The Halloween History of the Headless Horseman

The Halloween History of the Headless Horseman

This article is an excerpt of GolfBlogger’s book: Things In The Basement: A History of Halloween Horrors, available on Amazon at the link.

Headless Horsemen have figured in the imaginations of many cultures, and have now become a fixture in modern horror and Halloween celebrations. Some compilations of Grimm’s Fairy Tales include an encounter with a headless horseman. Bavarian folklore apparently contains tales of Headless Horsemen who patrol the forests.

In India, a character called the Dund rides about headless, although his noggin is tied to his saddle. The Dullahan of Irish folklore is a headless spirit seen riding a headless horse. In some variants, it’s a headless coachman. The Green Knight of medieval legend is beheaded by Gawain, but rides away carrying carrying his own head.

In a 1777 work by the German poet G.A. Burger, Der Wilde Jager, a ghostly huntsman is condemned for his cruel demeanor on earth. He rides with his hell hounds through the woods and chases innocents. The poem is based on German folklore and in some versions, he’s headless.

The best known of the Headless Horsemen, however, appears in Washington Irving’s 1820 story, The Legend of Sleepy Hollow. It is this version of the story that has become Halloween legend.

Irving was not above borrowing folklore for his tales, especially from the Dutch—as in his popularization of the Dutch Santa Claus. New York, originally New Amsterdam was Dutch in origins, and Irving’s Knickerbocker Tales focused on their descendants.

In Irving’s story, the Headless Horseman is the ghost of a Hessian who was decapitated by a cannon ball during the American Revolution. His spirit haunts the town of Sleepy Hollow.

The Hessians were mercenary soldiers from the German state of Hesse-Kassel hired by King George III to fight against the Continental Army during the American revolution. It was the Hessians who were caught by surprise at the Battle of Trenton after Washington crossed the Delaware River.

The Hessians also featured prominently in the Saratoga Campaign in New York in 1777. The Hessian force there contained a large number of cavalry. However, in the dense upstate New York woods, the horses were abandoned, and the Hessians fought on foot. The Hessian forces under British General Johnny Burgoyne were defeated by the Colonials under Horatio Gates and Benedict Arnold.

In either case, the Hessians developed a reputation among the colonists for brutality against the local populations. Whether that was true, or only propaganda is unclear. Their reputation, however, plays a part in the Legend of Sleepy Hollow.

The Washington Irving tale of horror is well known. It’s set in the town of Sleepy Hollow, which, Irving reveals early in the story, is a magical place haunted by the spirit of a headless Hessian trooper. The plot revolves around a schoolmaster named Ichabod Crane, who is in pursuit of Katrina van Tassel, a wealth heiress. Unfortunately for the skinny and somewhat meek Crane, his competition for Katrina is the local bully, Brom Bones.

The subject of the horseman comes up at a local party, where the various young men of Sleepy Hollow are telling ghost stories. Brom Bones claims to have raced the Headless Horseman for the stakes of a bowl of punch. In the race, he claims that the Horseman was unable to cross the water under the town’s bridge. Even with this lightheartedness, however, Crane is nervous.

Irving notes that the time of year is autumn, but does not specify whether or not it is Halloween.

On the way home from the party, Crane imagines all sorts of scary things in the woods. Eventually, he is joined by another rider. When he realizes that it’s the Horseman, he flees, hoping to reach the bridge for the safety of town.

Crane nearly makes it. But, at the last minute, the Horseman throws his head, knocking the schoolteacher from his mount.

That’s the last we hear of Crane. The next morning his horse is found, as is a shattered pumpkin, but there’s no sign of the schoolteacher. His fate is never actually revealed by the storyteller.