The headless horseman gallops through the folklore of Germany, Ireland, Scotland and North America. Though he appears singly there may be more than one, as in tales from the German Rhineland.
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Celtic and German pagan culture sometimes overlap because the Celts occupied a broad swath of what is now Germany during the Iron Age (1200 - 600 BC). One example of crossover is the Wild Hunt, where the mythical Welsh king Gwyn ap Nudd is among the leaders. Other leaders of the Hunt include Norse god Odin or his wife Frigg; heroic figures such as Siegfried of Xanten; and multi-faceted ancient goddess Frau Holle or Hulda of German origin.
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In America, the headless horseman is best known from The Legend of Sleepy Hollow, an 1820 story by American author Washington Irving. Trivia - in 1819, he wrote the tale of Rip Van Winkle, who slept for a hundred years. It's not surprising to find Irving suffered from insomnia.
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According to The Legend of Sleepy Hollow, which takes place during the Revolutionary War (1775 - 83), the Headless Horseman is a Hessian German soldier decapitated by an American cannonball at the Battle of White Plains in Oct, 1776. The Hessians served as auxiliary troops for the British.
In this case, the soldier was buried without his head. He rises up at night in search of it, with a flaming jack o' lantern as replacement. In modern tales he appears at Hallowe'en.
In Irish folklore, the dullahan or dulachán (dark man) is a headless, demonic fairy who carries his head beneath his arm. His whip is made from the spine of a human corpse. A death is said to occur if the dullahan stops riding. He calls a name and the person drops dead.
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In another version he's the headless driver of a black coach called the Cóiste Bodhar or Death Coach. The dark carriage is known throughout mythology of northwestern Europe. In Scotland it appears along the Royal Mile to pick up the dead.
Also in the northwest arises a similar figure, a rampaging headless fairy called the gan ceann (without a head). Menacing as he is, unlike other headless horsemen he can be frightened away by gold in his path or worn by a person.
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In Germany, stories of Headless Horsemen center around the Rhineland-Palatinate, or Middle Rhine region. Some scholars think Irving's story is inspired by a German tale from Johann Karl August Musäus's retellings of German folktales (Volksmärchen der Deutschen, 1783).
The German Headless Horsemen are revenants who fall into the category of Wiedergänger, the Undead who rise again. They wander the countryside seeking atonement for their sins or crimes. They're dangerous to encounter as they can kill with a touch.
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The Horseman might have to do one or more good deeds to make up for his transgressions in life. Instead of shaking hands with the recipient he holds out a tree branch, and the person takes hold of the other end. This causes the branch to die instead of the person.
Many cultural and mythological traditions were brought to North America by German settlers from the Rhineland-Palatinate area. These include the Christmas figure of Belsnickel, who brings treats for good children and birch switch to whip the naughty into shape. Another is the Irrwurz or Mad Root of folklore.
In Cape Breton, Nova Scotia, Canada, the headless horseman tale crossed the pond with Scottish settlers. A man named Ewen, who desired to be a chieftain, lost his head at a clan battle on the Isle of Mull near Scotland. Both he and his horse are headless, and to see him is a sign of a death imminent in the family.
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