The Legend of Sleepy Hollow Easy Halloween Lesson Plan


Many of our middle school students will be familiar with The Legend of Sleepy Hollow. With all the many film and television adaptations that have been produced over the years, many of them have been exposed to the story!

However, many of them have not read the actual text! Why? Well, Washington Irving seems to like his long description and silver-tongued vocabulary. In short, it’s a tough read for many middle school students.

That said, you know I’ve got your back!

Simplified Adaptation of The Legend of Sleepy Hollow

Now included as part of my The Legend of Sleepy Hollow resource, you will receive a simplified version of Irving’s short story. This adaptation remains true to the original story, but tones down some of the difficult early 19th century language. This more accessible version will allow students to dive deep into literary analysis!


In my classroom, I like to use this story to take a look at the characters and Irving’s use of characterization. I ask my students to examine closely the characters of Ichabod Crane, Brom Bones, Katrina Van Tassel, and The Headless Horseman.

Students also work on their paragraph writing skills as they write a character sketch for each! As a bonus, I’ve also included a context clue vocabulary assignment for students to practice identifying unknown words!

This is such a fun way to incorporate a little spookiness into your classroom this fall season! I love the way holiday lesson plans seem to engage students–even the reluctant ones–in learning on a deeper level!

If you’re looking for more spooky short story fun, check out the bundle!

Until next time,

Brenna (Mrs. Nelson)