88: Halloween Horror Folklore: The Scary Origin of Jack O' Lanterns, The Real Story Behind The Headless Horseman, and All Hallow's Eve Folklore
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Of all 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. Well, 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 that 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 this pleasure?' Jack asked as he approached the devil. He was a smug man. No one 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 of the line 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 to pay the tab. And 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 in his pocket, he couldn't change back into his devilish form. Stingy Jack only agreed to let him free if the devil spared Jack's life for at least 10 years. And the devil agreed. But once the 10 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 one last snack before he took him to the underworld. And once Satan was up in 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, 10 years later, Jack passed away as an old man. Not a single person in the village attended his funeral other than the priest who read him his rites. Remember, he was not very well liked. Jack awoke outside of the pearly gates of heaven awaiting his judgment.

But St. Peter, unsurprisingly, rejected him. And that only meant one thing. Jack's soul was finally the devil's. After years of being humiliated by Jack, the devil 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 hollowed-out turnip and scratched into the outside was the face of the devil.

He placed a candle inside and Jack was forced to 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 these vegetables had the face of the devil, they could be used to keep the devil away. In old Celtic traditions, villagers carved frightened faces into crops like plums,

beets, turnips, and potatoes to ward off lost dead souls and fairies from the underworld to stop them from coming in or trying to take them to the other side. Imagine coming upon someone's garden only to see decaying and twisted faces carved into their entire 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.

Would you believe me if I told you there was a podcast that was haunted? Well, it's called Two Girls, One Ghost. Hosts Corinne and Sabrina didn't want to believe it at first, but seven years later and hundreds of encounters submitted by listeners later, they can no longer ignore it. Two Girls, One Ghost is the most haunted podcast in America. We're talking ghosts, EVPs in episodes,

Spirits making contact with listeners, orbs darting through their YouTube videos, and so much more. Paranormal enthusiasts Sabrina and Corinne explore the deepest, darkest, spookiest places in the world, delivering doses of research, history, and spine-tingling tales.

If possessed kids crawling backwards up walls, campers entranced in fairy orgies, and creatures chasing drivers down back roads is your thing, tune into Two Girls, One Ghost wherever you listen to podcasts. New episodes are released every Thursday and Sunday.

And now you can join Sabrina and Corinne every Tuesday on Patreon and share your own haunting tale live in their campfire stories. Satisfy that spooky itch and entertain your inner witch with two girls, one ghost. But be warned, side effects may include a haunting or two. So listen at your own risk.

This is Heart Starts Pounding. I'm your host, Kaelin Moore. If you're new here, welcome to our playground for the darkly curious. We have episodes every Wednesday night at 7 p.m. PST, and that's midnight on the dot if you're listening from the underworld.

I 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 the 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 it's 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 just wanted to take a sec to say thank you to everyone listening to the ad-supported version of this show. Thanks to your support, we were able to donate the sponsorship dollars from the first few episodes this month towards Hurricane Relief for victims of Helene and Milton.

Specifically, we gave to places that I'm going to link in the description. But if anyone's listened to the Appalachian Horrors episode, you'll know that I have family connections there and I love the folklore and legends from the region so much. So we wanted to just do whatever we could. Thanks to the community that we have at Heart Starts Pounding, we were able to make this donation. So I just wanted to take a sec to say thanks, you guys.

Okay, now I want to get into one of the most famous Halloween legends of all. But in true Heart Starts Pounding fashion, there is a little 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 Sleepy Hollow in New York from Connecticut, and though he hadn't really made any friends yet, he had received a personal invitation from the most beautiful girl in Sleepy Hollow, who also happened to be from the wealthiest family in Sleepy Hollow, to attend her party that night, October 31st, Katrina Van Tassel. A

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, the residents were all 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 ghost 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 the lore of Sleepy Hollow. He didn't really care much for 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 seemed to be talking to another guy.

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 kind of confused, but agreed. And the two danced wildly to a few songs. But this angered Brahm. 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 at that point, claiming that they had seen this 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, but it wasn't.

and every night he woke from it to trot around Sleepy Hollow and find his head. Braum said that one night he saw the horseman himself. He was out riding his horse when all of a sudden he heard the echoey, haunting sound of hooves on cobblestone. That was 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 see who it was, the man turned around. And that's when he realized the rider had no head, just an empty space above his neck. Brom grabbed his reins and galloped away, but the horsemen followed, gaining ground fast. The horsemen had almost overtaken Brom's horse when they got to the church bridge. As they crossed,

Brom turned around and watched as the horsemen disappeared into thin air. "Remember," Brom told the group, "he can't cross the church bridge."

At this point in the story, Ichabod was shaking. He was so freaked out and he really didn't want to hear any more ghost stories that had been quite enough. He looked over to Katrina to see if she maybe wanted to dance again, but she was looking at Brom, completely captivated by his story. So he just decided he should leave.

People were still arriving to the party when 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 he 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 in his direction. "'Hello?' he shouted."

but there was no friendly call in return. So he kicked his horse, begging it to go 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, they were 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 Brahm told him and got a chill. But Brahm was just saying that to impress Katrina, he thought, and he trotted forward. But the mysterious writer behind him was getting closer.

It's probably just Brahm playing a prank on him, trying to scare him away. So Ichabod decided that he should face him. So he turned around, but no one was there. The sound of 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 that's when Ichabod could see that through the mist, there was the outline of the rider still approaching. He thought to himself how bad he was going to pummel Brahm when he saw him, but he watched as the head of a black horse emerged out of the fog. Then, hands on reins. Then, the body of the rider wearing all black. And then, where the man's head should be,

was just a pumpkin with the most depraved and twisted grin carved into it. Ichabod watched as the horse kicked up its front legs into the air and the rider effortlessly held on with one hand, never taking its carved eyes off of him. This was the horseman Brahm had warned him about. The locals were right.

Ichabod kicked his heels into the sides of his horse, and this time it obliged and it took off running. The cemetery whipped by him, the graves were bouncing up and down in his vision as his horse galloped, but he could have almost swore that he saw the earth was turned up near one of the graves.

almost like someone had emerged from their casket. But there was no time to think about that because the rider behind him was getting closer. His neighbor's old horse that he had borrowed was no match for the ghost horse behind him, and he was being overtaken fast.

That's when he had an idea though. The cemetery was attached to the old stone church. And if he could just make it over to the church bridge in front of it, the writer would disappear. So Ichabod pulled the reins tight and his horse followed, bounding over the stone wall and cutting through the graveyard towards the church bridge.

But the rider did the same and he stayed hot on his heels. The church bridge was getting closer and closer and Ichabod was almost there. He dug his heels into the side of the horse even harder, begging him to speed up. The headless horseman was now only a few feet behind him, but Ichabod might still make it. He was about to cross over the stone bridge. Safety was just on the other side. And as his horse took his first step onto the bridge,

He turned around to face the headless horseman, to watch him evaporate like Brahm 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 its 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 Katrina's home for their own, 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 there was 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 really missed him all that much. But one thing did stick out to them. They had never heard a version of the Headless Horseman tale that included a pumpkin. That was really 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. More after short break.

Okay, I have to tell you guys about a new podcast that I've been listening to. It's called Ominous Thrill, and it's a monthly anthology of horror, thrillers, and suspense that I would describe as Black Mirror meets American Horror Story. The episodes are fully sound designed and have actors playing all the parts, so it feels almost like you're watching a movie or a TV show.

Each episode delivers a thrilling new character-driven story that spans genres like psychological horror, thriller, and suspense, creature features, and grounded tales where obsession, love, rage, and revenge class in the murky worlds of the supernatural and paranormal.

I'm a huge fan. I love listening to audio dramas. I really feel like I'm so immersed in the story when I listen to Ominous Thrill, and I really think you guys will like it too. You can listen to Ominous Thrill wherever you get your podcasts.

I love the legend of Sleepy Hollow, but you might be shocked to know that 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, though, he fired a cannonball from atop a hill and he 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 led to the American soldiers winning back control of the war.

He was buried in a grave eight 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 the 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 a lot 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 for you to decide. For our last tale, I'm gonna take you back in time with me, thousands of years to the origins of Halloween.

So Halloween itself has ancient Celtic pagan roots in the festival Samhain. Samhain was celebrated as early as 300 BC and translates to summer's end. It was the 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 other world was intensified.

See, it was believed that the veil between life and death became thinner on that one spooky evening, and spirits, fairies, 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 known as the Crone.

The Crone goes by many names, including the Old Woman, Grandmother, the 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 celebrations of Samhain thought it was important to make sure that she was happy or else she would steal their loved ones as they slept.

But over the years, paganism was replaced by Christianity and Samhain transformed into All Hallows' Day, a day the Catholic Church would never admit being inspired by paganism. They tried their best to separate the images.

But it was inspired by paganism and very much so, especially the night before All Hallows Day, All Hallows Eve, the October 31st celebration of those who were killed for their Christian faith.

If you were to go to an All Hallows' Eve, say a thousand years ago, you would see a celebration very similar to Samhain. A large bonfire would be burning in the clearing of the woods, tended by priests instead of druids.

People would be gathered around the 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. And 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 Kyiv around 945 AD.

Olga's husband was the leader of the region's army called the Rus, and this worried Olga because tensions had been rising in the area between the Rus and another army, the Drevlians. But he insisted that he was okay and he wouldn't let anything bad happen to their family. One night, though, 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 ended up homeless, but not Olga. A fire had been ignited inside of her and she wouldn't rest until she avenged Igor's murder.

So one day, after Ruth's army officials came to Olga's home to inquire if Igor's son was in any position to take over his military position, they were disappointed when they saw that the boy was only three years old. He just 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 they agreed that Olga could take over Igor's position until her son was old enough. But little did they know that Olga's entire military strategy was to kill as many Drevlians soldiers as she possibly could to avenge her husband.

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

Olga was completely disgusted at this proposition. Her husband's body wasn't even buried yet. And here was Mal asking him to marry her for no reason other than to take control of her military. She could have written back and said no in big capital letters. She could have given him a piece of her mind, but she didn't.

Olga was really smart and she was very calculated. She knew that this was her chance. So she wrote back to Mal the following, quote, "'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 Kyiv in their boats and not get out. They should remain there and she would come greet them with her soldiers.

So that day, a bunch of Olga's soldiers greeted the prince's fleet at the docks and brought them through the city. She made sure that they were treated like royalty. People were gathering 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 they were 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 these long and deep trenches dug, almost like moats that weren't full of water. One of the Drevlian generals turned to ask Olga's soldier what they were for. And as he did, the Rue's soldiers pushed the visiting army into the trenches. And the walls were so smooth on the sides,

There was nothing they could cling to 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 the men were buried alive.

After Mal hadn't heard from his men in a while, he sent over another group of soldiers to Kiev to inquire about the marriage. And when they arrived, Olga offered them a bathhouse so they could bathe after their long and grueling journey. And 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. So Mal was waiting at a large table in his castle for his bride and figuring that she would just be a few more minutes, he and his men 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 Drevlian soldiers as she could get her hands on. And her story stayed alive as it was told every All Hallows' Eve by a massive bonfire.

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 also, before we leave, I just wanted to mention two things. The first being I was recently on Neil McRoberts' podcast, Talking Scared. He typically interviews a lot of really good horror authors like Stephen King. But he had me on for his holiday Halloween episode. And we had a great conversation with lots of scary movie and scary book recommendations. So be sure to check that out wherever you get your podcasts.

And also, some of you did reach out after my cursed cemeteries episode saying that the way I clean graves might not be the perfect way to do it, which is actually great for everyone at the cemetery because I've only ever cleaned my ancestors' graves, so it's really just my great-grandfather that's going to come haunt me. If you want to go clean graves this Halloween, there are better, safer ways to do it than the Scrub Daddy version I suggested, all of which can be found online.

online. So take care of this holiday. I'll be spending this Halloween 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 programming here at Heart Starts Pounding, beginning with a look into the dark side of YouTube families.

Heart Starts Pounding is written and produced by me, Kaylin Moore. Heart Starts Pounding is also produced by Matt Brown. Additional research by Marissa Dow. Sound design and mix by Peachtree Sound. Special thanks to Travis Dunlap, Grayson Jernigan, the team at WME, and Ben Jaffe. Have a heart pounding story or a case request? Check out heartstartspounding.com. Until next time, stay curious. Ooh, ooh, ooh, ooh, ooh.