The Historical Headless Horseman

Headless Horseman

Every Halloween, he wanders around the woods and roadways, as he rides his horse mysteriously, and not to mention frighteningly, without a head—the Headless Horseman—indeed, makes one of the most ghastly horror stories. The rider, usually either carrying his head with him; or a jack-o’-lantern as a substitute to his head; or just completely without a head would vanish the existence of those who ever walked his path. That is generally how the infamous Headless Horseman is depicted. Such image was popularized by the American short story written by Washington Irving, “The Legend of the Sleepy Hollow”. But throughout history, the element of a headless rider has also been applied in several folklores throughout Ireland; Scotland; Germany; and India, aside from America.

Overview of The Legend of Sleepy Hollow

The story is set in 1790 in what is known to be the superstitious eerie secluded Sleepy Hollow in the historical Tarrytown, New York during its Dutch settlement. Apart from being rumored to be bewitched early into the Dutch settlement, the place is said to be haunted by the Headless Horseman, the most notorious of all ghosts that haunt the place.

The Headless Horseman was a Hessian trooper who was decapitated by a cannonball in the Battle of White Plains in 1776 during the American Revolutionary War. Although his body was recovered from the battle and eventually buried in the cemetery of the Old Dutch Church of Sleepy Hollow, his head, however, was lost. And every Holloween, the Hessian trooper’s malevolent ghost rises from his grave in a furious search for his head.

The legend tells of the ill-fate of an outsider, Ichabod Crane, a lanky schoolmaster from Connecticut. Amidst the spooky village of Sleepy Hollow, arose the competition for the hand in marriage of Katrina Van Tassel, the daughter and sole child of a wealthy farmer, Baltus Van Tassel between Ichabod Crane and Abraham Van Brunt, a jockey skilled in racing who often won in competitions, bagging several prizes and whose large build and strength earned him the alias “Brom Bones”.

Aside from Ichabod’s interest in Katrina, he saw that marriage to her was an opportunity to procure Van Tassel’s wealth. However, Brom got in the way of his pursuit of Katrina, as Brom played a series of pranks on him, thus, putting his goal of winning Katrina’s heart and obtaining Sleepy Hollow’s fortune at stake. Soon, tension among the three grew as well.

The ambitious Ichabod, then, attended a harvest party held by the Van Tassels at their homestead. Ichabod enjoyed the event, as he partook in the feast and even got to dance with Katrina. Brom, however, got jealous at the sight of the two dancing. When the music stopped, they all gathered around to share ghost stories. Although Ichabod’s motive really was to propose to Katrina after the guests leave, unfortunately, his plan of securing the hand of the maiden failed. It left him dismayed riding home.

On Ichabod’s way home, the ghost stories he heard from the harvest party stimulated his imagination, as he passed by places purported to be haunted. Suddenly, he was terrified to have encountered the gigantic Headless Horseman. Thereafter his encounter with the Headless Horseman, there was no sight of Ichabod, but only his wandering horse; trampled saddle; discarded hat; and a mysterious shattered pumpkin. So Katrina was left to be wed with Brom, who suspiciously appeared to know a lot more about the hapless tale of Ichabod and would even burst into laughter when the shattered pumpkin was brought up.

In the story, it would seem as though the Headless Horseman was actually Brom disguised as the ghost. However, old country wives believe that Ichabod was spirited away by supernatural means.

Other Tales on Headless Riders

The Dullahan or Dulachán

In Irish folklore, they have another version of the headless rider, the Dullahan or Dulachán which is not a man, but rather a demonic fairy who has the power to lash out the eyes of those who lay eyes on him and even end a life of a person immediately just as it utters the person’s name. It rides a horse and wields a whip made of a human corpse’s spine, while it carries his head under his lower inner thigh and sometimes holds it up to see a further distance.

The Gan Ceann

Another distinctive version from Ireland is the Gan Ceann, meaning without a head in Irish Gaelic. It is basically just another version of the Dulluhan which is a small figure that drives a black carriage instead of a horse. Wearing a gold object or putting a gold object on his path can fend off the Gan Ceann.

Tale of Ewen

In Scotland, there is a tale of a headless horseman named Ewen. It was in a clan battle in Glen Cainnir on the Isle of Mull that he was decapitated. He, as well as his horse, lost their heads in the battle. And losing his head in the battle also lost him the chance to be chieftain.

Gawain and the Green Knight

Around the 14th century, there was a poem written by an anonymous writer which gives an account of when the Green Knight came to Camelot and challenged King Arthur’s knights to test their loyalty and honor. He gave them a dare wherein if done successfully, the successful knight will receive an axe blow in return. He asked the knights to chop off his head, and the brave knight who was able to do so must agree to meet with him again a year and a day later to bend his head in front of him. It was Gawain who beheaded the Green Knight. Thereafter, the Green Knight picked up his head and reminded him of the pledge before taking off.

Legends of the Brothers Grimm

The Legends of the Brothers Grimm, written by Jacob and Wilhelm Grimm, tells of two German folktales of witnessing headless horsemen in Saxony.
The first is about an encounter of a woman from Dresden with a headless horseman sitting on his grey horse at a place called “Lost Waters” near Dresden, Saxony on an early Sunday morning. She was out to gather some acorns when she suddenly heard a hunting horn. After hearing it again, there she turned around and met with the headless horseman who, then, introduced himself to as Hans Jagenteufel, a man with a former life of wickedness.

The second tale is about “The Wild Huntsman” named, Hackelberg. Despite the passing of this headless horseman, the sound of his hunting horn resonated from Brunswick, Lower Saxony, serving as a warning against riding the next day for hunters as a means of prevention from accidents.

In other German versions, the headless horseman hunts down the criminals who committed capital crimes.

The Jhinjhār

In contrast to most portrayals of the headless horseman, in India, specifically in the folklore of Rajasthan and Madhya Pradesh, the headless horseman which they refer to as Jhinjhār is usually considered as a heroic figure. The tales of Jhinjhār tell of the brave who have died protecting the innocents. They are either about a Rajput prince who persistently tried to save a village or caravan even after losing his head during his attempt of salvage or a Mughal cavalryman fighting for his prince.


Irving’s The Legend of Sleepy Hollow inspired several adaptations with its very first music adaptation around 1913 which is a piano suite entitled, In Sleepy Hollow by Eastwood Lane. Then, came its first Broadway musical around 1948 entitled, Sleepy Hollow with music by George Lessner and book and lyrics by Russell Maloney and Miriam Battista. Several others followed including film and television variations. The most popular of all films was the adaptation directed by Tim Burton in 1999 entitled, Sleepy Hollow. However, Burton made a few revisions in the story. In his version, Ichabod Crane was a police constable sent from New York City on a mission to investigate recent murders involving the decapitation of victims. And around 2013, the mystery series entitled, Sleepy Hollow was co-created by Alex Kurtzman; Roberto Orci; Phillip Iscove; and Len Wiseman, wherein Ichabod Crane is reimagined as an English professor and turncoat during the American Revolutionary War who decapitated a horseman who is purportedly Death. The horseman didn’t die, yet he once again finds the horseman years later when he awakens in 2013. He teams up with Abbie Mills, a lieutenant in the town of Sleepy Hollow’s sheriff’s department to terminate the murderous horseman.

Although there are several other versions of the Headless Horseman throughout the world, the Headless Horseman during the American Revolutionary War became the most popular and has made a mark in the history of Sleepy Hollow. And along with Irving’s short story, The Legend of Sleepy Hollow, it has given Sleepy Hollow the reputation of being one of the most haunted places in the world, as well as the Headless Horseman, himself, has gained the reputation of being the most frightening infamous ghost in American history.

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Legend of the Headless Horseman 2
Legend of the Headless Horseman