Study Guide

The Legend of Sleepy Hollow

The Legend of Sleepy Hollow Summary

In a sentence: Skinny dude with a funny name gets chased by a headless horseman and dies. Or runs away—unclear. The end.

Here is the (slightly) longer version:

Once upon a time, a guy named Ichabod lived in a little town called Sleepy Hollow. He was the town teacher and choirmaster. In other words, he was pretty important people. That's the backstory and this is where the craziness starts.

One day, Ichabod realizes that the richest guy in town has an only daughter who's pretty good lookin'. He decides that he's going to hit on her so hard that she'll have no choice but to fall in love with him. Flawless plan, clearly. Oh, there is one problem though. There's this other guy named Brom and he wants to kill Ichabod for taking his lady. Minor snag.

Ichabod lies low for a while because, you know, he doesn't want to die, but then something amazing happens. There's a party at his lady's place and he is invited. Booya. He gets dressed up, sprays on his finest Axe Body Spray (19th-century edition), and heads off on his borrowed steed.

The party is hoppin', but when it's over, his lady dumps him. Ichabod is making his way home, crying all the way, when he meets the Headless Horseman. Ichabod goes nuts trying to get away from him, and when he finally thinks that he's safe, the Headless Horseman throws his head at him, and knocks Ichabod off of his horse and onto the ground.

The next day, no one knows what happened to Mr. Crane. They see horse tracks, Ichabod's hat, and a pumpkin, and they all assume the Horseman got him. We hear that Ichabod ran away and became a judge. But Brom laughs mighty suspiciously every time they talk about Ichabod. Hmm, could it be? Nah, it was the Horseman. Right?

  • Section 1

    • Once upon a time, there was a place in the mysterious land of New York called Tarry Town. It was called Tarry Town because the husbands from the neighboring towns would stay there a little too long on market days. Get it? Because they tarry? In the town? Okay, moving on.
    • Not so far from Tarry Town is a little valley that's so quiet you can hear a pin drop. That little valley is called Sleepy Hollow.
    • The people who live in Sleepy Hollow are, well, sleepy. They dream fantastic dreams about magic, spells, witches, and anything supernatural you can imagine.
    • No one is sure why Sleepy Hollow is so full of ghouls and monsters. Maybe the land was cursed by a high German doctor or maybe it was cursed by a native witchdoctor. Who knows?
    • The worst of all the creepy crawlies is the Headless Horseman. He was a Hessian soldier (Hessian is a fancy word for the German troops hired by the British Empire) who got his head blown off in "some nameless battle." No big deal since he still rides fine, but legend has it that the horseman rushes to the church each night to find his buried head. So that's creepy.
    • We mentioned that the residents of Sleepy Hollow are a little special, but anyone who visits for a while seems to be drinking whatever the natives are drinking. That is, everyone who visits becomes superstitious, too.
    • The narrator wants us to know that he is totally not making fun of such an upstanding town as Sleepy Hollow. In fact, he loves it. Unlike most places in America, nothing ever changes there. Here comes our protagonist, Mr. Ichabod Crane. Tall, lanky, skinny, with a huge nose and bulging green eyes. Not your typical handsome hero.
    • Our man from Connecticut teaches in a run-down one-room schoolhouse and rules with an iron fist. He's a strong believer in the phrase "spare the rod and spoil the child" (1.9), but he doesn't consider himself to be cruel. He thinks he's doing his students a favor.
    • When school is out, everything is different. Mr. Crane is friends with his students—especially the ones with pretty mothers and sisters and even more especially the ones who can cook.
    • Ichabod has a huge appetite, and he doesn't make enough money as a schoolteacher to feed it on his own. So he's forced to live with the families of his students. He becomes a temporary handyman/nanny/whatever-they-want-him-to-be to pay for his rent.
    • In addition to being a teacher, Ichabod is the choirmaster. He prides himself on his singing and sings so loudly that he can be heard half a mile away.
    • As an educated man of letters, Ichabod is a big deal in the town. He has read several—count 'em, several—books all the way through. Everyone in Sleepy Hollow gets excited when they see such a smart guy.
    • All the ladies love a smart man, so this guy is the center of attention. On Sundays, he shows off, reciting poetry and generally acting like a nerdy Casanova.
    • Ichabod loves scary stories. The scarier the better. At least until nightfall, when he gets so scared that he freaks out at the sound of his own footsteps. 
    • To ward off his fears, Ichabod sings psalms, which impresses the pants off the townspeople.
    • He also likes to chill out with housewives and old Dutch ladies (we're sensing a trend). They trade scary stories about everything that can possibly be haunted. 
    • Of course, when he goes home, he's scared out of his wits, but everything is fine again when daylight comes.
    • Everything would have been fine for our dear protagonist, if it weren't for a meddling woman.
    • Katrina Van Tassel, the fairest lady in all the land, captures the heart (or should we say stomach?) of Ichabod. Her dad is Baltus Van Tassel, a rich old farmer, and she's his only child. Rumor has it that she's quite the coquette, or a flirt in old-timey speak.
    • After Ichabod visits her dad's farm, he knows that he has to marry Katrina so that it can all be his. We ain't sayin' he's a gold digger. Actually, we are.
    • The farm is overflowing with animals that Ichabod can just picture as food on his plate and money in his pocket.
    • Inside the farmhouse, it's like an old-school episode of MTV Cribs. It's a little weird that they decorate the place with ostrich eggs and artichokes, but hey, whatever floats their boat.
    • Now Ichabod has a mission: get the girl. But it's not going to be easy—he already has a rival.
    • Brom Van Brunt, who we imagine as a young and goofy Arnold Schwarzenegger, has been trying to date Katrina for a long time before Ichabod came around. This guy is big and brawny and everyone in town looks up to him. He has no game, but Katrina's not saying no either. 
    • Ichabod knows that he can't compete with Brom's manliness, so he goes undercover and tries to hit on Katrina under the guise of choir lessons. Since her dad is too busy watching the weathervane and her mom is too busy minding the farm animals, it works like a charm.
    • Suddenly, Brom isn't invited to the Van Tassels' anymore. Oh, and suddenly, Brom wants to kill Ichabod.
    • As you might have guessed, Ichabod is a wimp and won't agree to a duel, so Brom decides that he'll just play pranks on him instead. Of course, Ichabod thinks these aren't pranks, but hauntings. (It is Sleepy Hollow, after all.)
    • One day, while Ichabod is ruling over his subjects—er, students—he gets an invite to a big party at the Van Tassels'. Nice. He lets school out early so he can get a head start on looking good for his lady.
    • He puts on his only suit, brushes his hair by a broken piece of mirror on the wall, and borrows a broken down old horse from his landlord of the week. 
    • Clearly Ichabod isn't all that and a bag of chips. Most awkwardly, his horse is ragged and half blind, and its hair is matted with trash in it. Ichabod can't even sit properly on the thing and it looks like he is riding a kid's pony. Not exactly a knight in shining armor. (You should probably just go read this scene. It's kind of hilarious, and it's a great example of Irving's sarcasm throughout the story.)
    • Sleepy Hollow seems to be a pretty beautiful place. The narrator spends a long time describing the forest and all the antics of the woodland creatures. Ichabod enjoys the scenery as much as we do, especially because it makes him think of Katrina making him pancakes. We're not kidding.
    • After some more scenic descriptions, Ichabod arrives at the Van Tassel manor, where the party is bumping. Everyone is dressed to the nines, hair slicked in eel-oil and all. Even Brom is there, being as alpha male as normal.
    • Even though there are lots of buxom ladies around, Ichabod heads straight for the food. While stuffing his face, he imagines how awesome it will be when everyone has to listen to him after he marries Katrina. What a dreamboat.
    • Old Baltus is being a good host and telling everyone to enjoy their time. He seems like a pretty laid back guy.
    • Now, we dance! Well, Ichabod dances. Or shakes wildly. He isn't so good at this dancing stuff, but Katrina doesn't seem to mind how he gets down. 
    • Brom, on the other hand, is in the corner crying.
    • After his awesome dance, Ichabod goes to hang out with the old folks, who are telling stories about the American Revolution. You see, Tarry Town was no man's land, so all kinds of crazy stuff happened there during the war. The storytellers like to, um, elaborate a bit, though. 
    • After the war stories, it's time for more scary stories. Particularly ones about the Headless Horseman. 
    • Brom says that he challenged the Horseman to a race one time. He would have won, too, if the guy didn't disappear when they got to the church. (We totally believe him.)
    • Once the ghost stories are all told, the party is over. Everyone starts to head home, but Ichabod stays behind to talk to his ladyfriend.
    • We're not sure what goes down, but suddenly, Ichabod is sad and Katrina has dumped him. Our guy is heading home alone.
    • It's dark when Ichabod rides home, and you know what that means: all the scary stories come back to him. He's so freaked out that he only barely makes it past a particularly fearsome tree by kicking his trusty steed half to death.
    • And now, the scene we have all been waiting for: Ichabod is face to face with some sort of large black rider. Dun dun dun.
    • Ichabod tries to lose the horseman by speeding up. It doesn't work. He tries to fall behind the guy. It doesn't work. He's so scared now that he can't even sing.
    • Finally, Ichabod realizes who the rider is. You guessed it—the Headless Horseman.
    • Now things get crazy. Ichabod is trying to get to safety at the church, but he's a really (and we mean really) bad rider. The horse is out of control and nearly throws Ichabod off.
    • Finally, Ichabod makes it to the church. He thinks he's won, but he looks behind him to find that the Horseman is still there. 
    • The Horseman promptly throws his head (which he carries with him) at Ichabod and knocks him right off of his horse.
    • End scene.
    • The next day, no one knows what happened to Ichabod. He doesn't show up for breakfast, and he doesn't show up for school. Uh oh.
    • When people go looking for him, all they find are a bunch of horse tracks, Ichabod's hat, and a shattered pumpkin. What does it all mean?
    • Since they can't find his body—and this is Sleepy Hollow—they assume that the Headless Horseman has stolen him away. Of course.
    • No one is sad or concerned. Nope, they just move on and get a new teacher.
    • Some years later, a farmer tells the townspeople that Ichabod ran away and became a judge—but no one pays attention. No one even pays attention when Brom laughs every time people talk about Ichabod's abduction. Hmmm.
    • The story ends with a new tale about a haunted schoolhouse and a teacher who, like someone we know, loves to sing.
  • Postscript

    The Postscript

    • Mr. Knickerbocker is the author of the postscript. He tells us that he heard this story (the one we just read) from a guy in Manhattan.
    • Everyone who hears the story thinks it's hilarious. Oh, except for one curmudgeonly old dude. After everyone else has stopped laughing, old guy asks what the moral of the story is.
    • The storyteller replies with the most confusing nonsense—you'll just have to read it to believe it.
    • Old curmudgeonly guy seems totally confused and doesn't want to admit that he has no idea what this guy is talking about. Instead, he says that he doesn't think the story is 100% true.
    • The storyteller shoots back at him: "as to that matter, I don't believe one-half of it myself" (2.7).