Teaching The Legend of Sleepy Hollow

You are getting "Sleepy"...

  • Activities: 13
  • Quiz Questions: 34

Schools and Districts: We offer customized programs that won't break the bank. Get a quote.

Get a Quote

Nerdy boy meets pretty girl. Nerdy boy gets beat up by jock. Jock steals girl. Headless horseman comes and terrorizes everyone.

Yeah—this classic Halloween story's got something for all your students, and we're here to break it down for you. Mean jocks and all.

In this guide, you'll find

  • rigorous activities based on text evidence.
  • reading quizzes like whoa.
  • engaging pop culture resources beyond the not-quite-classic Disney animated film of the story.

Now hurry up and check out our guide—before you meet poor Ichabod's fate.

What's Inside Shmoop's Literature Teaching Guides

Shmoop is a labor of love from folks who love to teach. Our teaching guides will help you supplement in-classroom learning with fun, engaging, and relatable learning materials that bring literature to life.

Inside each guide you'll find quizzes, activity ideas, discussion questions, and more—all written by experts and designed to save you time. Here are the deets on what you get with your teaching guide:

  • 13 – 18 Common Core-aligned activities to complete in class with your students, including detailed instructions for you and your students
  • Discussion and essay questions for all levels of students
  • Reading quizzes for every chapter, act, or part of the text
  • Resources to help make the book feel more relevant to your 21st-century students
  • A note from Shmoop's teachers to you, telling you what to expect from teaching the text and how you can overcome the hurdles

Want more help teaching Teaching The Legend of Sleepy Hollow?

Check out all the different parts of our corresponding learning guide.




Instructions for You

Objective: Students are often under the impression that being the protagonist of a story is synonymous with being the good guy. And while that's often the case, it's not always true. Is The Legend of Sleepy Hollow an exception? Well, that's what your students will find out for themselves in this activity.

Students will work in pairs to examine the conflicting sides of Ichabod. They'll find evidence supporting both sides of this argument, and then come to a conclusion about which side has the more compelling evidence. Your class can complete this activity in about 45 minutes.

Materials Needed: Text of The Legend of Sleepy Hollow, access to this clip of the song about Ichabod Crane from Disney's The Adventures of Ichabod and Mr. Toad

Step 1: What better way to demonstrate a point about a character being more than he appears than by showing a cartoon man charm a lady while stealing a pie from her? Start by showing this classic Disney clip that introduces Ichabod to Sleepy Hollow. It's only about a minute and a half, and it's a great way to show how Ichabod seems like a nice guy while also proving there's something devious about him.

Step 2: Once they've all witnessed the pie theft, put students in pairs (or have them choose their own partners, whichever works better for your class's dynamic).

Step 3: Each pair is now going to look for conflicting evidence about Ichabod. One partner will go through the story and find a minimum of three direct quotes that point toward Ichabod being a pretty good fella, while the other partner will find three direct quotes showing Ichabod as a dishonest, disingenuous coward. For each quote, the student will write one or two sentences explaining how it works in Ichabod's favor or how it makes him look bad.

Since Irving spends so much of the story providing description, and since so much of it is about Ichabod, there'll be no shortage of examples. You can point out to your students that Ichabod is first introduced in paragraph 8, though, so they don't waste time looking at the parts before he comes in. This part of the assignment should take about 20 minutes.

Here's an example of a quote that paints Ichabod in a positive light:

…he had various ways of rendering himself both useful and agreeable. He assisted the farmers occasionally in the lighter labors of their farms, helped to make hay, mended the fences, took the horses to water, drove the cows from pasture, and cut wood for the winter fire. (par. 12)

An example of a quote not so favorable toward Ichabod might look more like this:

As the enraptured Ichabod fancied all this, and as he rolled his great green eyes over the fat meadow lands, the rich fields of wheat, of rye, of buckwheat, and Indian corn, and the orchards burdened with ruddy fruit, which surrounded the warm tenement of Van Tassel, his heart yearned after the damsel who was to inherit these domains, and his imagination expanded with the idea, how they might be readily turned into cash, and the money invested in immense tracts of wild land, and shingle palaces in the wilderness. (par. 23)

(If your class has an odd number of students, and one group has to include three, have one of the three look for quotes both in favor of and against Brom. It could be just as interesting to see if he's really a bad guy just because he antagonizes Ichabod.)

Step 4: After your students have found the required quotes, they get to pass judgment on Ichabod. Have them work together to write two or three paragraphs that explain their findings and determine what type of person they believe Ichabod truly is. This should also take about 20 minutes.

Instructions for Your Students

It'd be accurate to call Ichabod the protagonist of The Legend of Sleepy Hollow. But does that also mean he's a good guy? Well, there's no better way to find out than to dive back into the story and look for evidence. Your job here is to work with a partner to find different perspectives on Ichabod (i.e. both good and bad things about him), and then judge for yourselves what type of person he really is.

Step 1: Before you head back into the text, this will give you a little taste. Check out this Disney version of Ichabod from years ago. You'd think if anyone could erase all of a character's flaws and paint them as a perfect hero, it'd be Disney. But even the Disney folks show him committing petty theft.

Step 2: Now it's time to be assigned a partner. Together, you'll decide which of you will be pro-Ichabod and which will try to prove he's a creep. Once you know exactly what aspect of Ichabod you're looking for, go back into the story for direct quotes to support your side.

You want to find a minimum of three to support your point of view, and your partner will also find at least three. After you copy down each quote, write one or two sentences explaining how the quote supports your side of the argument.

Keep in mind that Ichabod is first introduced in the story in paragraph 8. From that point on, Irving writes so much description of him that you're bound to trip and fall over a usable quote if you're not careful.

Step 3: Once you and your partner have each found your quotes, you'll decide together whether Ichabod's a good guy or not. Whichever side you choose, you'll write two or three paragraphs explaining your decision. Your analysis should:

  • Reference some of the quotes you chose in support of your overall view of Ichabod.
  • Mention other parts you didn't use, if you feel there was more than enough evidence to support one side of the argument. (On the other hand…)
  • If you're 50–50 on old Ick, use your best quotes for each side of his character.