Then:

The Doctor gathered all of his companions that had been with him throughout the night along with Cherry to explain his plan. He smiled at all of then before he began with a nervous look around the room and he swallowed hard. Nobody was exactly calmed by this, and the Doctor's next statement didn't exactly help matters much.

"Okay Twilight, Shining... You know usually how I have great plans, and brilliant ideas to stop whatever we're facing?" He asked, and Shining and Twilight nodded politely although inwardly they were thinking "No, not really."

"Well..." The Doctor began before with manic frenzy he threw on his Stetson and cried "Look at me Horsey, I'm a target!"

Trixie gaped in shock as Twilight and Shining collectively facehoofed. They knew exactly what the Doctor was thinking, luring the Horse out into the open while they went and burned the bones but this was still a risky plan if either of the two were to be honest. Nopony still knew the limits of the Horse's abilities in single combat and what she could do yet. All they'd seen was just mere teleportation and sword swinging, and one lucky swing of that sword and they'd be out one Time Lord for all they knew. After all, they still didn't know just how many regenerations the Doctor was allowed access to. Hell, even the Time Lord himself didn't know. Technically, this was supposed to be his last body, and he didn't know if going into a different dimension rendered the laws of a Time Lord's Regeneration ability moot.

"So, this is your plan Doctor?" Trixie asked in disbelief. "Face down the Horse in single combat, mano-a-mano? Trixie says, no she asks have you ever heard of the concept of SUICIDE!?! Because that's exactly what this is!" She roared in the Doctor's face, making him wince a bit and take a step back.

"Now now, no need to get your horn in a twist, and believe me as I know it can happen seeing as how I've seen it, but I'm not going to face Horsey mano-a-mano. I'm going into battle with another ally by my side."

"Who, us?" Trixie asked. The Doctor smiled and booped her on the nose making Trixie's jaw drop.

"Nope, my wits." He laughed and Twilight facehoofed as the Doctor muttered to himself under his breath which went something along of the lines of "Ponies and humans, you're all the same, you don't think. Besides, didn't you hear the words "I'm a target?" Listen before you speak."

This was the best that could be understood of the Doctor's chastising. Trixie looked understandably insulted and harrumphed to herself before she muttered "Trixie is smarter then she looks." before turning to Twilight and hissing in her ear "Is he always like this?"

Twilight groaned before she responded "Pretty much. But don't worry, I'm sure the Doctor has a plan here, a good one that's better then he makes it sound."

Trixie crossed her front forelegs and said "Trixie is not exactly reassured. How certain are you? 100%?"

Twilight nodded before Trixie raised a eyebrow and the lavender unicorn quickly corrected herself with a "Okay, 65% sure."

Now:

The Doctor and the Headless Horse/Black Berry stared each other down, before it happened. Each drew their chosen weapon and the Horse struck first swinging it's sword but the Doctor managed to knock it out of the air and onto the ground with a sonic blast from his Screwdriver.

The Doctor looked incredibly pleased with himself, this could be easier then he thought it would be but his smirk soon vanished when the Horse regained it's sword and took a swing with this time the Doctor being too surprised to react as he was split right down the middle. But that was the odd thing, there was not a drop of blood, nor guts spilling out onto the street and no gore whatsoever. And then it got really odd, as the Doctor's body just flickered and vanished.

It was then the Doctor, the real one for all the Horse knew stepped out from a home's front doors.

"Well, you know what they say. No guts, no glory eh? Not in this case Horsey!" The Time Lord mocked. The reaction this comment generated was exactly the one the Doctor expected and the one he'd been wanting.

The Horse screeched in rage, she'd been tricked by a mere illusion! She swung her sword once more at the Doctor and he ducked his head to avoid it being lopped right off.

"Woah nelly, this is not how a second date is supposed to go!" The Doctor teased, and only succeeded in making the Horse madder then ever.

"Of course, I don't know how you'd be able to enjoy me on a second date considering how you have no... well, head, and plus I don't date dead ponies who also happen to be stropping maniacs. That's even below Jack's standards I think." The Doctor mused to himself as the Time Lord dodged another sword swing which tore apart his hat and cut some of his mane off his scalp as he let out a small yelp.

"That was my favorite hat..." The Doctor thought to himself. "Plus, I like my hair the way it is!"

"Rainbow, some help may be required here!" He yelled, and sure enough Rainbow Dash appeared and flew in only to kick the Horse into the town's well but soon as she did so black smoke clambered out of the well's pit and reformed into the Headless Horse, who reared up on her hind legs and whinnied in rage before bringing out her sword again and swinging it in a fanciful manner. "It's kinda elegant, in a I'm going to decapitate you and all your relatives and relations way." The Doctor mused to himself.

"Great, now we'll both die a horrible bloody and headless death." Rainbow said dryly. The Doctor ignored her.

"You know, if I liked to kill... and was partial to guns I'd just shoot her dead now, just like in that movie I watched once." The Doctor commented cheerfully before he straightened up his vest and his expression became grim.

"You know, this has been fun and all but now we really have got to have a serious talk. You were once a good pony Berry, until that prat of a father of yours messed you up and killed your coltfriend. I get it, you wanted revenge, but this has to stop now! You seem determined to play your role as a monster so you know what I'll have to do? Yeah, that's right. Play my role, as the pony who stops the monsters!" The Doctor began before with the final words his speech turned vicious and cold with Rainbow feeling a chill run down her spine at the words spoken. This was the Oncoming Storm, the Predator and now the Headless Horse was about to meet him. With a smirk, he pulled out a small walkie talkie and yelled into it.

"Trixie, Twilight, Shining, NOW!"

Sleepy Hollow Graveyard, a few moments before...

In the Graveyard, a hole had been dug, right in front of Black Berry's grave and inside lay dried up bones with the threesome standing above them all of their horns alight and glowing with magical auras, each in their own color with the magic still waiting to be used for it's purpose.

"So, you think the Doctor can handle her? T-The Headless Horse I mean?" Trixie asked nervously, while looking around her every so often just to make sure there were no more Weeping Angels in the area or anything that could even resemble one. She was still shook up quite a bit from her last encounter and near death from one and wasn't even bothering to hide her fear behind arrogance and bravado.

"I wish I knew Trixie, I really wish I did." Twilight murmured to herself. "I'd like to say he knows what he's doing but... well, he's the Doctor."

Then a thought struck Twilight, she'd just noticed somepony who could and should have probably been with them or the Doctor was missing and it wasn't Rainbow Dash or Cherry Berry.

"Hey Shining, where's Cadence? Shouldn't she be helping here?" Twilight inquired curiously and Shining frowned to himself.

"I have my reasons for keeping her out of this, Twily." He answered grimly and before Twilight could ask again he repeated himself with a "Just... reasons."

Twilight then got the sense that if Shining wanted his reasons kept private and didn't want anypony to inquire into them, they'd be that way... For now at least. She sent her brother a "We will talk about this someday" look which he caught. Then, before any more words could be said between the two, they heard the Doctor's voice come from a walkie-talkie resting on the ground nearby.

"Trixie, Twilight, Shining, NOW!" The Doctor's voice roared over the walkie-talkie, and all three ponies shared a look before with a flash and a small poof of a magical explosion the flames were lit and the bones were burning nicely. Twilight and her two compatriots let out identical sighs of relief, that should stop the Horse for good...

Or at least that's what they thought...

Back in town, the Doctor awaited for what he expected to come, the flaming of the Horse's spirit as it was finally laid to rest. But that's exactly what DIDN'T happen, much to Rainbow's and the Doctor's shock and horror. The Horse was still there, and madder then ever. it had felt what the Doctor's friends had tried to do, and it didn't like it.

"Aw come on, you gotta be kidding me!" Rainbow exclaimed at the sight of the still-there Headless Horse.

"Twilight..." The Doctor began nervously as he and Rainbow began to slowly back away from the Horse. "Please tell me you burned the bones."

His voice came out in a squeak, and the Doctor felt no shame in admitting he was afraid. He didn't know why the plan failed like it did, but he doubted he'd have time to wonder much longer.

"Yeah, we did! Is something wrong?" Twilight asked nervously only for the Doctor to swallow hard.

"Is some-" He began before snapping "OF COURSE SOMETHING'S WRONG! The Horse is still alive, well not alive but kicking and really rather hacked off!"

Back in the Graveyard, all three ponies shared a look. That wasn't good, not at all. Twilight began to panic as she paced back and forth muttering how the plan should have worked, before a thought struck her. She thought she may have just figured it out, even if the solution chilled her to her core.

"Doctor, it's the Horse's spirit! It's too angry now at everypony even slightly related to her father for even burning bones to work! I... I don't know how, but that's the truth!" Twilight yelled in fear for the Doctor's life. And then the Doctor realized it too. Of course, it made sense! There was only one way for the Horse to be defeated now, he just didn't know if it would ever happen. And yet he was about to be shocked, as striding out of the Town Hall was Cherry Berry.

"What do you want?" The Horse hissed in it's raspy voice.

"To say something that should have been said a long time ago. To say... I'm sorry." Cherry whispered, but the Horse still heard her.

"SORRY!?!" She roared. "Sorry can't make up for what's been done to me!"

With that, she plunged her sword into Cherry's chest as the Doctor let out a shout of "NO!" and Twilight heard him and exclaimed "What's happening? DOCTOR!" but Cherry still somehow found the strength to talk even as she coughed up blood.

"Maybe it can't, but maybe it can. There's something that should have been done long ago, something that should have been done on the night you first rose from the after-worlds to haunt this town with your curse. You had family, and you still do in me. What your father did was horrible, and a unforgivable act but I still want to make things right. M-My family, your family, forgives you and yet we u-understand you as well. You and I-Ichabod should have had a h-happy life, and i-it was taken from you. For that, me and all those who are descended from your father are very, truly sorry." Cherry coughed up before her eyes closed for the last time but her words had reached the Horse. It felt very, very ashamed of itself, and if it had a head would have been sobbing for all the meaningless deaths it had inflicted, either related to her father by blood somehow or not. And then, with a flash of flame and a final screech it was gone leaving only ashes in it's wake with Cherry's body crumpling to the ground no trace of the sword which had pierced her.

"Doctor, what's happening?" Twilight asked again, her mind considering the worst possibilities imaginable. The Doctor closed his eyes and let out a long sigh.

"It's over, it's finally over. The Horse, along... Along with your aunt are gone. I'm sorry Twilight." He whispered in sorrow. This whole night, it had been meaningless, hadn't it? Had he really achieved anything besides getting somepony very close to one of his friends killed? Twilight knew where his thoughts were heading, and even as she sobbed in mourning for her aunt reassured him.

"It wasn't meaningless Doctor, not really. You stopped a curse, and laid a pony to rest." She said and the Doctor chuckled sadly.

"No, it wasn't me who did this, it was Cherry. Your aunt, she may have had her faults but in the end she proved to be a pony to be admired... In the end." The Doctor said sadly, and for that Twilight had nothing to respond to.

Sleepy Hollow Train Station

The train whistle blew sharply that very next morning, it was almost time to go back home. Twilight took one last long look at Sleepy Hollow and sighed. With her aunt gone, there was nothing left for her here. In her mind, this had been the worst Nightmare Night ever. When she got back, all she wanted to do was just curl up in her bed and sleep the day away, this whole venture had exhausted her. Suddenly she felt a hoof on her shoulder. It belonged to Trixie.

"Listen, Trixie just wants to say she is sorry... For about what happened to Cherry. She was a real hero, although she never deserved what she got."

Twilight sniffed as she wiped away her tears as Trixie continued.

"You're a tough pony Twilight Sparkle, and you will recover... Although you will never be as Great and Powerful as the mighty Trrrriiiixxxxie!" The Showmare cried before with a explosion of magical smoke she was gone having vanished to parts unknown.

"Think she'll ever change?" The Doctor asked, having only caught the last bit and the explosion. Twilight looked up at him and smiled.

"You know, I think she already has..."

END

Author's Note

Well, that's the end of this little jaunt with the Doctor and his friends. I bet you weren't expecting not for the Doctor or Twilight to be the hero of this piece, but Cherry herself who went out like a good Mayor protecting her town should. Next, I just want to thank you all who've stuck with me through this story, as you guys took the time out of your lives to read this story out of the many others out here on Fimfic and for that I really thank you, and will leave you with this message just before I go.

THE DOCTOR, TWILIGHT AND SHINING WILL RETURN IN "NOW A PONY, ONCE A TIME LORD"...