The Story Behind The Legend Of Sleepy Hollow

Headless Horseman. (2022, September 13). In Wikipedia.

When I was a kid, I had this recurring dream about the Headless Horseman. He would take me on his horse through my neighborhood.

In the years after that, the dream faded away, and kept wondering where that dream might come from — I had never seen any kind of movie or read a book about this tale.

But there was this one game: Happy Harvest.

It was a social farming game where you could grow your crops and share things with your friends. It also had seasonal themes and always on Halloween, the Headless Horseman appeared on your farm and you had to complete quests for him to earn a couple of extra money.

I think that’s where it came from; but what’s the story behind the tale?

Searching for his head

The Headless Horseman is a character from the Sleepy Hollow Legend; he is searching for his or keeping it in his hand. I remember it as the horseman who keeps his Jack-o’-lantern head in his hand.

The story originally came from the book: “The Legend of Sleepy Hollow”, by Washington Irving.

In this “short story”, Irving portrays the Headless Horseman based on the folklore legend that has circulated around European and American culture.

In the 18th century, there was this man that presumably was killed in the Revolutionary War in America. His head was cut off by the Americans and that’s why he’s holding his head.

The original folklore

Obviously, this story was based on Irving’s book, but before this book was even written there was much old folklore around since the middle ages.

The Headless Horseman was often portrayed as a demonic character in European stories whereas in The United States it’s mostly seen as this Halloween story.

But what’s something that all of these stories have in common is that the horseman was killed and decapitated during some battle in a war.

Ichabod Crane

I got to know Ichabod Crane, a character from the Sleepy Hollow Legend when I first watched the Disney movie “The Adventures of Ichabod and Mr. Toad”.

The Legend of Sleepy Hollow. (2022, September 3). In Wikipedia.

He’s the one who gets chased by the Headless Horseman.

When he stays at a place called “Sleepy Hollow” in New York. He’s first introduced to the Headless Horseman in this super creepy house.

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Originally Published on Medium

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