About 150 years Ago, Sleepy Hallow was just a small town, not really worthy of being put on any sort of map. To be perfectly honest, that's just the way the townspeople liked it and wanted it to stay that way. The populace was quite small, about only one hundred ponies or so, and everypony knew each other quite well. Most ponies lived ordinary lives, with ordinary jobs not better then anypony else. But there was one, a exception. This one was named Blue Berry, and oh he was a rich pony beyond belief, with his own personal manor house on a hill that overlooked the town.

He was a cruel and nasty sort, and a pony nopony liked. Believe me, the feeling was quite mutual. Quite mutual indeed. They all thought he lived up there, alone with his money and with nothing to do but count it. Greystark Hall, it (The manor) was called although some called it Berry's Folly when they thought Blue Berry couldn't overhear them. He did hear, but ignored the nickname as he didn't care one jot what others thought. He never did.

However, some say his only saving grace was his daughter, a fair and elegant pony named Black Berry, whose fur and mane earned her that name she was given. Black Berry shared none of her father's traits, and was well liked by all.

But there was one pony who liked Black Berry more then anypony else, a simple beet farmer named Ichabod Crane. He was rather poor, and lived on a farm, with only the beets he gave to Sleepy Hollow's towns people to keep him afloat. He wasn't handsome either, so no one would expect anypony to actually take a liking beyond friendship to him.

But beyond all expectations, it happened. Black Berry did just exactly that. She fell head over heels for Crane, and her feelings were quickly returned, but that was where the trouble began...

Greystark Hall, library:

Blue Berry was in a unhappy mood, he'd heard all of the rumors going around town, about how his daughter was cavorting with a simple farmer. Something had to be done about it, but what?

Krack-Koom! The thunder went.

"That farmer, Icha-What's his name is ruining my family's hard earned reputation!" Blue growled to himself as he paced back and forth. "We've been around since for decades, and now look what's happening!"

"I've warned him time and time again to stay away from my daughter and look what's happening!" Blue snapped, thought obviously nopony heard him.

"He goes and ignores me! Why, I bet all of my money that they're..." Here he gave a shudder. "Having sex in a shed! Yeah, that's exactly what they are doing I bet!"

"I'll have no more of it, no sir!" Blue Berry snapped before a thought struck him, a absolutely downright evil thought. He now knew exactly what to do as he rubbed his hooves together and cackled as lightning flashed outside.

Back in the present time...

Everypony present took in Cherry Berry's story so far, each with varying reactions.

"Geez, this Blue Berry guy sounds like a real Grade-A jerk." Rainbow huffed as she crossed her forelegs. "If I ever meet him, I'm bucking him into the next century."

"You do realize he's probably long dead by this point, right?" Twilight deadpanned. Rainbow looked embarrassed as she rubbed her head in embarrassment. "Oh, right... But the point still stands!" Rainbow declared.

"Oh, how'd I'd like to give him the worse punishment I could think up!" Cadence snarled. She, as the Princess of Love found this Blue Berry fellow quite distasteful, to say the least. "Disrupting love, like that!"

"Trixie says she thinks she hates Blue Berry right now." Trixie commented as her horn sparked magic in anger. Twilight's and her brother's was doing the exact same. By now, everypony had cleared away from the stage as a hard rain came down. The storm that had been threatening the town for the past few hours had finally arrived and had broke wide open.

"Oh, I can see where this is going... I don't even need my Tardis to tell the ending here." The Doctor muttered sadly as he shook his head. Cherry nodded sadly, before she gave her reply.

"And you'd be right on the money with that one, trust me. It only gets worse from here..." She trailed off.

"How can it get any worse then this!?!" Rainbow interrupted and everypony glared at her. Cherry smiled sadly.

"Trust me, it can..."

Sleepy Hollow: 150 years ago, Nightmare Night...

Blue Berry made his way through the streets of Sleepy Hollow. Even if it was about to rain, colts and fillies still ran from house to house in various costumes, in order to please the Nightmare Goddess and hide from her gaze. Even now, through a hole in the clouds the shadow of the Mare in the Moon was visible awaiting it's time to return down to Equus.

But Blue Berry had a different purpose then everypony else as he made his way to Ichabod's farm house outside of town. In his saddlebags, Blue carried a meat cleaver grabbed from his kitchens. He crossed the fields of Ichabod's farm and entered the home. As he made his way through the home, he accidently bumped up against a cabinet and knocked over a vase which shattered when it hit the floor.

In paranoia, Blue looked around to see if Ichabod would come to investigate. He never did, and so Blue made his way to the bedroom. Sure enough, there was Ichabod sleeping in the bed, next to... At the sight of who Ichabod was sleeping next to, Blue's rage boiled over and he pulled out his cleaver and brought it down. Blood spattered the walls. The job was done, and no one would be the wiser on who did it. Blue smiled in a sick manner and left as quickly as he'd came. But he had forgotten one simple fact.

Love was one of the most important facets and laws of Equus. You break that law in some manner, and you bring grave consequences on you and your town. And Blue Berry had just done exactly that. Later that night, everypony would swear they would see storm clouds building right over Ichabod's home and the form of a headless horse appearing within them and rearing up on it's hind legs and whinnying. A curse had been created, and now it would bring it's power to the town of Sleepy Hollow for the next one hundred and fifty years on this very night exactly.

Present Time:

The story was done, and everypony present took it in.

"By Celestia..." Twilight whispered. "That's horrible. And you ACTUALLY celebrate this... This tragedy?" She roared and Cherry looked ashamed of herself.

"Yes, it was." Cherry Berry replied sadly. " And it's not a celebration, not really. It's a memorial. Ponies have just forgotten that. I'm ashamed to admit I, and by extension you and your family are related to that monster of a father. This whole town is cursed, and if history holds the Horse will appear again tonight. I'd hoped it wouldn't, but it probably will. I'd advise you to clear out now before things get any worse. And believe me, they will."

"No, we're not leaving. This monster has to be stopped, you've been afraid long enough." Twilight said defiantly as Shining looked at Cherry nervously while Cherry smiled at Twilight gratefully and whispered "Thank you..."

"S-So, you think it's entirely possible the Headless Horse will skip tonight?" Shining asked nervously, though he didn't believe his own words. The Doctor shook his head to answer Shining's question before replying.

"Hardly, there have already been murders tonight, both fitting the Hor-No, Crane's stropping mad style. He's very regimented, if history is correct. It's not a question of if he'll show up, but WHEN..." The Doctor trailed off ominously. In the distance, as he looked towards a group of trees he thought he saw a headless figure appear for just a brief moment, before vanishing into the shadows...

"So what do we do?" Twilight asked, genuinely terrified for her life although she wasn't showing it in front of Cherry. The Doctor smirked and gave her his answer, one that truly surprised her.

"For now, we enjoy the festival, and wait."

Author's Note

Okay, so now you know the truly tragic legend of the Headless Horse. I admit, I may have took a few liberties, but this is the way I wanted to tell the tale. Anyways, what'd you think of the chapter, which I believe to be one of the most wordy things I've ever written for Once a Time Lord's canon. Any comments or questions?

Edit: Added the italics to indicate the flashback moments.