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Short Stories Sleepy Hollow

STORY REVIEW: The Legend of Sleepy Hollow

Washington Irving

The Headless Horseman Pursuing Ichabod Crane” by Thomas Hawk is licensed under CC BY-NC 2.0.

First Things First…

I read this once, about seven or eight years ago, and created a study guide about it for an educational company I was doing freelance work for. It was cool getting paid to read a classic story that I’d never read before.

It’s easy to think of any version of Sleepy Hollow as a great Halloween story, but it’s always been an ideal November story for me, so I’m excited to revisit it now.


3 Things I Like


3. What Ever Happened to Ichabod Crane?

The narrator makes it very clear at the end of the story that it’s NOT clear what actually happened to Ichabod. He might’ve been killed or abducted by the Headless Horseman (if the Horseman was even real). Or he might’ve left town after his harrowing experience, out of fear of the Horseman and Hans Van Ripper, and embarrassment over being rejected by Katrina.

If he did leave, he may have become a judge in Connecticut. He might even be the lanky old man from the postscript who asks what the point of the story is.

Then again, the entire story might be made up. The narrator even says he doesn’t believe half of it himself. And being that this is a legend, I like leaving Ichabod’s fate and the Horseman’s existence ambiguous.

2. A Sleepy Town Full of Phantoms and Reverie

Photo by Melissa Mullin on Unsplash

Washington Irving goes into great detail with many of his descriptions—about characters, parties, and the town itself. His description of Sleepy Hollow makes it feel alive, which is ironic, since it really is a sleepy town. Its superstitions play a huge role, though, and they add to the spookiness of the story. Here’s how he introduces the town…

“A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere. Some say that the place was bewitched by a high German doctor during the early days of the settlement; others, that an old Indian chief, the prophet or wizard of his tribe, held his powwows there… the place still continues under the sway of some witching power that holds a spell over the minds of the good people, causing them to walk in a continual reverie. They are given to all kinds of marvellous beliefs, are subject to trances and visions, and frequently see strange sights, and hear music and voices in the air. The whole neighbourhood abounds with local tales, haunted spots, and twilight superstitions…”

The entire story isn’t as scary as I hoped, but it’s at its best in these and other descriptions regarding the town’s favorite local legend, the Headless Horseman, and the phantoms that terrorize Ichabod when he travels alone at night.

1. Ichabod Crane

Ichabod is far from the typical protagonist. He doesn’t have the looks (one of the first descriptions of him says he could be mistaken for “some scarecrow eloped from a cornfield”), or even the personality to be sympathetic. He’s actually rather conniving in the way he woos Katrina. He’s more interested in her for the house, land, and potential feasts he’ll inherit than he is because of her personality or even her beauty.

Ichabod seems bright, too, in the way he uses his position in town to pursue her, rather than competing openly with Brom Bones, which surely wouldn’t go well for him. He’s cowardly, but at least he recognizes a fight he can’t win.

As it turns out, he loses anyway, since Katrina rejects him before he leaves (or is taken) from town. But all his unsavory characteristics (even the way he tends to befriend his students with attractive older sisters or with mothers who are great cooks) make him interesting to read about.


1 Thing I’m Mixed On


1. The Headless Horseman

This is the character who’s hurt most by the fact that the story is only a little spooky, but actually pretty tame.

The Headless Horseman has a cool backstory. He’s supposedly the ghost of a Hessian soldier during the Revolutionary War who had his head blown off.  But when he chases Ichabod during the story’s climax, it’s not as exciting as it should be. This should be a more gripping part. And it ends very abruptly. I actually like the slower parts of the story, where Irving sets the scene and gets into very detailed descriptions about the town, its superstitions, and Ichabod, more than I like the action.


1 Thing I Don’t Like


1. Katrina Gets the Short Shrift

Katrina is a hugely important piece of the story, since she’s Ichabod’s primary motivation. And, if it is really Brom posing as the Headless Horseman who chases Ichabod from town, she’s his motivation, too. But Irving doesn’t go into nearly as much detail about her as he does about Ichabod, Brom, Sleepy Hollow itself, or even her father’s party. Maybe he wanted her to be more mysterious, and maybe he never explains why she rejects Ichabod because Ichabod kinda sucks as a person and deserves to be played.  For me, though, that’s one thing I would prefer an explanation about.

I also wish Katrina was more fully fleshed out so I knew more about why everyone likes her. I hope it’s not just about her beauty or future inheritance.

The Review

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The descriptions bring this story to life, even if they’re long-winded. Unfortunately, the action involving the Headless Horseman—the most well known aspect of the story in pop culture for years—doesn’t quite live up to the hype.

 Still, Ichabod is a classic character, and Sleepy Hollow is a classic setting. It’s a very good story just based on those two things, and the town’s superstitions add a lot to the mood.

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