[4] Author Gary Deniss asserts that while the character of Ichabod Crane is loosely based on Merwin, it may include elements from Youngs' life.

He is described by Irving in the story as "tall, but exceedingly lank, with narrow shoulders, long arms and legs, hands that dangled a mile out of his sleeves, feet that might have served for shovels, and his whole frame most loosely hung together.

His head was small, and flat at the top, with huge ears, large green glassy eyes, and a long snipe nose, so that it looked like a cock perched upon his spindle neck, to tell which way the wind blew."

Ichabod was also known as "the singing-master of the neighborhood" and often on Sundays would "take his station in front of the church gallery, with a band of chosen singers; where, in his own, he completely carried away the psalm from the person."

In the story, he was "esteemed by the women as a man of great erudition, for he had read several books quite through, and was regarded a master of Cotton Mather's History of New England Witchcraft, in which, by the way, he most firmly and potently believed."

Irving describes Ichabod as "a man of some importance in the female circle of a rural neighborhood; being considered a kind of idle, gentleman-like personage, of vastly superior taste and accomplishments to the rough country swains, and, indeed, inferior in learning only to the parson."

In the story, Irving writes regarding Ichabod: "he would have passed a pleasant life of it, despite the Devil and all his works, if his path had not been crossed by a being that causes more perplexity to mortal man than ghosts, goblins, and the whole race of witches put together, and that was—a woman."

This attracts the attention of the town's rowdy, Abraham "Brom Bones" Van Brunt, who also wants to marry Katrina and is challenged in this only by Ichabod.

During his journey home, Ichabod encounters another traveller, 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.

However, before Ichabod can react, the Headless Horseman throws his severed head at him, knocking him from the back of his own horse and sending him "tumbling headlong into the dust."

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."