The Legend of Sleepy Hollow Lesson Plans

The Legend of Sleepy Hollow is a fun ghost story by early American writer Washington Irving. Read the whole story online at Project Gutenberg.

The Adventures of Ichabod and Mr. Toad includes Disney’s terrific cartoon version, voiced by Bing Crosby. It makes a great choice for Hallowe’en party entertainment, or to follow up a reading of the story.

In nDisney’s version of The Legend of Sleepy Hollow, schoolmaster Ichabod Crane seeks the hand of a wealthy landowner’s daughter. His rival, Brom Bones, is a local hero, a rough sportsman with a gang of friends who join him in bullying Ichabod Crane. At the end of a lavish harvest festival, Ichabod takes the chance of speaking to the girl he admires, is rejected, and leaves the party in a bad mood. He is chased by a headless horseman carrying a Jack o’ Lantern in place of a head, and disappears forever.

Washington Irving was also the author of Rip Van Winkle and an important contributor to the American image of Santa Claus.

Online resources

Lesson plans and resources available online:

  • Edsitement’s Sleepy Hollow lesson plan asks the question, “How did Washington Irving write a story that still captures audiences hundreds of years later?”
  • Identify subjects and predicates from the book’s sentences in an online grammar quiz.
  • A PDF file from Theater IV has a variety of worksheets and activity pages.
  • A package from Raz-Plus has activities and information, including what students should know about attending a live theater performance.

The Legend of Sleepy Hollow is a wonderful read aloud, filled with  marvelous descriptions and humor. Once you’ve read it, choose from these cross-curricular connections to extend the learning and the fun.


  • The important characters of this story are described in lively language, with lots of detail. Katrina van Tassel, the girl whom both Ichabod and Brom are courting, is described only in terms of her appearance, with a passage later about her parents suggesting that she might be spoiled. Have students flesh out the character of Katrina in a character sketch.
  • Many people have made plays from this story — your class can do it, too! Write and stage the play for your school, or film it for your class website.
  • While this story is accessible to younger readers, the vocabulary can really be challenging. Collect words from the story in a pocket chart or on chart paper and see how many new ones you can learn while you’re reading the story.

Social Studies

  • Sleepy Hollow is a real place, and the character of the place is important to the story. Irving says that the people of Sleepy Hollow are inclined to see ghosts, and says of visitors to the area, ” However wide awake they may have been before they entered that sleepy region, they are sure, in a little time, to inhale the witching influence of the air, and begin to grow imaginative, to dream dreams, and see apparitions.” There is no Google Earth Tour online yet for this story, so here’s your chance!
  • The Smithsonian has an intriguing lesson using “The Legend of Sleepy Hollow” to explore contagion. With Coronavirus still among us, this topic is often on our minds.
  • The life of a teacher during Colonial times (and after, in many areas) was difficult. Ichabod Crane, like most teachers, earned very little and was given a place to live by parents of his students. Things were different for students, too — not least because of the use of corporal punishment, which is described in the story. Use a Venn diagram to compare school in Irving’s day to your modern school.
  • Sleepy Hollow had lots of local ghost stories, the most exciting one being the story of the Headless Horseman. Have students research local ghost stories. If there are no local ghost stories where you live, discuss why that should be. Is Irving right in thinking that some places encourage superstitious attitudes? Is your town too new to have developed any ghost stories? This is a good opportunity for surveys and oral history projects.
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  1. I would like to access this information. When I click on the links it says page NOT FOUND.

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