Lesson Plans: Grades 6-8

The Legend of Sleepy Hollow

Created September 17, 2010


The Lesson


The Legend of Sleepy Hollow

Washington Irving

Credit: Photograph courtesy of the Library of Congress

Washington Irving's tale of the Headless Horseman has become a Halloween classic, although few Americans celebrated that holiday when the story was new. In this unit, students explore the artistry that helped make Irving our nation's first literary master and ponder the mystery that now haunts every Halloween -- What happened to Ichabod Crane?

Guiding Questions

  • How does "The Legend of Sleepy Hollow" still capture the imagination of readers today?

Learning Objectives

After completing this lesson, students will be able to

  • Summarize the plot of "The Legend of Sleepy Hollow."
  • Adapt passages of "The Legend of Sleepy Hollow" for a contemporary audience.
  • Analyze the characterization of Ichabod Crane and Brom Bones in "The Legend of Sleepy Hollow."
  • Offer an imaginative response to the conclusion of "The Legend of Sleepy Hollow."

Preparation Instructions

  • This lesson plan consists of four learning activities that you can use together as a unit or adapt separately to your curricular needs.
  • Review the suggested activities, then download and duplicate any online materials you will need. If desired, you can bookmark specific web pages so that students can access relevant online materials directly.
  • For background on Washington Irving and additional teaching resources on "The Legend of Sleepy Hollow," visit these websites accessible through The Center for Liberal Arts on EDSITEment:

Lesson Activities

Activity 1. Introducing The Legend of Sleepy Hollow

Ask students to share what they already know about Washington Irving's "The Legend of Sleepy Hollow," which may be familiar to them from the film adaptation by Tim Burton or the animated version by Walt Disney. Then have students read the story, first published in 1820. Ask students to compare Irving's short story (one of the first examples of this genre) with the tale that has become part of American folklore. Consider, for example:

  • The proportions of humor and terror in Irving's telling.
    The "Legend" has gained a reputation as a ghost story over the years, but Irving shaped it as a comic tale of self-delusion leading to its own downfall. Ask students to point out "the scary parts" of the story. How scary are they in Irving's hands?
  • The prominence of the Headless Horseman in the original story.
    Hollywood has made this frightening apparition the signature image of the tale, yet Irving presents him as a creature of hearsay and foolish superstition who remains indistinct even when he finally appears. Ask students to point out descriptions of the Headless Horseman and evaluate his impact on the narrative.
  • The underlying dynamics of Irving's plot.
    At its core, the "Legend" is a fabliaux-like tale of rival suitors, with a suggestion that their affections are being manipulated by the lovely whom they both desire. And as in a fabliaux, appetite is the driving force behind the plot, in this case the appetites of Ichabod Crane -- for food, wealth, admiration, and romance. Ask students to summarize the story's plot from this point of view, as a chain of events set in motion by the ambitions of Ichabod Crane. Then examine the part suspense plays in the narrative. To what extent does this indispensable ingredient for a mystery advance the plot?
Activity 2. Language in The Legend of Sleepy Hollow

Though the story Irving tells in "The Legend of Sleepy Hollow" will be familiar to most students, many of the words he uses will likely puzzle them. In the first paragraph, for example, words like cove, denominate, implore, inveterate, propensity, vouch, advert, and repose may frustrate young readers. Take advantage of the print-out format that online texts make possible by having students underline unfamiliar words as they read "The Legend of Sleepy Hollow." Then divide the class into small groups, assigning a section of the story to each group, and have students use context clues and dictionaries to produce an annotated edition of the tale.

  • When students have shared and compared definitions, explore the contribution of hard and far-fetched words to Irving's style by having students re-write short passages of the story in the simpler, more direct manner a writer might use today. Talk about what is lost and gained in these transformations. To what extent does Irving's use of unusual terms serve to characterize the narrator of his story, creating an impression of voice and personality? To what extent does his style serve to keep readers at a distance from the story, inviting us to watch it unfold as informed observers rather than become emotionally involved?
Activity 3. Characters in The Legend of Sleepy Hollow

The two main characters of "The Legend of Sleepy Hollow," Ichabod Crane and his nemesis, Brom Bones, are often assumed to be figures of American folklore, although they are in fact Irving's original creations. Have students examine the techniques Irving uses to create the impression that these characters have a life of their own outside his story.

  • Compare Irving's descriptions of the two characters' physical appearance (Crane in paragraph 8, Brom Bones in paragraph 26). Call students' attention to the way Irving assembles a picture of Ichabod Crane out of separate elements, enhancing his ungainliness, while he presents Brom Bones in broader strokes, conveying an impression of energy and strength. Ask students to illustrate these passages to help them analyze Irving's literary technique, which produces a sharply drawn portrait on the one hand and a catalog of personal qualities on the other.
  • Compare the social frame Irving sets around his two main characters when they are introduced into the story. We see Ichabod Crane lording it over his pupils, accommodating the rustic families that take him in, showing off his singing talents and education for impressionable ladies, and trading superstitious tales with the local gossips (paragraphs 9-19). By contrast, Brom Bones comes into the story as the chief candidate for Katrina's love, the dominating figure in the community, and the leader of a pack of fun-loving friends (paragraph 26). Ask students how these associations play on our prejudices and color our opinions about the two characters.
  • Explore the contrasting values these two characters represent. Students might recognize them as those arch-rivals of youth culture, the nerd and the jock, but Ichabod and Brom can also be interpreted in terms of city culture and country life, the virtues of art and the vitality of nature, imagination and reality, wish and will, brains and brawn, or the outsider and the native son. Have students generate further points of contrast between these two characters in order to see how Irving has set them up as almost archetypal opposites across a range of value systems.
  • Finally, explore the students' response to these two characters. Point out that to some degree "The Legend of Sleepy Hollow" is the story of an underdog who goes up against the local hero. Do we pull for the underdog in this contest or enjoy the spectacle of his defeat? Do we side with the local hero or find ourselves drawn to the comical figure who will be his victim? Talk about the ways Irving manipulates our sympathies in his story, shading from ridicule of Ichabod toward a more affectionate point of view by letting us see more and more of the story through his eyes (for example, in paragraph 22, paragraphs 38 and 56, and at the story's climax in paragraphs 61-65).
Activity 4. Concluding The Legend of Sleepy Hollow

Irving ends "The Legend of Sleepy Hollow" with an air of mystery, leaving us to wonder if the Headless Horseman really did carry away Ichabod Crane. Few students, however, will doubt that the Headless Horseman was Brom Bones in disguise, and might consider Irving's conclusion an exercise in empty atmospherics. Yet there is a real mystery left unsolved at the end of the story: What happened to Ichabod Crane?

  • After we see him knocked from his horse by a flying pumpkin, Ichabod vanishes without a trace, though Irving gives us a rumor that he went on to become a lawyer and eventually a judge (paragraph 69). To sharpen students' analysis of Ichabod's character, ask them to evaluate this rumor: How plausible is it? How well does it square with what they know about Ichabod Crane?
  • Have students brainstorm their own solutions to Irving's mystery, imagining what could have happened to a character like Crane. Point out that his story is set "some thirty years" before its publication in 1820 (paragraph 8). What was happening in the United States at that time? What famous Americans might he have encountered? What historic events might he have witnessed? Encourage students to speculate boldly on the later career of this literary character, then have each student write a story about some episode in Ichabod Crane's life after "The Legend of Sleepy Hollow" or an imaginary obituary summing up what he made of himself after his fateful encounter with his own worst fears.

Extending The Lesson

Critics consider Washington Irving a pioneer of American humor, the first to capture the democratic spirit of ridicule that we later find in the work of Mark Twain. You can explore this aspect of American literature further with the EDSITEment lesson plan, "Mark Twain and American Humor," which focuses on Twain's story, "The Notorious Jumping Frog of Calaveras County," another tale of the outsider outsmarted by native wit, as well as stories by George Washington Harris and Nathaniel Hawthorne.

Selected EDSITEment Websites

The Basics

Time Required

4-5 class periods

Subject Areas
  • Literature and Language Arts > Place > American
  • Art and Culture > Subject Matter > Folklore
  • Literature and Language Arts > Genre > Fables, Fairy tales and Folklore
  • Critical analysis
  • Critical thinking
  • Interpretation
  • Making inferences and drawing conclusions