Veracity in Storytelling
Veracity in storytelling is a defining theme of “The Legend of Sleepy Hollow.” The story is distantly removed from the reader—Crayon has found the story in Diedrich Knickerbocker’s papers, who is dead, and who at the end of the story writes that he heard it from an old gentleman, who claimed to not have even believed half of it himself, ultimately getting much of the story from primary or even other secondary sources. Thus, even where the story is told with confidence, the narrator has given us reasons to doubt evrything. We become critical readers, unlike Crane, who believes the ghost stories he reads.

The narrator also admits to complete ignorance of one of the defining moments of the story—Katrina’s imagined rejection of Ichabod—as well as to its ending. He does, however, relay a scene which he can only have knowledge of if Crane (or the horseman) has told his story. There were no other witnesses. Given the narrative frame of the tale, we know that the narrator is not omniscient but has had to rely on others' tales.

Yet, the narrator has not demonstrated that factuality is the point. It is likely that the point of telling the story, just as it has been passed along from one person to another, is in the telling, the enjoyment of the tale. On the one hand, we are critical readers, because otherwise we would not figure out who is playing the role of the horseman. On the other hand, we shouldn't act like a boring schoolmaster but like a true listener, enjoying the tale.

Crayon almost seems to be challenging the reader to enjoy the story even though he doubts most of it, for in the postscript to the story, in which we find out that the previous narrator does not even believe it, the one man who does not enjoy hearing the story says that the reason he cannot enjoy it is that he does not believe it. This man is presented negatively as some kind of dour doubter, however, thus emphasizing the fact that one is better off suspending disbelief, at least enough to enjoy the tale as it is presented. This is a lesson for some literary critics and professors who lose the joy of reading in the course of minute interpretation.
The Power of Imagination
The power of imagination is very prominent in “The Legend of Sleepy Hollow” and throughout Crayon’s collection as a whole. In “The Legend of Sleepy Hollow,” Ichabod is a rather comedic and foolish protagonist. This comes, largely, from the strength of his imagination, and this leads to his downfall.

Ichabod’s primary enjoyment is reading stories about ghosts, demons, and witches, or hearing stories about the same; yet, because his imagination is so powerful, he pays for this dearly, having great frights every time he walks or rides home after dark. The littlest things frighten him, and he can convince himself that almost anything is supernatural.

Ichabod’s imagination thus makes his life more difficult, but it does not seem to alter his behavior, since his imagination leads him to think the supernatural things are real. He continues to read these stories, and he continues to walk home after dark. His imagination in its fantasizing function does, however, seriously affect his life in that it reinforces his impotence. Ichabod’s imagination is so powerful that he believes himself essentially already the owner of the Van Tassel farm. Because he gets so much joy out of this fantasy, he forgets that he has to put forth an effort to make it into a reality, so he does not.

Ichabod also tries to woo Katrina, imagining his future life with her. But he does not take Brom seriously enough as a rival, nor does he do anything to prove that he could be a husband who would offer anything to Katrina besides singing lessons. Thus Ichabod’s powerful imagination renders him impotent in reality.

The Legend of Sleepy Hollow Themes
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Veracity in Storytelling
Veracity in storytelling is a defining theme of “The Legend of Sleepy Hollow.” The story is distantly removed from the reader—Crayon has found the story in Diedrich Knickerbocker’s papers, who is dead, and who at the end of the story writes that he heard it from an old gentleman, who claimed to not have even believed half of it himself, ultimately getting much of the story from primary or even other secondary sources. Thus, even where the story is told with confidence, the narrator has given us reasons to doubt evrything. We become critical readers, unlike Crane, who believes the ghost stories he reads.

The narrator also admits to complete ignorance of one of the defining moments of the story—Katrina’s imagined rejection of Ichabod—as well as to its ending. He does, however, relay a scene which he can only have knowledge of if Crane (or the horseman) has told his story. There were no other witnesses. Given the narrative frame of the tale, we know that the narrator is not omniscient but has had to rely on others' tales.

Yet, the narrator has not demonstrated that factuality is the point. It is likely that the point of telling the story, just as it has been passed along from one person to another, is in the telling, the enjoyment of the tale. On the one hand, we are critical readers, because otherwise we would not figure out who is playing the role of the horseman. On the other hand, we shouldn't act like a boring schoolmaster but like a true listener, enjoying the tale.

Crayon almost seems to be challenging the reader to enjoy the story even though he doubts most of it, for in the postscript to the story, in which we find out that the previous narrator does not even believe it, the one man who does not enjoy hearing the story says that the reason he cannot enjoy it is that he does not believe it. This man is presented negatively as some kind of dour doubter, however, thus emphasizing the fact that one is better off suspending disbelief, at least enough to enjoy the tale as it is presented. This is a lesson for some literary critics and professors who lose the joy of reading in the course of minute interpretation.
The Power of Imagination
The power of imagination is very prominent in “The Legend of Sleepy Hollow” and throughout Crayon’s collection as a whole. In “The Legend of Sleepy Hollow,” Ichabod is a rather comedic and foolish protagonist. This comes, largely, from the strength of his imagination, and this leads to his downfall.

Ichabod’s primary enjoyment is reading stories about ghosts, demons, and witches, or hearing stories about the same; yet, because his imagination is so powerful, he pays for this dearly, having great frights every time he walks or rides home after dark. The littlest things frighten him, and he can convince himself that almost anything is supernatural.

Ichabod’s imagination thus makes his life more difficult, but it does not seem to alter his behavior, since his imagination leads him to think the supernatural things are real. He continues to read these stories, and he continues to walk home after dark. His imagination in its fantasizing function does, however, seriously affect his life in that it reinforces his impotence. Ichabod’s imagination is so powerful that he believes himself essentially already the owner of the Van Tassel farm. Because he gets so much joy out of this fantasy, he forgets that he has to put forth an effort to make it into a reality, so he does not.

Ichabod also tries to woo Katrina, imagining his future life with her. But he does not take Brom seriously enough as a rival, nor does he do anything to prove that he could be a husband who would offer anything to Katrina besides singing lessons. Thus Ichabod’s powerful imagination renders him impotent in reality.
Lack of Class Structure in America
The theme of lack of class structure in America is most clear when reading “The Legend of Sleepy Hollow” in the greater context of The Sketchbook of Geoffrey Crayon, Gent., which offers the European contrast. It is still apparent here, however. Sleepy Hollow is an old town inhabited mostly by descendants of its original settlers. This would seemingly make it prone to family prejudices, a younger parallel to the European aged communities, yet there is no evidence of this kind of hierarchy. Instead, people are valued for their merits, such as their book learning or their ability in teaching, activities requiring strength, or singing.

Katrina Van Tassel is desired by almost every eligible young man in Sleepy Hollow, being the rich farmer’s daughter. In Europe, her lack of title would have limited those who would be interested in her to others of similar status, but in America (or at least this sleepy town) her abundance of resources, combined with her good looks, youth, and charm, are enough to make her very desirable. This is more of a unique money issue than a general class issue. Even as the most desired bachelorette in the neighborhood, moreover, she ends up choosing between a well-liked but irresponsible and rowdy young man, with no fortune that we know of, and a very poor and homeless school teacher with an obsession with ghost stories.

In their community, Ichabod is recommended by his comparatively good education; Brom, by his physical skills and likable personality. Their titles, families, and even money are not explicitly brought into consideration. This contrasts greatly with, for example, “The Pride of the Village,” another story in Irving's collection, in which a beautiful and virtuous young English woman ends up dying of heartbreak because the man she loves could not conceive of marrying her because of her comparatively low class.
Abundance of Resources in America
Although the source for “The Legend of Sleepy Hollow” is believed to be an old European folktale, in the context of The Sketchbook of Geoffrey Crayon, Gent., it is a very American story. This is clear, first of all, in the fact that it is set in America at all, when the primary cohesive factor of the collection is Crayon’s travels in Europe. Thus its being set in America is not just arbitrary but is an active choice and is thus essential, and this is reflected in several themes. While Europe has history, America has youth, promise, and resources.

Ichabod, like Rip Van Winkle, is indolent and impotent, barely able to provide for himself, producing nothing. He is, however, still able to eat almost constantly, as his appetite demands, because of the plentiful resources available in Sleepy Hollow. That this abundance is important is very clear, for almost half of the story is spent describing commodities: the Van Tassels’ land, farm, animals, house, possessions, and food. Whereas Katrina is described as youthful and pretty, each individual animal, each dish, is described in much more sensuous detail than she is. Thus resources become one of the most important features of the story, which goes along with Crayon’s belief that America’s advantages are in its natural resources and beautiful landscapes, while if one is looking for the best people and histories, Europe would be the better place to go.
Lack of History and Continuity in America
The lack of history and continuity in America, like the lack of class structure, is apparent in “The Legend of Sleepy Hollow” and is even more apparent in the rest of the collection, which offers the European contrast. Sleepy Hollow’s overabundance of ghost stories, when compared to other American neighborhoods, is explained by the fact that it is an old village, whose inhabitants are largely descendants of the original settlers. Thus, even though it is an American village, it is presented as more like a European village than most American neighborhoods, which allows it to have legends.

However, its youth in comparison to European towns is still very clear, as when Diedrich Knickerbocker says, facetiously, that the story he is going to relay happened during a very “remote period of American history, that is to say, some thirty years since” (274). In Europe, thirty years is barely a generation, not quite "history," but in America, even a twenty-year nap like Rip Van Winkle’s can result in missing a defining period of history.

Knickerbocker also emphasizes that a town like Sleepy Hollow is unusual in America, for most towns do not develop ghost stories, since no ghosts would come back to haunt people who move along so quickly. Sleepy Hollow is disconnected from other towns to the degree that even though Crane is alive somewhere, the people of the town never hear about him. The lack of history and continuity give people in America more freedom, such as freedom of movement, because it is accepted that people come and go and have to succeed on the basis of their talents. People do not have to live up to any expectations set by the generations that came before them.
The Natural and the Supernatural
Irving paints a strong contrast between the natural setting of Sleepy Hollow and the supernatural superstitions of the townspeople. Were it not for the people, with their stories of ghosts and their fears of ghosts, there would be no ghosts. Meanwhile, much of the tale focuses on the natural setting: the birds, trees, and the rest of the flora and fauna of the area, as well as the bodies of water, all described in beautiful detail.

Was Ichabod hit by a ghostly head or a natural pumpkin? It seems clear that the natural explanation should make more sense. But in Sleepy Hollow, there is a vibrant tradition of privileging ideas of the supernatural, and despite all the natural evidence, many people in the town blame the Headless Horseman for Ichabod's disappearance.

Finally, folklore about supernatural beings often focuses on ways that they can be controlled by natural things. For instance, because of the idea that ghosts haunt specific areas, people imagine that they cannot cross a bridge over a body of water, which would take them into a new area. Althouh the supernatural is by definition beyond the natural world, people seek to rationalize, contain, and contain it through storytelling and folklore.
Human Selfishness
Although “The Legend of Sleepy Hollow” is a light-hearted story, told in a humorous manner, it does not paint the most flattering picture of humanity—it probably does not “prompt a benevolent view of human nature” as Crayon says he desires to do in his writing. This is particularly true in the rampant selfishness seen in most of the characters. Most obviously, Ichabod desires Katrina most of all for the increase to his material wealth she would represent, and he even imagines himself selling off her family’s farm once it would be in his possession, for the money. Even when Ichabod shows his better characteristics, helping out around the farms he stays at and keeping the children and wives happy, his primary goal in doing so is to keep his hosts content so that they will let him stay, and continue to feed him.

Yet this is not the only example of greed or selfishness. Katrina uses Ichabod to secure Brom’s affection---she may understand Ichabod’s true motives, but either way, it cannot be denied that she does not hesitate to use him to suit her purposes. That this selfishness, or at least self-centeredness, is not confined to a few characters becomes very clear when Ichabod disappears. A search party is created, but only because Hans Van Ripper wants his missing saddle back, and when there is no sign of Ichabod, nobody cares. This is because has no debts, the assumption being that if he had owed anyone any money, they would have put much more effort into finding him. Thus Sleepy Hollow is a collection of people who, as in most places, put their self-interest first.