The story opens with a long descriptive passage offered in the first person by the narrator, who is revealed at the end of the story to be a man in a tavern who told the story to “D. K.” Irving’s contemporaries, and readers of the entire Sketch Book, know that “D. K.” is Diedrich Knickerbocker, the fictional author of an earlier book of Irving’s. The narrator describes the story’s setting, creating images of a quaint, cozy Dutch village, “one of the quietest places in the whole world,” in a “remote period of American history” that seemed long-ago even to Irving’s original readers. The village is not just far away and long ago; it is a magical place, “under the sway of some witching power, that holds a spell over the minds of the good people, causing them to walk in a continual reverie.”
In this land lives Ichabod Crane, a schoolteacher and singing instructor who comes from Connecticut. His last name suits him. He is tall, lanky and sharp-featured, with clothes too small and ears too big. Crane is a serious and strict teacher, but liked well enough by his students and their families. He has apparently no real friends in the community, but is welcome as he passes from house to house eating whatever he can help himself to in exchange for doing light chores and entertaining the housewives with his stories and gossip. He is much admired for his intelligence, for, unlike the rest of the village, he has “read several books quite through,” and he is especially interested in tales of witchcraft and magic. Several local tales feature the ghost of a Hessian trooper, who was killed by a cannonball and who rides through the countryside each night looking for his missing head.
One of Crane’s singing students, Katrina Van Tassel, has caught his eye, and he dreams of marrying her. Katrina is eighteen years old, plump and ripe, and “a little of a coquette.” Crane desires her not because of her beauty or her personality, but because her father is wealthy and there is always wonderful food at the Van Tassel home. He fills his thoughts with images of roast pigs and pies and sausages, and imagines selling off the Van Tassel land to buy a homestead in the wilderness where he and Katrina “with a whole family of children” could go in a covered wagon. So Crane begins to court Katrina.
Because she is beautiful and wealthy, Katrina has other suitors. Chief among them is Brom Bones, a man who is everything Ichabod Crane is not: strong, rugged, handsome, humorous and clever. Katrina seems content to be courted by two men, and does not discourage either man’s attentions. Brom’s natural instinct is to fight with Crane, but since Crane will not fight Brom resorts to playing a series of practical jokes on Crane instead.
One evening, Mr. Van Tassel hosts a big party for everyone in the village. Crane dresses up in his finest and makes himself look as handsome as he can. He is so awestruck by the tremendous foodladen tables at the party that he decides to ask Katrina for her hand. After an evening of swapping ghost stories with his neighbors, he approaches his intended bride. Although the discussion is not recorded, a few minutes later he leaves the house “with an air quite desolate and chop-fallen.” Feeling dismal, he begins the long ride home alone. Remembering all the ghost stories he has heard and told that evening, he gets more and more nervous.
Suddenly, he sees a large shadowy figure on the road ahead. It appears to be a headless man riding a horse, and Crane can just make out the shape of a head resting on the pommel of the saddle. Terrified, he races away, chased by the headless horseman. He is unable to escape. The last thing he remembers is the sight of the rider about to throw the head at him; struck by the flying object, he is knocked unconscious to the ground.
The next morning Crane does not come to school, and he is never seen in the village again. A search party finds his hat and a bundle of his possessions, and nearby on the ground a smashed pumpkin. Brom Bones marries Katrina, and for the rest of his life gives a knowing look and a laugh when the mysterious disappearance of his rival is mentioned. Though some in the village may suspect that Brom was responsible for Crane’s disappearance, most of the women maintain that Crane was carried away by the headless horseman. Crane himself has become the subject of the kind of ghost story he so loved to tell.
Ira Mark Milne (Editor), Short Stories for Students – Presenting Analysis, Context, and Criticism on Commonly Studied Short Stories, Volume 8, Washington Irving, Published by Thomson Gale, 2000.