MLP Halloween Special: Attack of the Headless Horseman!

by Smoker

Rating: teen
Tags: Other, Comedy, Rarity, Random, Adventure, Pinkie Pie, Crossover, Human, Applejack, My Little Pony: Friendship is Magic
Length: 2738

On one frightful Nightmare Night, the Headless Horseman shows up to wreak havoc on Ponyville! Oh no!

The Headless Horseman, aka Dullahan, aka that guy with the pumpkins, has come to Ponyville to set things on fire, and generally wreak havoc. Will the ponies be able to stop him? Or will Ponyville be burned to a crisp?

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A little something I whipped up to celebrate Halloween. Btw, happy Halloween, Fimfiction!

Also, the crossover tag isn't just for the classic Headless Horseman story; this incarnation of the Horseman is actually based on a version of him from a certain video game. I don't want to spoiler it - the game will be listed in the A/N at the bottom!

Published 2014-10-21 19:00:03 UTC
Last updated 2014-10-21 19:00:03 UTC

The Spooooooky Chapter

“Ooh, I just LOVE Nightmare Night!” Pinkie Pie squealed. She wore green suit with a tail that flopped behind her as she bounced, and a green-painted paper mache alligator head enveloped her face. Upon her back sat Gummy, who was painted bright pink. His head had darker pink fluff on it, as well as his tail.

One of Gummy’s eyes winked. “Oh, don’t worry, Gummy! That paint will wash off lickety-split at the end of the night!” Pinkie chirped happily.

She turned back to the streets of Ponyville, and gasped. “Applejack! Hi!” she cried, rushing up to her farmer friend.

Applejack turned to Pinkie. This year, she had chosen to dress up as a cow, her coat painted white and black, and a couple of ice cream cones over her ears to represent horns. “Howdy, Pinkie.” She greeted her friend, smiling. “Awful nice night for a party, inn’it.”

“Are you kidding?! It’s a SUPER-nice night for a party! The sky is clear, the moon is full, a flaming pony is flying down and laughing maniacally, the stars are shi-wait, WHAT?!”

The two turned and saw a small, shadowed figure in the distance, which was rapidly growing. It was indeed a flying pony, but he had no wings. That was the least of the oddities about this pony, though.

As it came closer, the pony was revealed to actually be a horse, black as night. Its eyes were a burning green, and its hooves were literally burning green, the sickly lime-colored flames trailing behind the horse as it flew. It wore black armor, and it almost appeared to be grinning.

The most odd thing about it, though, was that there was a human figure riding on the horse’s back. It wore black armor very similar to its horse, and clutched reins in one hand. The most striking feature about the human, though, was that it had no head: where it’s neck should start, there was only a green hole, burning with the same flames that erupted from the horse’s hooves. To top it all off, the human’s free hand held a jack-o-lantern, which grinned diabolically.

Now the entire town was staring at the human as he rode around on his flying horse. And then, the human began to roar a strange, rhyming battle cry:

“Prepare yourselves, the bells have tolled! Shelter your weak, your young and your old! Each of you shall pay the final sum! CRY for mercy, THE RECKONING HAS COME!”

And with that, the human threw his pumpkin head down at the nearby town hall. It exploded on contact with the hall’s roof, causing flames to spew everywhere. Soon, the town hall was burning like it was kindling.

That got ponies screaming.

Even worse, the human materialized more pumpkins from nowhere, throwing them sporadically at random houses all over Ponyville.

“Oh my gosh! Is that – is that the Headless Horseman?!” Pinkie gasped.

“What? You mean that myth from when we were foals?! The one alongside Princess Luna and the Boogeyman?!” Applejack yelped. “And – and he’s real?!”

“Never mind all that!” Pinkie cried, pulling out a pad of paper. “I want his autograph! Yoo-hoo! Mister Horseman!” She called up at the figure which circled around the town.

“There’s no time for autographs, Pinkie! Ponyville is literally on fire!” Applejack cried. “We gotta put these things out!” With that, she put a hoof to her mouth and whistled loudly, drawing the crowd’s attention. ”Everyone listen up!” she yelled. ”We’ve gotta put out these fires! Now, are there any clouds that the pegasi can use-“

“There isn’t so much as a scrap of vapor!” one Pegasus called.

“Yeah! That jerk Rainbow Dash used what little clouds there were to make her costume!” another Pegasus shouted angrily.

“Costume?” Applejack questioned.

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“Beep beep! I’m a cloud!” Rainbow Dash chirped happily. She was completely hidden inside a small cloud, with the exception of her tail, which stuck out behind her. Her eyes peered through the front of the cloud as she happily, obliviously glided along, high in the sky, somewhere far from Ponyville.

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Applejack stuck a hoof to her face. “Twilight, why do you and your rain spells have to be stuck in Canterlot this weekend…” she muttered. Then she began to yell again, stamping a hoof. ”Listen up, y’all! We’re gonna have ta do this the old-fashioned Earth Pony way!”

She gestured to a large, shallow barrel of water, which she had been setting up to use for apple-bobbing. “Take buckets, fill ‘em with this here water, and use it to put out the fire!”

“How?! There aren’t any buckets!” One stallion questioned.

Applejack paused. “I… didn’t really think of that.” She admitted.

“Here we go, Applejack!” Pinkie cried, and to Applejack’s astonishment, the pink pony had a massive pile of metal buckets behind her.

“What – how –“ Applejack stuttered.

“I have secret bucket stashes all around Ponyville, in case of bucket emergencies.” Pinkie said happily. “And this definitely qualifies! EVERYONE GRAB A BUCKET AND POUR!” She cried out the last bit in a shrill, piercing voice.

The town’s populace sprang into action. Ninjas, cowboys, aliens, dragons, goblins, and many other costumed ponies all grabbed buckets, filled them with water, and began to toss the water at the buildings. The earth ponies and unicorns splashed water at the flaming walls of the buildings, while the pegasi flew up high and poured water onto the roofs.

As Applejack picked up a bucket, she bumped heads with another pony. “Applejack!” the other pony cried, and Applejack saw that it was Rarity.

Rarity looked quite fashionable, even in this apocalyptic scenario. She wore a black jumpsuit, studded all over with gleaming diamonds, causing her to look like the night sky, shimmering as she walked. “Quite the Nightmare Night this is turning out to be, eh, darling?” Rarity said with a raised eyebrow.

“Rarity! Thank Celestia!” Applejack grabbed her friend by the shoulders. “Listen, I’ve seen you make dresses; you can lift a bunch of needles and fabrics and junk with ease. Can you do that with the buckets; use a bunch of them at once?”

Rarity scoffed. “It’ll be easy as making my morning tea.” She bragged, her horn glowing. Over a dozen buckets raised from the pile, encased in Rarity’s light blue magic. She began to dip them into the water bucket, and soon had a chain going, rapidly filling and pouring, filling and pouring.

“The sky is dark, the fire burns! You strive in vain, as fate’s wheel turns!” the Horseman yelled, cackling as he threw another pumpkin.

“Ah, shaddup!” Applejack yelled back at him, tossing water and putting out a patch of fire before galloping back for a refill.

Despite the Horseman’s taunting, though, the ponies were actually doing well. Many unicorns had taken to copying Rarity’s strategy, levitating a half-dozen buckets at a time, and the pegasi were taking up to three buckets at a time; one in each hoof, and one in their mouth.

After ten minutes, the ponies were moving like well-oiled machines. The Headless Horseman desperately tossed pumpkins left and right, but the ponies put out the fires almost as soon as they appeared.

Finally, Applejack tossed one last bucketful of water onto a nearby house. “Beat that, ya big rat!” Applejack cried at the Horseman.

The Horseman yelled once again, only this time he wasn’t mocking or joking; this time, he sounded genuinely angry. “My flames have died – left not a spark! I shall send you MYSELF, to the lifeless dark!”

“Oh, pickleberries.” Pinkie Pie mumbled as the Horseman swooped to the ground. Two spectral green blades appeared in his hands, and he began to ride through the streets, cackling as he slashed his swords at ponies, causing them to flee in terror.

“Everyone gang up on him!” Applejack cried. The horseman had been expecting something like that, though: raising one of his swords, he yelled another rhyme. “Soldiers, arise! Stand and fight! Bring victory at last to this fallen knight!”

As he chanted, pumpkins, similar to the ones he had been throwing, sprouted from the ground. They wore evil grins, and giggled. They rose from the ground on green tendrils, and began to whip their vines at the nearest ponies.

“Dangit!” Applejack cried. “Focus on the pumpkins, everypony! Rarity, Pinkie! Let’s beat this guy into next Nightmare Night!”

“Of course!” Rarity said, brow furrowing.

“Whee! Let’s go!” Pinkie cheered, bouncing along. “Hey! Mr Horseman! Over here!” she screamed in a shrill voice. The horseman wheeled his horse around, galloping at Pinkie Pie.

As he approached, Pinkie reached out and borrowed a staff and white beard from a colt who had been dressed as a wizard. “Can I borrow these for a sec? Thanks.” She said happily, before putting on the beard. As the horseman neared, she held out her staff.

“YOUUU… SHALL NOT…. PAAAASSSSS!!” She cried, and just as the horseman reached her, she swung her staff at the horse’s knees.

The monstrous creature of nightmares abruptly tripped over the staff, causing the horse to slam into the ground, and the rider to fall off.

“Nice work, Pinkie!” Applejack called to her friend. “Now let’s finish this guy!”

“Thanks!” Pinkie said to the colt, handing him back his beard and staff. Then she bounced toward the horseman.

As Applejack, Rarity and Pinkie closed in, the horseman cackled, and melted into shadows. “Where could I be – where do I hide?” He taunted. “Find me before my blade finds your side!”

“Crud.” Applejack muttered. “Split up! He can’t be far!” She called to her friends.

Rarity rushed to the shadowy alleyways, lighting her horn up to check in the darkened corners.

“Ya-ta-da-la-da, ya-tata-ta-la-da! This is the song when looking for the horseman!” Pinkie said, singing a small tune as she looked under rocks and pressed her face to windows.

Applejack’s keen eyes whisked around, looking for the horseman’s figure. Then, something: a flicker on the rooftop. Before Applejack could register the sight, a blur leapt from the rooftop, and landed in front of her: the Horseman, blades gleaming.

“It is over, your search is done! Let fate choose now, the righteous one!” He sang, even as he swung his blades viciously at Applejack.

“Whoa nelly! Girls! I could use some help here!” Applejack cried, leaping over a low swing of the sword.

Thinking quickly, Rarity tore down a big banner reading “Happy Nightmare Night” and tossed it at the Horseman. The knight was momentarily disoriented as the cloth went over his eyes, and he removed it, just in time to see Applejack’s hind hoof flying towards his face.

In a surprisingly adept maneuver, though, the Horseman raised his swords, quick as lightning, and caught Applejack’s hind leg between the flats of his blades, not an inch from his face. As though he’d practiced it before, the Horseman spun around, twirling his blades, before slamming them to the ground. Applejack cried out as she felt something snap in her hind leg.

As Applejack curled up on the ground, clutching her leg, the horseman gloated. “Your body lies beaten, battered and broken! Let my curse be your own, fate has spok-“

He was cut off when Pinkie leapt onto his back. She smashed her hooves onto the back of his armor. “You big meanie-pants! Leave us alone!” she cried, banging her hooves like a drummer.

“Off of me, you worthless cur!” The Horseman roared, reaching behind him and grabbing Pinkie. “You filthy, mangy, waste of fur!” he roared at her. Pinkie could see clear down his neck-hole, into the unnatural, green light in his chest. “I’ll cut your head off so you’ll look like me!” The Horseman continued, holding his blade to Pinkie’s neck. “I’ll make it slow – just wait and see!” He said cruelly.

“Yoo-hoo! Darling!”

The Horseman turned around, to see Rarity levitating a sofa with her magic.

“Be a gentlecolt and hold this for me, will you?” She said cheerfully, before flinging the sofa at the Horseman. The human was knocked over with an anguished cry.

“Thank heavens for Quills and Sofas.” Rarity commented as she rushed with Pinkie. The Horseman, trapped under the couch, cackled.

“So eager you are for my blood to spill!” He chuckled. “But to vanquish me, t’is my head you must kill!”

This gave the ponies pause. “Kill?” Rarity said quietly.

Abruptly, a pumpkin rolled out of the Horseman’s neck-hole like a bowling ball, coming to a stop in front of Rarity. It glared at her and stated, “Go ahead, scum – finish me off! Kill me so that you may laugh and scoff!”

“Now hold on a minute, pardner!” Applejack said, crawling over. She was surprisingly resistant to the pain in her hind leg as she said, “I don’t know where you come from, but here in Equestria, we don’t kill ponies – or people. We reason with them.”

“You speak nonsense, don’t waste your breath.” The Horseman’s head sighed. “Just finish me and grant me an honorable death.”

“No, darling, there must be another way.” Rarity said. “How about you just leave and never come back – that will work for both of us!”

The Horseman’s head groaned. “Look, did I mention there’s candy inside of me.” He said, abandoning his rhymes for the first time.

“CANDY?!” Pinkie cried, and before anyone could stop her, she had smashed the pumpkin open and begun to root through the head’s contents.

“Pinkie! What have you done?!” Rarity shrieked.

“I’ve gotten myself some yummerlicious candy, that’s what I’ve done!” Pinkie said, holding up a cookie shaped like a jack-o-lantern. She bit into it, savoring the taste. Then she saw the others staring at her. “What?” She questioned.

“Um… you… ya kinda…” Applejack stuttered.

“By the way, does it feel a little drafty all of a sudden?” Said Pinkie – or rather, the pony skeleton where there used to be Pinkie. The animated skeleton then looked down at herself. “Eeek!” she cried.

“Pinkie, calm down!” Rarity said, her own voice on the verge of panic. “I’m sure there’s some way to-“

“I’m a skeleton! This is AWESOME!” Pinkie cried, dancing around. “Hang on, hang on, I have jokes for just such an occasion!” She pulled out a list from somewhere or another, and began reading.

“I won’t have a dance for this Halloween. Why? Because I have no-body to dance with!

“Why do dogs like chasing me? Because they’re after my bones!

“Y’know, these jokes are good – they really tickle my funny bone!”

Rarity and Applejack groaned. “Say, Applejack,” Rarity said, desperately trying to ignore Pinkie’s terrible jokes. “You seem awfully okay for someone who had their leg broken.”

“Ah, it was just sore.” Applejack said, standing up. “Ah’ve had a kink in Bucky Mcgillicuddy for a while now, y’see, and that twist was just what he needed!”

Rarity rolled her eyes as Applejack flexed her leg. She turned back to Pinkie to see that the pony was back to normal – costume and all. “Oh, good. It’s not permanent.” Rarity commented, wiping sweat off of her forehead.

“It’s not?” Pinkie asked, looking up. Glimpsing her hoof, she frowned. “Aww man! Now I don’t have an excuse to tell more skeleton jokes!”

“Thank Celestia.” Applejack and Rarity commented. Then Applejack noticed something. “Hey – looks like the Horseman’s pumpkin minions have gone right ta sleep.”

Indeed, the minions were lying on the ground, and their jack-o-lantern heads were rolling around aimlessly. Pinkie walked over to one, then picked it up, a mischevious grin coming onto her face.

“Hey Rarity – think fast!” Pinkie cried, chucking the heavy pumpkin at Rarity. The unicorn cried out as the pumpkin squashed onto her head, resulting in her having an organic pumpkin mask.

Pinkie giggled as Rarity glared at her through the eyeholes of the mask. “Are you feeling vine, Rarity? orange you feeling cheerful?”

“That’s it! I’m done! We’re done here!” Rarity said, throwing her hooves up. “Goodnight, everypony!”

Author's Note

Apologies; this chapter scared me so much that I forgot how to make a proper ending.

By the way, in case you couldn't tell, the horseman in this fic was inspired by the headless horseman in the game "World of Warcraft". Seriously, over half of his lines are taken word for word from him.

And again, happy halloween, ~~everybody~~ everypony!