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Ichabod comes from the biblical name of the grandson of Eli the High Priest and son of Phinehas. Irving might have borrowed the name from that of Ichabod B. Crane, a colonel in the US Army during the War of 1812 whom he had met in 1814 in Sackets Harbor, New York.
According to a notation by Irving, the character of Ichabod Crane was based on a schoolteacher named Jesse Merwin, whom Irving befriended in Kinderhook, New York, in 1809. According to an 1894 article in The New York Times, "it [was] claimed by many that Samuel Youngs was the original from whom Irving drew his character of Ichabod Crane".
As described in the story, Ichabod Crane follows strict morals in the schoolroom, including the proverbial "Spare the rod and spoil the child"; outside the schoolroom, he is shown to have few morals and no motive but his own gratification. Despite being thin, he is capable of eating astonishingly large amounts of food and is constantly seeking to do so. In addition to this, he is excessively superstitious, often to the extent of believing every myth, legend, tall tale, etc. to be literally true. As a result, he is perpetually frightened by anything that reminds him of ghosts or demons.
A turning point in the story occurs when Ichabod becomes enamored of one Katrina Van Tassel, the daughter and only child of a wealthy farmer named Baltus Van Tassel, who pays little attention to his daughter other than to be proud of her merits when they are praised. On account of both of her beauty and her father's wealth, which he is eager to inherit, Ichabod begins to court Katrina, who seems to respond in kind. This attracts the attention of the town rowdy, Abraham "Brom Bones" van Brunt, who also wants to marry Katrina and is challenged in this only by Ichabod. Despite Brom's efforts to humiliate or punish the schoolmaster, Ichabod remains steadfast, and neither contestant seems able to gain any advantage throughout this rivalry.
Later, both men are invited to a harvest festival party at Van Tassel's where Ichabod's social skills far outshine Brom's. After the party breaks up, Ichabod remains behind for "a tête-à-tête with the heiress", where it is supposed that he makes a proposal of marriage to Katrina but, according to the narrator, "Something, however ... must have gone wrong, for he certainly sallied forth, after no very great interval, with an air quite desolate and chapfallen", meaning that his proposal is refused, allegedly because her sole purpose in courting him was either to test or to increase Brom's desire for her. Therefore Ichabod leaves the house "with the air of one who had been sacking a henroost, rather than a fair lady's heart."
During his journey home, Ichabod encounters another traveler, who is eventually revealed to be the legendary Headless Horseman; the ghost of a Hessian soldier who was decapitated by a cannonball during the American Revolutionary War. Ichabod flees with the Horseman chasing after him, eventually crossing a bridge near the Dutch burial ground. Because the ghost is incapable of crossing this bridge, Ichabod assumes that he is safe. However, the Horseman throws his own severed head at Ichabod, knocking him from the back of his own horse and sending him "tumbling headlong into the dust". The next morning, Ichabod's hat is found abandoned, and close beside it a shattered pumpkin. Ichabod is never seen in Sleepy Hollow again, and is therefore presumed to have been spirited away by the Headless Horseman. Later, "an old farmer, who had been down to New York on a visit several years after, and from whom this account of the ghostly adventure was received" suggests that Ichabod had been frightened, both of the Horseman and of the anger of his (Ichabod's) current landlord, into leaving the town forever, later to become "a justice of the ten pound court" in "a distant part of the country." Katrina marries Brom, who is said "to look exceedingly knowing whenever the story of Ichabod was related, and always laughed heartily at the mention of the pumpkin", which events "led some to suspect that he knew more about the matter than he chose to tell"; therefore, it can be assumed that he himself was the Horseman, whose legend he took of advantage of his rival.
In reality about Ichabod's fate, he returned to Connecticut without his horse.
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