The Legend of Sleepy Hollow

8 ways to start a deeper conversation.

Contains spoilers for the entire book.

Discussion topics

Topic 01 of 08

What makes Sleepy Hollow such a dreamy, haunted place?

There is no single right answer. Bring your own reading.

What makes Sleepy Hollow such a dreamy, haunted place?
Keep the conversation going
- How does Irving's humour sit beside the spooky atmosphere?
- Which description stayed with you?
What kind of man is Ichabod Crane, and did you like him?
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- What does his appetite for food and wealth say about him?
- Why does he believe every ghost story?
What does Katrina Van Tassel really think of Ichabod?
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- Does she encourage him only to tease Brom?
- What does Ichabod actually want from her?
What does Brom Bones represent, set against Ichabod?
Keep the conversation going
- What did you make of their rivalry?
- Who is the better match for Katrina?
What happens at the Van Tassels' party that sets up the night ride?
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- What did the ghost stories told that night add?
- Why does Ichabod leave so downcast?
How did the night ride and the chase affect you?
Keep the conversation going
- Was it a ghost?
- What did you make of the shattered pumpkin found the next morning?
What happened to Ichabod, according to the different versions?
Keep the conversation going
- Why does Irving leave it open?
- Which version do you believe?
Why do you think this story has lasted so long?
Keep the conversation going
- What does it say about how legends are made?
- What did you make of the postscript about whether the story is true?

There is no single right answer. Bring your own reading.