'The Legend of Sleepy Hollow' Essay and Discussion Questions

"The Legend of Sleepy Hollow" tells the fictional story of Ichabod Crane, a schoolteacher who competes with another suitor for the hand of Katrina Van Tassel. However, instead of getting the girl, Crane ends up experiencing a very strange and spooky event.

Written by Washington Irving, the short story was first published in 1820 and continues to be a popular Halloween tale today, especially because it includes a ghost story about a mysterious headless horseman. 

A short piece of gothic literature filled with pranks and humor, "The Legend of Sleepy Hollow" is one of Irving's most enduring works. While the story prompts scares and laughs, it also warrants discussion and literary analysis. Here are a few questions about "The Legend of Sleepy Hollow" that you can use for study or conversation. 

Essay and Discussion Ideas

• What is important about the title?
• What are the conflicts found throughout the story? 
• How does Irving reveal character?
• What are some of the themes? How do they relate to the plot and characters?
• Is Ichabod Crane consistent in his actions? Is he a fully developed character? Why?
• Do you find the characters likable? Are the characters persons you would want to meet?
• Discuss some of the symbols in the story.
• Compare "The Devil and Tom Walker" with "The Legend of Sleepy Hollow." What is similar and what is different in terms of plot, storytelling, and themes?
• What is the primary purpose of the story? Do you find the purpose important or meaningful?
• How essential is the setting to the story? Could the story have taken place anywhere else? Does the setting represent or allude something?
• What supernatural or surprising events are employed by Washington Irving? Do you find these happenings believable?
• What is the role of women? 
• Does the story end the way you expected? Why?
• Would you recommend the story to a friend?
• Would you read other works by Washington Irving based on your reading of this story?