October After Dark: The Headless Horseman of Sleepy Hollow

SPEAKER_00 0:00

Hey everyone on this week's episode of Whispers from the Mist, Conversations from the Spiritual Byway. Today we are heading to Sleepy Hollow, where we will explore the legend of the Headless Horseman, the history behind the story, and why it still gives us chills today. So with this introduction, let's take this conversation a little bit further down the spiritual byway. Hello everyone and welcome to another October edition of Whispers from the Mist, Conversations from the Spiritual Byway. I am here. Well, I'm Michelle, and I am here, and I'm here with Stacy. Hi, Stacy. Hi, Michelle. How are you? How are you? I am doing all right. How are you? I'm doing well. I mean, I love October. You all know that. We're going to be talking about Sleepy Hollow today, my childhood nemesis. But before we jump into Sleepy Hollow, I have to make a correction that has to do with the last episode we recorded on vampires. I know you know what I'm going to say because I sent you notes and I'm like, I have to correct this, and why wouldn't you stop me in a moment? But when I was talking about Bram Stoker Stoker and the fact that he wrote Dracula, I stumbled over his name the first time, but the second time I said it, I called him Bram Stroker. Which is perfect. Stoker. When I listened to that, I spent like a half an hour trying to figure out how to edit that out, and I couldn't do it. And I'm like, well, I'm human. Hopefully, people were not listening that closely, like you do when you edit it and you listen to it over and over and over again. But yeah, um, it's Brahm Stroker. Stoker.

SPEAKER_01 1:48

I said it wrong again. I feel like you want it to be Bram Stroker.

SPEAKER_00 1:52

I think everybody wants it to be, but it's Stoker. It's stoked our imagination. That's why I have to remember it. He stoked our imagination as Brahm Stoker.

SPEAKER_01 2:01

That's a very valuable and important correction.

SPEAKER_00 2:04

Well, I thought it was. I'm like, people are probably just thinking, where is her mind at? Or maybe I'm the only one that has a dirty mind. I don't know. Don't think so though.

SPEAKER_01 2:12

No, definitely not the only person that has a dirty mind. Even if you're spiritual, you can have a dirty mind. Like we're human. Oh, well, thank you so much for that correction. Yeah.

SPEAKER_00 2:22

I'm like, I can't believe I'm gonna have to say this, but I just wanted people to know I recognize my air and I'm taking accountability for it. Well, the other day I was on Instagram and I was just kind of what do they call doom scrolling. I was scrolling through and I came across an article or a real, I can't even remember what it was right now. And it was talking about an individual. And the way I read it, and maybe I just put my own spin on it, this individual dressed up like a ghost, was in a cemetery, and when people walked out, he would jump out and go woohoo or boo. And then he got arrested.

SPEAKER_01 3:04

I can imagine that that would not go over well. But my question is, what was he actually arrested for? Because it sounds like he was just scaring people, which is not illegal.

SPEAKER_00 3:19

So it's not illegal, but some people might see it as harassment. Um my biggest thing was how would I feel if I was walking through a cemetery and someone jumped out and went boo or woo? How would I feel? And I really had to think about it. And I think if I was there for the reason of just taking a stroll, looking at the different headstones, exercising, that would be one thing. But if I was there and I just attended a funeral, I would not be very happy.

SPEAKER_01 3:51

I've spent so much time in cemeteries. I think we've talked about this in the past because they're great for running, they're great for walking, and they're safe because a lot of people driving cars don't go over roughly like 10 miles or five to 10 miles per hour. So it's easy to see people, easy to get out of the way and all of that stuff. But if I'm just there casually and somebody scares me, I would probably find it hilarious. But if I'm there honoring a family member or somebody that I have laid to rest, I think I would be a little perturbed.

SPEAKER_00 4:23

So I had to look it up. Like, is this a real story? Did I get the details right? And the only story when I went to the internet was about a man who lived in Portsmouth, England. He had been out drinking with friends and they were at the Kingston Cemetery in Portsmouth. They were playing a little bit of football, and they got a little rowdy, and one of them started pretending to be a ghost. So I don't know where I got was dressed up like a ghost, but the only story that I could find that was similar had to do with this gentleman. And I found this at thegardian.com. I'll put the actual article in our show notes.

SPEAKER_01 5:03

It's a tough one. I I understand both sides on this one, but I'm also like so easygoing. If it was inappropriate, I probably would like throw time and place. Yeah. But at the same time, it's pretty funny.

SPEAKER_00 5:17

Yeah, I'm pretty type A, but maybe they were just playing football, which is probably the English version, and he was just going woo whenever he scored. I don't know.

SPEAKER_01 5:27

He wasn't playing football in the cemetery, was he? It sounds like they were. Oh, so to me that is extremely disrespectful.

SPEAKER_00 5:34

But what I read on Instagram was just a man was dressed like a ghost in a cemetery. That's how I read it. Doesn't mean that's how it was written. That's how I interpreted it. I was like, would I be offended? So I thought I'd bring it here and ask, would you be offended?

SPEAKER_01 5:50

Yeah. I would be more offended by the um playing, I think, football in the cemetery than I would about anything else. Yeah, I would agree.

SPEAKER_00 5:59

That would be a little disrespectful. So well, that's the story I wanted to share before we jump into Sleepy Hollow. And I am going to give you 10 seconds to tell me some of the characters in Sleepy Hollow. You can include the town. So one would be Sleepy Hollow. Ichabod Crane. Yeah. Headless Horseman. And that's where my brain ends. I know there was a love interest who I now remember is Katrina, and there was her Paramour or want to be Paramour, and his name was Brom Bones. What a name. But um this book was written by Washington Irving. Washington Irving was born in New York City in 1783. So that would have been just right after the American Revolution. And he grew up in a city that still was very deeply connected to its colonial past. And he became one of the first American fiction writers to gain a major readers readership in Europe and the United States. So his background was Scottish and Cornish, but as a writer, he became very fascinated by old New York, especially the Dutch period when New York was also, or not also, it was known as New Amsterdam. And long before Sleepy Hollow, he even created a fictional Dutch historian named Dietrich Knickerbocker, who was a comic literary persona who wrote about Old New York and Dutch settlers. And when I was doing a research on Mr. Knickerbocher, because I'm like, was it a pseudoname that Washington Irving created? But it wasn't. It was a character. And just for kicks and to get the hype going, like before the book came out, Washington Irving would put missing person ads in the newspaper for this gentleman, Knickerbocker, which I thought was interesting. Yeah, that's very interesting. Irving also knew the Hudson Valley landscape personally. And so when he would go to write, he would always go back to old churches, farmhouses, local history, and the sense that these Dutch settlers really had a commitment to holding on to stories and passing them from generation to generation. So how do you think he came up with the idea for Sleepy Hollow? I think Sleepy Hollow just came from those generations of superstitions, folklore, old stories, like I said. But the Hudson Valley is very near where a battle took place during the Revolutionary War. It was a Battle of White Plains. And this happened on October 28, 1776. Okay. Now, Irving makes his horsemen that he writes about, a Hassan Hassan trooper who he says that during this particular battle was hit with a cannonball in the head and lost his decapitated. So that was his story. I'm gonna go through his story as a recap in just a minute. But that's how he came up with the idea of this particular headless horseman.

SPEAKER_01 9:12

I'm going to take a guess that it was because he witnessed something along those lines and he kind of created it from there because what a lot of people do when they experience trauma is turn it into a story to move forward with.

SPEAKER_00 9:26

I'm sure somebody did, but probably not him, because I think he was born a year after the Revolutionary War. So he probably grew up hearing about this.

SPEAKER_01 9:35

Yeah. Well, and it could have been like a a story that was told over and over again that scared him as a child and kind of haunted him too.

SPEAKER_00 9:43

Do you want me to tell you the summary? Let's hear it. I'm ready. Okay. Before we get into the different versions of Sleepy Hollow, I want to go back to the original story. The legend of Sleepy Hollow was written by Washington Irving and first published in 1820. What I'm sharing here today is a retelling of this story. So this story takes place in a quiet little area along New York's Hudson River near Terrytown, and it's called Sleepy Hollow. Sleepy Hollow. And Irving describes it as this almost dreamlike place where people are especially drawn to strange stories, old legends, ghost tales, and things that can't always be explained. Aren't we all? So it's good to know even back then there were people like us. And the biggest legend of all was that of the headless horseman. According to the story, the horseman was once a Hassan soldier who fought during the American Revolution, and he was supposedly killed when a cannonball took off his head. Sounds like a miserable way to die.

SPEAKER_01 10:44

I was gonna say it sounds quick but miserable.

SPEAKER_00 10:47

Yeah. His body was buried in the local churchyard, but people believed his spirit still rode through sleepy hollow at night searching for its missing head. That is what stuck with me. I'm gonna a hundred percent blame this story for my fear of being decapitated and losing my head. 100%.

SPEAKER_01 11:05

As a child, totally valid.

SPEAKER_00 11:08

I saw the Disney version, so I'm blaming Disney for this one. And washing.

SPEAKER_01 11:12

That's an interesting that it scared you so much and it was Disney because you would think that they would have lightened it a bit.

SPEAKER_00 11:18

Well, they did, and we're gonna get into that when we talk about that version. So I'll just keep continuing. I'm just telling you like one of the biggest fears of my life is that. So I'm blaming the story for having that long-rooted terror about that. Okay. So I just said his body was buried at the local church. He's searching for his missing head, and this is the world that Ichabod Crane steps into. Ichabod Crane is a school teacher from Connecticut. He's tall, thin, a little awkward, but he's educated and absolutely fascinated by the supernatural. He loves hearing stories about ghosts, witches, spirits, haunted places, and unexplained things. The problem is he also believes a lot of what he hears. So he may enjoy a ghost story while he's sitting safely inside with other people, but once he's outside alone at night, every sound suddenly feels scary or suspicious. Every shadow looks like something, every noise in the woods feels like it could be following him. While he's living in Sleepy Hollow, Ichabod Crane becomes interested in Katrina Van Tassel, the daughter of a wealthy farmer. But Ichabod isn't the only person who's interested in Katrina. There's also Braum Bones. He's strong, he's confident, he's athletic, a great horseman, and known for practical jokes. He's not very happy that Ichabod is now competing for Katrina's attention. And one autumn evening, Ichabod was invited to a gathering at the Van Tassel home, which was Katrina's home. There was food, music, dancing, and eventually, as the evening gets later and later, they start to tell ghost stories. And of course, someone starts talking about the headless horseman. They talk about the Hassan soldier, they talk about the old church in the graveyard, and they talk about a bridge near the church that is supposedly very important to the legend. The story goes that if someone being chased by the horseman can get to the bridge and cross it, the ghost will just disappear. Now, you've got to remember that Ichabod already believes in this kind of thing. It wasn't a big sell to him. So these stories, they don't just entertain him, they stay with him. And later that night, Ichabod leaves the Van Tassel home. Now, I'm gonna pause here. How many times have we gone to slumber parties or events where it's all fun and games when we're surrounded by people, but when we have to go home, when we have to face the night, it suddenly takes on a whole new vibe.

SPEAKER_01 13:47

I remember many a sleepover party, friend's house overnight, like doing the whole bloody Mary thing in the bathroom, and then I'd go home and I'd be by myself and I'd be afraid to go pee in the middle of the night.

SPEAKER_00 14:00

I still am afraid to look in the mirror at the middle of the night. I don't like to.

SPEAKER_01 14:04

No, I I'm not a fan of looking in the mirror in the middle of the night because I I don't know. I'm I might be a weird one here, but if I get up in the middle of the night to go to the bathroom because I am female, I don't need a light. So I just walk into the bathroom and leave the lights off and use the bathroom, wash my hands, and leave because I know where everything is, right? But the mirror is super creepy with no light on and and nothing along those lines. So maybe I'm the weird one. I don't know if anybody else goes to the bathroom with the lights off at night, but I do. I just my dog's not on the floor by my bed, and I trip over. My dog's usually on top of me in bed, so she's fine. Yeah, she's fine.

SPEAKER_00 14:39

Okay, so again, later that night, Ichabod leaves the Van Tassel home. Something seems to have happened between him and Katrina. Irving never really tells us exactly what, but Ichabod leaves the house feeling disappointed. And now he has to ride home. He's alone, he's in the dark, and all those ghost stories from earlier in the evening start replaying in his head. So now the road feels different, the trees look different, every sound seems louder, and then he notices something. There is another rider on the road. And at first he can't tell who it is, but the rider seems to be following him. And when Ichabod slows down, the rider slows down. And when Ichabod speeds up, the rider speeds up. And then Ichabod realizes something is very wrong. He looks at the rider who appears to have no head. Instead, it looks like he's carrying his head with him. Ichabod becomes convinced that the headless horseman is now chasing him, and now it turns into a full-on race through the darkness because Ichabod remembers the story about the bridge. If he can just get across it, maybe the horseman will disappear. So he pushes his horse faster, he reaches the bridge, he crosses it, and for just a second he thinks he's safe.

SPEAKER_01 15:58

He turns around and the horseman is still there.

SPEAKER_00 16:02

And instead of disappearing, the rider throws what appears to be his own head directly at Ichabod and it hits him. And Ichabod falls, and then he disappears from the story. The next morning people go looking for him. His horse is found, his hat is found near the bridge, but Ichabod, he's gone. And next to his hat is something very interesting, a shattered pumpkin. Ichabod is never seen in Sleepy Hollow again. Later people hear rumors that maybe he survived the night and just left the area. And Kurtrina, well, she eventually marries Brahm Bones. So that's kind of where it ends, but Irving does give us one final clue. Whenever people tell the story of Ichabod's disappearance, especially the part about the pumpkin, Brahm seems to react like he might know just a little bit more than everybody else about the story. And that leaves us with the real mystery of the Legend of Sleepy Hollow. Was Ichabod actually chased through the woods by the ghost of a headless Hizan soldier? Or did Brahm Bones know exactly how superstitious Ichabod was? Did he dress up like the horseman and chase him through the woods and throw a pumpkin at him? Washington never tells us. And I think that's part of why the story still works. There's enough there to explain it away, but there's just enough left unanswered to make you wonder. Was it a prank? Was it fear? Or did Ichabod Crane really encounter the headless horseman? What do you think? What do you think? I'll tell you what my young self thought. It was a horseman. There was no joking about it. He came across the horseman that night.

SPEAKER_01 17:42

I would agree with that as a younger human soul. That would be where my head goes too. But I think now and understanding what we have learned about spiritual activity and entities and all that jazz, I find it more likely a prank.

SPEAKER_00 17:58

And if I'd ever read the book, well, it would have been when I was older. So I probably would have been a little more discerning. But the book wasn't released as just like the headless horseman. It was released as a part of a larger story that was first published in 1820. And the book was called The Sketchbook of Jeffrey Crayon Gent. That's interesting. Yes. Interesting, enduring. So we have this book first published in 1820. And then in 1949, October 5th of 1949, because October must be a popular month for a lot of people, Disney released a full-length film. Actually, I'm just gonna say Disney released a show called The Adventures of Ichabod and Mr. Toad. So I didn't realize it was part of a series. And the legend of Sleepy Hollow, the headless horseman part was the second part of the cartoon. The first part was Mr. Toad, as in Mr. Toad's Wild Rided Disneyland. Did you know that? I did not know that. So that's a piece of trivia. I learned something new. You learned something new. But later, Disney separated the Sleepy Hollow segment and released it as The Legend of Sleepy Hollow, and it aired on television under that title in 1955, and then received a separate theatrical release in 1958. Now, Bing Crosby was the narrator of The Legend of Sleepy Hollow, Disney's version. He wasn't Ichabod Crane's voice, he was the narrator. And the cartoon, because I just re-watched it to see if it had the same effect on me, it was almost like a musical because there are at least three songs in there that Bing Crosby seen. One of them is about Ichabod Crane, one of them is about Katrina, and the other one is about the headless horseman.

SPEAKER_01 19:58

I kind of love that. I'm a big Bing Crosby fan. I mean, I don't like a lot of the stories that have come out about him, and he apparently was not the greatest guy in his family life, but I don't like to believe that because he has such a beautiful voice.

SPEAKER_00 20:15

He has, he seems like an angel. And if you think back to the time when this cartoon was being released, you have a sweet voice telling a sweet story. I again just re-watched that part of Ichabod Crane and the Toad, however it went. And it reminded me a lot of Beauty and the Beast. The opening in that provincial town and all the women swooning over Ichabod Crane at points. Braum was just like gased on a little bit. So I wouldn't be surprised if later artists, Disney Imagineer, didn't draw on that as some reference because it so reminded me of the beginning of Beauty and the Beast.

SPEAKER_01 20:58

Oh, that's interesting.

SPEAKER_00 20:59

Yeah. So they bring you into the story. It's all sweet, it's all smooth sailing, it's kind, it's funny, ichabod. They make him very superstitious. And one of the songs I think he's walking up and there's a ladder there. He won't walk under the ladder. A black cat walks by, he won't touch the black cat, and then he spills salt later and has to throw it over his shoulder. So he's very superstitious. They set that up very, very good. He also very much likes to eat. That was his one of his main motivations in life. And he likes money. Katrina's father was very wealthy, and so he had money in his eyes every time he thought of her. Also, I didn't remember that part.

SPEAKER_01 21:40

Interesting.

SPEAKER_00 21:41

So it all starts out very lovely, very smooth, and then it gets more dramatic. The song about the headless horseman comes, and then the headless horseman scene, which terrified me as a child. And in my mind, again, there was no way that it was anything other than the ghost of a headless horseman. I don't even think I was old enough. To differentiate that there could have been someone playing a joke like that when I first started.

SPEAKER_01 22:05

Right. It's an interesting thing because we are essentially trained to believe whatever they're telling us. So of course it's terrifying. Can you imagine? Well, I I can imagine because I believed it. I think because the story leaves so much to the imagination, too, that makes it just a little bit more scary. Exactly.

SPEAKER_00 22:26

Yeah, you're left to your own interpretations. Watching it as an adult, I could see where it could have been a prank. But I don't know how someone pulls off that prank still. I don't know. But then after the Disney version, they're just not gonna let the headless horseman rest because in 1999, a movie starring Johnny Depp as Ichabod Crane was released, and it was called Sleepy Hollow, and it was one of Tim Burton's creations. And you said you saw that movie.

SPEAKER_01 22:56

Yes. It's been a long time. I haven't watched it recently. I watched it many years ago. I'm a big Johnny Depp fan, though. So he is the reason that I watched it. You know, Captain Jack and all that.

SPEAKER_00 23:08

I love it. So in this retelling of Sleepy Hollow, Ichabod Crane is not a school teacher. He is an investigator that was sent to Sleepy Hollow to investigate a series of decapitation murders. Tim Burton was really good to stay true to the names of the different characters, such as Katrina, Braum, the Headless Horseman, but he builds in a whole gothic murder mystery around the story. So the biggest shift in the story is, you know, when Irving first wrote it, we question whether the horseman was real. In Burton's story, the horseman is absolutely supernatural, but someone is using that supernatural force as part of his crime. But I've never seen the movie again. Too terrified by a cartoon to watch the actual movie. But that's kind of the gist of that. And then in 2013, I believe this was on Fox, but I could be wrong. No, it is on Fox. Sleepy Hollow premiered, and it ran from 2013 to 2017. And it moves Ichabod Crane from the revolution into modern day America. And the headless horseman in this series just becomes a part of a much larger mythology involving witches, demons, apocalyptic themes, and supernatural forces. So now we're really far from Irving's original story. Now we have the recognizable main ingredients, Ichabod Crane, The War, Sleepy Hollow, and the Headless Horseman. But it's different because now you're bringing in everything else that there could be into the show. Interesting. Yeah. It's fun. It is fun because it's folklore. It came from somewhere. And over the years, and as we grow and change as a society, the stories morph and change into what we may find interesting and entertaining. But you're talking about a story that was told around a campfire or around the fireplaces while they're trying to keep warm. And this is how they entertain themselves. And this is how they grow as a community. They keep their kids in line. They keep other people in line by telling these stories over and over. And it becomes part of their tradition, which now is part of our tradition. I mean, I could never look back at my childhood during my favorite month of October and not have watched that show, even though it terrified me.

SPEAKER_01 25:35

So I think even though things scare us, we always have these memories, right? As an adult, we look back and we're like, hey, like I that was terrifying, but I'm gonna do it again. And you end up creating these traditions and talking about the core piece like you just brought up. I think it's really cool. Well, not psychologically, probably not really cool that they use scare stories to keep kids in line, but you know, I understand at the same time, it's entertainment, right?

SPEAKER_00 25:59

It is, and I don't know if it was just to keep kids in line, but that's what it would do for me if someone told me not to go in the woods after dark because there's a witch that if you find her house and you eat the candy off her house, she's gonna throw you in her stew. Like that would keep me out of the woods. I'm just saying. I was very susceptible. I was very easily persuaded to be on my best behavior. And I continue to be. Even though I call it Braum Stroker instead of Stoker. Braum Stroker. So just a quick recap, and then we can think about closing up this episode if you want to, Stacy. When Washington Irving wrote the story, he left it very ambiguous. Maybe the horseman was real, maybe he wasn't. When Disney did their cartoon, the horseman feels terrifyingly real. In Tim Burton's series, the horseman was real and he was part of a murder mystery. And in the TV series, the horseman just became part of an entire supernatural universe. Which version do you like best?

SPEAKER_01 26:58

I'm not sure. I'm gonna have to now I I kind of want to go on a sleepy hollow spree and try to watch and make an appending.

SPEAKER_00 27:06

Would you go from the Disney version all the way through the TV series? TV series is a commitment. It's four seasons.

SPEAKER_01 27:13

Yeah, I don't I don't know if I would want to dive into the TV series. I think I want to see if there are any like major horror options that they I'm sure that turn Sleepy Hollow into like super horror.

SPEAKER_00 27:26

Yeah, and you know, Sleepy Hollow took place in New York, which of course is on the East Coast, and there's a lot of history there, and a lot of it comes with a haunted portion now. And when you think of that, you're thinking of old towns, churches, graveyards, settlements, revolutionary war, battlefields, Gettysburg was out in that direction. It's just so many layers of history out there.

SPEAKER_01 27:52

It's very true. Very, very, very true.

SPEAKER_00 27:54

To revisit a couple more stories because it is fascinating.

SPEAKER_01 27:57

I I think that's also the the charm of the area that you're talking about, too, the East Coast. I always made the joke with you in the past that you can take two steps and find something haunted in this area. And that's I think my favorite thing about living on the East Coast is there's so much rich history here.

SPEAKER_00 28:16

Well, anything else you want to share about Sleepy Hollow? Do you think we did it just as I hope we did and I hope everybody keeps their heads? I hope so too. That's a very good way to shift into listener questions. That's so funny. Well, your first question is what do you think? Do you think that Ichabod Crane encountered the headless horseman? Or do you think it was his rival Rom Bones behind it? This is question number two. Which version of Sleepy Hollow do you remember the most? And number three, if you had to ride through Sleepy Hollow at night alone, what would scare you the most? If anything?

SPEAKER_01 28:58

Those are great questions.

SPEAKER_00 29:00

Yeah, I would not ride through Sleepy Hollow alone at night. I would have a car now, as most people would, I think, and just zoom through it or just be in before dark.

SPEAKER_01 29:11

Yeah, be in before dark. In those areas, it's probably the safest thing to do. I think so.

SPEAKER_00 29:16

Well, with that, Stacy, would you like to close out this episode? Absolutely.

SPEAKER_01 29:21

I hope everybody stays here.

SPEAKER_00 29:24

Trust what you know. And meet you along by way. Thank you so much for taking the time to be here with us walking and scratching us here. Whatever you are on your journey right now, just know you're not alone. We're here for you, and we're all in this together.