Background: The informant grew up in Sleepy Hollow, New York, home to the Legend of Sleepy Hollow.

Context: I asked him about The Legend of Sleepy Hollow, and he sent me a video telling it to the best of his memory.

“The story goes, The Legend of Sleepy Hollow, there’s this place, like the pilgrims, ooo America, this undiscovered land, creepy, scary, lots of woods. There’s this one place called Sleepy Hollow, where it is now in New York. It’s haunted, there’s lots of ghosts there, it’s a quiet little grove, and then when you go in, there’s lots of spirits, it’s very scary. That’s the story.
That’s what’s happening there. But then scariest one of all, is supposedly there’s this guy called the Headless Horseman, who’s the ghost of a Hessian soldier during the Revolutionary War, whose head got shot off by a cannon, so at night he rides around looking for his lost head. And that’s the setting of the story. What happens is this guy named Ichabod Crane comes and he becomes a school teacher in Sleepy Hollow. He’s a very frail, skinny, skittish man, and after he teaches, he loves talking to the housewives about all the gossip, hearing all the gossip, and they start telling all these ghost stories. He is just so scared, he’s such a scared person- they really freak him out. He’s just living in Sleepy Hollow, hearing all these scary stories, being very scared.
He goes to this ball or something, or some town celebration, and he sees this girl who is the daughter of the wealthy family in town. I think her name is Katrina Von Tassel, and he instantly falls in love with her, I think wants to marry her, maybe he asks her to marry him and she’s like no. Whatever. So he’s beefing with this other guy, I don’t remember his name, he’s like the big man around town, he’s tall, strong, he’s like the manly man. They’re both fighting over Katrina. The other guy sees that Ichabod is into her and he doesn’t like that.
Later that night when Ichabod leaves the party to go home, he’s riding his old, slow, brown horse home through the dark woods at night in Sleepy Hollow. He hears a horse behind him. He’s looking, trying to see what it is, and then he sees this dark figure in the night. And it’s a black horse, and sitting on top of it is a man all covered in black with no head. He’s like ‘oh my god it’s the Headless Horseman!’ So he starts running, the horse is chasing him, he’s riding on his horse, the other horse is chasing him, they go over the famous Sleepy Hollow bridge, and then he’s like “aaa.”
The story ends and it’s basically up to you to decide whether that was the actual Headless Horseman chasing him or that was the guy who he was fighting with who also owns a black horse, who knows that Ichabod Crane is a scaredy cat, and was basically trying to intimidate him. “

Reflection: this legend reflects many of the values of the culture that produced and tells it. It tells that underdog stories are valuable–Ichabod is the protagonist, not the manly man. It also speaks to the fear of the unknown in Early America, and the nature of the Headless Horseman speaks to a trauma from war, in this case, the Revolutionary war. This legend is commonly known as an authored story written by Washington Irving. It has been told folklorically since it was written down, and it was likely inspired by folklore before it was penned.

For further reading, here is the text of Washington Irving’s story: https://www.gutenberg.org/files/41/41-h/41-h.htm