In the Hudson Valley of New York, Dutch settlers have an established history. Ichabod Crane, a schoolteacher, is new to the Hudson Valley town of Sleepy Hollow—unlike the descendants of its early Dutch inhabitants. Sleepy Hollow is dreamy, whimsical, and full of supernatural lore. There are legends that the town itself has been enchanted or bewitched. Among many superstitions and tales in the region, the most prominent is that of the Headless Horseman: a Hessian trooper who lost his head to a cannonball.

Ichabod came to Sleepy Hollow from Connecticut in order to teach. Like many residents of the town, he enjoys sitting comfortably around the fire with older Dutch women, exchanging ghost stories. He is a “man of letters” and thus admired for his knowledge. As a schoolmaster, Ichabod plays an integral role in the community, specifically with the country women. He is also a well-known singer in the town; many come to him for lessons. One such pupil is Katrina Van Tassel, a Dutch heiress to her father’s farm. Ichabod is attracted to Katrina and particularly fascinated by her wealth. He makes plans to woo her so that he, too, might inherit her family’s abundant farmland.

Much to his chagrin, Ichabod isn’t the only pursuer of Katrina. Brom Van Brunt, nicknamed Brom Bones for his powerful physique, also seeks Katrina’s hand. Brom’s presence discourages most other suitors. Ichabod, however, continues his pursuit confidently. Brom ridicules Ichabod. He even trains a dog to whine in a “most ludicrous manner,” introducing the dog to Katrina as a competitor with Ichabod’s own musical teachings. The two men continue to butt heads over Katrina with neither gaining an absolute upper hand. One evening, Ichabod is invited to the Van Tassels’ home for merry-making, or a gathering with dinner and dancing. Ichabod spends extra time getting ready, attempting to make himself look both presentable and like a cavalier. He also borrows a horse from his neighbor, Van Ripper. The horse is vicious and broken down, his mane is tangled and knotted, and there is a “lurking devil” within him. Upon this steed, Ichabod sets out for the Van Tassel home.

On his journey, Ichabod becomes increasingly enchanted by the expanse of farmland he encounters. Apples, corn, and pumpkins all excite him as he thinks about the delicacies they will soon be made into: cider, cakes, pies, and more. He arrives at the Van Tassels’ castle in the evening and finds Brom Bones already there. Brom has ridden his horse, Daredevil, who is mischievous and not unlike his rider. The food-motivated Ichabod is immediately drawn in by the alluring spread on the table—sweets, fruits, meat, and cream. As Ichabod indulges in the culinary delights before him, he thinks about how wonderful it would be to be “lord of the scene” if Katrina were to marry him. He is enraptured by the status enjoyed by Van Tassel, fantasizing about what it would be like to raise his social standing and be selective about the company he keeps.

Music plays, and people begin to dance. The musical Ichabod is talented in dance, too, and draws a crowd of admirers. When the dancing fades, Ichabod joins the older members of the community who have gathered around, telling stories. Sleepy Hollow is situated near the former British-American line of the Revolutionary War, making it a location full of all kinds of stories. The narrator notes that sufficient time has passed for people to embellish their stories without scrutiny, as folklore is often situated in truth. War stories are told, but the local ghost stories and legends make up the bulk of the conversation.

Sleepy Hollow is said to be a hub of these supernatural happenings. Ghost stories are closely entwined with the town, as if a “haunted contagion” is blown through the air. Common legends are reiterated, such as seeing a mysterious woman in white who shrieks in the night, or hearing mourning cries at the tree where a Major André was hanged. No story brings quite as much excitement as that of the Headless Horseman, who has been seen tethering his horse in the graveyard of an old church. Even skeptics have allegedly seen the horseman—Brom Bones discredits him as a jockey who needn’t be feared.

Before the evening closes, Ichabod speaks with Katrina. The specifics of their conversation elude the narrator, yet it seems that the conversation goes poorly and possibly in favor of Brom Bones. Ichabod leaves the estate without noticing the riches he so desperately wanted just hours earlier and mounts his horse to ride home. The crestfallen Ichabod becomes spooked on his journey back. Each noise he hears and unsettling image he sees he attributes to the natural world around him. Suddenly, the figure of the horseman begins chasing Ichabod. He is terrified, and his horse ceases to obey his orders. The horseman throws his severed head at Ichabod; Ichabod tries to dodge it but is knocked off his horse. The following morning, the horse is found—but Ichabod remains missing. At the site of the encounter, all that remains is Ichabod’s hat and a smashed pumpkin. He is not seen again.

There is speculation in the town about what happened to Ichabod, yet no one knows for sure. Many think he was embarrassed by Katrina’s refusal or that he did not want to return to Van Ripper after losing his horse. During these conversations, Brom Bones always lets out a chuckle at the mention of the smashed pumpkin, implying he may know much more about that night than he says.