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 York State Library 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.