History Behind The Headless Horseman Legend

Take a step back in time when the night was feared. Within the encroaching darkness, danger awaited. A time when frightful tales warned of evil spirits roaming the land. A time when the thud of hoofbeats or the rattle of a carriage would strike terror in the hearts of those who huddled in rooms lit by wood fires and candles. A time when a fearsome specter prowled the gloom of the night looking for victims, souls he could take—a horseman missing his head. 

The Headless Horseman by Anita Dickason. Research on the origins of the legend of the headless horseman.

In many ancient cultures, heads were believed to contain the mortal’s soul. A trophy to be taken during battles, adding prestige and power to the warrior, or planted on a stake as a warning to all evildoers. It’s not surprising a legend arose of a headless horseman. The origin of stories dates back to the Middle Ages in European history, 500 A.D. to 1500 A.D. and occurred in more than one country.

Irish Legend

The earliest version, the Dullahan, meaning dark man, is from Irish folklore. According to some theories, the tale originated in ancient Celtic mythology. The forerunner of the Dullahan was a fertility god, Crom Dubh—a god demanding blood sacrifices by decapitation. After Christianity arrived, Crom Dubh turned into the Dullahan, a demonic creature roaming the countryside on horseback, carrying his severed head under his arms or high above him. Some claimed his whip was the spine of a human’s corpse.

The Dullahan was a messenger of death, an omen of doom. When the Dullahan stopped, someone died. He would point his whip at a mortal or call out a name. The person immediately dropped dead.

In another Irish version, the headless Dullahan drove a black funeral coach drawn by headless horses, a “death coach”. Seeing the Dullahan’s coach outside a house meant someone inside was about to die.

Scottish Legend

The Scots had their version of a headless horseman. In this case, the headless rider was based on a real person by the name of Ewan of the Little Head from the Maclaines of Lochbuie. Ewen, the son and heir of a Maclaines chief, was decapitated by a follower of his father during a clan battle in the 1500s. As the legend goes, his maddened black horse carried the headless body until, exhausted, the horse stopped, and the body toppled to the ground. Ever since, some say, Ewen has stalked the Maclaines, riding to claim their souls. Others believe an encounter with Ewen, the Headless Horseman, is an omen of imminent death.

An American Classic 

Within United States history, the headless horseman was forever immortalized by author Washington Irving in his short story written in 1820, The Legend of Sleepy Hollow. Historians believe tales of a headless horseman in Germany may have influenced Irving. Irving had traveled to Germany and was familiar with German folklore. 

I did discover one interesting detail. Many of the current renditions of the headless horseman include a pumpkin that isn’t present in ancient mythology. It would seem this detail was added to the legend by Washington Irving, an intriguing twist to the conclusion of his story. Read about the Jack O’Lantern.

The Traditional Tale of the headless horseman began…

The Legend of Sleepy Hollow is a story about a schoolteacher, Ichabod Crane, who moved to Sleepy Hollow and his encounter with the headless horseman. 

According to Wikipedia, “Irving, while he was an aide-de-camp to New York Governor Daniel D. Tompkins, met an army captain named Ichabod Crane in Sackets Harbor, New York during an inspection tour of fortifications in 1814. Irving may have patterned the character in “The Legend” after Jesse Merwin, who taught at the local schoolhouse in Kinderhook, further north along the Hudson River, where Irving spent several months in 1809. The inspiration for the character of Katrina Van Tassel was based on an actual young woman by that name. Irving had stayed with her family for a short time, and asked permission to use her name and loosely base the character on her. He told her and her family that he liked to give his characters the names of people he had met.”

Here, in Washington Irving’s words, is his description of the headless horseman: 

“The dominant spirit, however, that haunts this enchanted region, and seems to be commander in chief of all the powers of the air; is the apparition of a figure on horseback without a head. It is said by some to be the ghost of a Hessian trooper, whose head had been carried away by a cannonball, in some nameless battle during the revolutionary war; and who is ever and anon seen by the country folk, hurrying along in the gloom of night, as if on the wings of the wind.

His haunts are not confined to the valley, and especially to the vicinity of a church that is at a great distance. Indeed, certain of the most authentic historians of those parts, who have been collecting the floating facts concerning this spectre, allege that, the body of the trooper having been buried in the churchyard, the ghost rides forth to the scene of battle in nightly quest of his head; and that the rushing speed with which he sometimes passes along the Hollow, like a midnight blast, is owing to his being belated, and in a hurry to get back to the churchyard before day-break. 

Such is the general purport of this legendary superstition, which has furnished materials for many a wild story in that region of shadows; and the spectre is known, at all the country firesides, by the name of the Headless Horseman of Sleepy Hollow.”

Washington Irving’s story is considered one of America’s foremost ghost stories and iconic American folklore. Though written over 200 years ago, Irving’s words still have the power to keep a reader turning the pages. For a unique Halloween read, this is one book I highly recommend. On a cold autumn night, settle back in a chair with a favorite beverage. Be prepared to be entertained with the rest of this timeless classic of suspense and frightful fun, The Legend of Sleepy Hollow. 

I’m always “On The Hunt” for new stories. If you have a question or a comment, please let me know.

Anita Dickason

P.S. You may recognize the story of the headless horsemen from the Film Sleepy Hollow directed by Tim Burton, which loosely follows the story of Ichabod Crane who sees the headless man in the town of Sleepy Hollow; and thus begins the legend of the headless horseman. 

From IMBD: “The Curse of The Headless Horseman (Christopher Walken) is the legacy of the small town of Sleepy Hollow. Spearheaded by the eager Constable Ichabod Crane (Johnny Depp) and his new-world ways into the quagmire of secrets and murder, secrets once laid to rest, best forgotten, and now reawakened, and he too, holding a dark secret of a past once gone.”

About The Legend of Sleepy Hollow

Washington Irving’s classic, “The Legend of Sleepy Hollow,” has been making spines tingle since 1820! Irving tapped into a timeless fear: the prospect of a late night journey shrouded in fog turning suddenly fatal. Our imaginations conjure every conceivable danger, but in one of history’s most famous encounters, one Ichabod Crane comes—dare we say it, face to face? —with the “specter known at all the country firesides,” the Headless Horseman of Sleepy Hollow. A classic, distinctively American tale, that evokes additional terror as Halloween comes and goes each year, this is the original, 1820 version, as originally found in Irving’s collection of short stories entitled “The Sketch Book of Geoffrey Crayon, Gent.

Find it on Goodreads and Amazon

Anita Dickason

Anita Dickason is a retired police officer with a total of twenty-seven years of law enforcement experience, twenty-two with Dallas PD. She served as a patrol officer, undercover narcotics officer, advanced accident investigator, tactical officer, and first female sniper on the Dallas SWAT team.

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