Sightings - Headless! The Legend of Sleepy Hollow

Episode Date: October 20, 2025

New York, 2011: Every town has its legends—but in Sleepy Hollow, legend and nightmare are one and the same. This Halloween, a young cyclist learns the Headless Horseman still rides. Thanks to this week's sponsor MEUNDIES! Visit ⁠meundies.com/sightings⁠ to grab some cool glow in the dark underwear for spooky season. Use promo code SIGHTINGS for up to 50% off! Sightings is a REVERB and QCODE Original. Find us on instagram ⁠⁠@sightingspod⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices

When you're with Amex Platham, you get access to exclusive dining experiences and an annual travel credit. So the best tapas in town might be in a new town altogether. That's the powerful backing of Amex. Terms and conditions apply. Learn more at Amex.ca. dot c a slash ymx october

has a way of blurring the line between legend and reality especially when the fog rolls in and the moon hangs low over long forgotten roads but in some towns the plastic skeletons and animatronic zombies decorating front yards aren't nearly as terrifying as what thunders through the darkness behind you. Because some creatures don't need a head to hunt you down. Welcome to sightings, the series that takes you inside the world's most mysterious supernatural events. Each episode brings you a thrilling story that puts you at the center of the action, followed by a discussion that dives into the accounts that inspired the story,

and our takes on them. I'm MacLeod. And I'm Brian, and we are just over a week from Halloween, so I thought it was the perfect time to tackle one of the most famous spooky season stories of all time, the legend of Sleepy Hollow. There's a whole lot more to this tale than meets the eye, and today's story is bound to make you second guests traveling alone on back roads at night. Will you survive a ride through Sleepy Hollow? Find out on this episode of Sightings. My name is Paul Littlefield. My name's Paul Littlefield. I'm in my 20s now. and live in the city, but I grew up in the Hudson Valley, just outside Terrytown,

which means I lived practically next door to Sleepy Hollow. Yeah? That Sleepy Hollow. The one in all the Halloween stories, Headless Horses, Curse Bridges, all that? Does that make me sound jaded? I mean, I honestly never bought into any of it growing up and hated the tourist buses that came rolling through each October. My whole life basically turned into a Halloween theme park. each fall with hayrides and branded coffee mugs and way too many pumpkin decorations.

But seriously, a legend of a headless guy on a horse? It sounded like something a bunch of drunk colonists made up to mess with their neighbors. Then again, this wouldn't be a Halloween story and a true one, no less, if there wasn't some truth to the matter. And all I know is I've got my truth. And not to be, um, oh, what's the word? literary or anything, but what happened to me when I was 15 made me realize that maybe, just maybe. Some legends exist for a reason. Back then, I was completely obsessed with cycling.

I joined the team as a freshman and was already training for state competitions by my sophomore year. I pretty much lived on my bike, spending every free moment exploring the back roads that wound through Westchester County. I could tell you which shoulders crumbled after the winter thaw and which driveways had loose dogs that like to test sprint speed. So when people told me to stay off certain streets after dark because of old legends, eh, I'd shrug. Honestly, the only thing I thought I was likely to meet out in the boonies was a raccoon.

But that fall, my teammates started talking about seeing things during their own nighttime rides. One day, Mike Rodriguez claimed he'd seen shunies. shapes moving through the fog near the old church cemetery. Then this other guy claimed he chased a lantern light down Bedford Road, but he had no idea who was making it or how. I treated all of it like a workout game. If my friends wanted to be spooked, I'd pace them past the churchyard and cemetery with my headlight on low and calling out to any ghosts that might be listening. Nothing ever happened, of course. But still, the rumors kept spreading,

and soon enough, some of my teammates were quietly changing their favorite loops. Even the team captain told me he'd stopped taking roads that ran past the old Dutch church, at least after dark. When I pressed him about why, he just shook his head and said he'd rather not talk about it. I wrote all of it off as nerves and imagination and people psyching themselves out because of the local folklore. But then, I had my own.

encounter. It was a solo ride in mid-October. The sun had already set, but I had good lights on my bike and knew the roads like the back of my hand. I remember pushing myself pretty hard, working on my climbing technique on some of the steeper hills near, sleepy hollow proper. I'd stopped about halfway through my route for some water and to check the time. It was my usual spot, just a quiet stretch of road that ran parallel to the woods. And then I heard a branch snap in the trees. At first I didn't make much of it. It could have been a deer, or maybe just an old branch falling. But then I heard something else, something rhythmic, almost like hoofbeats. I looked up from my water bottle and scanned the tree line. The moon was pretty bright that night

so I could make out shapes in the distance. And there, maybe 50 yards away. I saw what looked like a silhouette of someone on horseback, just standing there at the edge of the road up ahead. Now, I should mention that there are still a few horse farms in the area, but, I mean, who rides a horse at night? I called out asking if everything was okay and got no response. The figure just stood there, perfectly still. By then, my curiosity had gotten the better of me, so I turned my headlight up to try and illuminate the thing, but it was gone. which didn't seem possible because it was a horse, right? So I clipped in and rode to the spot where I thought I'd seen the rider,

but there was nothing there, just empty forest and the sound of wind through the leaves. I probably should have let it go right there, but I rode just a bit further, and then I saw them. Hoof prints, fresh ones by the look of them, pressed deep into the dirt and damp leaves. and I'm not going to lie that left me shook because if what I'd seen was real if there really had been someone

on horseback out there then where are they gone I didn't tell anyone about what happened that night partly because I wasn't sure I could trust my own eyes and partly because I'd been so stoic all these weeks before I mean think of it

Paul Littlefield the guy who spent half his time debunking ghost stories, claiming he'd seen a horseman in the dark. So I just kept my mouth shut and continued my regular routine as fall deepened into late October. Soon the trees were turning brilliant shades of red and gold, and the morning mist made everything look like something out of a fairy tale. It was awesome, minus the strange horsemen lurking in the night, of course. Now, as Halloween was rolling around, Coach Brennan decided he'd create a route for us that rolled past all the landmarks connected to the Sleepy Hollow legend. The old Brooklyn. bridge, the church cemetery, all the areas where Washington Irving supposedly got his inspiration

to write the story. And now, given my prior encounter, I was slightly nervous about said route, but I kept my head down and ventured out on my own one night, hoping to pull the time that would impress the coach and the entire team. The ride was going fine. Until I reached a stretch of road I'd somehow never really noticed before. There was the old cemetery set back from the pavement, Not the famous one, mind you, because this one was partially hidden by a stone wall and overgrown with ivy. And even though 90% of me wanted to keep going, to keep posting time, the other 10% won out. So I slowed down and stopped to take a closer look. And yeah, it was a cemetery.

Nothing unusual there, but I don't think I'd ever noticed before how old the headstones were. Some were so weathered that I couldn't even make out the names or dates. And as I stood staring at them, the wind suddenly picked up, sending leaves flying all over the headstones. And of course, right then is when I heard it again. Hoofbeats. But this time they weren't distant. They were clear, rhythmic, and growing closer. So I turned towards the source of the sound.

And what I saw... Well, I don't think I'll ever forget what I saw that night. because about a hundred yards down the road silhouetted against the evening sky was a figure on horseback a tall rider dressed in what looked like a long cloak or coat and perfectly motionless but as I stared trying to make sense of what I was seeing I realized something was wrong with the silhouette the proportions were off somehow because even though the rider had broad shoulders and a powerful build, the spot where the head should have been was empty.

There was just nothing. I blinked hard, convinced I was seeing things, but when I opened my eyes, the figure was still there. And now, it was moving. The horse beginning to walk in my direction with that same steady rhythm I'd been hearing. I tried to clip my foot back into my pedal, but I was too scared to move correctly,

so my foot caught air, and as I looked up again, I realized the horseman had closed half to distance between us already. And now I could see with absolute clarity that where his head should have been, there was nothing but empty space above the collar of a dark jacket. I stumbled backward, grabbing for my handlebars, but I faltered. The front wheel turned sharply, and the whole bike toppled over, taking me down with it.

I hit the dirt, hard, scraping my knee and jamming my shoulder. But when I looked up, the road was empty, no horse, no rider, no sound except for my own ragged breathing in the distant hum of traffic from the highway. I rode home as fast as I could until my breathing settled and my hands unclenched and the roads picked up the normal noises again. But as I peddled down those familiar streets, I couldn't shake what I'd seen. And for the first time in my life, I was genuinely... deeply afraid of something I couldn't explain because I knew with absolute certainty that what I'd encountered on the road that night

was real. Hey, McLeod, guess what? What? It is our favorite time of year. Spooky season? It is, but it's also fall, which is my favorite time of year, aside from spooky season.

So the leaves are turning, We're getting ready to layer up. I love a good sweater. Guys, though, if you are still rocking old beat-up boxers under those flannels and jeans, it is time to upgrade to me, undies. They're just like so soft, so breathable, perfect for crisp fall mornings, chilly nights, and everything in between. Oh, McLeod, you should become their new spokesperson.

I'm serious, though. And I got some as well, and I love the really cool patterns on all of them. And this is something that I'm sure that sightings listeners will love. Miundis has a limited edition Halloween line just in time for spooky season with fun prints, including McLeod, some that glow in the dark. Are you serious? Well, good. Now I won't need nightlights when I get scared from our stories. So take it from us because we wear them.

Meundies is your new fall essential. And right now, sightings listeners, that means all of you can get cozy and spooky for less with deals up to 50% off. at meundies.com slash sightings and enter promo code sightings. That's meundies.com slash sightings. promo code sightings for up to 50% off. Meundies comfort that's made for fall. Thanks meandies for sponsoring this episode. After that second encounter, I couldn't just pretend nothing had happened. I mean, I'd the thing twice now, and both times it had seemed as real as my own bike beneath me. So instead of continuing to ride it off, I decided I needed to understand what I was dealing with. I started with

Washington Irving's original story, which I'd somehow managed to avoid reading despite living in the shadow of it my whole life, and honestly the similarities between what Irving wrote and what I'd experienced were unsettling. The description of the horseman, the way he appeared and disappeared, even the area where I'd seen him, it all lined up with the old tale. When I kept digging, I learned about revolutionary war battles fought in our area, and the series of unmarked soldier graves scattered around. One account from 1778 described a Hessian officer, apparently a German mercenary, who'd been decapitated by a cannonball during a retreat through Sleepy Hollow.

Though his body was found days later, his head was never recovered. He was buried in the cemetery that, according to old maps, sat exactly where I'd had my encounters. And the more I learned, the more I began to think that maybe Irving hadn't just pulled his inspiration from thin air. I tried to put it all out of my mind, but the nights made it impossible. I dream of cycling down those same dark roads, always with the sound of hoofbeats echoing behind me. I'd look over my shoulder, and I'd see that same headless figure bearing down closer and closer until I'd wake up in a cold sweat. I never told my parents about any of this.

What would I even say, that the town's Halloween mascot had crawled into my head and set up shop? But my teammates noticed something was off. I'd started avoiding routes that went anywhere near the cemetery. And when Coach led us on another practice loop that passed the church, I kind of freaked out a little bit. The ride started off like usual. There were ten of us in a tight pack, but as we approached that familiar stretch of road,

my heart started pounding. Then, faint but unmistakable, I heard hoofbeats, and I nearly lost control of my bike right then and there. The guys asked if I was okay, and I just told them I hit a pothole. But inside, I was falling apart. Later that night I realized something had to give.

Either I'd face this thing head on or spend the rest of my life haunted by shadows and phantom sounds. So, a few days before Halloween, I made the choice. I mapped the same route as the night of my first encounter and told myself I'd ride it start to finish. No detours, no backing down. The fall air was crisp and a light fog was starting to roll in from the Hudson River as I rode toward Sleepy Hollow. Even though my heart

rate was elevated, I felt filled with purpose, not fear. I was hunting for answers. I reached the cemetery, just as the fog began to thicken around the old headstones. The mists gave everything a feeling straight out of a horror movie, but I didn't back off. I dismounted my bike and stood in the silence, waiting. And for several minutes, nothing happened. I even started to think that I'd been wrong, that maybe it all had been in my head. And there it was, those hoofbeats again, slow and steady at first, but close, so close I could feel the vibrations in the road. then through the mist the horsemen emerged moving at a full gallop right towards me every instinct told me to run but i forced myself to stand my ground i needed to see this thing clearly to know what it was but as it grew

closer all i saw was pure horror the horse was massive jet black with red eyes that seemed to glow in the moonlight And the rider, well, he was exactly like the old stories described. A tall figure in a dark military coat, hands tight around the reins, leather gloves creaking. But where his head should have been, there was just empty, terrifying space. He was maybe 50 yards away when my nerve finally broke. I grabbed my bike, clipped in, and launched forward. The road tilted downward, giving me speed, but the hoof-beats. thundered behind me. No matter how fast I rode, the horseman kept pace. I took every turn I could

think of, trying to lose him in the winding back roads. But he followed my every move, never falling back, never giving up. And slowly, inevitably, I could hear him getting closer. At one point I risked a glance back and saw the headless shoulders hunched low, cloak billowing behind him. But I kept pedaling like my life depended on it, because I'm pretty sure it did. My lungs burned, my legs screamed, but I had no choice but to keep going, keep going, keep going. As I rode, I remembered the old stories about the bridge, how the horseman couldn't cross water, and I realized that reaching it just might be my only hope. I bent low, cutting through the fog until the outline of the old covered bridge emerged ahead. I peddled even harder, the sound of hooves so close that I could

feel the ground vibrating beneath my wheels. I looked back one more time and impossibly, the Horseman's hand looked like it was on fire or was holding something on fire, I don't know. I hit the bridge at full speed at centuries-old wood groaning under my bike. Behind me, I heard the Horseman's mount skid and stumble just before the bridge's entrance. And for a moment, I thought I'd made it. Then I heard hooves clopping on wood. The story's got it wrong. It was still coming after me.

I don't know how much further I made it. I just remember pedaling as fast as I possibly could when something struck the back of my helmet with tremendous force. The impact sent me tumbling from my bike, and I hit the pavement hard, rolling end over end towards the woods before everything went black. When I came to, the first thing I noticed was the silence. No hoofbeats, no movement,

just the gentle rustle of wind through the trees. I sat up slowly and found my bike still overturned on the side of the road. I tried to get up, but my body ached all over, and my head throbbed. I reached back with shaking fingers and felt something sticky on the back of my helmet. For a heart-stopping second, I thought it was blood. But when I pulled my hand forward, I realized it was pumpkin pulp. The stuff was everywhere all around me, all giving off a slightly charred smell. And I realized then a flaming pumpkin had hit me in the back.

back of my head. I tried to make sense of it as I finally managed to pull myself to my feet. Had someone been playing a prank? Maybe my whole chase had been staged somehow by my teammates. But, I mean, that didn't add up. The figure I'd see him, the horse, the way he moved, that was no one in costume. Besides, who could ride a horse like that, keeping that speed on narrow roads in the dark? My front wheel was jacked, badly bent, so I ended up walking home, trying to come up with a story that would satisfy my parents. I ultimately told them I'd hit a patch of loose gravel and crashed, not a total lie, at least. Years have passed since then, but I've never forgotten that night. Even now, in the city, when I ride home late and the streets are quiet,

I sometimes catch myself listening for the sound of horse hooves that shouldn't be there. And every once in a while, usually when I'm pushing hard or taking a turn a bit too fast, I swear I can hear them. That steady rhythm keeping pace behind me, never quite catching up, but never falling behind either. Maybe it's just my imagination. Or maybe it's a phantom echo of a real experience. Or maybe somewhere out there in the dark, a headless rider is still making his rounds. homing the back roads of the Hudson Valley on moonlit nights,

waiting, and I wonder if one day will come looking for me again. Sightings will be back, just after this. Sightings will be back just after this. Welcome back, dear audience to sightings. I am winded from that intense chase. I have not gone on a bike ride in a long, long time. My legs are burning at the very thought of this episode. Right off the bat, Brian, I have to say, this was so much fun.

Thank you for writing this story. What a novel perspective on this sleepy hollow leg. I, it's pretty apparent this was more a play on the classic story than something that actually happened, right? Right? Please tell me. I, I haunted down a person who had this experience and... What? No, yeah.

You got me. You almost got me there. Yeah, it is kind of a modernization of the classic tale, following a lot of the same beats, but kind of giving it, you know, that kind of meta vibe a little bit. You know what's interesting? I don't know if I really know much. about the original story. I remember the like Disney animated a little like kind of short film almost. And then did you see Tim Burton's movie? I think I saw it. I forgot most of it. I kind of I remember the thing that I remember is Christopher Walken's head. Yes. And his like

sharp teeth. Sharp teeth. Yeah. Yeah. No, it's a fun movie. But we'll get into the story that that kind of informed the legend. But it's kind of taken on a life of its own and Sleepy Hollow has become a place that isn't kind of the canon of supernatural lore in a way. Like, everyone knows what it is. Everyone knows that it represents a headless horseman for the most part. And that's why I just thought it was the one to do right before Halloween. I think it's perfect. I think it was a perfect choice.

So I guess let's kind of journey to Sleepy Hollow, which, again, everyone, if you didn't know, it is a real place in Westchester County, New York. It's about 30 miles north of New York City. And it is a town, like a little hamlet, I guess, right out. side of Terrytown, New York, on the Hudson River. Right. But it's the place where Washington Irving, who wrote the original legend of Sleepy Hollow story, grew up or spent at least a formative part of his teenage or childhood years. And this story was published all the way back in 1819 or 1820.

Okay. But the story itself, for those who aren't familiar with the tale, it follows Iqabod Crane, who moves to Sleepy Hollow to teach children. And he also happened to be the singing master in town, which is where he seemed to basically. used it as a way to meet women. And one of the people he ended up setting his sights on was Katrina Van Tassel. She was the daughter of a very wealthy man. So one night he intends to make his affections known to her. And this happens like three-quarters of the way through the story. The first three-quarters of it is basically the leaves are beautiful. And Iqabod Crane was teaching children. And occasionally he would sit and read for a while. And like just a lot of very

idyllic kind of. No mention of headless horsemen. No mention of creepy things. It's just, you know, slice of life. Yeah. But on the night that he goes to Katrina Van Tessel's house, there's a party happening. And at that party, there's people talking about spooky ghost stories. And one of them is the tale of the fearsome headless horsemen that lurks in the area, who is allegedly a Hessian soldier, which is a German soldier who lost his head and has been looking for it ever since. Later that evening, he apparently tries. to woo Katrina and it fails. Washington Irving kind of has this weird plot device where a narrator who doesn't know all the details is telling the story. So he's like, I don't actually know what happened, but then he rode away into the night. What a great way to like establish tension and mystery. Mystery is really the operative word there. To establish mystery, an unreliable narrator. And to give it the feel of like journalism almost. It feels real in that sense. Absolutely.

Yeah. And it feels real. then when we're recounting when Iqabod is beginning the long ride home on a borrowed horse that is apparently really old and slow. So as he's riding home, he is pursued, of course, by a giant horseman who's following him. And at first it's just a menacing figure on a horseback who's following him from a distance. Then he picks up the pace and Iqabod looks back and realizes that the horseman is headless, just like the stories that he was hearing at the Van Tassel party. then of course it turns into an outright chase and Iqabod is losing the race basically because his horse is old and decrepit but he's still holding on he's just like if I can only make it to the bridge the horseman can't follow me because apparently that was part of the story and indeed the horseman stopped right before hitting the bridge but then he lifted up his head which he had been holding in his hand apparently and whether it was a head or a pumpkin we don't actually know but he then threw it at Iqabod,

So in the actual story, it's not made clear that it's not a pumpkin in the story. It's not. The story at first describes it as he lifted his head, threw it at Iqabod, and then we kind of lose Iqabod's perspective a little bit. Yeah. Because then the next morning, the horses still standing there by the bridge. There's Iqabod's bag or something is there, but surrounded by pieces of a shattered pumpkin. Oh, okay. But Iqabod is never seen again. So it kind of creates this whole idea of, like, was it a prank? Because in the story, there's also this other suitor of Katrina Van Tassel, who's this strapping young man named Braun, who could have theoretically been pretending to be the headless horseman and threw a pumpkin at him as a prank or to scare him away or something like that. Right. But the fact that Iqabod completely vanished and was never seen again is kind of strange.

So pretty much that's just the end of the story, the original story. That's pretty much the end of the story. Okay. I personally want to think that the horseman was real and not just a prank, especially because Iqabod vanished. But what's kind of interesting here is the kind of thought experiment of the kind of thought experiment of, is there any truth to this legend at all? You beat me to it.

That's the thought that's been running in my head is like, where did he get this story? Did he just make it up out of whole cloth or? He didn't. So that's what's kind of cool about this. So this was written in 1820, 35, 40 years after the Revolutionary War. And apparently after the Battle of White Plains, there was a headless corpse of a Hessian soldier who was found decapitated by a cannonball in Sleepy Hollow. Okay.

And it had been after a violent skirmish and someone found the body. And then Van Tassel, who was a real person, buried it at the old Dutch church, which also pops up a lot throughout the story. And it was believed that the Heshin would arise at night in search of his head. And anyone who would run across his path would be faded to die. Wow. Bookmark that. Heshen. Can you go on, what was a German, Heshen is a German soldier?

What were they doing over here? They're kind of mercenaries. Mercenaries. So they were paid to come and fight. Okay. But Hessians in particular were noted for being excellent marksmen and excellent horse riders. And were they fighting for us or for the English? Good question.

They fought for the British Crown. Okay. Which means that they were kind of the enemy to the locals in the area. It just feels so like no good deed. Like here we are. You have like Van Tassel, this like moral gentleman being like, well, he was an enemy combatant, but it isn't right to leave a child of God out here rotting. So I'm going to bury him at the church, at our church. And then he's like, ah, F you, I'm going to come out and take heads. No good

deed. What's really cool, though, I think, and I don't know whether this factored into Washington Irving storytelling or not, but this Sleepy Hollow story and this idea of this Hessian who lost his head and is looking for it, what's really cool is that there are lots of other stories from around the world, that go way back, that feature a headless entity, usually on a horse, who lurks in the night. Huh. And do they all chase people or? Usually they kind of do.

So, yeah. So in Ireland, there's this headless demonic fairy, which sounds kind of neat. Yeah. Called Adelaan. Sorry if I butcher that, everyone from Ireland. But he's usually riding a horse. He's carrying his head. Even scarier than that.

he has a whip made from a human spine. Oh, whoa. And his job is basically to ride around really fast and potentially chase people. But when he stops riding his horse, he calls out a name and the person who he named immediately dies. Ah. I guess another variation on that tale is that he is the coachman for death's coach. Oh.

So however you want to coin it, basically, he's associated with death and dying and bad omens and things like that. And were there, you said plural. Were there other cultures where there's a similar type figure? Oh, yeah. No, I'm just getting going here. Oh, okay. All right. So in Germany, there were a whole lot of stories about Headless Horsemen, apparently. Most of them were in the Rhineland area of Germany, which Sleepy Hollow was on a river.

So does that mean anything? I don't know. But German, just like our Hessian soldier. Indeed. But what's cool about these guys is that most of them were fated to kind of wander the earth until they atoned for their sins. Oh, okay. But at the same time, there was also, I guess, low. that they killed victims by simply touching them. So it's like if they catch you,

which kind of vibes with the sleepy hollow of it all? Yes, exactly. But what I can't quite square is that if they are wandering the earth until they atone for their sins, murdering people doesn't seem to... Right, right, a good way to atone for their... Yeah, that wasn't a thought-out plot device.

But that was interesting. In Scotland, there are accounts of a horseman who was decapitated in a clan battle. What's cool about him, though, is that when he is seen, his horse also doesn't have... a head. That just went from like kind of like creepy to like, wow, that's upsetting. A poor horse. The visual wrongness of it is somehow more upsetting than just a headless

horseman. Leave it to Scotland. You leave it to Scotland, absolutely. The final one also comes from America, like Sleepy Hollow, but this comes from Texas. So in Texas, there's stories of something called El Merto, which I guess implies that it has some kind of Mexican or Spanish cultural origins. It's been around since the mid-1800. hundreds. In this case, El Merto, this entity, his horse can supposedly produce lightning bolts from its hooves, which is pretty cool. That is pretty cool. And the theory for how this thing seemed to come about is that the man who became this entity was a horse thief, who was killed to set an example, basically, to not steal horses, obviously. He, like, vowed his eternal, like,

vengeance, sort of. Well, I guess I would, too, because what they did was they cut his head off. They mounted his body to a wild horse, they tied his head to the pommel of the saddle, and then just, you know, slap the horse and set it off into the wild. Oh, wow. With the dead rider on him. To be like horse thieves, cattle rustlers out there take note. And then when he's seen, when he's been quote unquote seen by other people since then, his head is always, you know, hanging there on the side of the horse attached to the pommel of the saddle. Wow. Man, so like gruesome and like gothic. And that's why folklore is fun, everyone. That's right. But it's like, it actually makes sense. It's also folklore is fun, but it also kind of provides an interesting throughline or connection to the past of our current folk tales and stories. Because all these people in Sleepy Hollow, Van Tassel sounds like a Dutch name, like we're themselves, immigrants. And the fact that there's all these stories around the world feels like, oh, it makes perfect sense that some version of those tales from the places they came from transferred across the ocean and became like revised and made new. and specific to, you know, America, their new home. Absolutely.

No, and that's what's, I think, really compelling and interesting about this. And then it was obviously immortalized by Washington Irving, who made it his own even further. Especially hearing the fact that, like, this was a very specific German folk tale and that it was a Hessian soldier. And so whether it was Germans living in Sleepy Hollow who kind of started telling the story or people had heard that story of Germans and the German was buried and, like, scenes start. bringing to my mind of like, well, what would this have actually been like at the time, this real guy deciding to bury this enemy combatant in the town's church? I can imagine there being a lot of contentiousness around that. And then add the fact that it seems pretty clear that the Hesians head was taken off by a cannonball. Yeah. Which to me implies that there probably wasn't

any head left to bury with the body. Yeah. So you're burying a headless body who's eternally missing that important part of him. Yeah, yeah. I mean, it's like, it's just classic fodder for ghosts. One thing I did read is a professor who said that, quote, the headless horseman as a supernatural entity represents a past that never dies, but always haunts the living, which I think is really cool and is very kind of indicative of the Sleepy Hollow story and the iterations that have come since where like this entity comes alive, it torments people, it reflects. some past horror of some kind.

Yeah, and I mean, a war is about as horrific as it gets. Absolutely. And I guess in a weird way, given how famous the story has become and how it's kind of taken root and kind of taken over the town of Sleepy Hollow, it seems like he was right. The past doesn't die, you know, in this case. It is still there. It is still with us.

Kept alive through a pretty stellar story. Which is so awesome. But listeners, if you have seen a headless horseman, let us know. If you are from Sleepy Hollow, Hit us up on Instagram at SightingsPod or drop us a message on Spotify. We have lots of people doing that. We love reading those and responding to those. Now, with that said, we're two weeks away from Halloween.

Brian, take us one step closer. Where are we going next week? Well, next week is actually going to be our 50th episode. Whoa, that's massive. Yeah. We should do something to celebrate. We're going to actually be bringing to life some of our very, very favorite spooky listener stories. Oh, that's perfect.

I know. Doing a Halloween listener's stories because they're always like the creepiest ones. Oh, absolutely. They always freak me out the most. Oh, that's perfect. So, oh, that's a good, good reminder to listeners. If you have stories of Headless Horsemen from Sleepy Hollow or anything at all that you think would be fun to share, send those stories to stories at sightingspodcast.com. That's right. We won't be able to get them in next week's episode, but we plan on doing lots more of these. So send them our way. We can't wait to do more. Keep enjoying your spooky season, and thanks for hanging out with us for a little bit. That's right. We'll see you next week. Same time, same place, right here on sightings.

Sightings is hosted by McLeod Andrews and Brian Sigley. Produced by Brian Sigley, Chase Kinzer, and McLeod Andrews. Written by Brian Sigley. Story music by Jack Staten. Series music by Mitch Bain. Mixing and mastering by Pat Kicklater of Sundial Media. Artwork by Nuno Sarnatus. For a list of this episode sources, check out our website at sightingspodcast.com.

Sightings is presented by reverb and cue code. If you like the show, be sure to subscribe on your favorite podcast platform, so you're first to hear new episodes. And if you know other supernatural fans, tell them about us. We'd really appreciate it.