Stories, they make up a lot of plenty of small town's myths and folklore. But most of the time, that's all they are really. Just stories. But there is one exception to the rule. The Legend of Sleepy Hollow and the Headless Horse. You know the one, the tale of a horse who roams the moors every Nightmare Night looking for his lost head. And if he doesn't find it, he'll take yours just to substitute. He's not picky. But like I said before, most don't believe in him and think he's just a tale to scare foals into doing what they're told.

"Eat your dinner or the Headless Horse will take your head!" They say. But tonight, on that very special night known as Nightmare Night when myths and horrific gothic legends are celebrated the Headless Horse will come alive once more. And this time around, a certain group of ponies will be caught in the thick of it...

The train whistle of the Friendship Express cut through the evening sky like a banshee's wail as the train trundled down the tracks with it's passengers sitting comfortably inside the cars.

"Well, I must admit when your Aunt Cherry, the mayor of Sleepy Hollow asked you to come to her town just to join in the fun and you asked me to come along I was... skeptical to say the least. Let's face it, Nightmare Night is about getting scared and after the things I've seen kids in costumes and a few bad props won't work on me." The Doctor said as he sat in a chair with Twilight and Shining across from him. Cadence sat next to the Doctor, across from Shining. For Cadence, it had only been three days and three nights since the Windego Invasion, though thanks to time travel for everypony else it had been a bit longer.

"So, what changed your mind?" Cadence asked curiously.

"...The candy." The Doctor admitted with a flush. "Hey, where's Rainbow?"

"I don't know... Last I checked she'd gone to the bathroom." Shining remembered.

"Got to be one long line then." The Doctor joked and Cadence and Twilight stared at him in disgust. It was then Rainbow returned carrying a bunch of candy.

"Eh, dare I ask?" Twilight said, not really wanting to know.

"There was this trolley mare going around offering free candy. So I took some." Rainbow replied, looking rather unashamed of herself.

Cadence raised a eyebrow.

"Some? You look like you took the whole trolley supply." She said, and Rainbow flushed red knowing she'd been caught as she sat down with Twilight moving over to make room for her. The candy went on the table separating the two seats.

"Rainbow, you do realize there will be plenty of candy when we get to Sleepy Hollow right?" Twilight deadpanned.

"Hey, it was free candy! So sue me." Rainbow retorted. Twilight sighed while Shining muttered "Just one more hour of this... Just one more hour and I'll be free."

Sleepy Hollow, around the exact same time...

Meanwhile, in Sleepy Hollow some final preparations for what the town considered the biggest night of the year were well underway. Tents had been set up a few days before for a festival celebrating the legend that put the town on the map. In one particular tent, a blue unicorn with a very light blue, almost white mane got ready for her contribution that was part of a play on the Headless Horse.

"Oi! Hurry up in there you dratted mare! The last of the rehearsals is about to go on! And we need you!" A male stallion's voice called into the tent. Another voice, angry as well called back at it.

"Don't get your fur in a twist! The Great and Powerful Trixie must not be rushed!" The titular mare yelled before stepping out of the tent in a starry cape and witch's hat.

"There, you see? If you let me, I can come out looking quite sexy. Don't you think?" Trixie asked seductively as she glanced at the stallion who's fur was stone grey. The stallion had a grape colored mane as well. His name was Written Script, and he wasn't pleased with Trixie's arrogance in the slightest.

"Be lucky you're the only mare with a talent for special effects we could find, otherwise if I had my way I would have replaced you long ago in this whole... fiasco!" Script snapped and Trixie huffed as she walked right by him.

"You just don't understand Trixie's art form." She said.

Written muttered "Oh, I'll give her art form all right..." under his breath.

Soon, they were at the stage, and by now the moon had fully risen casting it's moonlight on the town square where the stage itself had been constructed. The wind from a nearby storm that was coming in blew through tree branches, and they swung and swayed from the gusts. The whole thing added all up to a rather eerie effect.

"Well, I'd say we are ready." Written said as he looked around the area. "Yeesh though, if I were more superstitious I'd say in weather like this it would be a bad night to put on a play. But as they say, the show must go on!"

Suddenly, everypony who was there heard the loud rumble of thunder and lightning flashed. And in that brief moment, on the stage a dark figure, one who looked to be missing a head was visible. But it was soon gone. Script turned to Trixie.

"Please tell me that was one of yours..." He hissed.

"No, though Trixie must give props to whoever did it." Trixie said in confusion.

"...Gotta be somepony playing a prank. It's just got to be... It can't really be him." Script whispered in denial. But inwardly, he didn't believe his own words and was mentally thinking about going home and grabbing his black cat for a good luck charm. Script took a few quick calming breaths, before regaining his composure.

"Alright ponies, just forget about what we saw and think nothing of it! Somepony is just pulling our legs!" Script ordered. "Now, let's take this thing from the top!"

As the first few lines were recited, Trixie frowned. She knew exactly what she saw, and she knew it looked far too real and had too much mass for it to be more then just a prank by somepony skilled in special effects and illusions. Plus, that would require somepony to be as skilled as her and nopony was. Suddenly her thoughts were interrupted by Written Script's voice.

"Alright Trixie, are you ready?"

"Y-Yes." Trixie stammered. "Trixie was born ready!"

An hour later...

About a hour later, the Friendship Express was pulling into Sleepy Hollow Station and already the passengers were beginning to disembark. The autumn air was cold and crisp, even as more thunder rumbled in the distance. All around the station, jack-o-lanterns had been set up, their interiors lit up by candlelight.

"Ooh! I'm in the spirit of Nightmare Night already, aren't you Shiny?" Cadence said in glee as she nuzzled up against Shining, making him blush and stutter out "Y-Yeah. I'm with you there, huh?"

The Doctor rolled his eyes in mock disgust and said "Ponies..." although it was clear by his tone he didn't mean it in any insulting way.

"Oh yeah, this is going to so awesome!" Rainbow Dash whooped. "If only I'd brought a costume then I'd be all set!"

"Maybe there's a costume shop in town for those who need one at the last minute." Twilight suggested with a smile. "Oh, I can't wait to see what my Aunt Cherry Berry's got planned for this year! I wanted to go last year, but I was so absorbed in my books it... It may have slipped my mind." Twilight admitted with a blush.

"Well, I intend to play pranks! This is THE night of the year for them." Rainbow Dash said with a grin. "I'll just grab myself a super-scary costume and frighten the fur off anypony I choose!"

Twilight chuckled and rolled her eyes good-naturely as she was used to Rainbow's antics. Suddenly there was a loud scream and she and the Doctor shared a look, with the Doctor breaking out in a smile.

"Now that's the kind of thing I like to hear!" The Doctor laughed before galloping off in the direction of the scream with Twilight running after him calling "Hey, wait for me! Just slow down! DOCTOR!"

Rainbow, after seeing this, leaned over to Shining and muttered "That stallion has issues." Shining could only nod in agreement.

When Twilight finally caught up with the Doctor, she found him (Along with several other ponies) standing outside a tent near the town square. Inside the tent, was the body of a stagehand who was missing something rather... important. Twilight glanced at the body and looked rather green.

"Well... I don't think this is what they meant by fun frights." The Doctor said, referring to a nearby poster for the play. "This isn't fun at all."

"Tell me about it." Twilight agreed. Then Trixie's mocking voice came from behind her.

"Aw, does Twilight Sparkle not have the ability to handle the sight of a headless pony?" Trixie mocked, though she inwardly was rather disgusted herself. She just wouldn't admit it in front of Twilight, who right now was grinding her teeth at the sound of Trixie's voice.

"What are you doing here Trixie?" Twilight asked in annoyance.

"Trixie's business is Trixie's own. So never you mind!" Trixie snapped. "Never thought I would see you again Twilight Sparkle."

"Believe me, I'm overjoyed at the prospect." Twilight deadpanned and Trixie faked being hurt as the Doctor watched the whole thing like a tennis match.

"So, you two... Uh, know each other?" The Doctor asked nervously. He got conflicting answers.

"Yes." Trixie said while Twilight said "No." It was then Cherry Berry, who was a mare with deep red hair and a matching coat walked up. She began shooing everypony off and attempting to reassure them by saying. "Now now, I'm sure this is a one time incident. Nothing to worry about."

"Nothing to worry about?" The Doctor exclaimed. "He's missing his HEAD!"

Written leaned over and whispered "Cherry, earlier I thought I saw-" but Cherry hushed him and hissed "Say nothing!" before she quickly changed the subject by walking over to Twilight and hugging her. Twilight returned the hug.

"So nice to see you again. Tell me, is your brother here?" Cherry asked.

"Yes, but shouldn't we be worried about...?" Twilight trailed off but Cherry waved a hoof dismissively.

"Hardly. The police will catch whoever did this. So, a hero of Equestria now are we?" Cherry began. "Tell me more."

"Believe me, I've got a lot to tell you." Twilight replied in a excited tone of voice. "There was this one thing me and my friends did the other day..."

"You can tell me more back at the house. Believe me, you will want to see what I've done this year!" Cherry said excitedily, and although Twilight looked curious she took one last look at the dead body behind her. Trixie stuck out her tongue, which Twilight responded to in kind. The Doctor sighed, it looked like tonight was going to be very interesting indeed...

"And just when I thought there would be nothing for me to worry about tonight..." He muttered before letting out a long sigh.

Author's Note

Well, I hope you enjoyed the first chapter to what's the start to a new adventure for the Doctor and the whole gang, plus Cadence and Rainbow to boot. Like I told Gallent, this will just be to tide you over until I get to work on the real sequel to Once a Time Lord. Anyways, what do you think?