The Legend of Sleepy Hollow: One of the Most Famous Early Works in American Fiction

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The Legend of Sleepy Hollow is a short story of speculative fiction by American author Washington Irving, contained in his collection of 34 essays and short stories entitled The Sketch Book of Geoffrey Crayon, Gent.. Written while Irving was living abroad in Birmingham, England, The Legend of Sleepy Hollow was first published in 1820. Along with Irving’s companion piece Rip Van Winkle, The Legend of Sleepy Hollow is among the earliest examples of American fiction with enduring popularity, especially during Halloween because of a character known as the Headless Horseman believed to be a Hessian soldier who lost his head to a cannonball in battle. The story is introduced at first by describing the area of Tarrytown, then leading into Sleepy Hollow, described as a quiet, calm place where superstition and ghost stories run amok. Soon after that, the narrator describes the first and one of the most important characters, Ichabod Crane, a bony school teacher whose objective is unknown to the reader (at the time).


In any story plot is divided into 5 crucial parts: Introduction/Exposition, Rising Action, Climax, Falling Action, and finally Resolution/Denouement. The first plot part chronologically (after introduction) is the Rising Action. This is the point in the story where the central conflict is introduced. In this case, the conflict is introduced as soon as Ichabod Crane learns of the massive wealth Katrina van Tassel has at her disposal, so he quickly makes it his objective to marry her. Unfortunately for Ichabod, another guy already had his eye on Katrina and isn’t going to give her up without a fight. This leads us into the climax of the story. Ichabod (after sweet-talking Katrina into it) gets invited to a great party at Katrina’s house. Unfortunately, it doesn’t go well for him and she ends up dumping him for Brom van Brunt, the resident tough guy. He starts his long, sad trek back home but gets rudely interrupted in the middle of it by the fabled Headless Horseman! He falls off his horse amidst the panic and disappears into the forest. After Ichabod disappears, nobody could care less. They simply move on, get a new schoolteacher, and burn his books. He just becomes another wordless victim to the phantoms of Sleepy Hollow. Nobody can say they really liked him anyways. The story finally concludes with a conversation between two men. Guy 1: ‘What was the moral of the story?’ Guy 2: ‘There wasn’t one.’Guy 1: ‘So the story wasn’t true?’Guy 2: ‘Of course it wasn’t.’


Foreshadowing is a prominent theme in The Legend of Sleepy Hollow. The use of foreshadowing can even be found in the introduction, where it states that the town of Sleepy Hollow is obsessed with the paranormal and ghost stories, implying that this would play a big part in the story. Even the setting oozes foreshadowing, with Sleepy Hollow being described as “A place given to superstitions. The land seems to cast a spell over its inhabitants. The source of dreamlike apparitions is the landscape itself, which provides the perfect backdrop for ghostly encounters—including frightening ones.” The setting foreshadows Ichabod’s encounter with a ghost by providing just the right place for it. Even more setup for the encounter with the Horseman is that at the time Ichabod is going home from the party, it is exactly ‘the witching hour’, a time where it is said that spirits and ghost come out.

Point of View

There are two points of view primarily used in books: First person PoV and third person PoV. In the first person point of view, the narrator is one of the characters in the story, usually the protagonist. The story is seen through the eyes of the character, and is described as such. The pronouns, “I and me” are prominent here. The other point of view used in books is third person PoV, which is more commonly found in literature. Here, the story is described as seen through the eyes of an onlooker, where the narrator is not a character in the story, but outside of the action. There are two types of third person PoVs. In the third person omniscient point of view, the narrator knows everything, including the thoughts and feelings of all the characters. In the third person limited point of view, the narrator sees things through one character’s eyes and reveals that character’s feeling and thoughts. The narrator can describe what other characters do or say, but not what they feel or think. We can safely say that the Legend of Sleepy Hollow was told from the third person limited point of view. The narrator wrote the story but he heard it from an old man, like a ghost story. As such many facts are forgotten or mixed-up, much like a real urban legend passed down by mouth. For example, he doesn’t know what Katrina says to Ichabod before he runs off. The story is generally described from an outsider’s point of view, as well.

Point of View (Part 2)

Point of view also affects the information that a reader receives. The Legend of Sleepy Hollow was clearly written in the third person, limited point of view and that affects how we perceive the story as such. The main difference is that, from how this story was told and where it originated, we have a hard time figuring out the truth. In some areas the author would be able to describe the characters in great detail, but in others simply lacking the facts that have been forgotten or changed. The narrator know just as much as the characters do, if not less.


There are four types of characters commonly found in literature: round and flat, and dynamic and static. A round character is complex, showing many different qualities—revealing faults as well as virtues. A flat character is one-dimensional, showing a single trait. A dynamic character develops, changes, and learns something during the course of a story—unlike a static character, who remains the same. Ichabod Crane can actually be described as a rounded character. Although his most-obvious trait is his Greed, Ichabod is actually a rather multi-faceted character. Beyond his selfish ambitions, Ichabod is also superstitious, imaginative, has a (typically unhealthy) sense of curiosity, and even has some positive traits thrown in for good measure.,. Brom Bones is similar to this. He has many qualities from being strong, playful, and clever. He was also planning to marry Katrina so he used his knowledge of Ichabod to scare him away. Although, Katrina seems to be a fairly flat character. She seems to be the “popular girl” of the story, who the male characters are attracted to, but not much else.


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The Legend of Sleepy Hollow has quite a few themes going for it. One of these is the theme of Wealth. We get a pretty good idea of what Baltus’s pad looks like, and—well, it’s pretty awesome. But just like with everything else in the story, Irving calls into question what being rich really means. Can Baltus really be rich if he doesn’t live in a marble-floored mansion with mountains of gold and silver? Or is being wealthy just having more than enough to get by? Wealth separates the hungry and skinny (Ichabod) from the full and fat (Baltus), but can anyone really go hungry when trees are overflowing with fruits? Irving leaves those questions for you to figure out. Another central theme in The Legend of Sleepy Hollow is the Supernatural. Okay sure, the supernatural can be scary, but isn’t there more to it? Are there different types? Can it be funny? Is it real or is it total fluff? And most importantly, was it Brom or the Headless Horseman? We know that’s a lot of questions, but ‘The Legend of Sleepy Hollow’ seems like an investigative report about all things supernatural. We end up with more questions than answers, but one thing’s for sure in our sleepy little town: whatever it is, the supernatural is going to come for you. Finally, another theme found in The Legend of Sleepy Hollow is Truth, Dreams, apparitions, specters—Sleepy Hollow has them all. But here’s the question: are they real? Well, that’s a question the Sleepy Hollowers have some difficulty untangling—something’s definitely in the water there. Thanks to our super unreliable narrator, we have to second-guess nearly every word in the story. Is there any sincerity? What’s real and what’s not? And most importantly, does it matter?


There are two primary types of conflict in The Legend of Sleepy Hollow: internal conflict and external conflict. With an external conflict, a character struggles against an outside force, like another character. But an internal conflict is the opposite of this. An internal conflict is when a character struggles with their own feelings and/or beliefs. As for the conflict in The Legend of Sleepy Hollow, Ichabod is a nerdy, for that time, schoolteacher who moves to Sleepy Hollow from Connecticut. Ichabod is a bachelor but becomes infatuated with one of his music students, the young lady Katrina Van Tassel. Ichabod vies for her affections against another suitor named Brom Van Brunt. Much of the conflict involves Brom humiliating Ichabod; it was kind of like the mean jock picking on the skinny nerdy guy in high school. Thrown into the mix is the legend of some guy who got his head blown off by cannon during the Revolutionary War. Apparently, he rides around at night and is known as the Headless Horseman. We can easily describe this as the external conflict. There is also an external conflict in the story, as well. Ichabod would be afraid because he got into his head that the Headless Horseman was real and was frightened from then on. His unkindness forced women to despise him and his way with the ladies made men and women both despise him even more. He would eat so much food that no one would ever want to invite him over for dinner. His ego and morals would never let him have very many friends or dinner partners.

Characters (Part 2)

Characters are defined through characterization. Specifically, Direct characterization and Indirect characterization. In direct characterization, the writer directly explains a character and their attributes. But in indirect characterization, the writer only gives clues to the character by describing their behavior, thoughts, and appearance, and leaving it up to the reader to figure out the character. Ichabod Crane is the embodiment of indirect characterization. The author describes in great detail, Ichabod’s lanky appearance, his greedy and selfish thoughts, and even his name gives a bounty of clues to his character. Irving does anything but directly tell you about Ichabod. Katrina van Tassel, on the other hand, is not like this at all. She gets little time in the spotlight of characterization, but when she does, it is direct as can be. As much of her flat character that can be described is described in full detail.

Symbolism and Allegory

A beautiful use of symbolism can be found in The Legend of Sleepy Hollow, right at the beginning of the tale. Irving describes the Headless Horseman as being the ghost of a dead Hessian soldier. At first glance, this may not mean much. But after a closer look, you will see that this has many layers of symbolism behind it. In short, Hessians were German soldiers who were hired to work during the Revolutionary War. Instead of using the magical, spooky creature that was popular in folklore, Washington Irving turns the Horseman into the ghost of a guy who fought in a very real war. Roots the whole thing in history a bit more, don’t you think? Its not difficult to think that the residents of Sleepy Hollow became obsessed with ghosts after the war, and its easy to assume that it somewhat traumatized them. And what’s the perfect symbol to embody their trauma? A headless Hessian horseman, of course. These people are Dutch, after all, so they probably knew the horseman myth. Plus, Hessians often rode horses, and a cannonball could take off your head—it’s a no-brainer to put the two together. It seems like the townspeople of Sleepy Hollow have collectively dreamed up the very thing that attacked them just a short while ago. One last thing. Hessians were kind of like mercenaries, and mercenaries are thought to be very greedy people. Imagine that. The greediest guy in Sleepy Hollow is attacked by greed itself.

Antagonist and Protagonist

Any good story has an antagonist and a protagonist; and The Legend of Sleepy Hollow is no different. An antagonist is someone who is usually considered as the ‘villain’ of the story, but they aren’t always a bad guy. Likewise, the protagonist is usually the ‘hero’ of the story, but doesn’t always have to be a good guy. In The Legend of Sleepy Hollow, Irving liked to mess with the rules a bit, choosing Ichabod as our protag. Ichabod seems like the least likely to be the protagonist, and you wouldn’t be wrong if you were thinking like that. So Ichabod feels more like an anti-hero than the hero. The same can be said for the resident antagonist, Brom Bones. Funnily enough, Brom seems to be the character accompanying all of the traits that a typical American hero would have, not the villain! It is in this way that Brom Bones can be seen as the anti-villain. These mismatched roles can be faulted upon from how the story was told; from the side of Ichabod Crane.


Washington Irving (1783-1859) published “The Legend of Sleepy Hollow” in 1819 as part of a collection of stories titled The Sketch Book of Geoffrey Crayon. One important event that happened recently to the writing of the story was the Revolutionary War. In this war, Britain hired German mercenaries called Hessians to fight against the Americans. The effect of this can even be seen in The Legend of Sleepy Hollow, where Irving describes the Headless Horseman as the spirit of a dead Hessian whose head was shot off by a cannonball. That very Hessian was buried in the Sleepy Hollow cemetery in an unmarked grave in 1812. In the late 1700s, near the end of the Revolutionary War, the Hudson River Valley area was equivalent to the wild west – an area of lawbreakers and lawmakers, rife with rivalries and fighting between British loyalists and American raiders. Also, the area was known for its abundance of Hessian soldiers. Washington Irving wrote The Legend of Sleepy Hollow during a tour of Europe, and this affected him as such.

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