang over the treetops!

Ichabod: Oh my!

Brouwer: I will never forget it.

N1: Brom rises, and all eyes turn to him.

Brom: I too have seen the Headless Horseman. I was coming home one night when he rode by.

Jansen: What did you do?

Brom: I wasn’t afraid. I offered to race him for a glass of cider.

Ida: Well, did you win?

Brom: I would have won. But just as we came to the old church bridge, the Horseman vanished in a flash of fire.

Martha: Ah yes! It is said that the Horseman cannot pass the old church bridge.

Brom (looking at Ichabod): So if the Horseman comes after you, head for the bridge. If only you can reach the bridge, you will be safe.

GARY HANNA

Scene 7

N2: On his way home that night, Ichabod, pale as a tombstone, trots along on Gunpowder. The shadows are long in the moonlight.

Wolf: Ah-rooooooo!

N3: Ichabod flinches.

Ida (offstage): Take care not to be on the roadway at the witching hour!

Ichabod: Keep it together, Ichabod.

N1: Suddenly, there is a rustling in the bushes.

N2: Something huge appears in the shadows.

Martha (offstage): Every night he rides in search of his head.

N3: Ichabod’s hands tremble as he clutches the reins.

Ichabod: Who’s there?

N1: The figure is atop a powerful black horse.

Ichabod: I say, s-s-s-sir, who are you?

N2: The figure does not respond. Ichabod kicks Gunpowder, and the horse takes off.

N3: When Ichabod looks back over his shoulder, he is horror-struck by what he sees chasing him.

Whole Class: The Headless Horseman!

N1: The head that should be resting on his shoulders hangs from the saddle in the form of a fiery jack-o’-lantern!

Ichabod: Fly, Gunpowder, fly!

N2: Away they dash, sparks flashing under Gunpowder’s hooves.

Brom (offstage): If only you can reach the bridge, you will be safe.

Ichabod: The church bridge!

N3: Ichabod cracks his whip wildly in the air.

Ichabod: Hyaw, hyaw! Come on, Gunpowder!

N1: Gunpowder’s hooves pound as they cross the bridge. Ichabod looks back again, expecting the Headless Horseman to vanish. Instead, he sees the ghoul raise an arm and hurl its head . . . at him!

Ichabod: Ahhhhhhhhhh!

N2: All goes dark.

Scene 8

N3: Several months later, guests gather for the wedding of Brom Bones and Katrina Van Tassel.

N1: The villagers sit by the fire telling tales to the new schoolmaster.

Brouwer: The next morning, Gunpowder wandered home, but Ichabod did not return.

New Schoolmaster: What happened to him?

Jansen: Nobody knows. A search led to the bridge. Ichabod’s hat was found next to the brook, and close beside it, a shattered pumpkin.

N2: Brom Bones chuckles to himself.

Ida: Mr. Crane was never found.

Hans: It is said that on quiet evenings, you can hear the ghost of Ichabod Crane whistling near the schoolhouse.

N3: Knickerbocker walks onstage.

Knickerbocker: Others heard that Ichabod was alive and well—just scared out of town by the ghost. They suspected that perhaps Brom Bones knew more of this matter than he chose to tell. 

If You Lived in Sleepy Hollow 

It’s 1790. You’re 10 years old. And sorry, you kind of smell.

By Adee Braun

STEVE MACKAY PHOTOGRAPHY/GETTY IMAGES

It’s dark outside when you wake up. Your two little brothers are still sleeping on the narrow straw mattress you share.

You shake them awake, then groggily get dressed. Your clothes smell as bad as they look: rough brown pants, a grimy shirt, a simple wool vest that your sister made, and a coat to keep out the autumn chill. Your leather boots are caked in mud and cow dung.

Normally you would be heading to school, but it’s harvest time, and your whole family must pitch in to gather wheat from the fields.   

You miss going to your one-room schoolhouse. You like learning about the American Revolution and all the battles that were fought in the Hudson River Valley, where you live.

Sometimes your teacher comes over for dinner and entertains you with thrilling stories about General George Washington. You remember the blasting cannons and ringing bells when Washington was elected president last year—the first president of the brand-new United States of America!

Working the Land

Your mother calls you in Dutch to come eat breakfast. (Your family came here from the Netherlands 130 years ago when New York was still a Dutch colony, and your family speaks English and Dutch.) After you eat, you grab your sickle and head to the fields. Reaping is hard work, and by noon, you’re tired and sweaty.

Thankfully, it’s time for a well-earned meal of bread, turnips, cabbage, and porridge with grated cheese that your mother makes from the milk of your cows. (She keeps the best cheeses to sell at market.)

When you were little, you and your friends would play in the woods, pretending to be soldiers of the Continental Army. Now that you’re older, your time in the woods is spent fishing and hunting with your dad. But there’s no time for hunting or fishing today.

Ghost Stories

At the day’s end, your family gathers for a simple meal. After supper, you and your brothers sit by the fire, telling ghost stories. If she isn’t too tired, your mother will sing an old Dutch folk song.

As a bright moon rises, you drag your weary body to bed. You drift off to sleep to the sound of the wheat fields rustling in the wind.

Activities (9) Download All Activities
Quizzes (2)
Quizzes (2)
Answer Key (2)
Answer Key (2)

More About the Story

Skills

text features, vocabulary, fluency, close reading, supporting details, figurative language, character’s motivation, foreshadowing, author’s craft, synthesizing, mood, narrative writing

Complexity Factors

Levels of Meaning

This play is a delightful take on a classic and chilling story about rivalry and superstition. The nonfiction essay provides background on the play’s setting by exploring what life was like for a child at that time.

Structure

The play is chronological. The essay, written in second-person present tense, describes a typical day in 1790 Sleepy Hollow.  

Language

The texts include some higher-level academic vocabulary, such as superstitions, mischievous, groggily, and reaping, as well as metaphors, similes, and hyperbole. 

Knowledge Demands 

The play and the essay are set in the late 18th century, which is likely to be unfamiliar to many students.

Step-by-Step Lesson Plan

1. Preparing to Read

Preview Text Features

  • The illustrations, map, captions, and informational text accompanying this play provide information about the time period in which the play takes place. Read these features together as a class.
  • Distribute our text features activity and have students complete it in small groups.

Introduce Vocabulary

  • Distribute our vocabulary activity sheet to preview challenging words and their meanings.
  • Highlighted terms: superstitions, lanky, wages, struts, mischievous, brooding, witching hour, clutches, reaping

Set a Purpose for Reading

  • Ask a volunteer to read aloud the Up Close box on page 17.

2. Reading the Play

Assign parts and read the play aloud as a class. Then discuss the first few close-reading questions as a class. Divide students into groups to answer the rest, along with the critical-thinking questions.

Close-Reading Questions (20 minutes, activity sheet online)

  • In the beginning of the play, Knickerbocker calls Sleepy Hollow “a place of superstitions.” What details support this statement? (supporting details) Ichabod is reading A History of Witchcraft; Ida and Martha tell him about ghosts in the town.
  • Why does Ichabod shiver at the end of Scene 1? What can you tell about him from this scene? (inference) He shivers because the darkening sky makes him think that the Wailing Widow’s ghost is nearby. You can tell that Ichabod believes in witches and ghosts, and he’s easily scared.
  • In Scenes 2 and 3, how do you know that Ichabod likes Katrina? What does Van Ripper suggest about why Ichabod might like her? (inference) In Scene 2, Ichabod looks at Katrina “adoringly.” In Scene 3, he says he has noticed “her many charms.” Van Ripper suggests that Ichabod likes her because her family is wealthy.
  • In Scene 4, Brom says that Ichabod has “dinner plates where his ears should be and shovels for feet.” What does he mean? Why might he be saying this? (figurative language/ inference) Brom means that Ichabod has huge, gawky ears and feet. Brom is probably jealous that Katrina is fond of Ichabod. He wants to make Katrina see Ichabod as unattractive.
  • When Ichabod asks Katrina to dance in Scene 5, she “glances slyly at Brom.” Why? (character’s motivation) She is enjoying the attention of both Ichabod and Brom, and she is having fun making Brom jealous.
  • How does Ichabod feel as he listens to ghost stories in Scene 6? What clues tell you this? (inference) He feels terrified. The stage directions say he is trembling and gulping, and he stutters as he says “W-w-who?” He responds to the stories with exclamations, including “Heavens!” “When the Horseman what?!” and “Oh my!”
  • Brom looks at Ichabod when he says “So if the Horseman comes after you, head for the bridge.” What hint does this line give about what will happen later? (foreshadowing) In the next scene, the Horseman does come after Ichabod, who heads for the bridge.The line also gives the reader a hint that Brom Bones might be involved in the chase.
  • In Scene 7, why do Ida, Martha, and Brom have lines from offstage? (author’s craft) These lines repeat what the characters said earlier; they are offstage to show that Ichabod is recalling their words and hearing them in his head.
  • Which parts of the article on page 21 are similar to what happens in the play? (synthesizing) The village teacher comes over for dinner; people enjoy telling ghost stories; they have memories of the Revolutionary War.

Critical-Thinking Question (activity sheet online)

  • Who do you think the Headless Horseman might be? What clues make you think so? (inference) The Headless Horseman is most likely Brom Bones. Some clues include: In Scenes 4 and 5, Brom shows that he is jealous of Ichabod, so he might have wanted to chase Ichabod away; in Scene 2, Katrina says that Brom has a black horse, and the Headless Horseman is “atop a powerful black horse”; in Scene 8, Brom chuckles when Jansen mentions the shattered pumpkin; at the end, Knickerbocker says that “perhaps Brom Bones knew more of this matter than he chose to tell.”
  • Do you find this play scary? Why or why not? (mood) Answers will vary. Some students will say yes, because the characters tell ghost stories and Scene 7 is very suspenseful with many scary details. Others will say no, because details in the play make it clear that the Headless Horseman is not real, it’s just Brom Bones.

3. Skill Building

Featured Skill: Inference

  • Distribute the inference activity. Have students complete it in small groups. It will prepare them to respond to the writing prompt on page 20.

Differentiate and Customize
For Struggling Readers

Work together with students to find clues in the play that suggest that Brom Bones is the Headless Horseman. Provide explicit explanations where necessary.

For Advanced Readers

Ask students to read “Rip Van Winkle,” also by Washington Irving. (You can find numerous versions adapted to their reading level.) Guide them to find similarities and differences between that story and “The Legend of Sleepy Hollow.”

Text-to-Speech