Washington Irving Society

Wednesday, October 1, 2025

BY TRACY HOFFMAN

Several years ago, the Washington Irving Society posted the “31 Days of Washington Irving” on Instagram. I was thinking about that Instagram project, so for fun, I gave ChatGPT a prompt requesting the following: “Give me a description of 31 ways to teach ‘The Legend of Sleepy Hollow’ by Washington Irving.”

Certainly, my prompt could be better, as the first suggestion needs help: “Chapter Summaries.” Clearly, that’s not going to work, but students could still write quick summaries for each page of reading, since “The Legend of Sleepy Hollow” has no chapters.

Another suggestion “Rewrite the Ending” made me laugh since Irving already gives us a variety of endings. Maybe Brom Bones, disguised as the Headless Horseman, scares Ichabod away, as a traditional reading of the story, or maybe Katrina herself is the Headless Horsewoman, if you want to explore non-traditional options. Despite my chuckles, Washington Irving would probably appreciate students exploring other endings. I rather like the idea, now that I’ve thought about it for a few minutes.

Although a handful of individual assignments don’t make sense, the categorizing of lessons seems useful. ChatGPT suggests the following categories for teaching “The Legend of Sleepy Hollow”:
• Reading Comprehension & Analysis
• Creative Activities
• Literary & Historical Connections
• Critical Thinking & Writing

I’m left wondering how else I might group lessons. For one, I’d like a Theoretical Approaches category. If I had all the time in the world, both to plan 31 lessons on the story and also 31 days in a future classroom setting, I’d love to do a lesson on gender, one on race, disability studies, and more. ChatGPT’s category of “Reading Comprehension & Analysis” could apply to my additional idea, but I would still want to lump such lessons into their own category.

Another bucket for me would be Biography, if I were teaching a class solely on Washington Irving, with all the time in the world. You could potentially create one lesson on Irving’s biography as it applies to “The Legend of Sleepy Hollow,” even though most classrooms don’t have that kind of time. Of course, that could also tie into “Literary & Historical Connections.” In fact, that’s how ChatGPT organized one biographical suggestion.

ChatGPT also says in its response to my prompt, “These strategies work well in middle and high school English or literature classes.” I should check to see what this instrument says if I narrow the search to university classrooms.

I’m wondering how many high school students find “The Legend of Sleepy Hollow” approachable.  And I would be fascinated to see elementary or middle school students reading the original tale aloud or quietly, to find out how readily they can move through an Irving read.

Instead of scrutinizing all the suggestions, I’m going to narrow the list of 31 items to a shorter list of potential approaches to the story. Some may be suitable for your classroom and some may not, but I’ll throw out all the ones sparking my own interest:

1. Setting Study
   Examine the role of the Hudson Valley setting and how it contributes to the mood.
2. Tone & Mood Word Wall
   Build a wall of descriptive words used in the story and their effects.
3. Vocabulary in Context
   Pull archaic or challenging vocabulary from the story and practice using it.
4. News Report Assignment
   Students write or perform a colonial-era news report on Ichabod’s disappearance.
5. Sleepy Hollow Soundtrack
   Curate a music playlist that fits the story’s themes and tone.
6. Compare with Original Folktales
   Read German or Dutch folklore sources and discuss Irving’s influences.
7. Character Diary Entries
   Write diary entries from the point of view of Ichabod, Katrina, or Brom.
8. Create a Sleepy Hollow Map
   Design a map of the village and forest using textual clues.

I personally want to try the Sleepy Hollow Soundtrack idea. I should be playing appropriate music when students enter the classroom, or when I’m moving through PowerPoint slides. Letting one class put together a playlist and then letting another class listen to their choices could be a worthwhile activity. I love giving quizzes at the beginning of class, so I can also imagine adding an extra credit question on a “Sleepy Hollow” quiz: “Identify one song you can hear playing in the background of Irving’s short story.”

To be honest, I need to do more with German and Dutch folklore. On Monday, my Washington Irving class read “The Specter Bridegroom,” set in Germany. This afternoon, we are tackling “The Haunted House” and “Dolph Heyliger.” At the very least, I’ll introduce them to Reichart’s Washington Irving and Germany (1957). The next time I teach “The Legend of Sleepy Hollow,” I need to dig around for some Dutch folklore, too.

By the way, I have narrowed my ChatGPT search to include “in a university classroom,” and I’ll share my finds, with commentary, next Washington Irving Wednesday.