Teaching “The Legend of Sleepy Hollow” in the High School Classroom

2025 Halloween photo of myself as Ichabod Crane with the AP U.S. History teacher as the Headless Horseman

November 5, 2025

BY CHERYL WEAVER

“Irving is really haunting the text!”
—11th-grade student after class

I was initially uncertain about how to teach this text. Irving’s work had never appeared in any anthologies my district provided, and I hadn’t encountered Irving—at least in my memory (a Rip Van Winkle moment?)—until graduate school. I developed three main instructional objectives:

  • Thematic: The story serves as part of the narrative of a new nation, emphasizing identity as beyond the individual and situated within societal constructs.
  • Comprehension: Focus on Irving’s detailed descriptions of characters and settings, helping students understand why he invested so heavily in these descriptions.
  • Vocabulary: After reviewing the story, I identified a few words that might require additional support for my students.

Here’s an overview of the short plan I developed, incorporating various activities:

Day 1: Students were tired from taking the PSAT in the morning, so to introduce the story, I showed the 1949 Disney adaptation. We used a short worksheet to explore questions about the post-WW2 context and what this adaptation reveals about the United States at that time.

Days 2-4: I gave a brief PowerPoint presentation on Irving and began reading the story with the students. Using an “I do, we do, you do” approach, I read and annotated the text on the first day, having students note brief subtopics for each paragraph. This helped them practice organizing their writing. On the second day, we annotated together, and on the third day, students read and annotated a section individually. We concluded with a 20-question multiple-choice assessment to gauge their understanding and identify areas needing review.

On the last day, Halloween, I read the story’s conclusion dressed as Ichabod Crane. To strengthen cross-curricular connections, this unit aligned with the students’ AP U.S. History studies; their history teacher dressed as the Headless Horseman!

To further engage students and assess their understanding of the text’s connections, we started two class days with a game I designed. Topics included natural imagery, real and fictional characters, settings, and vocabulary, specifically focusing on last names and the term “cognomen” from “The Legend of Sleepy Hollow.”

Overall, students enjoyed the unit and made insightful connections between Irving’s role in crafting history and identity for the newly formed nation. One student remarked, “Irving is really haunting the text!”

Now, I’m beginning to introduce “Rip Van Winkle,” aiming for a culminating project where students can choose between a creative writing option, a traditional analysis essay, or a visual design incorporating elements of Irving’s story and themes.

I eagerly anticipate sharing my students’ creations with you!

Ichabod Crane in the Twenty-First Century High School Classroom

Photo by Cheryl Weaver

October 29, 2025

BY CHERYL WEAVER

“That all this might not be too onerous on…his rustic patrons, who are apt to consider…schoolmasters as mere drones.”

The first time I encountered Irving’s work—aside from vague childhood memories of Disney’s 1949 The Adventures of Ichabod and Mr. Toad and my young adult adoration of Tim Burton’s 1999 Sleepy Hollow—I sat enthralled as my graduate school American Lit professor regaled me with Irving’s importance. Who knew, I thought, as I considered the context of Irving’s Rip Van Winkle, that Irving’s project played such a role in creating an American cultural identity? Roughly ten years later, my interest in Irving reignited when I was awarded a fellowship through the Women’s History Institute at Historic Hudson Valley. My research centered on women’s letters and the United States Post Office, but archivist Catalina Hannan’s knowledge and enthusiasm for Irving piqued my interest once again.

At the May ALA conference, I attended a panel hosted by the Washington Irving Society and met the Society’s President, Tracy Hoffman. We spoke briefly at the WIS Business Meeting: she, thinking ahead about the direction of the Society, and I, puzzling out how I could contribute, turned to pedagogy—not an altogether drastic turn considering Ichabod Crane’s occupation. We made tentative plans to develop instructional materials and methods for engaging learners of all academic levels in the serious study of the author. Ideas began percolating in my mind about how I could fit Irving thematically into my current curriculum.

I teach Language and Literature at a public high school boasting a robust International Baccalaureate program. My students are academically successful, with the expected mischievous nature of young people. (There are a few young Brom Boneses in my midst—harmless, though boisterous.) I needed to hatch a plan to cover the author and share my own adoration of his work. But I had some fundamental questions to consider first.

What exactly do my high school students know about Irving? Sure, most are familiar with the broad strokes—a headless man atop a strong steed, knife in hand, roaring and galloping toward his frightened object desperate to escape across a bridge. But would they be interested in the original text? Further, how could I frame Irving within the parameters of my course and work on stronger cross-curricular planning?

And then it hit me.

Could I position Washington Irving as America’s first influencer? Could that be a starting point to engage my students in reading Irving’s text? Could my larger curricular focus on identity use Washington to consider individual, regional, and national identities and how those are formed?

Those questions frame the unit I’ve just begun on Irving’s stories, timed to coincide with the same historical period in my students’ course on U.S. History…and Halloween. A few days in, students seem to be receptive (more on that to come!), and I anxiously await their reaction when I appear in class on Friday as Crane before they head to their history class, taught by a certain headless horseman.