Halloween Horror Folklore: The Scary Origin of Jack O' Lanterns, The Real Story Behind The Headless Horseman, and All Hallow's Eve

Written By Kaelyn Moore

Let's look into the legends, folklore, and history of the Halloween holiday. What does the devil have to do with jack o' lanterns? Who is the real headless horseman and where is he buried? And what stories were told around a fire at an All Hallow's Eve celebration thousands of years ago?

Subscribe on Patreon for bonus content and to become a member of our Rogue Detecting Society. Patrons have access to ad-free listening and bonus content. And members of our High Council on Patreon have access to our after-show called Footnotes.

Apple subscriptions are now live! Get access to ad-free episodes and bonus episodes when you subscribe on Apple Podcasts.

Follow on Tik Tok and Instagram for a daily dose of horror.

SOURCES

  1. https://secularhumanism.org/2021/02/the-occult-feats-of-mystics-and-saints/

TRANSCRIPT

Of all of the halloween traditions, Jack O’ Lanterns might be the most synonymous with the holiday. Every year, millions of families scoop out the goopy innards of Pumpkins and carve creepy little faces into them that glow in the candlelight.


But what most people don’t know, is the folklore behind why we carve Jack O’ Lanterns. What if I told you that those little porch decorations have demonic origins?


This is the legend of Stingy Jack


In a small village in Ireland hundreds of years ago, lived a devious man named Stingy Jack. Jack was known to be the most manipulative, conniving, and thoughtless man in all of Ireland. He was the type of guy who never offered anyone help. He cheated at every card game, and he was willing to do whatever it took to scheme the other villagers out of their money. His reputation was so big that it’s said to have reached the ends of the earth, and even well beyond that. 


See, one day the devil learned of Stingy Jack. He thought jack was the most vile man he had ever heard of, and for that reason, he had to have his soul.


So one halloween night, as the owls sat on tree branches, and a breeze kicked up dried leaves, Jack stumbled home from a pub. That night, the veil between the living and the dead thinned and the devil was able to slip through into our world. He waited for Jack in the crisp autumn air by a water well.  


To what do I owe the pleasure? Jack asked as he approached the devil. He was a smug man, no one else would ever dare joke at a time like this. The devil was almost offended, but he appreciated the lack of humility. It made him want Jack’s soul even more, and he made his intentions known to the drunk man.


Jack knew that this was the end for him, so he asked the devil for one last wish. Could they go back to the pub and have one final drink together. Then Jack would follow the devil down to hell. 


The devil obliged, but at the end of the night, Jack said he didn’t have any money left to pay the tab. Being the manipulative man that he was, he got the devil to turn into a coin, and when he did, Jack grabbed him quickly and threw him in his pocket. 


See, Jack was not a god fearing man, but in his pocket he carried a cross, and as the devil sat there next to it, he couldn't change back. Stingy Jack only agreed to let him free if the devil spared Jack’s life for at least ten years. The devil agreed.

But Once the ten years were up, the devil came straight back, eager to collect Jack’s soul. But Jack had other plans. He begged the devil to climb up an apple tree in his yard to get him a snack before he took him to the underworld. And once Satan was up the tree Jack carved a big cross into the trunk, trapping Satan up in the gnarled branches. Only when Satan agreed to the terms of Jack’s deal, which was to stop trying to drag Jack’s soul to hell forever, did Jack remove the cross. 


Finally, years later, Jack passed away as an old man. Not a single person in the village attended his funeral other than a priest who read him his rites. 


Jack awoke outside of the pearly gates of heaven, awaiting his judgment, but St. Peter unsurprisingly rejected him. That only meant one thing, Jack’s soul was finally Satan’s.


After years of being humiliated by Jack, Satan had finally won. And to celebrate, he came up with the most heartless punishment he could imagine. With a sick smile on his face, He handed Jack a hallowed out turnip and scratched into the outside was the face of the devil. He placed a candle inside, and Jack would spend eternity walking the black, empty, depths of purgatory with just his devil’s lantern. This earned him the name Jack of The Lantern, or Jack O’Lantern


For centuries, faces have been carved into autumn vegetables in remembrance of Jack’s story. Some cultures believed even though they had the face of the devil, they could be used to keep the devil away.


In old Celtic traditions, villagers carved frightening faces into crops like beets, turnips, and potatoes to ward off lost dead souls and faeries from the underworld to stop them from coming in or trying to take them to the other side. 


Imagine coming upon someones garden, only to see decaying and twisted faces carved into their whole harvest.


It’s a horrifying sight, but it’s not the only piece of dark history of halloween we’re going to learn about today.more after a short break


This is heart starts pounding, I’m your host Kaelyn Moore. 


If you’re new here, welcome to our playground for the darkly curious. We have episodes every Wednesday night at 7pm PST, that’s midnight on the dot if you’re listening from the underworld.


I’ve spent a lot of time this month looking up creepy stories for you all, from houses haunted by ghosts to houses haunted by bad people, to creepy basement stories and cursed cemeteries, all in the name of Halloween season. But I wanted to take some time THIS episode, and actually share some spooky stories about Halloween itself.


The history of the holiday is long and rich. It blends Pagan rituals from Ireland with Christian mythology. Some say it’s the day where the veil is the thinnest, and our world can interact with the next. Ghosts and demons can slip through.


And that’s exactly what we’re going to explore today. 


But before we do I want to take a second and say thank you to everyone listening to the ad supported version of the show. Thanks to your support, we’ve been able to donate the sponsorship dollars from the first few episodes this month toward hurricane relief for victims of Helene and Milton.


Specifically we gave to [insert] for the Appalachian region. If you’ve listened to the Appalachian Horrors episode, you’ll know of my family’s connection there, and I love the folklore and legends from the region so much we’re doing another appalachian horror episode for this months bonus episode.


We at heart starts pounding wanted to make sure we helped out in any way we could, and just know that by listening to the ads on our show, you helped make a real world different. So thank you.


Ok, now, I want to get into one of the most famous halloween legends of all. But, in true heart starts pounding fashion, there’s a bit of truth behind this legend, and we’re going to talk about that as well. This is the legend of sleepy hollow


Ichabod Crane approached the iron gates of a beautiful federal style mansion nestled in the woods. Lanterns flickered outside illuminating guests while they hitched their horses to posts and entered, and beautiful string quartet music drifted out of the palladian windows. 


Ichabod had been excitedly awaiting this party all day. He had just come to the town of Sleepy Hollow in new york from connecticut, and though he hadn’t really made many friends yet in town, he had received a personal invitation from the most beautiful girl in town who also happened to be from the wealthiest family in town to attend her party that night, October 31st. Katrina Van Tassel


A chilly breeze rustled through the orange and red leaves as he hitched the horse he borrowed to a post, and he entered the party.


One thing to know about Ichabod, he was not really loved by everyone in Sleepy Hollow. See, all the residents of sleepy hollow were really similar, they had all grown up in the quiet and dreamy town, and they heard the legends and stories.  And as a result, they were all very superstitious. They knew about the ghosts that stalked through the cemeteries. They knew which part of the woods to not go into at night, and they loved sharing these ghost stories with one another.


Ichabod, on the other hand, was unfamiliar with all of the lore of the town, and didn’t care much about it. He seemed most interested in marrying into the wealthy Van Tassel family at any cost. 


So as Ichabod entered the party, everyone kind of looked at him and rolled their eyes. But he didn’t care because he was laser focused on Katrina, who was standing by the fireplace looking like an angel. She was with a small group but was talking to….another guy. Brom Bones.


The handsome, universally beloved Brom Bones. He was the complete opposite of the arrogant and self-obsessed Ichabod, and for that reason, he was a total threat. Ichabod stormed straight up to Katrina and interrupted their conversation by asking her to dance. She seemed confused but agreed, and the two danced wildly to a few songs.


This angered Brom, and when Ichabod and Katrina came back to the group, he propositioned the newcomer. “Hey Ichabod, do you want to hear a ghost story?”


Ichabod….did not. Ghost stories really terrified him. But it was too late. Brom had already started. 


“Have you heard about the headless horseman who haunts Sleepy Hollow?” He asked him. Ichabod was trying to look tough, but he was already starting to feel nauseous.  


Everyone chimed in, claiming that they’d seen the headless horseman at some point. Legend said that he was the ghost of a Revolutionary War soldier who lost his head in battle from a cannonball. It was believed his grave was in the churchyard cemetery, and every night he woke from it to trot around Sleepy Hollow looking for his head. 


Brom said that one night he saw the horseman himself. 


He was out riding his horse, when all of a sudden, he heard echoey, haunting sound of hooves on cobblestone, the first sign the horseman was near. Then he saw a man in all black in the distance riding his horse. But when Brom called out to him to see who it was, the man turned around. That’s when he realized the rider had no head, just an empty space above his neck.


Brom grabbed his reigns, and galloped away but the horseman followed, gaining ground fast. The horseman had almost overtaken Brom’s horse when they got to the Church bridge. As they crossed, Brom turned around and watched as the horseman disappeared into thin air . Remember, Brom told the group, he can’t cross the church bridge. 



At this point, Ichabod is almost shaking, he’s so freaked out, and he really didn’t want to hear anymore ghost stories, that had been quite enough. 

He looked over to Katrina to see if she wanted to dance again, but she was looking at Brom, completely captivated by his story. So he decided that he should just leave.


People were still arriving to the party as Ichabod bolted out of the front door back down the steps. The chill of the air had turned icy cold and now, it was so dark that the woods in front of him looked like an endless abyss. 


He grabbed his horse and set off thinking to himself how silly this town was. He missed connecticut, the people of Sleepy Hollow were too simple for his liking. They talked about such banal things at parties like ghosts, who talks about ghosts at a party when you could talk about much more interesting things like money.


Eventually, he got far enough away from the party where all he could hear was the sound of the breeze and the labored breathing of the old horse


But then he heard something in the distance

It was so dark, far too dark to see, but someone else must have left the party, because behind him, he could hear hooves coming towards him.


Hello? He shouted, but there was no friendly call in return. 


He kicked the horse, begging it to go just a tad faster, but the old thing couldn’t go very fast. In fact, it seemed like it was slowing down. 


Again, he heard the hooves in the distance behind him, this time, getting closer. Up ahead was the safety of a few homes with flickering lanterns out front, but to his left coming up, he could just barely make out the iron gate of the old cemetery. The one where all the revolutionary war soldiers were buried. 


He remembered the story Brom told him and got a chill. But Brom was just saying that to impress Katrina, he thought, and trotted forward. (SFX echoey Neigh), but the mysterious rider behind him was getting closer. 


It’s probably just Brom playing a prank on him, trying to scare him away. So Ichabod decided he was going to face him

But when he turned around, no one was there. The sound of the hooves in the distance had disappeared, and he was left looking out into the darkness. The cemetery on one side of him, and the woods on the other. 

A thick fog started collecting near the cemetery, and Ichabod could see through the mist, the outline of the rider. Still approaching. He thought about how bad he was going to pummel Brom when he saw him.


But he watched as the head of a black horse emerged out of the fog, (SFX- hooves) then hands on reigns, then the body of the rider wearing all black, and then…. Where the man’s head should be was a pumpkin, with the most depraved and twisted grin carved into it. 


Ichabod watched as the horse kicked its front legs in the air and the rider effortlessly held on with one hand, never taking its carved eyes off of him. This was the horseman Brom had warned him about, the locals were right. 


Ichabod kicked his heels into the side of the horse, and this time, it obliged and took off running. The cemetery whipped by him, the graves bounced up and down in his vision as the horse galloped, but he could have almost swore he saw the earth turned up near one of them, like someone had emerged from their casket.


But no time to think about that, the rider behind him was getting closer. His neighbor’s old horse was no match for the ghost horse behind him, and he was being overtaken, fast. 


That’s when he had an idea. The cemetery was attached to the old stone church. If he could just make it over to the church bridge in front of it, the rider would disappear. Ichabod pulled the reigns tight and the horse followed, bounding over the stone wall and cutting through the graveyard towards the church bridge. But the rider did the same, and stayed hot on his heels.


The church bridge was getting closer and closer, Ichabod was almost there. He dug his heels in the side of the horse even harder, begging him to speed up. The headless horseman was now only a few feet behind, but Ichabod might still make it. 


He was about to cross over the stone bridge, safety was on the other side. As his horse took his first step onto the bridge, he turned around to face the headless horseman, to watch him evaporate like Brom said he would, but that’s not what he saw. Instead, he saw a large orange object hurtling towards him, and the black horse behind him up on his hind legs again. The last thing Ichabod remembered, was the pumpkin head of the rider making contact with his skull.


The next morning, as party guests were leaving the Van Tess’s for their homes, a few of them came upon the grisly sight at the church bridge.


They saw Ichabod’s hat lying on the stone bridge, and the pulpy, gory mess of a smashed pumpkin beside it. But no sign of Ichabod anywhere. 


No one ever knew what became of Ichabod, he was never seen again. The townspeople all whispered about what could have happened, but in all reality, none of them missed him all that much. But One thing stuck out to them. They had never heard a version of the headless horseman tale that included a pumpkin. That was strange. They didn’t have much time to think about it, though, because soon Brom and Katrina were married, and it was the biggest to do in all of Sleepy Hollow.


It wasn’t until years later that Sleepy Hollow started sharing their new legend. One about the outsider who couldn’t outrun the Headless Horseman on Halloween night. 

I love the legend of Sleepy Hollow, but you might be shocked to know it’s not just a legend, there are parts of that story that were inspired by true events.


There really was a revolutionary war soldier who was decapitated by a cannonball in the real town of Sleepy Hollow the night before halloween in 1776. Lieutenant Ephraim Fenno was an american soldier who arrived in the area to save the American Troops. The first day he was there, he fired a cannon from atop a hill and blew off the head of a German man who was fighting for the british, killing his horse in the process. The horrific scene shocked the British, and ultimately lead to the American soldiers winning back control of the war. 


He was buried in a grave 8 miles outside of Sleepy Hollow, but locals swore they would see his headless body rise from the grave each night and search the earth for his head. 


The legend of Sleepy Hollow is probably a blend of this tale, and the legend of Dullahan, a Celtic legend of a headless soldier who carries his rotting head in his hands as he scours the earth for victims to bring back to hell with him. His head is said to have the most twisted and devilish expression as it decomposes in his arms.


Sometimes, he can be seen holding a human spine in his other hand, and he’ll whip anyone who looks at him in the eyes, permanently blinding them. 


The only word he ever speaks is the name of the next soul he plans to take, and the only way he can be stopped is by throwing gold in his path. 


But the legend leaves it up for interpretation, was it really the devilish headless horseman that took Ichabod to hell with him, or did Brom scare him off in an attempt to win over Katrina? I guess that’s up to you to decide. 


For our last tale, I’m going to take you back in time with me, thousands of years, to the origins of Halloween


Halloween itself has ancient Celtic Pagan roots in the festival Samhain (sow-when). Samhain was celebrated as early as 300 BC and translates as Summer’s End. It was a festival of fire, used to usher in the dark half of the year,


Samhain was the most important moment of the Celtic year where connection to the Otherworld was intensified.


See, it was believed that the veil between life and death became thinner on that spooky evening, and spirits, faeries, and other creatures of folklore would come roam the earth. Locals would dance around massive bonfires set by Druid priests, and toss crops in as sacrifices to the gods for protection. 


One of these gods, was The Crone.

The crone goes by many names including, The Old Woman, Grandmother, Wise One, Divine Old Woman. Some call her the Old Wife of Thunder because of her violent and turbulent nature. She was said to use her wand of power to strike the earth and create frost and death wherever it landed.


The crone is a gatekeeper between life and death. She decides who stays and who goes, so celebrators of Samhain thought it was important to make sure she was happy, or else she’d steal their loved ones as they slept. 


But over the years, paganism was replaced by christianity, and Samhain transformed into All Hallow’s day, a day the Catholic Church would never admit to being inspired by paganism, the tried their best to separate their images.


But it was, and very much so, especially the night before All Hallow’s day, All Hallow’s eve, the October 31st celebration of those who were killed for their christian faith. 


If you were to go to an all hallow’s eve, you’d see a celebration very similar to Samhain. A large bon fire would be burning in the clearing of the woods, tended by priests instead of druids. 


People would be gathered around this fire, not dancing as wildly, remember these were roman catholics, but they, too, would be sharing stories about gods and demons. About people who stood in their faith in the name of God and witnessed miracles. One of these stories, was the tale of Olga Of Kiev.

Olga was a young woman living with her husband, Igor,  and three year old son in the far eastern european territory of Kiev around 945 AD. Olga’s husband was the leader of the regions army, called the Rus. And this worried Olga. Tensions had been rising in the area between the Rus and another army, the Drevlians. But he insisted that he was ok, he wouldn’t let anything bad happen to their family.


But one night, her worst fears came true. Just after midnight, a couple of Drevlian soldiers broke into their home and killed Igor in front of her. 


Now, women at this time had few options, and many women would have been left destitute without the help of their husbands, some would have wound up homeless. 


Not Olga. A fire had been ignited inside of her, and she wouldn’t rest until she avenged Igor’s murder. 

One day, other Rus army officials came to Olgas home to inquire if Igor’s son was in any position to take over his military position, and they were disappointed when they saw that the boy was only three years old. He wasn’t ready yet, but Olga insisted that she could take over until her son turned 18. She knew military strategy, she had learned everything from Igor, they spoke about his job every single night. 


The military officials, looked at each other hesitantly, but agreed that Olga could take over Igor’s position. 


Little did they know that Olga’s entire strategy was to kill as many Drevlian soldiers as she possibly could. 


The night before her first strike on the opposing army, however, she received a letter. It was from the Prince of the Drevelins, a scrawny and evil man named Mal. He was proposing marriage to Olga, as a way to bring the two armies together.


Olga was disgusted at this proposition. Her husband’s body wasn’t even buried yet, and here Mal was, asking him to marry her? For no reason other than to take control of her military. 


She could have written back NO in big capital letters, she could have given him a piece of her mind, but she didn’t. Olga was smart, and she was calculated, and she knew that this was her chance.


So she wrote back to Mal the following “Your proposal is pleasing to me, indeed, my husband cannot rise again from the dead. But I desire to honor you tomorrow in the presence of my people.” She specifically instructed Mal to send over members of his army to discuss the marriage. They should arrive in Kieve in their boats and to not get out. Remain there and she would come greet them. 


That day, she had her soldiers greet the prince’s fleet at the docks and bring them through the city. She made sure that they were treated like Royalty, people gathered in the town square just to catch a glimpse of the visiting army.


“Now we’ll take you to the royal court, where you shall meet your future princess” one of Olga’s soldiers remarked. The army men gave wicked smiles, like he was about to go claim what was rightfully theirs. It was disgusting. 


The soldiers brought Mal’s men over to the royal court, where outside, there were long and deep trenches dug, almost like a moat that wasn’t full of water.


One of the generals turned to ask the soldier what they were for, and as he did, the Rus soldiers pushed the visiting army into the trenches, the walls were so smooth, there was nothing they could cling to crawl their way out.


The last thing the soldiers saw as they looked up, was the stone cold face of Olga staring down at them, before chunks of cold dirt hit their faces. Olga listened to the screams with glee as all of the men were buried alive. 

After the Mal hadn’t heard from his men in a while, he sent another group of soldiers over to Kiev to inquire about the marriage.

When they arrived, Olga offered them a bathhouse, so they could bathe after their long and grueling journey. Once the soldiers were inside, she locked the doors and set the bathhouse on fire. 

Finally, Olga sent word to the rest of the Drevlian soldiers to prepare a big feast. She said that talks about the union had gone splendidly, and she would be arriving at their capital for the wedding. 

The day of the event, however Olga was nowhere to be found. Mal waited at a large table in his castle awaiting his bride. 

Figuring she’d just be a few more minutes, they drank beer and started eating. By the time Olga and her men showed up, they were completely drunk. Mal stood to greet his future wife, and Olga plunged her sword into him, avenging her husband Igor.  The other soldiers were slow to respond and they were slaughtered in their seats at the table. 

Olga went on to be deemed a saint within the catholic Church after she converted later in life. She spent the rest of her days dedicated to killing as many Drevlin soldiers as she could get her hands on, and her story stayed alive as it was told every All Hallow’s eve by the massive bon fire. 

So, this halloween, as you carve your Jack O’Lanterns and tell ghost stories, remember some of the roots and legends of the holiday. Think of Olga and her bloody quest, remember the soldier who lost his head on halloween, and think of naughty jack as you carve your pumpkins.

And take care this holiday, I’ll be spending it watching scary movies and trying to get my dog to wear the alligator costume I bought him, which I’m sure is going to be a losing battle. And I’ll catch you next week as we start the rest of our fall programing here at heart starts pounding beginning with a look at the dark side of youtube families.

Kaelyn Moore
Previous

The Disturbing World Of Youtube Family Channels
Next

America’s Most Cursed Family: The Dark History Of The Lemp Mansion