Murder in Sleepy Hollow

Cassie: Hello, everyone, and welcome to another episode of The Obscure. How are you, Ava?

Ava: I’m doing well. Can you believe that we’re already a month into the new year? Time’s flying by.

Cassie: It really is.

Ava: I swear, I’m still writing 2024 and it’s not even January anymore! But aside from that, all is well. How about you?

Cassie: I’m managing—it’s a little cold for my liking. I never really seem to get used to the cold.

Ava: Ugh, tell me about it. At least I don’t have to work outside. I just go out for food or coffee. And even then I just have Jake grab it on his way home.

Cassie: What a guy. Yeah, you know, we’re lucky. We get to sit inside and just talk about whatever we want, and that just so happens to be murder and mysteries—our specialty.

Ava: So true. And today we have a really intriguing case.

Cassie: Oh, yes, we do. But before we dive in, we want to tell you all about our friends over at Basic. Whether you’re an athlete, an office worker, or a fellow podcaster, getting the nutrients you need is easy with Basic. They offer daily vitamins, protein powders, and custom meals shipped straight to your door. Use our code “OBSCURE” for 20% off your first order of $50 or more and get back to the basics.

Ava: And can I just say, their stuff is delicious.

Cassie: Absolutely, I don’t know why I didn’t try it sooner.

Ava: Same here.

Cassie: Alright, are you ready to talk about this?

Ava: I’m ready.

Cassie: Our story today focuses on the events of last October, focusing on I. Eli Crane—a journalist for the Connecticut Herald.

Ava: What does the “I” stand for?

Cassie: “Ichabod”. His full name is Ichabod Elias Crane.

Ava: Yeah, you can’t really blame the guy for going by Eli.

Cassie: Definitely a unique name. Although Crane worked for the Connecticut Herald, he was in New York following a story that captivated him personally.

Ava: So his paper didn’t officially send him there?

Cassie: No, he was following the story on his own terms, driven by personal intrigue.

Ava: Honestly, I’d do the same thing if a story I was following was close to home.

Cassie: And it’s easy to see why he was intrigued. Every ten years—dating back to 1894—during the second week of October, someone in the town of Sleepy Hollow either goes missing or is found murdered.

Ava: Woah, that’s creepy. Always the second week?

Cassie: Yup.

Ava: People— If you knew something like this was happening, why wouldn’t you leave town for a week? Take a little vacation instead of courting danger.

Cassie: Well, that’s what the local residents advise. Or at least leaving before nightfall. But the police haven’t been much help. The last case involved Jillian Castle, who was found murdered in the woods, and Art Hampton was arrested for that one. The cases in 2004 and 1994 were labeled missing persons—both assumed to have left to California. The police have answers, whether true or not, but nothing that fully satisfies the mystery.

Ava: And what do the locals believe?

Cassie: This is where it gets eerie. The local theory is that the ghost of a Hessian soldier—who lost his head in the Revolutionary War—roams on horseback during that week, searching for his head.

Ava: Glad everyone is thinking clearly. Nothing says “logical” like a headless ghost. Have any locals actually seen him?

Cassie: Some claim they have. And here’s the chilling detail: every victim that’s found is missing their head.

Ava: So the theory goes that he’s picking off and trying on heads as he rides through town?

Cassie: That’s the idea.

Ava: Lovely.

Cassie: And then there’s Ichabod Crane. He hears all about these legends and the accompanying warnings—and instead of taking the advice to stay away, he decides he wants to be there during murder week.

Ava: Seriously? Who doesn’t take those warnings?

Cassie: Nobody claimed he was the smartest. Many warned him not to be out at night. He even met with Police Chief Brom Van Brunt, who cautioned him about being there.

Ava: Woah, that’s another name. Brom Van Brunt.

Cassie: (Laughing) We’re full of them today.

Ava: Wait, I thought he didn’t believe that they were connected.

Cassie: Still claims not to. Chief Van Brunt maintained that any recent murders were nothing more than copycats looking for notoriety. Yet Crane was undeterred.

Ava: Of course.

Cassie: Witnesses say Crane became utterly obsessed with the case. He spent days poring over records and old newspaper clippings. One witness even said he saw lying on the ground at a site where a previous victim was found—as if trying to recreate the scene.

Ava: Lying there like he was trying to immerse himself in the moment? That’s intense.

Cassie: Intense indeed. He was even arrested one night for breaking into the cemetery where locals claim the ghostly horseman is seen among the graves.

Ava: So , he wasn’t just a casual investigator—he was actively engaging with the legend, even mimicking it?

Cassie: Exactly. And get this, the witness who found him lying on the ground at the murder scene said that he had a photo of the murder in one had, which he used to check that he was in the exact position, and that he covered his face with a black towel—almost as if trying to become “headless”.

Ava: That’s disturbing. I mean, I get doing on-site research, but that crosses a line.

Cassie: Unsurprisingly, none of the locals were fans of his methods. His behavior grew more erratic over time, and by the end of his visit, many described him as paranoid, jumpy, and anxious—convinced he was next.

Ava: Well he sounds like such a people-person.

Cassie: Oh yeah. You just have to look at his blog to know that. The way he writes about the town is as if the whole place was full of blood lust. And he writes multiple times that he knows he’s next on their list. And as it turns out, he was.

Ava: But before we get to that. Let’s take a break so I can tell everyone about our partner of the show, Nuve.

Cassie: Oh, yes, do tell.

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Cassie: You’re getting good at that.

Ava: Aww, thank you, means a lot. So, Mr. I. Eli Crane…he’s a paranoid mess, thinks he’s about to get beheaded, stays in the town anyway like a dummy…what becomes of him?

Cassie: On October ninth—during the infamous murder week—Crane’s anxiety reached a fever pitch. He was shaking, sweating, and constantly looking over his shoulder.

Ava: Just leave town!

Cassie: Well, he doesn’t. That night, multiple people reported hearing bloodcurdling screams. Security cameras capture Crane running, glancing fearfully behind him, as if something was relentlessly chasing him.

Ava: Do the cameras pick up what he’s screaming at?

Cassie: They don’t. There was nothing behind him. Still, he was seen ducking as if to evade a blow, and even throwing objects behind him, as if trying to slow down an unseen pursuer.

Ava: A full-blown breakdown—or perhaps the ghost?

Cassie: Whatever it was, by the next morning, he had vanished. All that was found were the items that he’d dropped along his path, ending at an old bridge that leads out of town.

Ava: So he did skip town.

Cassie: That’s what authorities think. In fact, there was never even an official case opened. But, here’s the thing, his paper, the Connecticut Herald, confirms he never returned to work. And his last blog post is timestamped at 8:07 P.M. on October ninth—a post that sends shivers down my spine.

Ava: What did the post say?

Cassie: It was a short one—“It’s real. It’s all real. And I know what’s happening. If I go missing, start with Brom”.

Ava: Ooh, that’s chilling. Did Brom say anything about it?

Cassie: So far, Brom has only dismissed it as Crane losing his grip.

Ava: And that’s all we know?

Cassie: That’s where the story ends and speculation begins.

Ava: Mmm, did he uncover too much?

Cassie: Or did he fake it? Try to join the legend?

Ava: Or is there really a ghost?

Cassie: You know, I want to investigate it, try to get some answers, but I’m almost afraid to.

Ava: Yeah, I don’t blame you. No telling what you find.

Cassie: And so, for now, we’ll have to accept that there are no answers to this one. Guys, if you enjoyed this episode, be sure to like, subscribe, rate, and review, and let us know what you think happened in the comments. We’ll be back with another episode this Friday. Until then, have a great week—and we’ll see you next time when we talk about The Obscure.