The Legend of Sleepy Hollow

Reading Check and Short Answer Questions on key plot points are designed for guided reading assignments, in-class review, formative assessment, quizzes, and more.

Reading Check

1. When did the Headless Horseman lose his head?

2. Why does the name “Crane” fit Ichabod so well?

3. Who is the author of Ichabod’s favorite book, “History of New England Witchcraft”?

4. How does Ichabod become acquainted with Katrina Van Tassel?

5. What was the prize for which Brom Bones supposedly raced the Headless Horseman?

6. Where does Ichabod first encounter the Headless Horseman?

7. Where did the old farmer encounter Ichabod several years after his disappearance from Sleepy Hollow?

Short Answer

Answer each question in at least 1 complete sentence. Incorporate details from the text to support your response.

1. Why is the setting of the story called “Sleepy Hollow”?

2. What is most attractive to Ichabod about Katrina?

3. What does the old farmer report about Ichabod’s life after leaving Sleepy Hollow?

Paired Resource 

“How Washington Irving Shaped Christmas in America”

• This resource explains how Washington Irving, best known for his contribution to the Halloween holiday, also had a profound influence on the celebration of Christmas in North America, inspired by Christmas celebrations he witnessed in England.
• The full text of Irving’s book Old Christmas is available here from Project Gutenberg.
• How do Irving’s Christmas stories compare in mood and tone to “The Legend of Sleepy Hollow”? How is each a fitting companion to the related holiday?

Recommended Next Reads 

“The Castle of Indolence” by James Thompson

• “The Legend of Sleepy Hollow” opens with a quotation from “The Castle of Indolence” Canto I, Stanza VI. This poem, written by the Scottish author James Thompson, is an example of the Romantic writing style.
• This poem provides an opportunity to compare the Romantic and American Gothic styles of writing.
• This work connects with the theme of Tradition Versus Change in American Gothic Horror.
• Shared topics include supernatural influences and landscape description.

“Rip Van Winkle” by Washington Irving

• This short story is also told by Diedrich Knickerbocker, the fictional historian who narrates “The Legend of Sleepy Hollow.”
• It establishes the character of Rip Van Winkle, a Dutch American man who falls under a spell and sleeps for twenty years in the Catskills before awakening.
• This story shares the theme of Dutch Colonization and Heritage in New York.
• Shared topics include “larger than life” characters, the Revolutionary War, supernatural influences, and landscape descriptions.