Reading Notes: “The Legend of Sleepy Hollow”

Let's Talk About Literature
6 min readJan 5, 2023

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Photo by Antonio Gabola on Unsplash

One of the first things you might note about this story is that it has a subtitle, “Found among the Papers of the Late Diedrich Knickerbocker.” As you read, keep in mind that Knickerbocker is the narrator, and this subtitle is a framing device. This framing helps add the appearance of historical veracity, establishing a legend. You might notice other instances of this as you read.

The story begins with a description of Tarry Town as well as Sleepy Hollow, a small valley nearby. Sleepy Hollow is a promising retreat and “one of the quietest places in the whole world.” This helps paint a picture of a place where the supernatural seems to linger, a place with little change or development.

The residents of Sleepy Hollow seem to live in a drowsy, dreamlike state with their “marvelous beliefs” and superstitions. The most prominent tale is about the Headless Horseman.

Ichabod Crane is a tall, thin man who resembles a scarecrow. He’s not from Sleepy Hollow; he’s actually from Connecticut. He’s come to Sleepy Hollow to teach school.

Ichabod is a hungry guy, a man with a huge appetite. For this reason, it’s beneficial for him to be fair with the children. After all, he lodges at homes in the community due to his meager pay. He also uses his time in those homes to show the parents of his students that he’s not simply a “drone.” He frequently plays with with the children, and we get this image of Ichabod holding a child on one knee and rocking a baby’s cradle with his foot. This part of the story is important for a few reasons. For one, we learn that there is some tension related to book learning at school vs. practical learning at home. We also learn that Ichabod purposefully meets social requirements because they benefit him. In fact, his social life serves him well. Ichabod seems well-liked by people in town for all his faults.

You’ll also notice a few references to Cotton Mather. Ichabod is a “perfect master” of Mather’s History of New England Witchcraft. Ichabod spends his evenings reading spooky stories and telling others about them only to be frightened by fireflies and birds on his way home. The good news is that daylight puts a stop to these “terrors of the night.” Irving writes that it is “a woman” who crosses his path that causes “more plexity to mortal man than ghosts, goblins, and the whole race of witches put together.”

We meet Katrina Van Tassel, the daughter of a wealthy farmer and the object of Ichabod’s affections. She’s “a little of a coquette, as might be perceived even in her dress” as her petticoat displays “the prettiest foot and ankle in the country round.”

Katrina’s father is a wealthy and thriving farmer named Baltus Van Tassel. He is “satisfied with his wealth, but not proud of it.” His farm is described in great detail, as Ichabod imagines the many types of animals and how he’d eat them with gravy and onion sauce. Ichabod sees the farm in the many ways he can consume it. He’s greedy for wealth, food, and increased social standing. He’s already planning what to do with Katrina’s inheritance before they’re officially courting.

Of course, the relationship is not a done deal just yet. Ichabod has a problem: Katrina has other suitors. Irving compares Ichabod’s ordeal to being a “knight-errant of yore” fighting dragons, giants, and the like. His biggest opponent is Brom Bones, a man known for his physical prowess and mischievous pranks. In fact, other suitors have already decided to take “the war into other quarters.” However, Ichabod is persistent.

While Ichabod isn’t openly waging war against Brom Bones, Knickerbocker notes that tension is rising. While it seems that Brom would be the obvious winner, Knickerbocker notes that the hearts of women are riddles. So, the fight continues. All the while, Brom plays practical jokes on Ichabod, including vandalizing the schoolhouse at night to make Ichabod even more paranoid.

A messenger arrives at school one day to invite Ichabod to a party at the Van Tassel castle in the evening. So excited to get to the party, Ichabod shrugs off his responsibilities and excuses the schoolhouse early. He borrows a horse named Gunpowder. The “broken-down plough horse” has “outlived almost everything but his viciousness.”

The autumn day is gorgeous. As Ichabod rides, he sees things he can devour. Even in a peaceful, lovely moment, Ichabod is concerned with consumption. When he arrives at the party, it’s full of farmers and their families. Brom is there with his own horse, Daredevil.

Upon arriving, Ichabod’s first step is to admire the pastries. He gorges himself and thinks about how he’ll never associate with those of lower social and economic standing again.

Next, Ichabod takes to dancing. He prides himself in his dancing, and Katrina joins him. Is he finally gaining the upper hand? Notable at this point is Irving’s reference to a largely ignored group of people: the Black audience outside watching. They are likely enslaved people who are not invited to participate but rather watch the guests indulge from the outside.

Guests gather around and tell stories about the Revolutionary War. Those old enough embellish and fictionalize stories about the war in which each is a hero. We see that the town has been impacted by the war, much like other parts of the country.

Then, they get to talking about ghosts. This includes talk of the Headless Horseman, who loves to hang out near a church graveyard. Brom bones claims to have had a run-in with the Headless Horseman, even racing him to a bridge. Ichabod talks about Cotton Mather again as well.

After the party ends, Ichabod lingers to speak with Katrina. Knickerbocker isn’t exactly sure what happens, but he does know that Ichabod leaves feeling rejected. You might note here that Knickerbocker is not quite an omniscient narrator. Does this make him sound more realistic? What is Irving doing here?

As he rides home, Ichabod can’t stop thinking about the ghost stories told at the part. He imagines the ghouls and goblins as his imagination runs wild. He eventually sees the looming figure and imagines it is the Headless Horseman. As he rides, he loses the borrowed saddle and misses his path to return home. He embarks on a perilous race, holding on for dear life as he passes over the church bridge. He hopes the specter will disappear as it did for Brom Bones, but just as he reaches the other side, he sees the ghoul throw its head at him. He falls off his horse, and the figure disappears.

While the horse is found the next morning, Ichabod is never seen in Sleepy Hollow again. They do find a shattered pumpkin near the church bridge, however. As a reader, you may put together that the entire ordeal was likely a prank put on by Brom Bones.

The town mostly forgets about Ichabod, but one day a farmer returns with information that Ichabod is still alive and left to pursue teaching and politics elsewhere out of embarrassment. He seemingly became quite successful outside of the town. Meanwhile, Brom Bones and Katrina Van Tassel marry, and Brom seems to laugh every time somebody mentions Ichabod and the mysterious pumpkin.

A postscript follows the story. It reveals how Knickerbocker heard the story in Manhattan. A man who also overheard the story questions its veracity, and the storyteller himself acknowledges even he doesn’t believe the tale.

Next: Questions to Consider

Previous: Introduction & Context

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