Headless Horseman

Hello and welcome back to Fab Figmentals!

I’m Lindsey Morse, your guide through the realm of curious creatures, magical monsters, and beautiful beasts. Each episode, we dive into the folklore and history of a different legendary creature and share a story about it. And all through the month of October we’re paying special attention to some of Halloween’s most famous monsters. 

This week, we’re taking inspiration from one of my favorite Halloween classics: Washington Irving’s “The Legend of Sleepy Hollow.” 

As you probably already know, “The Legend of Sleepy Hollow” follows the misadventures of Ichabod Crane, a superstitious schoolmaster who comes face-to-face with the Galloping Hessian of the Hollow— better known as the Headless Horseman— a specter that’s believed to haunt the area near the town of Sleepy Hollow in New York’s Hudson Valley. 

Like many great scary stories, this one has roots intertwined in both fiction and reality; and looking back, it’s now difficult to determine just how much of the legend was invented by Irving. Given the history of that part of New York, it’s pretty clear the story was inspired— at least in part— by real life events.

During the American Revolutionary War, the area of Westchester County, New York, where “The Legend of Sleepy Hollow” is set, was a sort of no-man’s-land. After the Battle of White Plains in October 1776, the British occupied the area south of the Bronx River, and the Americans were based north of Peekskill, leaving the area around Sleepy Hollow an open stomping ground for all sorts of ruffians and raiders. Opposing forces often faced off there, and it wasn’t unusual for Patriot militias to get into skirmishes with Loyalist rangers, British infantrymen, or Hessian Jägers—renowned German sharpshooters who rode around on horseback supporting the British troops. Local legend holds that the  headless body of one of these Hessian riders was found in Sleepy Hollow and buried in the town’s church cemetery. Some say the rider was beheaded in a violent dispute; others claim that he was decapitated on the battlefield by a cannonball that blew his skull to pieces. Either way, his restless ghost is said to set out at nightfall, angrily in search of his missing head.

But let’s see what Washington Irving has to say about this famous undead equestrian. Unfortunately, the unabridged version of “The Legend of Sleepy Hollow” is a bit too long to share on our show, so we’re going to cut straight to the chase— pun intended. 

I’ll set up the story for those of you who need a refresher: Ichabod Crane is the protagonist of our tale. He’s a gangly, scarecrow-looking chap from Connecticut, and has come to Sleepy Hollow to work in the town’s schoolhouse. Overall, he’s a rather likable fellow, if a bit of a know-it-all, and he’s embraced by the local community. He babysits youngsters, gives singing lessons, and gossips with housewives. But he is not without his flaws. He’s a superstitious man, and he loves hearing and sharing ghost stories— though he has a tendency to take them to heart, and he often gets spooked when walking alone at night. He also lusts after women and money, and soon after arriving in Sleepy Hollow he sets his romantic sights on one of his students, Katrina Van Tassel, an 18 year old flirtatious beauty from a very wealthy family. 

Unfortunately for Ichabod, he’s not the only one with eyes for Katrina. Local golden boy, Brom Van Brunt, widely known by his nickname, Brom Bones, is also after her affections. 

Brom Bones does NOT like Ichabod going after his girl, and he acts out by regularly pranking the smitten schoolmaster. 

One autumn day, Ichabod receives an invitation to a party at the home of the Van Tassel’s, Katrina’s parents, and he’s sure that this will be his chance to properly woo her and win her hand. He spends the evening dancing and later trades ghost stories with the other guests. The star of this story swap is Brom Bones, who wows the crowd with wild claims that he recently outraced the Headless Horseman himself. As the party winds down, Ichabod hangs behind after everyone leaves in order to have a quiet word with his not-so-secret crush. 

We aren’t privy to what’s said, but we know it isn’t good for our bumbling hero. He sets out for home alone, devastated, but is soon haunted by the memories of the ghost stories he heard earlier at the party. Let’s join up with him here, as he’s making his way home in the dark, dead of night. 

A small head’s up: I’ve made a few small tweaks to the story so it stands alone. Now, here’s Washington Irving’s “The Legend of Sleepy Hollow.”

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It was the very witching time of night that Ichabod, heavy-hearted and crestfallen, pursued his travels homewards, along the sides of the lofty hills which rise above Tarry Town, and which he had traversed so cheerily in the afternoon. The hour was as dismal as himself. Far below him the Tappan Zee spread its dusky and indistinct waste of waters, with here and there the tall mast of a sloop, riding quietly at anchor under the land. In the dead hush of midnight, he could even hear the barking of the watchdog from the opposite shore of the Hudson; but it was so vague and faint as only to give an idea of his distance from this faithful companion of man. Now and then, too, the long-drawn crowing of a cock, accidentally awakened, would sound far, far off, from some farmhouse away among the hills—but it was like a dreaming sound in his ear. No signs of life occurred near him, but occasionally the melancholy chirp of a cricket, or perhaps the guttural twang of a bullfrog from a neighboring marsh, as if sleeping uncomfortably and turning suddenly in his bed.

All the stories of ghosts and goblins that he had heard in the afternoon now came crowding upon his recollection. The night grew darker and darker; the stars seemed to sink deeper in the sky, and driving clouds occasionally hid them from his sight. He had never felt so lonely and dismal. He was, moreover, approaching the very place where many of the scenes of the ghost stories had been laid. 

His heart began to thump; he summoned up, however, all his resolution, gave his horse half a score of kicks in the ribs, and attempted to dash briskly across the bridge; but instead of starting forward, the perverse old animal made a lateral movement, and ran broadside against the fence. Ichabod, whose fears increased with the delay, jerked the reins on the other side, and kicked lustily with the contrary foot: it was all in vain; his steed started, it is true, but it was only to plunge to the opposite side of the road into a thicket of brambles and alder bushes. The schoolmaster now bestowed both whip and heel upon the starveling ribs of old Gunpowder, who dashed forward, snuffling and snorting, but came to a stand just by the bridge, with a suddenness that had nearly sent his rider sprawling over his head. Just at this moment a plashy tramp by the side of the bridge caught the sensitive ear of Ichabod. In the dark shadow of the grove, on the margin of the brook, he beheld something huge, misshapen and towering. It stirred not, but seemed gathered up in the gloom, like some gigantic monster ready to spring upon the traveller.

The hair of the affrighted pedagogue rose upon his head with terror. What was to be done? To turn and fly was now too late; and besides, what chance was there of escaping ghost or goblin, if such it was, which could ride upon the wings of the wind? Summoning up, therefore, a show of courage, he demanded in stammering accents, “Who are you?” He received no reply. He repeated his demand in a still more agitated voice. Still there was no answer. Once more he cudgelled the sides of the inflexible Gunpowder, and, shutting his eyes, broke forth with involuntary fervor into a psalm tune. Just then the shadowy object of alarm put itself in motion, and with a scramble and a bound stood at once in the middle of the road. Though the night was dark and dismal, yet the form of the unknown might now in some degree be ascertained. He appeared to be a horseman of large dimensions, and mounted on a black horse of powerful frame. He made no offer of molestation or sociability, but kept aloof on one side of the road, jogging along on the blind side of old Gunpowder, who had now got over his fright and waywardness.

Ichabod, who had no relish for this strange midnight companion, and bethought himself of the adventure of Brom Bones with the Galloping Hessian, now quickened his steed in hopes of leaving him behind. The stranger, however, quickened his horse to an equal pace. Ichabod pulled up, and fell into a walk, thinking to lag behind,—the other did the same. His heart began to sink within him; he endeavored to resume his psalm tune, but his parched tongue clove to the roof of his mouth, and he could not utter a stave. There was something in the moody and dogged silence of this pertinacious companion that was mysterious and appalling. It was soon fearfully accounted for. On mounting a rising ground, which brought the figure of his fellow-traveller in relief against the sky, gigantic in height, and muffled in a cloak, Ichabod was 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! His terror rose to desperation; he rained a shower of kicks and blows upon Gunpowder, hoping by a sudden movement to give his companion the slip; but the spectre started full jump with him. Away, then, they dashed through thick and thin; stones flying and sparks flashing at every bound. Ichabod’s flimsy garments fluttered in the air, as he stretched his long lank body away over his horse’s head, in the eagerness of his flight.

They had now reached the road which turns off to Sleepy Hollow; but Gunpowder, who seemed possessed with a demon, instead of keeping up it, made an opposite turn, and plunged headlong downhill to the left. This road leads through a sandy hollow shaded by trees for about a quarter of a mile, where it crosses the bridge famous in goblin story; and just beyond swells the green knoll on which stands the whitewashed church.

As yet the panic of the steed had given his unskilful rider an apparent advantage in the chase, but just as he had got half way through the hollow, the girths of the saddle gave way, and he felt it slipping from under him. He seized it by the pommel, and endeavored to hold it firm, but in vain; and had just time to save himself by clasping old Gunpowder round the neck, when the saddle fell to the earth, and he heard it trampled under foot by his pursuer. The goblin was hard on his haunches; and (unskilful rider that he was!) he had much ado to maintain his seat; sometimes slipping on one side, sometimes on another, and sometimes jolted on the high ridge of his horse’s backbone, with a violence that he verily feared would cleave him asunder.

An opening in the trees now cheered him with the hopes that the church bridge was at hand. The wavering reflection of a silver star in the bosom of the brook told him that he was not mistaken.

He saw the walls of the church dimly glaring under the trees beyond. He recollected the place where Brom Bones’s ghostly competitor had disappeared. “If I can but reach that bridge,” thought Ichabod, “I am safe.” Just then he heard the black steed panting and blowing close behind him; he even fancied that he felt his hot breath. Another convulsive kick in the ribs, and old Gunpowder sprang upon the bridge; he thundered over the resounding planks; he gained the opposite side; and now Ichabod cast a look behind to see if his pursuer should vanish, according to rule, in a flash of fire and brimstone. Just then he saw the goblin rising in his stirrups, and in the very act of hurling his head at him. Ichabod endeavored to dodge the horrible missile, but too late. It encountered his cranium with a tremendous crash,—he was tumbled headlong into the dust, and Gunpowder, the black steed, and the goblin rider, passed by like a whirlwind.

The next morning the old horse was found without his saddle, and with the bridle under his feet, soberly cropping the grass at his master’s gate. Ichabod did not make his appearance at breakfast; dinner-hour came, but no Ichabod. The boys assembled at the schoolhouse, and strolled idly about the banks of the brook; but no schoolmaster. An inquiry was set on foot, and after diligent investigation they came upon his traces. In one part of the road leading to the church was found the saddle trampled in the dirt; the tracks of horses’ hoofs deeply dented in the road, and evidently at furious speed, were traced to the bridge, beyond which, on the bank of a broad part of the brook, where the water ran deep and black, was found the hat of the unfortunate Ichabod, and close beside it a shattered pumpkin.

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A common interpretation of this story is that the Headless Horseman is really Brom Bones in disguise, playing yet another prank on Ichabod. And that the poor schoolteacher is so terrified by the run in— or so embarrassed— that he quickly moves on from Sleepy Hollow to his next teaching stop. In fact, the end of the story, which we didn’t share here today, includes reports that Ichabod is indeed alive and well and went on to become an attorney and politician in another part of the country.

But I think it’s more fun to believe that he really was spirited away by the Headless Horseman. And, if you’re like me and enjoy indulging occasionally in the more supernatural explanations for stories such as these, perhaps you’ll be curious to hear that reports of other headless, horseback specters have been around since the Middle Ages. 

Ireland has the dulachán, a demonic fairy who rides around on horseback, carrying his head under his arm, and cracking a whip made from a human spine. 

There are rumors that Scotland’s Isle of Mull is haunted by the headless ghost of a man named Ewen, who was decapitated in a battle against a rival clan. Ewan’s ghostly apparition is said to torment the island to this day. 

And in English folklore, we find another piece of fiction featuring a headless horseman: one of the best known Arthurian stories, the 14th century Middle English chivalrous romance Sir Gawain and the Green Knight.

I think it’s incredible that there are so many different accounts of headless horsemen, and this time of year, it’s fun to embrace the holiday spirit by diving head first into creepy tales of ghouls and spirits such as these. But heed this warning: indulge in scary stories at your own risk. You never know when, like Ichabod riding home along on a dark road at midnight, they might come to life before your very eyes. 

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Thank you so much for listening to this episode of Fab Figmentals!

Research, writing, and sound editing are done by me, Lindsey Morse. Niall Cooper assists with writing and editing. Our theme music was created by Graeme Ronald. 

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If you’d like to support the show and hear more stories from me, please consider supporting the show on Patreon. You’ll also find a link to our patreon page on our website, fabfigmentals.com, and you can support the show for as little as a dollar per episode.  Last week, we posted a really fun bonus werewolf story, and we’ll have more bonus tales posting soon. 

Thanks again for listening, and I hope you’ll join me next week, as we continue our look at classic Halloween monsters. In our next episode, we’re heading to Egypt to talk tomb raiding & curses, as we turn our attention on a popular Halloween creature that— I dare say— is largely misunderstood: The Mummy. 

We’ll see you next time.