Activities for Teaching “The Legend of Sleepy Hollow” (Now part of a Secondary ELA Seasonal Blog Hop!)

“The Legend of Sleepy Hollow” is a ghostly story that commonly shows up in classrooms around Halloween.  There are a lot of ways to work with the text in the classroom.  It’s possible to stretch this story over a week with projects that analyze and examine the text as well as reach beyond it.


Activities for teaching “The Legend of Sleepy Hollow:”

Reading questions and graphic organizers provide a structured method of analysis.  The text can be challenging because of the old language and vocabulary.  Study the different ghost stories, compare Ichabod’s race with the horseman to the tales, or compare characters.

Include some differentiation by reading aloud to the class, finding an audio book version, or having students create a dramatic reading of the text.  (Bonus, have student’s create an audio version that you can use in later years.)

For an anticipatory set, students can discuss and/ or write about whether they believe in ghosts.  An expository essay about their own views– providing support on one side of the issue– is good practice at short, opinion-based essays (sometimes referred to as argumentative essays, as they lack research.)  Good practice as essay formation as well as making strong arguments.

Since there are many film versions of the story, comparing with all or part of one of the movies is an engaging higher-level-thinking activity.  The Disney version is a short, comical, animated film that fits well in the class.


Have students create a mobile or diorama of the food at the Van Tassel’s part or map the locations in and around Sleepy Hollow using details from the text.

Students can research then-and-now ideas related to the story, such as the town of Sleepy Hollow New York, or one-room school houses vs. modern schools.  Create a multimedia project their findings.

Analyze or discuss whether the story is a ghost story or a tale of a prank by Brom that ran Ichabod from town.  Students can take sides and argue their position.

The Headless Horseman’s Story is a fun writing project.  Students write from the point of view of the headless horseman, himself.  They’ll retell the chase with Icahabod but have creative freedom beyond that.  They may even decide if the horseman is a ghost or is Brom Bones playing a prank (both possible from the text.)


Group project ideas together to create a Choice Board or make Task Cards to provide student choice and engagement.  Or assign a whole-class project with resources and time available.  It’s a fun story with lots of opportunities to explore and examine.

These activities, and more, can be purchased in the money-saving bundle Legend of Sleepy Hollow Activity Bundle at my Teachers Pay Teachers Store.

Studying Rip Van Winkle?  Compare the two stories for similarities and differences.  Such as use of the supernatural and impact of setting.

Need other creepy stories for Halloween?  Or looking for a massive, money saving bundle full of Halloween activities?  Gotcha covered.

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7 Responses to Activities for Teaching “The Legend of Sleepy Hollow” (Now part of a Secondary ELA Seasonal Blog Hop!)

  1. Pingback: 5 Creepy Short Stories for Halloween – Ms. Dickson's Class

  2. Sherri says:

    “The Legend of Sleepy Hollow” was my favorite seasonal story when I was in middle school! I love all the activities and ideas you shared for this beloved classic!

  3. You can’t go wrong with this story! Students love reading stories from Washington Irving. Thanks for sharing.

  4. Always such a fun story to teach! Thanks for your ideas 🙂

  5. I have always LOVED “The Legend of Sleepy Hollow”. I always made it a part of my Halloween unit when I taught my enrichment class. My students loved reading the graphic novel version of it that I had. Thanks for sharing such great tips and ideas on how to successfully teach this class!

  6. Such great ideas for a legendary story. I especially love your writing ideas…what a cool way to incorporate student choice!

  7. Laura Torres says:

    I love the idea of a writing prompt on whether they believe in ghosts. That would make for some interesting reading!

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