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Ichabod Crane Flees The Headless Horseman

Postage Stamp: Legend of Sleepy Hollow

Ichabod Crane is a poor man with aspirations; a lover of ghost stories who fears the dark. In The Legend of Sleepy Hollow, Washington Irving creates an unsympathetic character as the subject of his American ghost story. Last week, Ichabod courted Katrina Van Tassel, hoping she would accept him as a suitor. One wonders why the poorest man in her social acquaintance thought the only daughter of the richest farmer in the region would marry him. Nevertheless, Ichabod approached Katrina expecting her approval. She declined his attentions. In this installment, Ichabod, heavy-hearted and crestfallen, [pursues] his travels homeward. 

Mounted on Gunpowder, Ichabod rides into the dark night. All the stories of ghosts and goblins that he … heard in the afternoon now [come] crowding upon his recollection. The night [grows ]darker and darker; the stars [seem] to sink deeper in the sky, and driving clouds occasionally [hide] them from [Ichabod’s] sight. Immersed in his disappointment, Ichabod approaches the scene of many local ghost stories .

Tulip Tree

An enormous tulip-tree stands before Ichabod in the center of the road. To stave off his fear, Ichabod begins to whistle. As [Ichabod] got closer, he [thinks] he [sees] something white, hanging in the midst of the tree: he [pauses] and [ceases] whistling. Ichabod examines the white substance and realizes it’s only a scar on the bark from a lightening strike. Ichabod’s fear gives way to relief and perhaps a cold sweat. Then, suddenly, Ichabod hears a groan. His teeth [chatter], and his knees [knock] against the saddle.

Another false alarm. The sound is from a breeze moving tree branches against each other. No doubt, Ichabod laughs at his fear. Perhaps he clutches Gunpowder’s reins a bit more tightly. The nervous rider looks ahead to a bridge consisting of logs laid side-by-side.

As [Ichabod approaches] the stream, his heart [begins] to thump; he [summons] up … all his resolution, [gives] his horse half a score of kicks in the ribs, and [attempts] to dash briskly across the bridge. Gunpowder has other ideas and runs into a fence. Ichabod’s terror grows. He jerks the reins, and kicks Gunpowder’s side. The horse stumbles into a thicket of brambles.

Ichabod applies both whip and heel upon the starveling ribs of old Gunpowder, who [dashes] forward, snuffling and snorting. The horse stops by the bridge, with a suddenness that … nearly sent his rider sprawling over his head. Picture ungainly Ichabod, his eyes wide with terror.

Ichabod’s eyes nearly pop out of his head when he looks at the side of the brook and sees something from his worst nightmare. The apparition is huge, misshapen and towering … like some gigantic monster ready to spring upon the traveller.

“Who are you?” Ichabod shouts with false bravado.

No answer.

“Who are you?” Ichabod shouts again, his voice quavering.

Still no answer.

Ichabod tells himself there’s nothing there, and begins singing a psalm to dispel the mystery before him. But, just as whistling didn’t dispel Ichabod’s fear, singing a psalm provides no relief.

Headless Horseman chases Ichabod

Just then the shadowy object of alarm put itself in motion, and with a scramble and a bound stands in the middle of the road. Though the night [is] dark and dismal, yet the form of the unknown [may] now in some degree be ascertained. He [appears] to be a horseman of large dimensions, … mounted on a black horse of powerful frame

The Midnight Ride Begins

With a sigh of relief, Ichabod remembers Brom Bones saying that he had outrun the Horseman. Ichabod urges Gunpowder forward. The stranger, however, [quickens] his horse to an equal pace. Ichabod [pulls] up, … into a walk, thinking to lag behind,—the other [does] the same. And then Ichabod gets a good look at his unwelcome companion. 

Black stallion

The rider [is] gigantic in height, and muffled in a cloak, Ichabod [is] horror-struck on perceiving that he was headless!—but his horror was still more increased on observing that the head, which should have rested on his shoulders, was carried before him on the pommel of his saddle!  

Ichabod whips Gunpowder forward; the horseman keeps pace. They [dash] through thick and thin; stones flying and sparks flashing at every bound. Ichabod’s flimsy garments [flutter] in the air, as he [stretches] his long lank body away over his horse’s head, in the eagerness of his flight

Bridge at Sleepy Hollow

Ichabod gains ground until his saddle girth slips. Ichabod seizes the pommel, and finally flings his arms around Gunpowder’s neck as the saddle falls to the ground. At an opening in the trees, Ichabod sees a bridge over a brook and the walls of a church further ahead. This was where Brom Bones lost his pursuer. “I just have to reach the bridge,” Ichabod thinks.

Ichabod hears the horse behind him and kicks Gunpowder in the ribs. Horse and rider gallop across the bridge, but the Headless Horseman rides hard behind him. The Horseman has his head in his hand as he prepares to throw it at Ichabod. The head sails through the air and collides with Ichabod’s skull. Ichabod falls off his horse. The Headless Horseman thunders by.

Ichabod Flees Headless Horseman

The next morning the [Gunpowder is] found without his saddle, and with the bridle under his feet, soberly cropping the grass at his master’s gate. Ichabod is missing. A search party locates the saddle, tracks from horses’ hooves, and Ichabod’s hat.

What happened to Ichabod? Did the Headless Horseman kidnap him?


Tulip Tree by Glyn Baker

Headless Horseman Pursuing Ichabod Crane by John Quidor

Jumping Black Stallion by Deathfly0

Sleepy Hollow. 1884.

Ichabod Crane and the Headless Horseman. Anonymous.

The Legend of Sleepy HollowGutenberg Project.

Jacqueline Smith.  “Halloween History: The Legend of Sleepy Hollow.” New York Historical Society. Oct. 25, 2013.

Author Sandra Wagner Wright

Sandra Wagner-Wright holds the doctoral degree in history and taught women’s and global history at the University of Hawai`i. Sandra travels for her research, most recently to Salem, Massachusetts, the setting of her new Salem Stories series. She also enjoys traveling for new experiences. Recent trips include Antarctica and a river cruise on the Rhine from Amsterdam to Basel.

 Sandra particularly likes writing about strong women who make a difference. She lives in Hilo, Hawai`i with her family and writes a blog relating to history, travel, and the idiosyncrasies of life.


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