The party eventually breaks up, and Ichabod stays behind to talk to Katrina. The narrator does not know what passes in this conversation, but Ichabod leaves the place looking rather crestfallen, and readers must use their imagination; it seems that in one way or another, Katrina was using him to secure his rival’s affections. Ichabod wakes his horse and sets off during the darkest and quietest hour of night. As he rides, all the ghost stories he has heard come back to him, and he gets more and more uneasy as he approaches the infamous church where the Headless Horseman most often rides.
He makes it past the fearsome Major Andre’s tree, but he has to calm himself by whistling. He then approaches the bridge that crosses the haunted stream, and his horse comes to a sudden halt. Ichabod sees a large, dark figure on the edge of the brook. He knows he cannot outrun a ghost or goblin, so he tries to summon his courage and asks, “Who are you?” He tries to get Gunpowder the horse to continue on, and he starts singing a psalm.
The figure goes into motion—he is a large horseman on a large black horse. The horseman rides along beside Ichabod and Gunpowder without saying anything or making any sign. Ichabod, bothered by this, tries to outpace him, but the horseman quickens his steed as well. Ichabod tries to lag behind, but the horseman keeps pace with him no matter what he does.
Ichabod tries to sing again, but his mouth is too dry with fright. He is not quite sure what it is, but something about his companion is greatly disturbing. When the horseman is suddenly in relief against the sky, Ichabod realizes something ever scarier—he is headless, and he has his head resting on his saddle in front of him. Ichabod panics and attempts to get away by suddenly dashing forward. The Headless Horseman easily keeps pace, however, and when they reach the road to Sleepy Hollow, the frenzied Gunpowder veers off in the opposite direction, toward the infamous church.
In Gunpowder’s frenzy, they gain some ground on the Headless Horseman, but Ichabod’s saddle starts to slip and falls off just as he grips Gunpowder’s neck to hold on. They approach the bridge by the church at which (in the stories that Ichabod has heard) the Headless Horseman vanishes. As soon as Ichabod gets across the bridge, he looks back to see if the ghost has vanished—but as he does, Ichabod sees the ghost stand up in his stirrups and throw his head at Ichabod. It hits Ichabod right in his head and knocks him off of his horse.
Gunpowder appears at Hans Van Ripper’s gate the next day without saddle or rider. When Ichabod has not appeared by dinnertime, either at Hans Van Ripper’s place or the schoolhouse, Hans becomes worried enough to send out a search party. They find hoof prints and the trampled saddle, and they finally find Ichabod’s hat lying next to a smashed pumpkin. They cannot find the schoolmaster, and though they search the creek for his body, they do not find it.
But since Ichabod was a bachelor and in nobody’s debt, the townsfolk decide that he has been carried off by the Headless Horseman, and they worry no more about it. Some say that he left town, partially in fear of the ghost and partially out of shame for having been summarily dismissed by Katrina. Brom Bones, who marries Katrina shortly afterward, also always seems to have a knowing look whenever the story is told, and he finds mention of the pumpkin especially funny.
The old country wives of the area, however, continue to hold that the ghost of the Headless Horseman spirited Ichabod away. This tale becomes a favorite story of the area. The schoolhouse is no longer used, and some say that it now is haunted by the ghost of the hapless schoolmaster.
Mr. Knickerbocher concludes the story with a postscript stating that he has printed this tale almost exactly as he originally heard it from a shabby old gentleman at a corporation meeting. When this man told the story, one gentleman did not seem to enjoy it as much as the others, and he said that he found some parts of it hard to believe. The narrator says that he does not believe half of it himself.
The primary theme in the final section of “The Legend of Sleepy Hollow” is the difference between truth and conjecture. What drives the plot is, first, Ichabod’s failure to understand the truth that he never was a viable suitor for Katrina, and then his failure to suspect that the “Headless Horseman” is just another practical joke on the part of Brom Bones. The importance of truth in storytelling is also central here. Who gets to be in charge of keeping the facts of a story separate from the conjectures, and who can evaluate the conjectures? Can wild tales like this one be verified, and it what ways does it matter or not matter if the story is exactly true or completely false?
One of the key moments in the narration, in the love triangle between Ichabod, Katrina, and Brom, is Katrina’s rejection of Ichabod. The reader sees none of this scene; we only know that he leaves her home dejected. The narrator does not know the details either, but he does not even know if this rejection really happened; he can only offer the reader conjecture, his best guess. Since the townspeople suspect that a rejection was one of the reasons he left town, such a conjecture has at least a minimal basis, and it would be quite understandable. Yet, what really happened? Did he take a liberty that she rejected, such as kissing her inappropriately? Did he make an offer that she rejected? Did he say something that proved his unsuitability for her?
The narrator, like the reader, has to use imagination to put in place this key moment in the story. It is a common narrative strategy to leave a key moment off stage or unsaid. Indeed, the reader knows how these kinds of experiences often go and can easily supply some realistic scenarios regarding rejected professions of love.
Yet, because the reader is given no clear view of what may have happened, the uncertainty in this scene leads us to question the reliability of all the rest of the story. Like the old men with their war stories, everyone has an interest in making the story the way he or she wants it to be. This point emphasizes how unimportant the literal truth is in a story, from a literary rather than a historical point of view. For the townspeople, who are not personally invested in Ichabod’s feelings, he is now just an interesting character in their local folklore, and maybe another ghost for the town to imagine they see or hear from time to time. They will tell the story in the way that makes it most fun or interesting or scary. Any teller of the story, at a number of removes from the actual story, has no reason to believe more than half the story anyway, but the present narrator tells the whole thing as he heard it (he claims) because the story is worth knowing in itself.
What happened to the protagonist is left unknown. Some say he ended up very successful in another state, some say he was spirited off by a ghost, and some say he left the town in shame, but the narrator has only other people’s conjecture on this matter. There is reason to believe, on the basis of the details of the story, that somewhere along the line Ichabod told his side of the story—Brom has never admitted to his role in the practical joke, and Katrina has never suggested knowing about it, so only Ichabod could have told the details of the dark night when Ichabod was chased by a horseman. Still, it is difficult to discern which elements came directly from him and whether they can be believed. The story is too good to be true, though it is believable in many respects.
Crayon’s choice to have the disclaimer in a postscript at the end of this tale, concluding the whole collection, emphasizes his opinion that the veracity of a story is insignificant for literary purposes, if it provides enjoyment and a positive moral result for the reader. Irving likely shared this opinion. It is hard to write fiction without an appreciation for the ways that fiction provides truth in a way different from fact-heavy histories.
Although Ichabod is so foolish, he has something in common with Crayon: both have very powerful imaginations. Ichabod’s causes him to believe in supernatural stories, and he even finds walking alone terrifying. He also can imagine himself as the lord of the Van Tassel farm so clearly that he forgets that he really has nothing to offer Katrina in a marriage, while another suitor could easily stand in his way. Crayon’s imagination, for his part, allows him comfort and keeps him happy with fantasies, but his imagination seems less foolish in the end because he uses his imagination to tell stories with a purpose. He gives pleasure and some measure of education, while Ichabod’s imagination is emotional and expresses unrealistic hopes instead of a literary perspective on reality.