Few things conjure up the feeling of a spooky autumn like Ichabod Crane riding his steed down a dusty road covered with fallen leaves in Sleepy Hollow, wary of the creature known as the Headless Horseman. The story has brought frightful joy to people for nearly two centuries, and will almost certainly continue to do so for many more.

Quick Facts about the Headless Horseman

• Its most famous appearance is in Washington Irving’s 1820 novel titled “The Legend of Sleepy Hollow”
• It is related to the Dullahann, a headless entity in Ireland that is said to take the dead away.
• The Headless Horeseman wears a long cape with a tall, standing collar.
• In “The Legend of Sleepy Hollow”, it carries a flaming jack o’ lantern which has the appearance of a “head”.

Where did the Headless Horsemen originate?

Stories about it have been around for a number of centuries. There is a strong chance that it comes from Ireland, where stories of a similar creature called the Dullahann have been told for hundreds of years.

In Irish folklore, the appearance of the Dullahann usually signals the death of a family member, similar to banshees. In some narratives, the Dullahann drives a black carriage, to carry the deceased away.

What does the Headless Horseman look like?

First, and possibly most creepy, the creature doesn’t have a head!

In American art and stories, the spirit is often visualized riding a black horse. It wears a long crimson cloak or cape that has a tall, standing collar. Many depictions show it carrying a jack o’ lantern in one of its arms, which could possibly be its – gulp – head.

The Dullahann has an even more gruesome appearance. It carries a severed head and uses a spine as a whip. The horse the spirit rides is also often said to be headless.

What are stories about the Headless Horseman?

In American folklore, the Headless Horseman is a character in Washington Irving’s story “The Legend of Sleepy Hollow”, written in 1820. The story is set in the small town, which is about 34 miles north of New York City and remains there today.

In his story, Irving tells us about two men who have fallen for the same girl – Katrina Van Tassel. The first man is Ichabod Crane. He is a heady schoolmaster and has a penchant for listening to tall tales and ghost stories in his free time. The second was Brom Bones, a muscular, cocky and somewhat arrogant young man who is skilled at horeseback riding.

One autumn night, on the way home from listening to ghost stories with locals at a tavern, Ichabod encounters the Headless Horseman. The spirit traps Ichabod on a bridge and throws its “head” at him. The next morning, Ichabod is gone and all that is found is a smashed pumpkin on the bridge and hoof prints nearby.

Though the story never declares it for sure, there is a strong chance that the Headless Horseman in Irving’s story is simply Brom – intent on winning Katrina Van Tassel’s heart – in disguise.

Festivals and Parades

The village of Tarrytown, New York, hosts a significant number of events each Halloween that revolve around Irving’s story. The Headless Horseman can be seen riding in the annual Tarrytown Halloween Parade. Storytellers recount the tale at the Old Dutch Church in Sleepy Hollow, close to the bridge where Ichabod met the Horseman. You can also visit Washington Irving’s old estate, and find other activities including hayrides and more. For more information, visit the link here.

The Horseman is also a significant part of Disney television history, and precedes Disney’s Boo-to-You Halloween parade. This parade can be seen at Mickey’s Not-So-Scary Halloween Party event that occurs several times a week during Halloween season.

The Headless Horseman in Writing, Art, Movies and Music

• A famous painting of Ichabod Crane being chased by the creature was made by Astoria Grand in 1858.
• In 1949, Disney released an animated film called “The Adventures of Ichabod and Mr. Toad”, which contained two separate cartoon segments. The first was “Wind in the Willows”, and the second was “The Legend of Sleepy Hollow”. The Legend of Sleepy Hollow cartoon helped to popularize the story and the spirit in modern culture.
• A movie titled “Sleepy Hollow”, was released in 1999. It starred Johnny Depp as Ichabod Crane, and Christina Ricci as Katrina. It is considerably more gruesome than the original story.
• The Dullahann makes an appearance in the Disney film “Darby O’Gill and the Little People”. It comes to take Darby away as he agrees to trade his life for his daughter’s life.