The Legend of Sleepy Hollow

In rural New England, ghost stories abound, and the local gossip thrives on tales of the supernatural. Sleepy Hollow, New York, in the 1790s is no exception. The legend of the Headless Horseman takes life in Washington Irving’s 1820 short story as part of The Sketch Book story collection.

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The Legend of Sleepy Hollow The Legend of Sleepy Hollow

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Table of contents

    “The Legend of Sleepy Hollow” Summary

    The Legend of Sleepy Hollow, the Headless Horseman, StudySmarterIllustration of the Headless Horseman, the fabled ghost that haunts Sleepy Hollow, Pixabay

    Just a few miles from the market town of Tarry Town in the state of New York lies a quiet, secluded valley named Sleepy Hollow. The area is well-known for its hushed and dreamy atmosphere where time appears to stand still. Some believe that the valley is bewitched, possibly by a German doctor or an old Indian chief. In any case, the seemingly enchanted environment is acknowledged by all who live and visit there.

    The locals, many of whom are descended from Dutch settlers, are very superstitious and have a collective arsenal of ghost stories and legends about the area. The most famous legend is that of the Headless Horseman. As the story goes, the Headless Horseman is the ghost of a Hessian soldier who was decapitated by a cannonball during the Revolutionary War. He is said to ride at night in search of his head, hurrying back to his resting place in the churchyard before sunrise. Among the ghosts and ghouls rumored to haunt Sleepy Hollow, the Headless Horseman is the most feared.

    The concept of headless horsemen comes from many different cultures’ folkloric traditions. This mythological creature appears in literature from as early as the fourteenth century in works such as Sir Gawain and the Green Knight (late fourteenth century) in which the Green Knight is beheaded and rides off carrying his own head. It is a prominent folkloric figure in Irish, Scottish, and Dutch traditions.

    The story continues with the introduction of Ichabod Crane, the main protagonist. Ichabod is the local schoolmaster and is known to be a strict but fair teacher and a scholarly man. He is extremely lanky, with huge feet and ears, large green eyes, and a long, sharp nose. Deeply superstitious, Ichabod is particularly affected by the tales and legends of Sleepy Hollow ghosts. His walks home from the schoolhouse at night fill him with terror.

    The Legend of Sleepy Hollow, One-room schoolhouse, StudySmarterIchabod Crane spends much of his time teaching in a schoolhouse like this, Pixabay

    To make ends meet, Ichabod also works as the local singing master and stays with his students’ families, rotating his lodging every few weeks. This arrangement works particularly well for Ichabod’s bottomless appetite for food, as his teaching salary alone isn’t quite enough to feed himself properly. He makes himself useful while staying with his students by helping out with the chores and taking care of the children. He also supplies local gossip and ghost stories from his native Connecticut, much to the delight of the housewives he stays with.

    Irving portrays Ichabod as a voracious eater. What does this say about his character? Do his dietary habits have any relation to his monetary ambitions?

    Ichabod Crane then falls in love with his singing pupil Katrina Van Tassel, the young and flirtatious heiress of the Van Tassel estate. Enraptured with both her beauty and fortune, Ichabod quietly courts her by using his tutoring as an excuse to visit her family’s farm. He is not alone in his pursuit of Katrina, however. The Van Tassel heiress is also courted by the rapscallion Abraham Van Brunt, known by locals as Brom Bones. Large, intimidating, and having a penchant for pranks and roughhousing, Brom has made short work of scaring away other potential suitors. However, Ichabod continues to court Katrina despite his daunting competition.

    Once Ichabod’s intentions toward Katrina become clear to Brom, he retaliates against the schoolmaster with childish pranks and shenanigans. In one instance, he and his gang smoke out Ichabod’s schoolhouse by stopping up the chimney. In another, they break into the schoolhouse and tear it apart. Further, Brom does everything he can to humiliate Ichabod in front of Katrina, even teaching his dog to obnoxiously whine during Ichabod’s singing instruction with Katrina.

    Throughout all this, Ichabod remains undeterred and is determined to win Katrina’s heart (and her vast fortune). His efforts are put to the ultimate test when he is invited to a party one night at the Van Tassel estate. Ichabod borrows a plow horse named Gunpowder from his current host Hans Van Ripper and cheerfully rides to the Van Tassel farm. He is determined to make a valiant and stately appearance.

    While at the party, Ichabod eats heartily and dances with Katrina, much to the dismay of Brom Bones. Later in the evening, Ichabod sits with some of the older partygoers and listens to their tales. Here he learns more about the local legends and ghost stories, including encounters with the infamous Headless Horseman.

    Brom Bones interjects at this point with his account of the Hessian ghost. While riding his horse Daredevil late one night, he came across the Horseman and brags to the party that he challenged the ghost to a race. However, just as he crossed the church bridge, the Headless Horseman suddenly vanished in a “flash of fire.”

    The party ends late in the evening, and most guests head home. Ichabod, however, stays behind to speak with Katrina. The narrator is vague about what exactly happens between the two lovers, but something goes wrong. Ichabod leaves the farm crestfallen and heads home, his hopes of winning Katrina’s hand completely dashed.

    After listening to ghost stories all evening, the ride back to Van Ripper’s farm is even more frightening than usual for Ichabod. Jumping at every rustle of the leaves, he struggles to control Gunpowder. To his horror, a dark figure on horseback approaches him. Ichabod attempts first to speed up, then slow down, but the figure maintains pace with him. As Ichabod steals a glance at the figure, he is terrified to discover it is headless and carrying its head on its saddle.

    Remembering Brom Bones’ encounter with the Headless Horseman, Ichabod tries to reach the church bridge in the hopes that the ghost will disappear at the threshold. He manages to cross the bridge, expecting to be safe. Instead of disappearing, however, the Headless Horseman throws his head at Ichabod, knocking him off of Gunpowder and into the dirt.

    The next day, Ichabod is gone, and Gunpowder has wandered back to Van Ripper’s farm without his saddle. All that is found of Ichabod is his hat, lying beside a shattered pumpkin.

    What does the shattered pumpkin symbolize?

    The Legend of Sleepy Hollow, Orange pumpkin in a field, StudySmarterA single, shattered pumpkin next to Ichabod’s hat is the only trace left of him, Pixabay

    Most residents of Sleepy Hollow conclude that the Headless Horseman carried off Ichabod Crane. It’s also noted that Brom Bones, who marries Katrina Van Tassel, displays a knowing air whenever the incident is mentioned. His behavior strongly suggests that he knows more about Ichabod’s fate than he lets on.

    The gentleman from whom the narrator heard the tale claims that Ichabod Crane is still alive. The combination of his rejection by Katrina Van Tassel, the frightening encounter with the Headless Horseman, and the fear of Van Ripper’s wrath for losing his saddle cause him to flee Sleepy Hollow. However, the more superstitious inhabitants of Sleepy Hollow hold firm in their belief that Ichabod met his end by the Headless Horseman.

    “The Legend of Sleepy Hollow” Characters

    Let’s look at the characters in more detail.

    Ichabod Crane

    The story’s main protagonist, Ichabod is the schoolmaster and singing master of Sleepy Hollow. He is tall and lanky, with feet like shovels and large green eyes. He is well-read and highly superstitious, with an insatiable appetite for food. Though he has stiff competition, he aims to marry the beautiful and wealthy Katrina Van Tassel.

    Washington Irving was notorious for naming his characters after real people he knew. The name “Ichabod Crane” comes from a United States Army Colonel whom Irving had met in 1814.

    Katrina Van Tassel

    Ichabod Crane’s love interest and heiress of the affluent Van Tassel estate. She is described as “coquettish” and is known to be a bit of a flirt. Katrina’s character is significantly less developed than her male counterparts, and she functions more as an object of conquest in the story.

    What does this say about the status/position of women?

    Abraham “Brom Bones” Van Brunt

    Ichabod Crane’s chief competitor in the battle for Katrina Van Tassel’s hand in marriage. Brom Bones is brutish and prone to roughhousing and pranks and is the opposite of the gangling and studious Ichabod. Despite his roguish behavior, he is seen as something of a hero among the inhabitants of Sleepy Hollow.

    Baltus Van Tassel

    Katrina’s father, the good-natured head of the Van Tassel household. Baltus is a loving and doting father, letting Katrina “have her way in everything.” While he is comfortable and generous in his wealth, he is not overly proud of it.

    Hans Van Ripper

    Ichabod’s bad-tempered and curmudgeonly host. He lends Ichabod the old and equally bad-tempered horse Gunpowder that Ichabod rides during his fateful meeting with the Headless Horseman.

    Do you think the name “Gunpowder” has any significance?

    The Headless Horseman

    The ghost of a Hessian soldier who was decapitated by a cannonball during the Revolutionary War. The Headless Horseman is said to ride at night in search of his head, returning to his resting place in the cemetery before sunrise. According to Brom Bones, the Horseman is unable to cross the bridge leading to the church.

    Diedrich Knickerbocker

    The narrator of the story, Diedrich Knickerbocker is a fictional New England historian that author Washington Irving frequently used as a vehicle to tell his stories.

    “The Legend of Sleepy Hollow” Themes

    Below are some of the main themes of the text. Are there others you can think of?

    Superstition and Tradition

    The residents of Sleepy Hollow are stubbornly convinced of the existence of the supernatural. Even when presented with eyewitness testimony that Ichabod Crane was not carried off by the Headless Horseman but fled the valley and became a politician, the Dutch wives of Sleepy Hollow (whom the narrator ascertains are “the best judges of these matters”) still hold fast to the belief that he met his end by supernatural means.

    The superstition of the Sleepy Hollow residents correlates with tradition, especially seeing as these descendants of Dutch settlers have a distinct set of practices and beliefs. Irving wrote “The Legend of Sleepy Hollow” in 1820 when the Industrial Revolution was in full swing. The existence of Sleepy Hollow as a place where time stands still and ancient superstitions are still held in high regard is indicative of the small pockets of societal resistance that held firm against the advancement of the Industrial Revolution. It’s a reminder that even as progress marches forward in an era of logic and reason, there’s still power in the beliefs and practices of yesteryear.

    Ichabod is a schoolteacher but repeatedly reads a book about witchcraft. What does this say about him? Where does Ichabod fall within the superstition versus tradition dichotomy?

    History and Legend

    The story of Ichabod Crane takes place “some thirty years since.” As Irving published “The Legend of Sleepy Hollow” in 1820, we can assume that the story takes place around 1790. This takes us to a particular time in American history. The United States was a young nation still healing from the wounds of the Revolution and trying to establish a sense of history and legend. Irving’s use of the fictional historian Diedrich Knickerbocker further drives the idea of a historical narrative in a time when little of it existed. The tale of the Headless Horseman represents a young country’s longing to establish legend and a sense of wonder.


    Ichabod Crane is the shining example of this particular theme. From his unappeasable appetite to his lust for the Van Tassel’s estate, Ichabod is a caricature of greed. Even his tenderness for Katrina Van Tassel leaves the reader wondering just how much of it stems from his actual fondness for Katrina and how much is influenced by his wanting to share in her inheritance. The passages in the story that describe Katrina’s estate and all the riches within it greatly outnumber the passages that describe Katrina herself. Further, Katrina’s beauty and desirability give the sense of her being more of an object of finery than a human being.

    Katrina’s father, Baltus Van Tassel, provides a counterpoint to Ichabod’s lust for food and finery. Baltus already possesses a staggering amount of wealth and seems wholly content in what he has. He even shares his wealth by throwing a lavish party that feeds and entertains those who possess much less than he does, including Ichabod.

    “The Legend of Sleepy Hollow” Analysis

    Let’s dive a little deeper by analyzing the text.

    Tone and Setting

    This Gothic tale is found “among the papers of the late Diedrich Knickerbocker.” Irving brings forth legend and history with his use of this fictional historian as the narrator of the story. Knickerbocker also gives the story a certain sense of folkloric authenticity, as his account is third- or even fourth-hand. Seeing how young a nation the United States was at the time of publication, this tone of an authentic historical and folkloric narrative is crucial in establishing a common American heritage within the story.

    Irving paints a vivid picture of the United States’ northeastern countryside with his ornate descriptions of the Hudson Valley and its surroundings. The story begins by plunging the reader headfirst into the beauty of Sleepy Hollow’s surrounding area. Irving gushes over the tranquil brooks and rivers, the active wildlife, and the overall stillness of this sequestered countryside in the American Northeast. He also sets the story squarely in the fall season with colorful descriptions of the ripening autumnal produce and the changing color of the leaves. This adds to the story’s ghostly nature by timing the events around Halloween.

    Do you think this text was influenced by Romanticism with its emphasis on nature?

    The Legend of Sleepy Hollow, Hudson Valley in autumn, StudySmarterThe Hudson Valley. This scenic area provides the setting for “The Legend of Sleepy Hollow.” Pixabay

    Irving utilizes these images of nature to evoke dread in some passages. The natural sounds of the valley haunt Ichabod during his walks through the darkened valley: “...every sound of nature, at that witching hour, fluttered his excited imagination; the moan of the whip-poor-will from the hillside; the boding cry of the tree-toad, the dreary hooting of the screech-owl.” The scenes that portrayed a place of beauty in previous passages are now designed to invoke a sense of terror in the reader. However, the tone of dread is balanced with a sense of humor. Specifically, passages that play on Ichabod’s amusingly large appetite or the pitfalls of courtship provide comic relief in an otherwise harrowing tale.

    Caricatures and Archetypes

    Irving makes great use of caricature in his characters. Ichabod Crane’s exaggerated comical appearance and love of knowledge present a stark contrast to Brom Bones’ equally exaggerated role as a Herculean competitor in the battle for a lady’s hand. These vastly different characters perfectly demonstrate the classic brain versus brawn archetype and further add to the folkloric feel of the story.

    Irving doesn’t stop in his archetypal character portrayal with Ichabod and Brom Bones. Katrina Van Tassel serves as the typical “fair maiden,” a character that is less of a developed human being and more of a living, breathing representation of the wealth for the lucky gentleman who marries her. Her father, the kindly Baltus Van Tassel, presents a flip side to this battle for riches. While Ichabod and Brom Bones engage in a fierce competition for wealth, Baltus already possesses that affluence and is satisfied with it. He represents the ultimate goal of financial security that men like Ichabod and Brom Bones crave.

    Facts Versus Fiction

    What happens to Ichabod Crane after his fateful encounter with the Headless Horseman? Irving carefully places clues that Ichabod Crane’s fate could be explained by logical means. The smashed pumpkin, Brom Bones’ skill on horseback, his motive in removing Ichabod as a competitor, and his “exceedingly knowing” disposition after Ichabod’s disappearance all point to the conclusion that he was the figure that frightened and hunted Ichabod. However, this conclusion is insinuated rather than definitively stated.

    Irving ultimately leaves the conclusion open to interpretation, challenging the reader to decide for themselves. The logical individual will undoubtedly conclude that the Headless Horseman was merely Brom Bones playing a prank, and Ichabod simply fled the area. However, the passionate believer in the unknown may prefer the enigma in the Dutch wives’ belief that he was spirited away by the Headless Horseman. In leaving the ending open, Irving allows room for a mystery that is true to the spirit of folklore.

    The Legend of Sleepy Hollow - Key takeaways

    • “The Legend of Sleepy Hollow” was written by Washington Irving in 1819 and published in 1820.

    • The inhabitants of Sleepy Hollow are very superstitious and believe several ghosts haunt the area, the most feared of which is the Headless Horseman.

    • The main character is Ichabod Crane, a schoolteacher determined to marry a local heiress named Katrina Van Tassel.

    • One night while in the woods, Ichabod encounters what appears to be the Headless Horseman. Ichabod disappears, never to be heard from again.

    • Washington Irving uses a fictional narrator named Diedrich Knickerbocker to give the story a folkloric and historic feel.

    • Irving utilizes natural imagery to give the reader both a sense of the setting’s natural beauty and a feeling of dread.

    Frequently Asked Questions about The Legend of Sleepy Hollow

    What is “The Legend of Sleepy Hollow” about?

    “The Legend of Sleepy Hollow” is about a New England schoolmaster named Ichabod Crane and his encounter with an infamous local ghost, the Headless Horseman. 

    Who is the author of “The Legend of Sleepy Hollow?” 

    The author of “The Legend of Sleepy Hollow” is Washington Irving.

    When was “The Legend of Sleepy Hollow” written?

    “The Legend of Sleepy Hollow” was written in 1819 and published in 1820.

    Who is the narrator of “The Legend of Sleepy Hollow?” 

    The narrator of “The Legend of Sleepy Hollow” is the fictional persona of Diedrich Knickerbocker, although the story was told to Knickerbocker by an unnamed gentleman.

    What is the tone of “The Legend of Sleepy Hollow?” 

    The tone of “The Legend of Sleepy Hollow” is folkloric, balancing terror with some moments of humor. Irving's tone is at times ominous and filled with dread, especially in passages describing Ichabod's walks through the valley after dark. At other points in the story, such as during descriptions of Ichabod's insatiable appetite or attempts to court Katrina Van Tassel, the tone is more lighthearted. 

    Test your knowledge with multiple choice flashcards

    What is Ichabod Crane’s main motivation in “The Legend of Sleepy Hollow”?

    Who is Ichabod Crane’s rival?

    Which of these themes are present in “The Legend of Sleepy Hollow”?


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