The Legend of Sleepy Hollow Lesson Plans | The Headless Horseman Book

"The Legend of Sleepy Hollow" by Washington Irving is one of the oldest American stories still regularly taught in schools. While this tale is often thought of as "scary", it actually contains a great deal of humor and thoughtfulness. Students will enjoy reading the characterization of Ichabod Crane and the origins of his legendary encounter with the Headless Horseman.

Student Activities for The Legend of Sleepy Hollow

Essential Questions for "The Legend of Sleepy Hollow"

  1. How do emotions affect our perceptions?
  2. How does the author use description to set the mood of a setting?
  3. What are superstitions? How are legends made?


Stories seem to survive year after year in every school about previous students and teachers. People tell stories all the time and exaggeration is common. Many times the fish was "this big" at each telling, but the space between the outstretched hands always seem to grow. There are neighborhood stories about a "witch" who lives alone on the hill. A story is all it takes to start a legend.

Legends are all around us. A legend is a story that has been passed down repeatedly, usually with exaggerated information. Legends are based on a real person, place, or event, and typically involve fantastic feats of some kind. Johnny Appleseed, King Arthur, and Robin Hood all have legends associated with them. While they were real people in a fixed time period, the stories passed down about them have obvious elements of fiction and fantasy.

Legends begin as a real story - though the facts may be a bit muddy even from the start. Legends grow and change with every telling. Sometimes changes are made or exaggerated to make the tale more exciting to those who hear it, or to teach a lesson. In this story, Washington Irving relates the start of a new legend, "The Legend of Sleepy Hollow".

Additional Activity Ideas for "The Legend of Sleepy Hollow"

  1. Create a graphic novel version of the story.

  2. Rewrite the story from the point of view of Ichabod Crane (or Brom Bones).

  3. Compare and contrast the characterizations of Ichabod Crane and Brom Bones in a T-Chart.

  4. Create a storyboard that illustrates Ichabod's imaginativeness with evidence from the text.

  5. Explore and depict themes, motifs, and symbols.

  6. Examine Irving's use of humor in the text by creating comic strips.

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