The Legend of Sleepy Hollow: Main Story Summary & Analysis

Irving uses this framing device—in which he is just presenting a narrative found within the papers of someone else—to give his story a claim to legitimacy and historical veracity.

Given that the Dutch had only been in North America for a few hundred years, the word “ancient” exaggerates the truth while also giving the story a ring of the legendary, and, by extension, claiming a history for the new nation of the United States that could support a cultural and literary tradition.

In the story, names tend to stand in for themes and characteristics—here, the town as a place that time forgot.

Knickerbocker does not often insert his own opinions and perspective into the story; here, it has the effect of further fleshing out the setting, as well as setting the stage for the contrast between an idyllic, peaceful village and its supernatural hauntings.

Again, the name “Sleepy Hollow” describes the town as well as Knickerbocker’s own descriptions, though more succinctly. The “witching influence” is portrayed as mysterious and even primordial, lending the setting a greater sense of natural history.

This is the first major example of reality, history, and the supernatural melding into one. The Revolutionary War certainly caused a great deal of death and destruction, but the “authentic historians” also chronicle entirely imaginative affairs. Telling stories, of course, is one way for the villagers to come to terms with the turmoil of the war.

Irving’s construction of a ghost story leads to some ambiguities—it isn’t always clear if Sleepy Hollow is more susceptible to actual ghosts and apparitions, or if the whole village, as a sleepy little town, is more prone to such imaginings.

The notion of Sleepy Hollow as a town that history passes by recalls Irving’s other famous story, “Rip Van Winkle,” but it’s also paradoxical—as the ghosts and spirits reveal, the town was influenced and even traumatized by the war.

Again, Irving’s language is used (often humorously) to create a sense of history where little exists: the “remote history” of the United States is just 30 years ago. Ichabod’s physical qualities are indicative of his dreamy, absentminded character—he seems to have fallen into his position without quite knowing why or how.

The prose in this section is witty, clever, and reveals Irving’s stylistic skill. The narrator seems to be representing the reader with the full gamut of Ichabod’s personality—he’s authoritative but distracted, strict but ultimately fair. Ichabod may not know what he’s doing “tarrying” in Tarry Town, but he has successfully appropriated, and embraced, the social role of schoolteacher.

In the early American republic, going to school was far from a given. Since most of the children would eventually be meant to work on and inherit their parents’ farms, it’s not surprising that there’s a tension between “book-learning” one hand and practical knowledge and getting children to work as field hands and help support their families as soon as possible on the other. Ichabod is acutely aware of this tension. He knows how to change his behavior based on the situation in which he finds himself—conscious that social relations are often a battle requiring strategy like any other. And it’s in his best interest to do so, since he can be sure to get a good meal out of it.

Given Irving’s constant but subtle irony, we might suspect that Ichabod’s voice is not as spectacular as he believes it to be.

Here’s another situation in which Ichabod adapts his behavior to his audience, knowing which aspects of his character to stress and which to hide in order to gain the most out of his acquaintances. Cotton Mather and his book will come up multiple times in the story, symbolizing both Ichabod’s abstract knowledge and his overly imaginative spirit.

The quotes in this section reflect the fact that Irving himself often employs the language of appetite and consumption even when talking about things other than food. Indeed, Ichabod’s appetite for meals and for stories is portrayed as one and the same, emblematic of his greedy nature. His ability to “swallow” stories whole also helps to explain why he’s unable to rid himself of them afterward and continues to be afraid.

Along with (and despite) his less admirable characteristics, Ichabod is clearly likable. As a newcomer, his likability gives him an entrance into the village folklore, which the reader has already learned about from the narrator earlier in the story.

Ichabod, unlike the Dutch wives, cannot simply tell stories and then go on living as if nothing had changed; for him, ghost stories become a part of reality rather than a break from it.

This (humorous) comparison of Katrina to ghosts and witches foreshadows just how much trouble Ichabod’s admiration of Katrina will get him into. The description of Katrina portrays her largely as another of Ichabod’s material desires, as something to be consumed—and ultimately as something to fight for.

Several paragraphs are taken up with this description, as seen through the eyes of Ichabod. Such detail regarding the farm’s abundance underlines Ichabod’s massive appetite—he’s not simply greedy for the trappings of wealth but for the consumption that goes along with it (somewhat understandably, given his humble status as a schoolteacher in rotating lodgings). Getting his hands on that farm would change his life, shoot him upward in society, and fill his belly for the rest of his life.

Mixed with Ichabod’s enormous appetite is his wild imagination, allowing him to picture himself married and settled down before his courtship has really started.

Abundance, here, is grafted onto the language of war, as the narrator begins to intimate that Ichabod will have to fight to achieve it.

Here we have an explicit comparison between Ichabod’s courtship of Katrina and the travels of a knight errant—another example of a fictional story seeming more attainable, more “real,” than reality. It also connects Ichabod to another knight-errant who’s imagination overpowers him: Don Quixote.

Another example of names serving as a powerful descriptor of characters or places. Brom Bones doesn’t exactly map onto the knight errant comparison—he’s mischievous rather than being a truly evil enemy. Brom’s reputation in the village backs up this characterization, and sets the bar higher for Ichabod to attempt to battle him. The surname “Bones” also connects Brom to the supernatural, but in a humorous way.

War is not always waged out in the open, but often takes place through more subtle, strategic moves. However, Ichabod’s choice to continue shows at least a bit of delusion compared to the other candidates.

The stage is set and any obstacles to a potential battle, such as Katrina’s parents, are swept aside.

Here, again, Knickerbocker inserts himself into the narrative to earnestly question the motives and actions of the characters—fitting with the conceit that he’s a real person considering a true story. In the initial battles between Ichabod and Brom, the result seems to remain a draw—even if Brom Bones has the upper hand in terms of dreaming up practical jokes to play.

In contrast to the earlier scene, here Ichabod is comfortably at the top of a different social hierarchy. His confidence at the schoolhouse is only increased by the invitation he receives to the quilting frolic, which confirms that he has at least succeeded in becoming one of the candidates to Katrina’s hand.

With the possibility of the abundance of Van Tassel’s farm replacing his meager income as a schoolteacher, Ichabod brushes aside his current duties—again, perhaps being overly imaginative about his ability to win over Katrina’s heart.

Irving, of course, helped to found the genre of American Romanticism, which believed in the primacy of the imagination above purely rational thought, the importance of personal freedom, and the authenticity of nature. But this description is more of a parody of romanticist prose, as Irving pokes fun at the battle into which Ichabod is riding.

By creating such an idyllic scene, the story sets up a future contrast between this peaceful afternoon and the same journey home later that night. Ichabod, once again, can’t help but consider nature not in its passive beauty but in terms of what it can offer him—particularly if he can win the battle for Katrina.

These kinds of details are typical of American Romanticism, a genre Irving is helping to forge through every description in his story.

The description of the guests’ clothing underlines Tarry Town’s status as a place devoid of history—though the ribbons suggest that even Tarry Town cannot fully escape changing times and traditions.

By now we should expect that Ichabod would make a beeline for the dessert table. The traditional Dutch food on offer adds another touch of tradition and age to the story. Ichabod’s gloating thoughts, meanwhile, reflect his sense of social competition and his acute desire to climb the social ranks.

This is the first moment at which it seems that Ichabod is finally gaining the upper hand against Brom Bones. The description of the black people outside, however, reminds us that beyond Ichabod’s social strivings, there were far clearer and more serious social hierarchies at the time—these black people were likely slaves.

Though Tarry Town seems not to have changed in years, the war certainly impacted the lives of its inhabitants. As major events recede into history, however, it becomes easier to build up stories and traditions around them—even if these tales blur the line between history and storytelling.

Given the blurred line between history and stories, it is unsurprising that war stories yield easily to ghost stories—especially since many of these tall tales draw on the historical war for their characters and plots. The supernatural is closer to reality in this village, particularly for Ichabod but to some extent for everyone.

Many of these ghosts, once again, were either real historical figures or have some kind of relationship to the Revolutionary War. The description of the church reveals how suitable it is for stories of haunting and ghostliness, since it is isolated, dark, and gloomy.

In the topsy-turvy world of Sleepy Hollow, those who are too anchored in reality will ultimately be punished by the supernatural. Brom Bones’s addition to the story are obviously boastful tall tales, but they underline his eagerness to seek out competition wherever he can find it. Looked back on from later in the story, Brom’s tales here will also suggest that perhaps he was laying the foundation for another of his pranks. Ichabod, for his part, believes too earnestly in the reality of the ghost stories to make up his own tales. He takes his tales from his book.

Again, Knickerbocker is not quite an omniscient narrator—there are things he doesn’t know, which paradoxically makes us more willing to accept his narrative as realistic. Instead he reads between the lines—something must have gone wrong if Ichabod is no longer enraptured by the abundance around him. The suggestion is that Katrina has rejected him, that he now knows he has no chance with her.

Sleepy Hollow’s picturesque isolation makes it attractive during the day, but an ideal setting for hauntings at night. Ichabod doesn’t need much more encouragement than that for his imagination to begin imbuing the nature around him with all kinds of supernatural qualities and creating his own reality out of them.

As we reach the climax, events begin to pile atop each other and the cadence of the prose grows quicker and more dramatic. Even as Ichabod is frightening himself into desperation, he draws on real historical events like Major André’s to justify his fear. By the time the massive figure rises out of the shadows, we are almost unsurprised, so well has Ichabod (and Irving) built up a foreboding of disaster.

Already, we see that Ichabod is not only frightened by the figure on a horseback, but by what that figure represents—particularly, here, the role it played in the story told by Brom Bones. While to the reader, Brom’s tale was obviously mere embellishment and bragging, Ichabod holds no such certainty. Given the framework through which he sees reality, he has almost no choice but to assume that the round object held by the horseman is his head—indeed, the narration encourages us to think so too.

Even while in a race for his life, Ichabod is fearful at having lost the saddle. We already know he prefers to avoid confrontation, so it’s easy to imagine how terrified he might feel about returning to the grumpy Van Ripper having lost the man’s saddle.

Again, Ichabod interprets his own reality in terms of the stories he’s heard, especially that of Brom Bones. In this case, though, the head is no longer simply an eerie, ghostly apparition but an object of battle wielded by the horseman against Ichabod.

Until this moment, we’ve experienced the climax solely through the eyes of Ichabod. Now, the perspective becomes a more distanced, objective point of view. Knickerbocker doesn’t explain the meaning of the shattered pumpkin—as readers more rational than Ichabod, we’re supposed to put the pieces together ourselves: that it is a pumpkin that hits Ichabod and not a head suggests the Horseman was no ghost, and the chase a prank. So: Brom Bones is a prankster and told the story about the Horseman being in this part of the forest. It seems very likely that Brom is pretending to be the Headless Horseman.

Ichabod’s pride in his intellectualism and singing chops is now portrayed as somewhat silly rather than as objects of admiration. Van Ripper’s attitude about school stems from the ambiguous position of Cotton Mather’s book, as both a repository of “book-knowledge” and of irrational supernatural tales. Ripper seems to think: if intellectual people believe in this nonsense, then I don’t want my kids wasting their time with school. Nevertheless, the other villagers easily assimilate this new element into the traditional town ghost stories.

Here, Knickerbocker introduces another element of uncertainty, with a competing conclusion of the tale. Ichabod left town not merely out of fear of the horseman, but more out of the more pragmatic fears of having lost Ripper’s saddle and the social embarrassment of having lost the battle for Katrina. Moreover, this conclusion suggests that in leaving the sleepy town of Sleepy Hollow, Ichabod himself became less dreamy, less focused on lucking into wealth and abundance through marriage, and instead diligently made a successful career for himself. In this conclusion, Ichabod’s path seems to mirror that of the United States, which at the time of the story’s publication was transitioning from a small-town agrarian society to one dominated increasingly by commerce, one where “striving” was valued and could make a career, one in which hard-headed reality was prized over fuzzy-headed beliefs in ghost stories.

Another hint that Ichabod’s perspective on what happened that fateful night is not the perspective the reader should adopt.

By ending with the opinions of the old Dutch wives, Irving can be sure that his tale will “count” as a ghost story—even if he’s introduced alternatives to the haunted, supernatural narrative. And even if the tale of the horseman isn’t “true,” it’s become solidly incorporated into the tradition and legacy of the town—and, by extension, of the budding American nation.