The Legend of Sleepy Hollow

There is a very old saying that fact is stranger than fiction and I’m sure you have encountered true stories that are far more bizarre and fantastic than those invented by the imagination. But then there is the story I am going to tell you today. I don’t know whether it belongs in the realm of fact or fiction. It is taken from various eye witness accounts of the events surrounding the area known as “Sleepy Hollow,” and concerning the Van Tassel girl, the schoolmaster and the horseman. But if it’s scientific proof or absolute certainty you want, that I cannot provide for you. I can only tell you what happened as near as I have been able to determine, and leave the question of believing it to you…

It may not come as a surprise to you (though perhaps it will) that New York as it is today is very different from how it was a few centuries ago. Nowadays, we think of skyscrapers and subways and the City That Never Sleeps. In those days, New York was almost entirely farmland and fishing villages. And close by the Hudson River, there was a little community known as Tarrytown, where the residents lived a very happy and peaceful life, and, come nightfall, avoided at all costs the wooded area known as Sleepy Hollow.

There were no wild animals or dangerous terrain in the woods and, in fact, by the light of the sun they were quite picturesque. But come nightfall, under the light of a full harvest moon, these same woods took on an air of foreboding which, as it always does, gave birth to legends and ghost stories, all of which I investigated in the course of my research. Some spoke of a lady in white, scorned on her wedding day, who had been seen calling out for her beloved, or the spectral dog who prowled the night. But most of the stories that grew from the imaginations of the townsfolk concerned a Hessian rider who had lost his head during the War for Independence, and rode nightly through the Hollow in search of it. Most of the sensible people of the region knew these stories and dismissed them as childish fancy, fit only for frightened children at Halloween dances…but they still reined their horses when they felt themselves drawing nearer to Sleepy Hollow.

Close by the hollow itself was a small village which bore the same name. And it was to this quaint, rustic backdrop, shrouded in mystery and fantasy, that Ichabod Crane came that fateful day.

Physical descriptions of Ichabod Crane are usually very similar. The first time you saw him, one farmer reported, you might, for a moment, think that a scarecrow had run away from his post. He was tall and almost impossibly thin. Six feet of solid skin and bone. He had large, nimble hands and even larger feet, which farmers often joked would come in useful when it came time to plant their crops. He had a smallish head with a largish nose that came almost to a perfect point, so that you might imagine he’d make an excellent weather vane. And when you were told that this apparition was to be the new schoolmaster, you wouldn’t be in the least surprised.

Yes, Ichabod Crane was that rarest thing in those days, a learned man. His books were his constant companion and he imparted their knowledge to children nearly as well as his absorbed it himself. His mind was quite keen and he seldom forgot anything he read. This was both fortunate and unfortunate, as it meant he absorbed the fantastical, the supernatural and the horrifying with far greater aplomb than would be healthy, especially for one with so active an imagination. The result being that you will never, if you live to be a hundred and seven, meet a more superstitious and fearful man than Ichabod Crane.

Some thought it odd that a man of learning would feel so overwhelmed by these superstitions, which we all know are based solely in ignorance of the world around us. When asked about this, the pedagogue would smile that awkward, wan smile for which he was known and say something like, “Well, of course, I take it with a grain of salt,” (this phrase usually compelled him to throw a pinch of salt over his shoulder, for fear of evil spirits), “but it is a mistake for science to assume it knows everything about the world in which we live. And, after all,” he would add, knocking on the nearest piece of wood he could reach, “one cannot be too careful.”

But despite his odd appearance and superstitious nature, Ichabod Crane was well admired throughout the village. He was gifted musically and would sing the loudest and the finest in church on Sundays, and offered music lessons to the ladies of the village in order to supplement his meager schoolteacher’s pay. He was charming, witty and quite elegant by the standards of the common farm folk he now lived with. He never failed to kiss a lady on the hand when they were introduced, nor doff his hat when one entered a room. Indeed, several of the ladies of the village (mostly the middle-aged ladies with no husbands and a talent for cooking too much food) found Ichabod very charming and he became very popular for this reason.

A little too popular, some might say.

For there was one pretty young maiden in town who had taken a liking to Ichabod’s gentility and bearing. An enchanting, alluring young vision named Katrina Van Tassel, daughter of the wealthiest man in that part of the country, and every bit as attractive as was the idea of being son-in-law to so rich a man as her father. It is therefore hardly surprising that Katrina would be the apple of every bachelor’s eye between Tarrytown and New Jersey. But though she had many suitors, there was one who stood head and shoulders above the rest.

And, no, I don’t mean the schoolteacher.

You see, before Ichabod Crane had come to town, all evidence indicates that Katrina had eyes only for Brom Bones. Big, strong, handsome, rough-and-tumble Brom Bones. Some thought he was nothing but a bully and, in truth, he did have a hot temper and a tendency toward jealousy, which is why so few of Katrina’s other suitors ever dared to make time with her. But he wasn’t really a villain deep down. Don’t get me wrong; He was a show-off, a braggart, a bit of a tussler when he’d had a few too many mugs of ale. But it was more a sense of mischief than malice that motivated him, and beneath all that bravado was a good heart that Katrina felt sure she could bring out.

When the lanky schoolmaster arrived on the scene, however, it is known that she was seen far less often with Brom and took many a moonlit walk with the pedagogue (a very old-fashioned word which means “school teacher,” but which it is impossible to describe Ichabod Crane without using). One or two thought she had lost her mind in throwing over Brom for the sake of Ichabod, but most recognized that she was just trying to make Brom jealous and maybe teach him a lesson about the right way to treat a lady. For as handsome and seductive as Brom was, Ichabod was an equal amount dapper and refined. Of course, had it come to blows, Brom would’ve reduced the schoolmaster to splinters with one punch, but Brom was too much of a gentleman for that. And Katrina didn’t approve of violence anyway, so Brom had to find other ways to exact his revenge on Ichabod Crane.

The following is an excerpt from the diary of a Sleepy Hollow housewife, who offers her account of a fairly amusing example of Brom Bones’ “vengeance”:

Mr. Crane came over today for my singing lesson. As he often does, he demonstrated the lesson himself, which was much higher in pitch than I would have thought him capable of singing. But just as he hit the highest note, a loud yowling sound, like an animal, rang through the house. Both Mr. Crane and I at first thought something had gone horribly wrong with his voice. Until we heard the sound of Brom Bones’ laughter just outside my parlor window and the yapping of the dog he had trained. A very mean trick to play on so lovely a man as Mr. Crane!

But, to his credit, Mr. Crane did not become angry with Brom. He merely chuckled quietly to himself and continued the lesson as if nothing had happened. A most curious man, this Ichabod Crane!

This reaction to such treatment was, I gather, fairly typical for Ichabod. The exception would, I suppose, be found in an old police report from this time, signed by Ichabod himself, along with the local magistrate, which states that Brom and his gang broke into Ichabod’s schoolhouse and knocked things over, rearranged the chairs, even tore a few pages out of Ichabod’s more “fantastical” books (from his personal library, of course, and not intended for use by his pupils) and pasted them on the walls. Ichabod’s rather extreme reaction was probably due to his initial assumption that evil spirits had done it, but when it was revealed to be the work of Brom and his “Sleepy Hollow Boys,” as they were often called, he at least made a show of being mollified.

Pranks of this nature were, I suppose, inevitable for a man like our friend the schoolmaster, but he took them in good humor. As his consolation, he had the thought of Katrina Van Tassel, and her father’s farm, and the good fortune that undoubtedly lay before him.

Poor Ichabod. He had no inkling that he was merely being used as a pawn in a game Katrina was playing with Brom. For all her admirable qualities, she was deucedly mischievous (a trait she shared with her admirer, Brom Bones) and something of a coquette, and didn’t for a moment foresee any unpleasant consequences from her actions. It was just a bit of fun, she would say with a light laugh. But she didn’t know how firmly the schoolteacher had pinned his hopes to this new prospect which he little suspected was nothing more than a cruel joke.

A biography of Baltus Van Tassel, Katrina’s father, describes the old man as being “very sociable and generous. He was never happier than when his home was full of people having a good time. He loved to host parties and dances for his friends and neighbors.” But of all the festivities this rotund farmer held throughout the year, his favorite was the Halloween dance. Every October 31^st, the entirety of the village was welcomed into the Van Tassel estate for the finest food, music and frivolity of the whole year. It was a dance to which Ichabod Crane was particularly looking forward. His skill at singing was matched only by his dancing, and he felt certain that tonight he would sweep Katrina off her feet and make her his own. He donned his best (indeed only) formal suit, busied himself at a piece of cracked mirror styling his hair, then set off on a borrowed plow horse, Gunpowder (whose name, no doubt, spoke to the power of his youth more than any fire he currently possessed), in the direction of the Van Tassel farm.

Ichabod had visited this fine estate on one or two occasions, but never failed to be spellbound by the beauty (and profitability) of the farmland. Nor the luxury of its interior and the almost unimaginable breadth of the buffet table. You see, despite his lanky build, Ichabod Crane was one of the world’s great eaters and absorbed succulent and savory foods better then he absorbed knowledge of the occult—a hobby and hindrance which, obviously, made his venturing forth on All Hallows Eve something of a challenge, but which he braved for the sake of Katrina.

And, indeed, Ichabod was the life of the party. He and Katrina moved across the dance floor like swans on the surface of a lake. Brom Bones tried to cut in, but could not keep up with the improbable grace of the pedagogue. All attempts to upstage or outshine the schoolmaster were, therefore, doomed to failure and Brom had no choice but to admit defeat…

For a while, anyway.

After all, Brom might not have been able to compete with Ichabod in grace or bearing. But his rival did have a weakness which Brom could exploit…and it was Halloween night! So, when the night was dark outside and the full moon rose in the sky and the men began the practice of entertaining their host and fellow guests with stories of the supernatural, Brom Bones stepped forth to seek his ultimate revenge on Ichabod Crane.

“I know most of you have heard the stories of Sleepy Hollow,” he said. “But, perhaps, for the sake of our new friend, Mr. Crane, you will not begrudge me repeating them here.” The crowd consented, never tiring of hearing the exciting stories. And there was no question which story was to be the highlight of the evening: The Tale of the Headless Horseman! I remind you at this point that the facts leading up to the horseman’s demise are entirely factual and beyond question. It is only after his death that we enter the realm of uncertainty:

“I need hardly tell you,” began Brom, setting the scene, “of how bravely the men of this territory fought to earn our freedom in the days of the war. And we most certainly know of the Hessian soldiers who were sent to cut them down, and of how courageously we beat them back. But never make the mistake of underestimating your enemy, and in truth, it must be said that the Hessians fought to the last man. And even when that last man was the only one still alive and still on his horse, he fought with the strength of ten, until one of our own grandfathers swung his sword and sliced off his head with one swipe.” A statement like this would have elicited cheers and huzzahs from the crowd, in which Ichabod Crane joined, half-heartedly, already beginning to turn pale.

Brom saw his rival’s cadaverous pallor, and with a grin, continued his story. “But mark my words! He didn’t fall. His head lay severed at the feet of his horse and blood streamed down his body. But he did not fall from his horse. He stayed rooted to the spot, and some who were there that day say he even spurred his horse and shouted a command because the steed rode off into the hollow. Our men did not give chase, believing the horseman to be dead. But answer me this, if he was truly killed, how did he come to be seen riding madly through the woods the following year? And on many cold, dark nights since?

“It’s true! The horseman still rides! You see, he lost his head that fateful night and he will never stop riding until he finds it. And if he cannot find his own head, he will find another that suits him just as well. And how do I know all of this?” added Brom, in a sudden inspiration. “Because last year, on this very night, I met this fearful apparition in Sleepy Hollow.” Spurned on by the excitement of the moment and the spite for his rival, Brom began improvising madly. “He charged full speed toward me, swinging his sword maniacally over his headless body. Laughing a wicked laugh that seemed to come from deep within his soul! But I wasn’t afraid. I spurred my best horse, Daredevil, and we rode like thunder to the covered bridge just past the old churchyard. For that cemetery is where the horseman’s power comes from, and once you cross the bridge, he cannot touch you.

“So let me caution all of you, that if you find yourselves riding through Sleepy Hollow tonight, do not stop, do not rest, do not slow down until you reach the covered bridge by the old church. Or else you might find yourself unwittingly assisting the Headless Horseman to…get a-head!” Of course, two hundred years ago, this was a new joke and the men laughed cathartically at the witticism, releasing their fright over Brom’s story. Even Ichabod Crane managed a hollow chuckle, which belied the fierce pounding of his heart upon hearing this account of the Legend of Sleepy Hollow.

A legend he little suspected he was about to become a part of.

From here onward, accurate accounts of what took place become fewer and farther between and we must rely on guesswork and conjecture. It is a matter of record that Ichabod Crane tarried after the other guests had left, in the hopes of having a private word with Katrina. It is well known that the schoolmaster set out on his way home a mere five minutes after this interview was terminated. I cannot say what passed between the two during this time, but we can draw conclusions from the morose countenance he wore when he reclaimed his mount from the stable. Yes, I believe that his hopes for Miss Van Tassel were dashed that night, and perhaps Katrina learned the dangers of playing with men’s affections, or perhaps not. We shall never know for certain. All that is known with any certainty is that Ichabod Crane left the Van Tassel farm, without stopping to admire it, a few minutes before midnight on his way home.

Among the diary entries, official reports and other verifiable documents I uncovered while trying to solve the mystery surrounding this story was the following account, to which no name was signed nor date given. I include it only because it is the only existing account of what may…or may not…have happened to the schoolmaster when he rode through Sleepy Hollow that night:

It was the very witching hour when Ichabod Crane found himself passing through Sleepy Hollow on his way to the Von Ripper farm where he had his lodgings. As the chill of the night air surrounded him, he gradually forgot his despair over Katrina, and his proper nature took over. Meaning his fear and superstition. He tried to persuade his horse to move faster, but all the spark had gone out of Gunpowder and he plodded along at his own pace. With each moment, Ichabod’s fears compounded. He started at the sounds of crickets or a bullfrog in the old mill pond. Once he was certain he heard approaching footsteps, only to see a couple of bulrushes blowing against a hollow log in the wind. This actually motivated Ichabod to smile and, as if to prove to himself that he wasn’t afraid, he even began singing one of his favorite psalms.

But his tranquility was short-lived, for a short time later, he heard a sound behind him which he knew for certain could not be bulrushes. A timid glance over his shoulder confirmed that there was another rider on the path to town. Ichabod tried to call to the rider, cordially, but the other gave no reply. Wary of this traveler, Ichabod spurred Gunpowder who grudgingly began to trot with more speed, in the hopes of putting some distance between himself and the stranger. But the stranger matched the speed of Ichabod’s horse and remained the same distance behind. Then, Ichabod reined Gunpowder in, planning to slow down and let this other ride pass. But, as before, the stranger slowed down and continued following Ichabod apace.

His heart pounding as though it were about to burst out of his chest, Ichabod’s neck continuously turned over his shoulder to keep an eye on this eerie companion. Finally, the path came into an open area where the trees did not obscure the moon and it threw the image of the strange rider into relief. And Ichabod beheld a tall, powerful rider all in black, with a long black cloak on a horse blacker than the midnight sky. But his imposing figure is not what caused Ichabod to pound his spurs into his horse’s ribs and take off at high speed.

For you see, the horseman was headless!

Looking over his shoulder as they raced on, Ichabod saw the Headless Horseman pick up speed and begin to chase them through the Hollow at top speed. Ichabod perceived a large, round shape on the pommel of the Horseman’s saddle. His head! thought Ichabod. He carries it with him until he finds one he likes better! Ichabod rode his horse harder than he would have ever thought possible until, at last, he was in sight of the old churchyard and the covered bridge. With one final crack of the whip, Ichabod tore across the bridge and didn’t stop or look around until he was well on the other side. And as he turned his head, he saw, to his horror, that the Headless Horseman was actually hurling his severed head through the bridge and straight at Ichabod. He perceived flames erupting from the head as it roared straight for his own, and Ichabod Crane was too terrified even to move out of its way and

The mystery document ends here.

We return now to the world of evidence and hard facts. The following morning, the sun rose on Sleepy Hollow as it always had. The good people arose and set about their work as they always did. Only at the Von Ripper farm was there any change in the usual routine. For their lodger, one Mr. Ichabod Crane, did not come to breakfast. Nor did he appear for luncheon or dinner. The children assembled at the school but their master did not arrive. Later that evening, however, Gunpowder did return, riderless.

The very next morning, the men of the village assembled to search the Hollow, a search which ended when they came to the covered bridge which separated the town from the old church. Masses of hoof prints in the earth spoke of a chase and a struggle between two men on horseback. To the side of the road, the schoolmaster’s hat was found. And, all around the scene, pieces of a shattered pumpkin shell complete with a melted ball of wax stuck to one large piece: A jack-o-lantern. No other trace of the schoolmaster was found.

So, my readers are asking, what happened to Ichabod Crane? Well, it’s difficult to say. Certainly the circumstances of his disappearance were somewhat fantastic. True, Brom Bones did seem to grin a trifle too widely at the mention of the pumpkin shell found on the scene, leading many to suspect that he knew more about the incident than he was letting on. And, yes, there were some who traveled to other parts of the country who claimed that they had met Ichabod Crane, settled down with a nice widow and her children and taking up the practice of law…

All that we know for sure is that Ichabod Crane was never seen in Sleepy Hollow again. Shortly thereafter, Brom Bones and Katrina Van Tassel were married. And every Halloween when the master of the Van Tassel Farm invited his guests to regale him with scary stories, the first one to stand up would invariably relate the tale of the old schoolmaster, never failing to omit the fact that those who had chanced by his now abandoned and rundown schoolhouse swear that they can hear a soft, angelic voice singing that same psalm that the pedagogue was so fond of.

We may never know the truth of what happened in those woods that night, but to the people of Sleepy Hollow, it is a matter of absolute fact that the poor, unfortunate schoolmaster was spirited away by the Headless Horseman.

THE END

If You Liked My Story, You Might Enjoy:

• The Adventures of Ichabod and Mr. Toad (1949) This Disney double feature consists of two stories with practically nothing in common. First, Basil Rathbone tells a comic adaptation of Kenneth Grahame’s “The Wind in the Willows,” then Bing Crosby tells and croons the story of Ichabod Crane. This is notable for being one of the few Disney animated films to end on a less-than-happy note.
• “Shelly Duvall’s Tall tales & Legends” (TV) Charles Durning narrates and Beverly D’Angelo and Ed Begley, Jr. star as Katrina and Ichabod.
• Sleepy Hollow (1999) Tim Burton made Ichabod Crane a scientist and a policeman who is sent to Sleepy Hollow to solve the mystery of the Headless Horseman. A loose, but enjoyable adaptation of Irving’s story which includes a chase scene closely inspired by that which appears in the Disney version (Burton often includes these little homages to Disney films as he himself got his start working on their animation staff).

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