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Chapter 1 ~ Vacation1,912 words
Chapter 2 ~ Work1,053 words
Chapter 3 ~ History Repeats1,233 words

Chapter 1 ~ Vacation

"Alright, Wonderbolts," Spitfire's voice carried throughout the now empty Baltimare Stadium, "Tonight's performance received amazing ratings. This has been one of the greatest season finale shows. Don't party too long tonight, though. Meet at the train station at 3 AM tomorrow and we'll be heading back to Cloudsdale. Just like we all agreed, I sent letters to each of your family and friends in your towns and cities so they can greet you at the station. After that, go home and get rest until spring. You all earned it."

All the Wonderbolts cheered and began to separate in their own groups to celebrate the end of another successful season. The only Wonderbolts left in the stadium were Rainbow Dash and Soarin.

It had been a few months by now since Blaze tried to destroy Dash and Soarin's relationship, and a lot has happened. Dash had joined the Wonderbolts, Twilight had mentored Starlight Glimmer in friendship, who graduated after defeating Queen Chrysalis, and honestly, life had been pretty good since then.

To Dash, life had been too good. Every day she waited for something to happen. Something that would put Equestria in harm's way once again. So far, nothing has happened but she wasn't going to let her guard down.

The two pegasi began to fly out of the stadium when Soarin spoke up.

"How does it feel knowing you finished your first season as a full Wonderbolt?"

"It's awesome," Dash smiled, "better than I imagined."

Soarin smiled back. "Good."

"So, what are you gonna do this winter?" Dash asked.

"I don't know," Soarin shrugged, "my parents are pretty busy in the weather factory and they don't think they'll have much time to relax this year."

"You should totally hang out in Ponyville! You can stay with me, and I'm sure my friends won't mind. Plus you can help get the town ready for winter. We start in two days."

"That'd be awesome! It'll be nice to spend quality time with my awesome marefriend!" Soarin pulled Dash into a hug as she laughed and blushed slightly.

"Alright, you goof," Dash yawned as Soarin let her go, "We both should get back to the hotel, the last thing we need is Spitfire screaming in our ears for oversleeping or something."

Soarin laughed. "Right."

The trip to Cloudsdale from Baltimare had been pretty quiet so far. Most Wonderbolts were asleep, and the rest whispered to each other about their winter plans. Even Spitfire was out. It was about 5 AM now, and they would be at the train station below Cloudsdale in an hour.

Dash fell asleep as soon as she had sat down. Soarin, who had awoken from his slumber an hour ago, admired Luna's night. That was when Airbrush walked up, a blanket wrapped around her.

"Hey, Soar," she said tiredly.

"Oh, hey Airbrush. Do you want to sit down? I can move Dash over a little to give you some space."

Airbrush looked over at the sleeping prismatic mare next to Soarin. She had her head rested against the window but the rest of her body took most of the seat. Airbrush shook her head.

"No need. I'm sure Wave Chill won't mind sharing the seat for once." She motioned behind her, where Wave Chill had been reading a newspaper. He recently had his luggage on the seat but moved it on the rack above when he tried to sleep.

"Go ahead," he said, eyes not leaving the paper.

"So," Airbrush sat down and wrapped the blanket around her self as she got situated, "planning to stay in Cloudsdale again?"

Soarin shook his head. "Actually, my parents are pretty busy with weather business and don't have much free time. I'm gonna be with Dash in Ponyville. Most likely for the whole winter."

Airbrush smiled. "It's good you two are gonna spend more time together. Wonderbolt life can be tough on relationships."

"Yeah, there have definitely been times where we argued because of the stress we had from it, but it obviously hasn't ruined our relationship forever."

"I hope it stays that way," Airbrush smiled before a question popped into her mind, "by the way, I heard Ponyville hasn't officially started their winter yet, did Rainbow say when they start?"

"Yeah, they get ready tomorrow. I never experienced winter except in Cloudsdale, so this will be new for me."

"Oh that's right," Airbrush nodded her head, "I forgot Cloudsdale doesn't do the same kind of preparations like the other ponies."

"I'll admit, I'm kind of nervous about that. Dash said she'll show me what to do, so that's good."

Before Airbrush could respond, the now awake Spitfire yelled through the Wonderbolt-filled cabin.

"Alright, everypony! We have ten minutes until we're at the station, so get your stuff together. Once you get off, find your families or friends and head on home."

"Well, I guess I should get my things together. I'll see you in the spring," Airbrush stood up and began to walk back to her original seat.

"You should come visit soon. I know Dash would love it," Soarin suggested.

Airbrush smiled. "Sure thing, Soarin."

Once the train had stopped at the Cloudsdale Ground Station, every Wonderbolt bolted towards their families and friends. Wave Chill was greeted by his little brother and father, Airbrush had her children, Spitfire to her mom, and Dash and Soarin to her friends.

"Hey, girls," Dash greeted as she slowly landed in front of her best friends. It was obvious that she was still half-asleep.

"I'M SO GLAD YOU'RE BACK I WAS SO DEPRESSED THE WHOLE TIME!" Pinkie screeched as she tackled the cyan mare.

"Thanks, Pinkie," Dash laughed as Pinkie let go.

"How was the tour?" asked Twilight.

"Super exhausting, but awesome."

"Oh, darling! You look exhausted! We should get that fixed up, especially in front of your prince charming!" Rarity exclaimed.

"If you don't mind me asking, Soarin, did anypony come to pick you up? Or are you going to be in Cloudsdale?" Fluttershy asked.

"Usually I stay with my parents for the winter, but it's going to be really busy in the weather factory this year," Soarin answered.

"So he's gonna be hanging with us in Ponyville! Is it cool with you guys?" Dash added.

"Soarin is going to spend all of winter, which is the most romantic season of the year, with his marefriend? THAT'S SO ROMANTIC!!!" Rarity squealed. Dash rolled her eyes.

"You thought when he looked in my direction it was romantic..."

"What? It was! I could see it in not only his eyes but in yours!" Rarity defended.

"I wasn't even paying attention until you screamed in my ear," Dash replied in a slightly annoyed tone.

"Well, you two definitely came back at the perfect time. Tomorrow is the winter preparations," Twilight explained, changing the subject.

"That reminds me, what do you all do? I never got to prepare for winter since I've spent them all in Cloudsdale," Soarin questioned.

"Twilight is in charge of organizing each group. Fluttershy leads the group that guides animals to good hibernate places, Pinkie leads the group that takes down the leaves of trees, Rarity leads the group that helps Fluttershy's group with guiding the birds to the south, and Applejack leads the group that collects the rest of unharvested fruits and vegetables," Dash explained.

"And what about your group?" Soarin asked.

"My group gathers the clouds from the weather ponies and places them in the right spot. Pretty much everything that goes on in the sky is what my group does."

"What group am I gonna be in?"

"You're gonna be in Rainbow's group. Fast pegasi like you and her will help speed up the process," Twilight stated.

Soarin nodded. Good, he thought, Not only will she able to explain what to do, but I'll also spend time with her.

The next morning, at Dash's home.

"Dash! Come on, we were supposed to meet Twilight at her castle an hour ago!" Soarin yelled.

Soarin didn't like waking up anyone, especially Dash, but he hated being late. He didn't understand, Dash seemed to look forward to this.

So why was she still sleeping?

"Dash?" Soarin peeked his head through Dash's bedroom door, only to see his marefriend lying in her bed.

"What?" Dash answered, not looking at him.

"We have to go, didn't you hear me cal- hey, you okay?" His voice went from a serious tone to a concerned one. He flew closer as she finally sat up.

"Yeah, just tired. Didn't get much sleep these past two nights," she assured, but Soarin wasn't convinced.

"You sure?"

"Soar, I appreciate your concern, but I'm fine. Let's just go to Twilight's."

Dash then finally sat up, and Soarin watched as she slowly walked out of her room. He was going to keep a good eye on her today.

"Where were you?" Starlight asked as Soarin and Dash flew into the castle.

"Overslept," Dash stated blankly.

Starlight and Soarin exchanged glances at each other, which both shrugged before following the pegasus into the Cutie Map room.

Soarin didn't really know Starlight as well as he knew Dash and her other friends. He knew what she had done, good and bad, but that was really it. When he had met Dash and her friends before Starlight joined the group, it was very easy to distinguish who was who. Twilight the bookworm, Applejack the farmer, Pinkie the party pony, Fluttershy the quiet one, Rarity the beauty guru, and Dash the athlete. He didn't really know what to make of Starlight.

"Rainbow Dash, you were supposed to be here with the rest of Ponyville an hour ago! Do you know how hard it is to lead a group of pegasi AND keep everything else organized?" Twilight lectured as Dash sat in her throne.

"Yeah," Dash answered, almost as if she wasn't really listening.

"What's up with her?" Starlight asked, to which Soarin shrugged once again as a response.

"She said she didn't sleep well last night."

They watched as Twilight continued to lecture Dash about punctuality, who wasn't paying attention whatsoever.

"Rainbow are you even listening to me? You are so out of it today!" Twilight said as she watched her friend slowly fall asleep.

"Yeah, yeah. I heard you. I'll get onto it," Dash yawned as she began to fly towards the entrance of the Cutie Map room, but was stopped by Twilight's magic.

"No. You are going to stay in here until I can find out what's wrong with you."

Twilight placed Dash back onto her throne gently as she walked over to her.

Starlight and Soarin watched the alicorn examine the loyal friend until she had come to a conclusion.

"Yeah, I'm not sending you out there with the other ponies."

"Why? What's wrong with her?" Soarin asked, worry growing each second.

"She's sick. Fever, exhaustion, absent-minded..." Twilight continued to list everything that Dash had been since that morning, "Soarin, you gotta do her job for her."

"What? But I don't even know what to do! She was supposed to show me!" Soarin exclaimed, surprisingly not waking up the now sleeping mare.

"I'll teach you," Starlight volunteered, "I had to fill in for Thunderlane last year, so I know what to do. Plus, I know that if you were in her place, she'd do the same for you."

Soarin nodded and they both left Twilight and Dash in the castle.

What could possibly go wrong?

Author's Note:

Welcome to That Winter in Ponyville! Thanks for reading my series so far. This could be the last one but who knows, I change my mind a lot...