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The Midnight Society: "The Legend of Sleepy Hollow" Discussion

Thursday, October 29, 2020

I don't know about where you are, but the past couple of days here in Georgia have been rainy and stormy, creating the perfect conditions for reading "The Legend of Sleepy Hollow." I also get up a lot earlier than the rest of my family to work, so it's always dark out, and this week I've had to look over my shoulder for the Headless Horseman more than once! 


Submitted for the approval of The Midnight Society: our discussion on Washington Irving's chilling tale, "The Legend of Sleepy Hollow."


1. What does Washington Irving do to create fear in his audience?

2. How is Brom Bones's horse, Daredevil, like him? How is Gunpowder like Ichabod? 

3. How does Ichabod Crane's vivid imagination lead to his downfall? 

4. Do you believe that the Headless Horseman was real? Or was he a creation of Brom Bones? 

5. How would the story be different if told from Brom's point of view? Katrina's? 

Bonus question: does the description of Brom remind you of another character you know of? If you're like many of my students past, you picture him exactly like a certain gentleman in a story about a beauty and a beast. 

I have to admit that one of my favorite parts of the story is at the end when we find out that basically because Ichabod was single and didn't owe anybody any money, no one in the village really cared what happened to him. That's cold. (And hilarious.) 

I look forward to hearing what you think! 

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