The Legend of Sleepy Hollow

Use these questions or activities to help gauge students’ familiarity with and spark their interest in the context of the work, giving them an entry point into the text itself.

Short Answer

1. “The Legend of Sleepy Hollow” is a popular Halloween ghost story. What would you consider some typical features of ghost stories? What tropes are often used in modern horror stories, shows, and movies? What about stories associated with Halloween? If a ghost story took place around Halloween in the 1700s in New York, what characteristics might it have that would make it different than modern ghost stories?

Teaching Suggestion: The final question of this prompt may provide an opportunity to better introduce the historical context of the story, which is important to understanding the plot and themes. These or similar resources may be helpful in providing additional information on the general setting, the origins of Halloween, and the local legend of the headless horseman. 

• In “What Was New Netherland?” the New Netherland Institute provides a brief history of Dutch colonization of North America to orient students to the historical context of the story.
• The article “The Headless Horseman” provides background on the likely origins of the legend of the headless horseman.
• The “Origins of Halloween” is an article on the origins of Halloween, including examples of headless ghosts or hunters.

2. “The Legend of Sleepy Hollow” is an example of the American Gothic genre. What characteristics are associated with Gothic literature, and what other stories might also fit into the same genre?

Teaching Suggestion: Students may be prompted with a list of other stories of the American Gothic genre, such as those written by Edgar Allan Poe or Nathaniel Hawthorne.

• This resource, “The American Gothic” by Dr. Kara Johnson for the Newberry Library, examines the foundations and characteristics of the American Gothic genre.

Personal Connection Prompt

This prompt can be used for in-class discussion, exploratory free-writing, or reflection homework before reading the story.

Ichabod Crane, the story’s protagonist, loves stories of ghosts, demons and witchcraft, only to be terrified to be out alone after dark. What ghost stories, monsters, myths, fairytales or stories do you find frightening (or did when you were a child)? What about them frightens you, and why do you still watch or read them? In these stories, is the suspense or the direct confrontation of the fear more frightening? Write an anecdote or a few paragraphs on your thoughts about scary stories.

Teaching Suggestion: Students might be interested to further explore the psychology behind a fascination with horror by reading and discussing the article below.

• This article by Haiyang Yang and Kuangjie Zhang discusses the psychological functions and appeal of horror and scary stories.