It could have been a good morning for flying.

Autumn had begun to creep in around the edges of the last day of summer, and though Summer Wrap-Up was only just officially beginning, the shift could already be sensed throughout Ponyville. It was felt in the cold wind that whistled through the streets, in the patchwork of reddening leaves which clung stubbornly to the trees, and the way the sunlight rising over the horizon was no longer the soft gold of summer, but rather a paler, whiter light.

The change of the seasons could be felt everywhere, Cherry Berry the balloonist observed; not just in Ponyville. Overhead, the weather team was busy sweeping away all the old summer rain clouds, leaving the sky above the town a spotless blue expanse. Along the horizon, Cherry could see a train of new clouds, as soft and white as fresh linens, trailing westward from Cloudsdale.

On the ground, a gaggle of ponies hurried down the street past the raised wooden platform where her pride and joy was tethered: her balloon.

Cherry’s balloon was more to her than just a machine for transporting her from Point A to Point B. The balloon was a part of her, a second body: both the wood of the basket frame and the fabric of the envelope were as pink as her coat and patterned intricately with swirling clouds and showers of stars that evoked the endless skies above. A glittering gold skirt and railing matched her own mane and tail.

The sight of her beautiful balloon waiting for her on the landing pad was enough to bring a smile to her face. And, given her latest run of bad luck, Cherry could use all the smiles she could get.

She didn’t expect many reasons to smile in her future.

It could have been a good morning for flying, Cherry repeated to herself, if I had a reason to fly today.

Cherry’s eyes fell downwards to the thick ledger book she held open in her front hooves. She ran the numbers — lined columns of jobs, trips, costs, expenditures, and incomes going all the way back to the beginning of summer — through her mind again, and again the numbers refused to add up.

Summer was always her busiest season; the skies were crowded with travelers and tourists, and paying jobs were plentiful. There was always work to be found, whether it was transporting supplies to remote camps in the Frozen North or ferrying tourists from Appleloosa to Manehattan.

Or rather there had always been work to be found, once upon a time. The summer that was ebbing all around her had been one of her least profitable summers to date. She wasn’t sure what had led to it — perhaps it had been the wild rumors of changeling swarms stalking the skies, perhaps it had been the rogue storms that kept blowing in off the coast, or perhaps she was just an unlucky pony — but Cherry had landed only a hoofful of jobs, and none of them had been particularly lucrative. Between the shortage of work and the ever-increasing prices on supplies like gas for the burner tanks, Cherry’s bit purse was feeling as empty as the sky overhead.

She barely had enough bits left to pay her expenses through the end of summer, and she definitely didn’t have enough to last through the long, slow winter when there’d be even fewer jobs.

If Cherry didn’t turn things around, she’d be in real trouble. She would have to hang up her aviator’s cap for the winter and find work on the ground just to make ends meet.

She closed her eyes and found herself taunted by visions of herself picking cherries, pruning trees, and baking pies. Being sequestered away in a kitchen, or stuck walking an orchard all day, was dreary work. She couldn’t fathom how other ponies found any fulfillment sticking their snouts in the dirt like that.

“Anything but that,” she whispered to herself.

Her natural-born earth pony talent — cherry farming, as it was depicted on her as a cutie mark depicting a cherry stem — would have kept her hooves on the ground, but Cherry Berry could not think of a worse fate than being down to earth.

She meant to fly, even if that meant flying against her own destiny.

“Hey!”

She gritted her teeth. When had everything — work, flying, even her life itself — become so difficult?

If she closed her eyes and quieted her mind, she could still remember when things had been different. She remembered a little earth pony filly who wanted nothing more than to reach the sky, who spent her youth with her head in the clouds wishing to fly like the pegasus ponies did. She remembered the first time she had flown her balloon to Cloudsdale, and the first time she had made the long flight to the skies above Cloudsdale, where not even the pegasi ventured.

The big sky, it was called.

From up there, everything looked small. Especially the ponies who had looked down on her and told her she could never fly.

It didn’t take long for the ponderous thoughts of ledger books and balancing accounts to intrude into her reverie. Her happy memories crashed headlong into a storm of worries about work, and money, and the future, and she was dashed back down to earth.

“I said, hey there! Hell-ooo? Do you talk?”

Somepony was talking to her. Cherry opened her eyes and looked around. The street in front of her landing pad was bustling with morning traffic, but none of the ponies who passed by so much as looked in her direction.

Then she looked down, and saw the filly.

She was short and scrawny, even for a foal, with a dusky orange coat and wild mane as purple as the night sky. She didn’t have a cutie mark, either, but she was wearing a pair of light blue saddlebags strapped across her back. Judging from the fraying fabric and mud caked on them, they had seen their fair share of use.

She’s a bit of a runt, Cherry judged unkindly, still sour about her prospects. The arrival of fall meant all of Ponyville had turned out for Summer Wrap-Up; earth ponies and unicorns combed the fields outside of town, taking the health of the trees and ensuring the local critters’ burrows were stocked with food for the winter ahead. Pegasus ponies ushered in the seasonal winds and rounded up migratory birds for their long journey south.

Unfortunately, with the town being so busy that day, even foals were left to wander the streets to get into trouble and bother grumpy balloonists who’d much rather be left alone to wallow in their own self-pity.

The sight of one such filly gawking at her did not help Cherry’s bad mood.

“Uh, can I help you? I’m a bit busy,” she lied, turning back to continue leafing through her ledger. She was in no mood for company, and definitely not the company of foals. Cherry struggled enough getting along with ponies her own age.

The filly spoke up behind her. “That’s your balloon, right? It’s really cool. Can I go for a ride on it?” Her voice was loud and raspy for such a pint-sized pony.

Scrunching her face into a frown, Cherry turned to shoo the filly away.

“Sorry, kid, but I don’t give free rides,” she said, and gave the filly a hard stare.

Cherry was about to turn back to her work but stopped when she noticed them: two stubby wings, as bony as the rest of the filly, were folded along her flanks. The filly kept them tucked close to her sides, almost entirely hidden beneath her threadbare saddlebags. They were so small Cherry had missed them the first time she had looked at her. They looked more like the wings one might see on a newborn, not a filly of school age.

“Besides,” she continued, her voice tinged with annoyance, “if you want to go flying why don’t you go help out the other pegasi? Aren’t you supposed to be rounding up some birds right now or something?”

The filly winced and rubbed the back of her neck but didn’t answer.

“I can pay,” she said, looking back up at Cherry. Her face had grown determined and, for a moment, she looked older than her age. “I wasn’t asking for a free ride. I really want to go. Please? I’ve wanted to fly for so long.”

A pegasus wanting to fly in a balloon? That’d be a first, Cherry thought. Most pegasi she had met responded to the idea of balloons with either condescending curiosity or outright derision. She wondered if the request was the filly’s idea of a joke.

“I don’t know if your parents gave you some bits and told you to get lost for the day but balloon rides aren’t cheap, kid. And they’re not for fun. This is a serious job, believe it or not. If you’re bored maybe you should go bother the party ponies at Sugarcube Corner or something. Some of us have real work to do.”

Anywhere but hanging out here, Cherry thought. Just leave me be.

The filly rummaged around in one of her saddlebags and Cherry’s ears perked up at the sound of clinking metal. The filly pulled a bit purse from her bag and held it out to her. Cherry snatched it, loosened the drawstring with her teeth, and counted the bits inside.

She wasn’t kidding — she really can pay. The filly had enough bits stashed away that she could pay for a trip all the way to the Crystal Empire if she wanted to, though Cherry was in no rush to tell her that.

Cherry weighed the hefty purse in one hoof and her ledger in the other.

This is seriously just my luck, she thought. Being reduced to flying pegasus ponies around, as if their usual derision wasn’t enough? She wanted to chuckle bitterly at the misfortunes the day seemed to already be piling on her, but stifled it.

Maybe the pegasus was having a laugh at her expense. Maybe she had come to gawk, or mock the odd earth pony who needed a wonky contraption to fly because she hadn’t been born with wings. But Cherry would get the last laugh; she would still walk away with the pegasus’ bits. One high-paying job might just save her from spending the winter on the ground. She could swallow her pride and suffer chauffeuring a filly around for that.

“Okay, fine,” she relented. “You’re in luck, kid. My balloon’s in pretty high demand but you just happened to catch me on a slow day. So where are you heading to, then? Cloudsdale? Stratusburg? Las Pegasus? I hope your parents know what you’re getting up to, because it’s gonna cost them a lot of bits.”

The filly reared and buzzed her tiny wings in a peculiar manner that evoked a bee or a hummingbird more than a pegasus. She may have been a pegasus, free to fly wherever she wanted, whenever she wanted, but Cherry couldn’t recall the last time she had seen one of her customers so excited to fly in her balloon.

Pony feathers she thought, I can’t remember the last time I was that excited to fly.

The filly composed herself. “Actually,” she said, grinning, “I don’t care where we go. I just wanted to fly. Anywhere.”

Cherry Berry wove a hoof through a loop of cord hanging just over her head and gave it a sharp tug. The burner system hissed to life as its flame heated the air within the balloon’s pink fabric envelope. The balloon woke from its torpor and struggle to rise upwards, like a dragon shaking off a long nap.

They were barely more than a few feet up in the air when her passenger clambered up so she was sitting on the edge of the basket railing with her hind legs dangling off into the open air.

“This is so cool!” the filly laughed without looking at Cherry. She was entranced by the sight of the ground beneath them. “Oh my gosh, I’m actually flying!”

“Yeah, we’re flying alright.” Cherry was still a little wary of the pegasus, but she couldn’t help but crack a wry smile at her unbridled excitement before resuming her gruff demeanor.

“Also get down from there or you’ll fall,” she snapped. “You may be able to fly but I have enough problems to deal with today that I don’t want to add watching you smack face-first into the dirt to the list.”

Cherry rummaged through the onboard supplies she kept tucked away in a corner of the basket: a toolkit for emergency repairs, a plethora of small instruments for measuring conditions like height and air temperature, and a neatly ordered stack of flight logs, maps, weather charts, and other navigation aids. She stacked the big toolkit case on top of her ledger and slid the impromptu platform against the railing for the filly to stand on.

The little pony added her own saddlebags to the top of the mess and, by balancing atop it on her hind legs, she was able to prop herself against the basket railing and look out without risking plunging over the edge.

She gazed up at the sky in wordless wonder while Cherry fired the burner again. The balloon ascended more gracefully than it had at first, passing first above the roofs of Ponyville, then through what was normally the pegasus cloud layer that rested a short distance above the town. The sky over the town was mostly empty in anticipation of the season change as the weather team dismantled the last few old clouds of summer. A few of them stopped what they were doing and watched the balloon ascend.

Cherry felt their eyes on her and all the old words that had haunted her as a filly came flooding back into her mind.

You? Flying? But you’re an earth pony!

Isn’t your place down there on the ground?

If you were meant to fly, you’d have been born a pegasus.

But Cherry wasn’t a filly anymore. She shook her head free of the voices and forced her mind to focus on the job at hoof. She found one of her navigational tools — a small instrument, no larger than a pocketwatch — among her supplies and checked the balloon’s ascent. They hadn’t risen very high off the ground, but it helped take her mind off the judgmental stares from the pegasi.

“So, this is flying,” the filly said.

“Yep. This is flying,” Cherry responded without looking up. She could feel the filly staring at her expectantly. An uncomfortable moment passed with no other sound but that of the wind passing over the ballon’s fabric.

“So you’re sure there’s nowhere you want to go?” she asked, again.

“Are you kidding? I could go anywhere!” the filly clamored. “Where’s your favorite place to fly? Have you ever been to Cloudsdale? How long have you been flying? Did you build this balloon yourself?”

Oh, great, she’s a talker.

Cherry rubbed her muzzle in exasperation. She shot her passenger a wary glance.

“I don’t know, I don’t really think about that stuff much. It’s just a job. It’s what I do.”

“But flying’s such a cool job! It’s the coolest job there is. I bet a lot of ponies must be jealous that you get to fly every day. Hey, I really like your goggles,” the filly rambled on, pointing at the aviator cap and goggles Cherry wore on every flight. “You look like a Wonderbolt.”

Truthfully, Cherry didn’t need to wear them while ballooning, but she secretly liked how stylish they looked on her. They might not have provided much practical value, but they reminded her of all the dashing aviators she had looked up to as a filly. And nopony had ever complimented her on them before; for a moment she felt a flicker of appreciation for the filly’s words.

“I’m Scootaloo,” the filly offered. “I probably should have told you that earlier but I was way too excited to actually get up in the air.”

Cherry sighed and gave up on her readings. She would have been fine going the entire flight without knowing anything about her passenger, but the filly clearly wasn’t going to let her work in peace.

“I’m Cherry Berry.” After a pause, she added, “Nice to meet you, Scootaloo.”

Scootaloo turned her curiosity to the equipment she had distracted Cherry away from: her set of flight instruments were probably as expensive as the balloon itself, and it had taken her years to acquire them all. They were brass and wood devices with crystal faces that each seemed to register a different number or measurement. They were earth pony inventions — altimeters and pyrometers and variometers and even a sparker for the burner system — painstakingly engineered and powered by ticking gears and finely-tuned gauges rather than unicorn magic.

“What’s that?” Scootaloo asked, pointing at the small device Cherry was still holding.

“It’s an altimeter.”

“What does it do?”

Cherry frowned. What kind of pegasus cared about earth pony technology? “Tells me how high up I am.”

“Wow.” Scootaloo looked at the altimeter like she had never seen anything like it before. “Can I hold it?”

“Sorry kid but this thing isn’t a toy. It took earth ponies a long time to figure out how to build instruments like this.” Cherry bristled but tried not to show it. “When you don’t have wings, flying takes a bit more work. Us earth ponies have to make do in different ways.”

Scootaloo, deflated, looked away. “Yeah, I’ll bet.”

Years of suffering naysayers had left Cherry a very aloof pony, but even she couldn’t help but feel a pang in her chest when she saw the disappointed look on the filly’s face.

“Just don’t drop it, okay?” she said as she handed the altimeter over. Scootaloo turned it over in her hooves gleefully but delicately, like it was a priceless treasure from the royal vaults of Canterlot.

“So these things help you fly?” Scootaloo asked as she handed the altimeter back. “You said flying takes more work for earth ponies, but I think it’s really cool that you don’t let that stop you. It’s really cool that ponies build things like this. I’ve never seen anything like it before.”

Cherry softened a little. As far as she could tell, Scootaloo wasn’t playing any sort of joke on her. The filly truly was keen on ballooning.

Maybe I misjudged her...

“Hey, speaking of flying, this thing does fly, right?” Scootaloo continued. “’Cause right now we’re just going straight up. How do you make it, you know, fly? Go places?” She waved her forelegs in a flapping motion that Cherry took to represent the act of flying.

In Cherry’s experience, very few of her passengers were interested in talking shop. Most of them just wanted to get from one destination to another with minimal interaction. She had not expected a filly — and a pegasus, at that — to be the first pony in a long time to show any interest in her craft.

When was the last time she had talked ballooning with anypony? Looking at Scootaloo, Cherry thought of herself as a filly. What she would have given to find a balloonist and bombard her with questions of her own!

“Oh no, it just goes straight up and down. Next stop, the moon!” she teased.

To her delight, Scootaloo craned her neck to gaze upwards. Cherry laughed. “Sorry, sorry. Bad joke. Yeah, I can move the balloon a little. These things,” she said and motioned at two smaller cords that hung to either side of the burner cord, “open the turning vents so I can make sure the basket’s facing the right way. Oh, and there's another cord that opens the parachute vent, that's on top of the balloon. The basket’s the big wooden box we’re standing in, by the way. The envelope up there is what most ponies call the balloon. They don’t know that balloons have different parts.”

“But,” she hastily added, “I don’t really do most of the flying.”

“What do you mean?” Scootaloo tilted her head. “Didn’t you say you can turn the balloon — err, the basket?”

Right on cue, the balloon finally reached the height Cherry had been waiting for. A wind was rising from the south, and it caught the balloon in its current. With the wind pushing behind them, they were borne along over the village’s outlying fields with surprising speed. Cherry took a deep breath in of the sweet southern air and enjoyed the gentle rocking motion of the basket as it gained speed.

Scootaloo also turned her face to the wind and let it whip through her mane. “How did you do that?” she asked in disbelief. “How did you make it take off like that?”

“I don’t have to do anything! The wind does most of the work for me. She’s the best copilot there is.” Scootaloo was looking at her with rapt attention, so Cherry let herself indulge her explanation. “Earth pony balloonists figured out a long time ago that they couldn’t fight it or fly against it the way pegasi and birds can.”

She pulled on the burner cord again to keep the balloon level as it bobbed along, heading north, away from Ponyville. “So instead, they decided to fly with the wind. Kind of like sailing a boat on the water. It’s more of an art than a science.”

Scootaloo grinned like it was the most thrilling story she had ever heard, and Cherry saw the reflection of the burner’s pilot flame dancing in her eyes. For the first time that morning, she could feel her own spirit begin to lift.

Cherry Berry had figured she’d fly an easy route; Scootaloo, after all, hadn’t specified any destination besides “flying around.” They’d float north, following the Foal Mountains and Unicorn Range past Canterlot in a circle around Equestria’s sprawling central valley before returning back to Ponyville. It would be an easy trip — Cherry had flown it so many times she knew the heights and directions of all the pegasus wind corridors by heart.

As she quickly realized, though, Scootaloo wasn’t looking for an easy trip.

“Can’t this thing go any higher?” the filly whined as they drifted towards Canterlot over the rolling hills outside Ponyville. The thrill of their initial takeoff had long since worn off. “I mean, this is cool and all, but it’s not really what I thought it’d be. Have you ever seen Rainbow Dash fly? She could’ve flown to Canterlot and back a dozen times by now!”

“Hey, if you wanted to fly the pegasus way, you didn’t have to hitch a ride with me,” Cherry said. Part of her couldn’t help but agree with the filly, though. What was she doing? Was she flying, or just going through the motions? Earth ponies hadn't spent centuries perfecting the art of ballooning just to glide lazily along whatever winds the pegasi allowed for them.

A cross-breeze blew across her face, and it brought with it an answer: the big sky.

Most ponies on the ground knew nothing about it, and those who did would never request such a trip. But Scootaloo, Cherry had decided, was no ordinary pony content with ordinary flying. The filly was hungry for something more than just a quaint balloon ride, and though Cherry didn’t know what drove that hunger, she knew what it was like to want to push the envelope.

She saw some of herself in Scootaloo, as different as they were.

“You know,” she began, “you’re right. Ballooning can be boring when you’re flying on all the boring old winds. Don’t get met wrong, it’s really helpful that the pegasi maintain such orderly winds for us to use, but it’s not very exciting, is it? I guess I’ve gotten so used to flying on them I forgot that. So, do you think you’re tough enough to fly the big sky?”

Scootaloo’s ears perked up. Cherry had gotten her attention. “The big sky? What’s that?”

Cherry pointed a hoof upwards. Overhead, the deep blue sky of autumn fanned out as far as the eye could see, and then some. High up, higher even than where the pegasi tended to the clouds and Equestria’s weather, was what earth ponies had called the big sky since time immemorial. Huge and wild clouds, worked and shaped by the hoof of nature rather than in a weather factory, drifted like whales through the ocean. It was as untamed as the Everfree Forest, and limitless in its expanse.

“You pegasi can fly pretty high, but not even you can fly that high on your own. I guarantee not even Rainbow Dash has been up there. It’s tough for a balloon to soar that high, but it’s downright impossible to get there on wings. Up there the air gets real cold and the winds get real wild. You can get blown any which way. You might even fly right into a storm, or get lost in a cloud as big as a mountain. But if you want something exciting, it can't be beat."

One look at Scootaloo’s face and Cherry had her answer. “Um, Cherry, I have one question,” the filly asked sheepishly before they began their ascent. "Will you show me how to fire the burner?”

The climb into the big sky was an arduous one. Scootaloo — with Cherry’s guidance — burned through a painful amount of the balloon’s gas supply on their way up. As the air grew colder and more turbulent around them, their ascent slowed. Cherry could feel her purse lightening with each pull Scootaloo gave on the burner cord, but she tried to chase the thoughts from her mind. She had left her job far below; she was flying, now, and she felt as light as a feather.

At least that was what she told herself.

It had been so long since she had flown that high she had almost forgotten what it was like — almost. Most of her work was spent flying routes between cities, close to the ground. Nopony ever had a reason to fly up into the wild reaches of the big sky, where not even pegasus magic held sway. Most ponies shunned and feared untamed nature, preferring the orderly pegasus skies; Cherry Berry found freedom in it.

And, judging from her enthusiasm, Scootaloo did, too.

The long flight gave the filly plenty of time to bombard her with more questions, but her chattering no longer annoyed Cherry the way it had on the ground. In fact, she welcomed talking to a kindred spirit.

“You fly for your job, right? It’s what you do?”

“Yeah. A lot of odd jobs. All the big shipping happens on airships, but a little balloon like mine can make supply runs to places where the big ships can’t land or dock.”

“Well how come your cutie mark isn’t related to flying?”

Cherry glanced at the cherry stem on her flank. Scootaloo was right; her special talent wasn’t in flying, it was in cherry farming. Flying didn’t come naturally to her.

How could it, as an earth pony?

“Ever since I was a filly, I’ve always wanted to fly. Maybe something’s wrong with me but I’m more comfortable up in the air than picking cherry trees.” Cherry laughed.

“So, you mean your job is flying and it isn’t even your special talent?” Scootaloo whistled. “I’ve never heard of a pony going against their cutie mark like that.”

“Cutie-schmootie. If my cutie mark is scared of heights, it can stay on the ground. I’d rather be in the clouds.”

Scootaloo fell into quiet contemplation; her eyes were unfocused and gazing at something Cherry couldn’t see. A silence fell over the two, and Cherry’s own mind began to drift. “I remember one afternoon, when I was a little filly, probably even younger than you, Cloudsdale passed over my village. I lived in the middle of nowhere; I mean my village would make Ponyville look like Manehattan. I had never seen a cloud city before.”

Even as she spoke, Cherry could picture the great city as clear in her mind’s eye as the day she had first laid eyes on it. “I remember I kept thinking it had to end, but it didn’t. It just kept going, from horizon to horizon. I thought it was bigger than all the rest of Equestria combined. I had never seen so many ponies in one place before; there must have been thousands of pegasi flying around up there. It was like looking up at another world. When I finally grew up and became a balloonist, Cloudsdale was the first place I visited.”

“You saw Cloudsdale? I’ve always wanted to go there someday!” Scootaloo beamed. “Do you remember anything else about it?”

“You mean you’ve never been? Not even when they parked it over the Highland Reservoir for that water funnel? I remember every pegasus in town had to help them funnel the reservoir up there.”

“I was, uh, too young to help with that,” Scootaloo said, looking away.

Cherry continued, “Cloudsdale is a hundred times cooler up close than from the ground. The acropolis — that’s the big cloud fortress where all the old pegasus commanders used to rule their legions from — is bigger than Canterlot Castle. It might even be older than Canterlot."

“There’s canals between the clouds that are so big you could float a whole row of balloons like this one through, side by side. And the weather factory there puts any of the workshops in Manehattan to shame. Cloudsdale alone makes almost all of the clouds for Equestria. They say the factory works around the clock and has never closed, not even for a day, since it first opened.” Cherry found herself half-wishing to see the city again. “A little pegasus like you really oughta visit. Have your parents take you next time they take a trip. I’m sure they must go there sometimes, every pegasus I’ve ever known does.”

Scootaloo didn’t respond. A melancholy settled over Cherry, unprompted. “You have no idea how lucky you pegasi are,” she said, unbidden. “I would have given anything to be born a pegasus. You have the whole world at your wingtips.”

“Well, being a pegasus isn’t always all it’s cracked up to be,” Scootaloo said at last. “The world feels pretty small to me. I’ve barely ever left Ponyville. I wish I could see the rest of Equestria, but…” she trailed off.

Cherry understood, or thought she did. “I had always wanted to fly, I had always loved looking up at the sky, but after I saw Cloudsdale that first time it took over my life. I wanted to visit those cities in the clouds, and see the world from up there. I wanted to be able to just fly over any mountain or ocean as easily as trotting across a meadow. Everypony told me I couldn’t, of course. Pegasi thought I was nutty, but even other earth ponies thought I should ‘mind my business’ and that the sky was ‘for pegasus ponies only.’”

But Cherry hadn’t minded her business. Even though she had only been a filly, she was relentless in the pursuit of her dream. She dug through her village’s paltry library, and when she couldn’t find any information on how to fly without wings, she had saved up her bits and sent away for more books. Her labors finally bore fruit, and she discovered that she wasn’t alone; earth ponies had been pioneering ways to fly — not through magic, but engineering — since long before the pony tribes ever united and Equestria was ever formed.

“I left home, traveled until I found a balloonist willing to take me on as an apprentice, and never looked back. Those were some good times,” Cherry said.

“What happened?”

“Well, my apprenticeship was fun, but after it ended came work. I wanted to fly all the time, and the only way to do that was to take jobs flying. Nopony was gonna pay me just to sail around the sky all day. It isn’t always fun — hay, it usually isn’t — but every now and then I get the chance to fly up high and remember what made me want to do this all in the first place,” she said.

She gave Scootaloo a reassuring wink, but couldn't shake the strange melancholy that still lingered over her. She tried to focus on the simple pleasure of flying, on her memories of her younger days, but her thoughts kept circling back to the same worries which had been haunting her: work, bits, winter.

The big sky was uncharted and ever-shifting. Weather almanacs and sky charts were useless, as the natural winds did not follow any careful pegasus planning. Cherry had to trust her instincts to guide the balloon; earth ponies called the art of sailing a balloon along uncharted winds steerage, she told Scootaloo, and it relied more on intuition and improvisation than any hard and fast rules.

Unfortunately, as she discovered, her sense of steerage was rusty. She really had gotten too accustomed to flying the wind corridors close to the ground. Those she could fly with her eyes closed, but it had been a while since she’d had to really focus and let the force of the winds guide her along. The balloon was pushed and pulled and swung around in aimless circles as she struggled to catch a strong wind to lift it out of the chaotic currents it was trapped in.

“I got this,” she told Scootaloo, her words ringing with the tinny sound of false bravado. She couldn’t bear to let the filly down — she couldn’t bear to let herself down, either.

It's just like the good old days, she told herself.

“Hey, look at the way those clouds are drifting.” Scootaloo pointed towards a colossal cloud bank that was blotting out the sky north of the balloon. The wall of clouds, muted and gray rather than the pristine white of pegasus clouds, rolled and clashed together like Wonderbolts jockeying for position in a race. “The winds are blowing them west, I think?”

“Yeah, we could probably catch that same wind, but I’m struggling to get much higher,” Cherry grumbled. “Even with the burner on full blast it’s tricky maintaining altitude.”

Scootaloo paced the basket while Cherry continued to finick between the burner and the parachute vent, alternating heating the air in the envelope and releasing it, trying to break free of the current they were trapped in.

“There!” she cried and pointed over the edge of the basket railing. “There’s some clouds beneath us. If we can just — “

“ — Catch an updraft and fire the burner at the same time, it might be enough. Good thinking, kid.” Cherry let the balloon descend at an angle toward the clouds which had gathered below them. It was a small cluster of stray pegasus clouds, drifting and glittering in the sun. The vapors rising off the clouds converged into a column of warm air which the balloon could ride for an added lift.

Buoyed by the updraft, Cherry gave the burner one last sustained pull. The balloon rose, and rose, and rose just far enough that it broke through into the higher winds of the big sky. The balloon caught the westerly wind, and they were away.

“That was pretty smart thinking!” Cherry called over the roar of the wind as the balloon picked up speed.

“Like you said,” Scootaloo said proudly, “it’s more of an art than a science!”

I’m starting to like this kid, Cherry thought.

Having finally broken through the turbulent zone between the end of the pegasus sky and the beginning of the big sky, the balloon was pushed higher and higher. The basket rocked back and forth, and Cherry wobbled for a moment before her muscles remembered years of previous flights and she steadied herself.

She looked over at Scootaloo. The filly was perfectly sure-hoofed; the violent motion of the basket didn’t seem to bother her at all.

“You’re a natural,” Cherry said, nodding at her. “Took me more than a few trips before my knees stopped shaking.”

The bumpy flight may not have bothered Scootaloo, but the altitude did; the filly was shivering in the cold, thin air. She clutched her forelegs tightly across her barrel and pinned her ears close to her head.

“Here,” Cherry said. She pulled her cap off and fastened it around the filly’s freezing ears. It was far too big for the little pony, but Cherry cinched the ear flaps closed under her chin to keep it in place. “If I had known we’d be flying the big sky today I would’ve packed a scarf.”

“Sorry,” Scootaloo said. “It was my idea.”

“Don’t worry about it,” Cherry said and smiled at her. The cold lashed her face and stung her eyes. “I haven’t had this much fun in a long time.”

Cherry’s balloon raced over Equestria, skirting along the edges of the great clouds that wandered the big sky. The sun was so close, Scootaloo said, that it looked like you could reach out and touch it. Beyond the clouds, the sky stretched on forever in all directions; an endless ocean with not another single ship in sight.

Below them, the central valley of Equestria appeared as little more than a quaint ring of mountains. A shining white needle — Mt. Canterlot — marked its southern edge, while a cloud hovered nearby over the northwestern mountains.

“That’s Cloudsdale,” Cherry said, pointing down at it. “See? Didn’t I tell you even pegasi look small from up here?”

“It doesn’t even look like a city!” Scootaloo laughed. She squinted. “It looks like one of the little clouds the weather team in Ponyville uses for rain.”

“I told you. How does it feel to be higher up than anypony else? Rainbow Dash could never cut it up here, but don’t tell her I said that. And hey," Cherry added, "you’re closer to Princess Celestia’s sun than even she is."

“Everything looks so different,” Scootaloo said. “It’s so small, but there's so much of it.” She glanced to the east, where the waters of the ocean could be seen. “I feel like we could go anywhere.”

“We can!” Cherry gestured around them. “You don’t think us earth ponies call it the big sky for nothing, right?”

“I’ve lived in Ponyville all my life,” Scootaloo said, “and from down there I always thought Cloudsdale was as high as anypony had ever gone. I thought being up there, flying around with all the other pegasus ponies, was the best thing that could ever happen to me. But there’s so much more, isn’t there?”

“A lot more,” Cherry said.

A sudden gust of wind blew the balloon off-course and it careened through a cloud. A fine mist filled the basket and Cherry felt a spray of ice cold water across her face and coat. Scootaloo yelped in shock.

The balloon floated aimlessly on, lost in the dark interior of the cloud. An occasional sunbeam pierced the gloom, only to be extinguished just as quickly. Scootaloo pulled Cherry’s goggles down over her eyes, but they fogged over instantly.

After an agonizing flight, the balloon finally burst out of the cloud and back into the cold sunshine and whipping winds. Both ponies were soaked to the bone, and the interior of the basket was slick with ice-cold condensation.

“You know,” Cherry offered as she shivered violently, “maybe that’s enough of the big sky for one day. Maybe we should head back down.”

Scootaloo’s teeth were chattering, but her eyes blazed with adrenaline. “Yeah, I'm thinking you're probably right.”

Cherry grinned. It had been an adventure watching Scootaloo touch the sky — not just the tidy, well-maintained sky of her fellow pegasi, but the real sky, the sky that existed even beyond their reach. She had discovered the real freedom of flying, just like Cherry had years ago.

But a question still lingered in her mind: why did a pegasus want to take a balloon ride in the first place? As she pondered it, more thoughts resurfaced. Cherry remembered the entire reason she had taken Scootaloo along was because she needed the filly's money, as sad as that was.

She didn't want to think about it. Making ends meet was a worry for the ground, and she wanted to fly. What would they do next? Cherry snorted; she wasn't ready to return to Ponyville.

“We don’t have to head back yet if you don’t want to,” she said, her voice more eager than ever before. “What do you say we go pay the unicorns a visit?”

Cherry guided the balloon as it circled the summit of Canterlot Mountain, descending in a lazy spiral back and forth between opposing winds. At last it came to float side-by-side with the snowcapped peak.

The top of the mountain may have looked like a fine point from the ground, but from the air it took on a different appearance. The top of the mountain was the size of a small meadow and covered in a deep layer of pristine snow. At the edges, the summit’s ridges gave way to sloping, slate-gray cliffs that stretched away to the valley floor. The white and gold spires of Canterlot gleamed against the mountainside hundreds of feet below them; from on high it looked like a dollhouse rather than a royal city.

“Wow! It stays snowy up here, even in the summer?” Scootaloo asked, leaning over the railing to study the snowy peak.

“You can thank the pegasi for that. I think they keep a warehouse full of snow in the city during the summer for maintaining it. Gotta keep it looking nice and majestic for the princess and all the nobleponies.”

The snow burned white as it reflected the sun overhead, and Cherry had to shield her eyes against it. “I’ve always loved views like this,” she said, turning away and gesturing across the valley. From their vantage point, they could see to the Unicorn Range in the west. “We may not be up in the big sky but there’s still a lot to see. I like flying by mountaintops — they’re the closest point between the ground and the sky, but you never see any ponies living on ‘em.”

“I think living on top of the world would be pretty awesome!” Scootaloo laughed and buzzed her tiny wings. She stared down at the royal castle below them. “We’re higher up than Princess Celestia! How many ponies can say that?”

“If you think the view here is nice, you should see Mt. Everhoof. Now that’ll take your breath away.” A vision of the mammoth mountain flashed across Cherry’s mind; she was pretty sure all of Mt. Canterlot would fit into its shadow.

“I spend so much time flying, sometimes I forget to look around,” she continued. “Everything looks so different from up here, doesn’t it? When I was a filly, looking up at Cloudsdale felt like I was looking at another world. When I’m flying, I guess it feels just like that, except the other world is the ground.”

The ground — she didn't want to think about the ground. Cherry wished she hadn't mentioned it. For a moment, she felt a surge of anger at herself; why couldn't she just enjoy a nice flight? Why did her dumb mind keep trying to prod her about all the problems waiting for her back on the ground?

A train whistled in the valley as it crawled along the tracks toward Canterlot. From their spot at the mountaintop, It looked like a tiny gray worm moving inch by inch across a lawn.

“Hey, Scootaloo, uh” — Cherry flicked her ears — “it’s been so long since I just flew for the fun of it I’d almost forgotten what it’s like. You know, I’m kinda glad you asked me to bring you along.”

“Really? You mean flying gets boring? How could flying ever be boring? It’s the coolest thing in the world!” Scootaloo gestured around them. “Or is it the raddest? Awesomest? I can’t remember, I’ll have to ask Rainbow Dash which it is.”

Cherry tensed at the question. Of course flying had its problems. Was Scootaloo really such a silly filly that she couldn't see that?

“Flying’s fine,” she said slowly, “it’s all the stuff that comes with it that isn’t so much fun. It's a lot of work, and everywhere you go ponies look at you funny, and you can't always pay your bills, and..." Cherry let her voice trail off. She was ashamed that she had almost begun ranting.

“You make it sound so bad, but I think ballooning’s awesome,” Scootaloo said, “and I think you’re super lucky that you get to do it.”

Cherry grinned. The filly had no idea how stressful it could be. How could she? She was a pegasus. Flying would never be work to her. “I think you’re the first pegasus I’ve ever heard say that."

A breeze raced over the mountain, shaking loose some of the topmost snow and sending it dancing and sparkling in the air. A small shadow passed overhead, darkening the sparkling white snowcap, and both ponies turned their heads.

“Hey look, a cloud!”

Scootaloo was right: It was a cloud, but, Cherry thought, not much of one. It was more like a loose thread of a cloud, frayed and torn off from a much larger one. Cherry had seen many wisps like it; the skies around Cloudsdale could be lousy with them at times.

The wisp fluttered and twisted loosely in the air like a pale ribbon, too jagged to float gracefully. It wrapped itself along the side of the balloon’s envelope and sank down until it was floating next to the skirt. Scootaloo pulled the oversized goggles down over her eyes. “I can just about…“

Before Cherry could stop her, the filly hopped, then hopped again, then leapt up into the air, buzzing her wings as hard as she could. She reached just high enough to throw her forelegs atop the wisp and pull herself up so she was sitting on top of it.

“Nice one!” Cherry called up to her.

“This is nothing compared to those big clouds higher up,” Scootaloo bragged. “I got this.”

The lopsided cloud drifted away from the balloon. Scootaloo clutched its surface tightly at first, but before long she grew bolder. She rose to her hooves, even though her legs were shaking, and hopped up and down on it. It curled and sagged under her hooves. “Most of the clouds in Ponyville are so high up I never get to walk on them! This is so cool!”

The breeze that had carried the wisp across the peak stirred and swelled into a gust. Even with Scootaloo weighing it down, the cloud began to thrash and tumble through the air wildly.

“H-hey!” Scootaloo let out a shout. She collapsed on top of the cloud again, clutching it with all four legs as it whirled farther and farther out from the balloon.

Cherry let out a chuckle at the filly’s fright.

“Alright, I think the cloud’s in a hurry to get somewhere. Just fly on back and we’ll be on our way, too.”

But Scootaloo didn’t budge.

“I…I…”

For a brief moment, the wisp stabilized and Cherry caught Scootaloo’s gaze through the goggles; the filly’s eyes were wide with panic.

And then the cloud was blown over the mountain’s edge and out into the open sky.

Scootaloo rode the wisp like a cowpony in a rodeo. The thin cloud was so fragile Cherry could see it shedding more and more tufts from its edges as it veered away. What was the filly getting playing at?

Cherry felt a familiar harshness come over her. Their flight had been fun, sure, but she didn’t appreciate whatever game Scootaloo wanted to play. She reminded herself that the filly wasn't her friend; she was a passenger. A paying passenger.

“Dang it, Scootaloo! Stop messing around already. Get back here!” She yanked on one of the turning vent cords to swing the basket around and keep the filly in front of her.

If Scootaloo heard her, she ignored her. The filly would not leave the cloud to fly back to her. Cherry felt her face hardening; the silly little pony was going to ride off on a cloud and leave her there.

This is why I don’t get along kids, Cherry thought, her simmering anger breaking into a boil. If she wants to fly off, I should let her. But her parents probably wouldn’t appreciate me letting her get blown off course to Celestia-knows-where.

Her mood soured once again, Cherry fired up the burner and caught the same wind that had ensnared the wisp. Everything was going fine, she thought. I was having such a nice flight.

That’s what I get for forgetting this is a job and not a joyride. Well, not anymore. Back to work.

Scootaloo was a distant speck, but the cloud’s erratic movements were slowing it down. Cherry’s balloon caught up to it quickly.

By the time she pulled the balloon up alongside the cloud, all that remained of it was a patch barely big enough to support Scootaloo, and Cherry knew that would give way soon and the cloud would evaporate into nothingness.

“Alright, it looks like your ride’s kaput, so will you get back in the balloon now so we can get going?” she asked sharply.

Scootaloo whimpered. She had buried her face in the cloud and was shaking.

“Scootaloo!” Cherry barked, “I’m tired of chasing you around! Now come on already!”

Cherry leaned over the basket railing and scooped the filly up in her forelegs. She tottered backwards on her hind hooves and set Scootaloo down on the floor of the basket. The filly was curled up into a ball.

The wisp, disturbed by the sudden movement, broke apart into a few strands of vapor that quickly disappeared into nothingness.

Exhausted, Cherry let herself slip down to the floor next to Scootaloo.

“What was that all about?” she huffed. “Don’t do that again. I’m not your foalsitter, you know.”

“I’m sorry,” Scootaloo said in a small voice. The filly slowly unwound herself and sat up but wouldn’t look at Cherry.

“Was that some kind of joke?” Cherry grumbled. “Making me chase after you like that? That was a really stupid game.”

“It wasn’t…I know…” Scootaloo said. She dabbed at her eyes. She was trying not to cry.

“You know not all of us are pegasi, right? You can’t just go flying off like that.” Cherry rubbed her eyes.

Cherry climbed to her hooves and pulled one of the turning vent cords to swing the basket around in the direction of Ponyville. “I think that’s enough flying for one day. I’m taking us back to Ponyville. You can find somepony else to chase you around.”

“The cloud — “

“I don’t want to hear it, kid. I've had a long day."

“ — I was scared — “

“You pegasi think that just because you have wings, and can fly, that — ”

“I can’t fly.”

Cherry’s words caught in her throat. She turned and stared, dumbstruck, at Scootaloo. The filly was still avoiding her gaze; she was rubbing one foreleg meekly against the other.

“I can't fly, okay? When the cloud flew away from the mountain, I couldn’t let go. I’m sorry. It’s my stupid wings.” Scootaloo scowled. She bit her lip so hard Cherry thought she might start bleeding. “They don’t work because they’re stupid and I’m stupid and I’m sorry I ruined everything.”

Scootaloo craned her neck over her shoulder and glared at her little wings so hard Cherry thought the filly would tear them off if she could. The filly angrily undid the flaps on her aviator cap and tossed it aside.

A pegasus with odd little wings who’d rather take a balloon ride than fly on her own. A pegasus who never got to walk on clouds or help out the other pegasi back in Ponyville. A pegasus who’s never been to Cloudsdale.

The realization froze Cherry to the bone; it was colder than the freezing cloud she had braved only a short time earlier.

She just wanted to know what it's like to fly, she thought bitterly and sank down onto the floor next to Scootaloo. And I blew up at her over a silly little cloud? What’s wrong with me? Who does that?

Except, Cherry realized, it wasn’t the cloud. She had been pushing the dread away all day, but it was still lingering in the back of her mind. All the flying and adventure had been little more than a distraction from her real worries.

She had been trying desperately to convince herself otherwise, but Cherry was still overwhelmed by the looming failure that hung over her. She had been trying to fly away from her problems, as if she could outrun winter forever. Maybe she had even succeeded for a time, but she had once again come crashing back down to earth.

But what about Scootaloo? What about the way she was smiling up there? The look on her face when we took off? The way she wanted to know everything about my balloon? About flying?

That wasn't a distraction, Cherry told herself sternly. That was real.

She reached out and laid a hoof on Scootaloo’s shoulder. The touch caused the filly to give up trying to be brave and she cried openly. She leaned against Cherry, and the earth pony wrapped a foreleg around her and pulled her close.

“I’m sorry,” Scootaloo echoed again.

“Hey, hey. It’s okay.” Cherry wanted to apologize, wanted to tell the filly that it wasn't her fault, but nothing came to her.

Cherry Berry wasn’t the most well-read student of Equestrian history, but even she was familiar with some its darkest moments: how the pony tribes had nearly wiped each other out through their disunity during the long winter of the windigos, how the spirit of chaos Discord had turned the land into a madhouse with ponies as his helpless playthings, how Nightmare Moon had nearly plunged all of Equestria into eternal night just to spite her sister Princess Celestia.

Somehow, making one filly cry felt like a greater crime than all of those historical evils combined. And she would not let that stand.

“I’m sorry, Scootaloo,” Cherry said softly. “I didn’t know about your wings. I wish you had told me — I feel so stupid. It's not your fault.”

Scootaloo’s tears slowed to a few sporadic sniffles. “I don’t like to talk about them,” she said. “Ponies make fun of me because I can’t fly.”

"I doubt any of those ponies have flown half as high as you did, today."

Scootaloo gave her a weak smile.

Cherry stood up and fired up the burner once more. The balloon, which had been drifting back towards Ponyville, rose and caught a warm wind. They began to double back north, back towards the valley.

It was a wind, and a route, that Cherry had flown many times before.

At that moment, she may have been the scummiest pony in Equestria, but it would be a cold day in Tartarus before Cherry held any pony back from flying.

Not on my watch, she thought. I can't go back and do this for myself, but I can still do it for her.

Scootaloo wasn’t looking outside the balloon, but she could still feel the abrupt change in direction. She looked up at Cherry through bloodshot eyes. In a small voice, she asked, “Where are we going?”

"I want to show you something."

Cloudsdale loomed over the valley, loftier even than the peak of Canterlot. The tall spires and friezes of the skyline shimmered and waved ever so slightly in the sunlight and breeze, mirage-like, while the earth far below was plunged into shadow by the city’s great wingspan. Rainbow flocks of pegasi, as thick as starlings, flowed in and out of the canals between the clouds in constant motion; blood coursing through the great colossus’ body.

The cloud city had not been built for flying machines, and most of the canals, especially towards the heart of the city, were so narrow only ponies might pass through them. But Cherry had made many trips to the city before, and she skirted the balloon around the outskirts until she found a wide shipping lane for balloons and other airships.

“I'm sorry nopony ever brought you here before, but I wanted you to see this place,” Cherry said as the balloon passed beneath a bridge flanked on each end by enormous cloud statues of pegasus legionnaires. The pair of statues were clad in their traditional banded armor and crested helmets to proudly welcome travelers to the home of the pegasus ponies.

Scootaloo stared, slackjawed, at the statues. Their unfurled wings fanned lazily in the breeze, giving them the appearance of being alive. You could stack town hall and Ponyville General floor to roof and they wouldn’t even reach the same height, Cherry thought as they passed beneath the statues’ gaze.

The canal was thick with air traffic; the balloon floated by a regal-looking pleasure yacht of an airship, its deck dotted with a party of unicorns in the fancy dress of the Canterlot court. Ahead of them, another earth pony balloon glided along the passageway before coming to rest at a cloud wharf.

Scootaloo’s gaze roamed, first from the airships, and then up and down the rows of cloud buildings that lined the canal. Many of the buildings were rectangular halls lined with columns in the classic pegasus style, though a few newer constructions, influenced by earth pony and unicorn architecture, occasionally cropped up between the larger, older buildings.

The balloon floated to the end of one canal before wrapping around into another one. But Cherry hadn’t brought Scootaloo to the great home of the pegasi just to float in traffic; she gave the filly an encouraging nod, and Scootaloo gave the burner cord a pull. The balloon rose out of the canal to float over the top of the city itself.

They passed over a sea of white and blue clouds that stirred with countless ponies of every color. The walls of Cloudsdale rose and curled like cresting waves around the austere colonnades and sharp porticos of the city. After clearing the rooftops, they flew over column-lined plaza with a rainbow fountain in the middle. It was packed with ponies, many of whom gazed up at the balloon as it floated over.

It was a pegasus agora, Cherry pointed out — and far from the largest one in the city.

Ahead of them, a tower of cantilevered clouds rose from the heart of the city, each connected by massive columns. A spiral staircase, as wide as an avenue, ran along the outside of it. A rainbow pool atop the highest cloud spilled over the side into a waterfall; the waterfall had no end, but rather dissipated into a fine rainbow mist that caused all the air around the tower to shimmer with a faint iridescence.

“That’s the acropolis,” Cherry said, pointing at it. “We can’t land there but we can get pretty close.”

As she predicted, a pair of armored legionnaires flew out to wave them away. The balloon glided around the side of the tower; Scootaloo marveled at the procession of pegasi shuffling up and down its stairs.

On the other side of the acropolis, they came into sight of the city’s grand agora, where yet more pegasi — and even a few griffons — thronged. It was a vast plaza dotted with tents, stalls, and carts. Many ponies seemed to come to the agora for more than commerce, as well, and they gathered around speakers who stood at podiums or on raised platforms to deliver lectures. Traders and orators both shouted over each other for the attention of the crowds.

“Hey, whaddya say we pick up a souvenir?”

Setting a balloon down in the middle of a crowded agora was tricky, but Cherry managed with only a few sneers from the pegasi nearby. A kindly trader even permitted her to tether it to his stall. Whatever the pegasi around them were saying or thinking didn’t matter; her attention was fixed entirely on just one pegasus.

Scootaloo pushed the basket door open. Cherry gave her an encouraging nod, and the filly took her first tentative steps out of the balloon and onto the cloud pavement of Cloudsdale.

“I’m really here,” Scootaloo said so quietly Cherry almost couldn’t hear her over the din of the crowd. She flashed Cherry a smile; tears were welling up in her eyes, but they weren’t the shameful tears she had shed earlier over her wings. Her face was too fierce, too proud, for any shame.

“I’m really here!” she shouted with newfound vigor, and skipped away into the crowd.

Cherry leaned against the railing of the balloon and let a few of her own tears fall quietly onto the cloud below. She really didn’t want to lose a new friend and kindred spirit. And, even if Scootaloo never wanted anything to do with her again, she really, really didn't want to ruin the joy of flying for her.

It didn’t take long for Scootaloo to return. Cherry had just finished dabbing her eyes when she saw the filly galloping back towards her through the crowd.

She skidded to a halt in front of the balloon, breathless.

“This place is everything I ever dreamed of,” she gasped. “There’s so many ponies! And these clouds! Oh, I could spend all day here! I could spend my entire life here!” Scootaloo climbed back into the balloon. She gave Cherry a knowing smile. “But there’s a lot more to see out there, isn’t there? All my life I've dreamed about coming here to Cloudsdale. But now that I'm here, this is just the beginning! I want to fly all over Equestria!”

“You sure you want to leave?” Cherry asked. “You can stay. As long as the guards don’t run me off, I don’t mind waiting. It’s, uh, the least I can do, really. For earlier."

“Thank you, Cherry. Thank you so much.” Scootaloo threw her forelegs around Cherry’s own and squeezed. With her free hoof, Cherry reached down and patted the filly on the head.

“Sure I can’t buy you something? A snowglobe? Postcard?” Cherry asked.

“I’m fine, really. I got to go to Cloudsdale!” Scootaloo laughed as the balloon took off. “I’ve wanted to do this my entire life. And now it’s really happening!"

The balloon cleared the top of the crowd just as a pair of legionnaires began pushing through the crowd towards them. Scootaloo gave the guards a wave as they sailed off towards the outskirts of the city; the guards grumbled but did not fly after them.

The sky over the weather factory was full of pegasus teams hauling clouds. More cloud wisps, detritus from the factory, floated through the air all around them like streamers.

“I really hate those things,” Scootaloo said, and suggested going around.

Cherry caught a draft and flew the balloon along the opposite edge of the city. They passed over a stately arena; within, crowds were cheering as pegasi in brightly-colored jerseys flew laps through cloud rings. Outside, the arena was flanked by a complex of smaller racetracks and gymnasiums.

To Cherry it was nothing special, but Scootaloo recognized the place instantly, even though she had never been there before.

“That’s the Cloudisseum!” she shouted. “Rainbow Dash told me stories all about how she trained there when she was growing up. She even went to flight camp there!”

Cherry joined her in looking down at the Cloudisseum. A class of flight camp students — all pegasus fillies Scootaloo’s age — were practicing flying drills in the air above one of the tracks.

Ever since they had left the mountain, Cherry had been mulling over what to say to Scootaloo.

"You know, I was never meant to fly either. Look at me; I'm an earth pony. By all rights I shouldn't be up here, but I am. If I can fly when even my cutie mark doesn't want me to, I know you can fly no matter what kind of wings you have. I know how ponies talk. They don't know what it's like. But you can't let that stop you — when you want something, when you really want it, when you can't live without it, you'll figure out a way to make it work. Does that make sense?"

Scootaloo nodded resolutely, and Cherry caught the breeze that would fly them back home to Ponyville. Behind them, the flight camp students rounded the Cloudisseum and disappeared from view.

The sun was sinking behind the horizon when Cherry Berry and Scootaloo came into sight of Ponyville. A cold and clear night, the first night of fall, was enveloping all as the lights of the town flickered to life and illuminated the purple gloom with a welcoming orange glow visible from miles away.

The twists and turns of their flight — soaring the big sky, the chase around the mountain, the trip to Cloudsdale — hung in Cherry’s mind like the dying sunset in the sky. Their initial departure was distant and hazy; in reality, it had happened only just that morning, and yet in the gathering darkness it felt to her as if time itself had been compressed somehow, and they had been flying for much longer than that.

Just as they passed over the first few homesteads on the edge of town, Cherry saw a shadow zipping up towards them from the ground. It was a pegasus stallion with a dark coat; one of the members of the local weather team. She thought she recognized him from the group they had passed on their flight out of town that morning.

“Hang on, ladies,” he shouted, waving them off with his forelegs. “We got a late takeoff coming through. Only be a minute and we’ll be outta your manes.”

Cherry let the balloon drop into a holding pattern and she and Scootaloo watched a stream of colorful birds take off from a field outside Ponyville, flanked by pegasi guides.

“They’re gonna have quite a flight ahead of them,” she remarked. “Strange time to be taking off. Going all night?”

“Yeah, they should’ve been out of here hours ago.” The stallion cracked a disarming grin. “I’m afraid something like this always come up during Summer Wrap-Up. Always a late flight, or somepony ends up taking them any which way but south. Night flying won’t be easy compared to the morning flights but hey, flying’s flying, right? Not gonna let a little darkness get us off schedule.”

Cherry didn’t detect any malice in the stallion’s voice. She smiled and nodded, and he gave them a friendly wave before darting off again to join the migratory flight as it headed south, over the Everfree Forest.

Something held Cherry back from resuming their descent. As they watched the birds disappear into the darkness, she was finally able to find the words she had meant to say earlier.

“Hey, Scootaloo,” Cherry said and laid a hoof on the filly’s shoulder. “About earlier..."

“It’s okay,” Scootaloo said in a voice that sounded like she had said it a hundred times before, “you didn’t know.”

“No, I didn't, but I wasn't gonna talk about your wings.” Cherry let a few strands of mane fall over her eyes; she didn’t attempt to brush them away. "All day, while we were flying, I kept looking for something, anything. I've been doing this for so long I just wanted to go back to what it was like to be young again and not have to worry about how I'm going to pay for my next tank of gas."

“But I can't do that. The sky's changed, and so have I. I can't just fly away from my problems and pretend like they don't exist. I have to learn how to fly with them, even when it's hard work."

"That sounds sad," Scootaloo said. "Don't you still like flying? I mean, you still want to do it, right?"

Cherry smiled. "Oh, of course! But it's different. I guess when you're older you'll understand. I thought I could just keep flying for myself, forever, but that wasn't really what I wanted. But watching you up there? That was the most honest fun I've had flying in years. You're a natural, Scootaloo. Maybe you can't fly like the other pegasi, but the sky's a big place and you deserve to be up there just as much as any of them."

“Nopony's ever told me that,” Scootaloo said. "Not even Rainbow Dash."

The bird migration was out of sight, but the balloon had yet to resume its descent. Scootaloo looked up at Cherry in the darkness. “I think earth ponies deserve to be up there, too. I'm glad they learned to build things like altimeters. I never knew there were so many different ways for ponies to fly."

They sat in silence for a long moment.

"I just wish today wasn’t over, you know? It feels like there's so much more left to see. There's so many places to go. Cloudsdale was cool, but I want to see what's past Cloudsdale.”

“Hey, cheer up,” Cherry said and slapped her on the back, “You know where to find me, and I’ll have a lot of free days this winter. It isn’t, uh, exactly my busiest season. We could do this again if you want.”

“Are you kidding? I’d go ballooning every day if I could!” Scootaloo buzzed her wings happily, but she was quickly overtaken with a glum look. “But it isn’t that. I had to work all summer just to save up enough bits to pay for the flight today. I worked so hard, I barely even got to see my friends ‘cause I was spending all my time sweeping Filthy Rich's store. But, hey, maybe we can do this again next year, huh?”

So that’s where she got all those bits from, Cherry thought. She didn’t say anything, but her eyes shifted to the purse resting in the corner of the basket. The money would go a long way come winter.

The words she had spoken to Scootaloo echoed in her skull: even when it's hard work. With a sigh, Cherry Berry pulled the parachute vent open, and the balloon began to descend once more.

Pony feathers, she thought.

“Hey, Scootaloo! You forgot something!”

It was well past dark by the time Cherry landed and tethered her balloon. Scootaloo had already disembarked and was plodding away into the darkened town.

“Wha—“ Scootaloo turned and had just enough time to catch her bit purse in her hooves as Cherry tossed it back to her. “But I thought you charged for flights!” she shouted, dumbfounded.

“Charge?” Cherry shrugged.

“You said flying’s expensive, and trips aren’t free. I’m pretty sure that was the first thing you told me, actually,” Scootaloo retorted. She looked from Cherry to the purse, then back to Cherry. Finally she relented, shrugged, and stuffed it back into her saddlebag.

One last, lingering blot of dread welled up in Cherry’s chest. Just think of the job. You need the bits. You’ll have to take a normal job down on the ground to get through the winter. Just take them. Come on, Cherry, you’re making a mistake.

“Oh, yeah,” she said, not trying to hide her grin, “that’s just for passengers, though. I’d never charge an apprentice balloonist for flying lessons. That is, you know, if you want to learn.”

No, I’m not.

Even in the darkened street, Scootaloo’s face lit up brighter than Celestia’s sun. Despite everything, it had been a pretty good day for flying.

“Hey, Scoot, I think you let too much heat out of the parachute vent. We’re descending a little too quickly. If you pull the burner we can — ”

“Are you kidding? I totally got this. Just watch!”

“Scoot, I really think — “

Cherry Berry’s balloon — her pride and joy, her loyal companion wherever she went — landed with an awkward thud against the roof of the Ponyville schoolhouse and scraped along the side, shearing off a line of shingles as well as gouging a deep scratch into the side of the basket. It slammed into the school’s bell tower and the impact staggered both Cherry and her young protégé. Scootaloo caught Cherry’s glare, blushed, and tugged her brand new, filly-sized aviator cap and goggles as far down her face as she could to hide her embarrassment.

Their crash landing had caused a gaggle of foals, along with their teacher, Ms. Cheerilee, to come outside in search of the cause of the racket.

“Scootaloo!” Cheerilee shrieked at the sight of her student attempting to untangle a balloon from the school roof. The schoolteacher pinned her ears and pressed her hooves to her head in disbelief. “What in Equestria are you doing?”

“Ya always gotta make an entrance, don’tcha, Scootaloo?” Apple Bloom, one of Scootaloo’s best friends, hollered.

“Woah! She’s flying a balloon!” a young colt said and whistled. “That’s so cool! It’s huge!” A chorus of voices rose from the class, echoing his excitement.

“Can you take me for a ride?” another foal shouted.

“Ballooning’s serious business!” Scootaloo answered in her gruffest Cherry Berry impersonation. “No free rides!”

Cherry Berry tapped Scootaloo on the shoulder. “Better not keep your adoring fans waiting. Or your teacher. Just because you’re training to be a balloonist doesn’t mean you can’t skip out on your other lessons,” she said. Her voice was gruff, gruffer than Scootaloo’s, but not without a hint of mischief.

Scootaloo cinched her saddlebag around her waist and pulled her goggles down over her eyes.

“Look out below!” she bellowed. The filly climbed up the basket railing and jumped out. She slid down the slanted roof of the schoolhouse, sprang off the edge with a push of her hooves, and buzzed her wings madly. Her trick worked; her wingbeats slowed her fall, and she landed safely on the ground amidst the throng of schoolfoals. They pressed in about her and bombarded her with a cacophony of questions while the long-suffering Cheerilee shook her head disapprovingly and began herding them back inside.

Scootaloo might not have mastered all the technical parts of flying down pat, and her steerage skill still needed some work, but she had a certain sense of style that Cherry was sure would carry her a long way up in the air. After all, she thought, ballooning was an art, and artists needed style.

“I’ve gotta get her back,” Cherry called down and gave a tug on the burner cord. Scootaloo lingered by the schoolhouse door to wave up at her. “You want to practice landings again after school? And maybe not, uh, on the school. Sorry for the ruckus, Cheerilee!” Cherry gave a rueful wave to the schoolteacher as the balloon departed.

“You know it!” Scootaloo shouted before Cheerilee finally wrangled her through the door and the two disappeared into the schoolhouse.

The damage to the schoolhouse wasn’t anything she and Scootaloo couldn’t patch up in an afternoon. The balloon was another matter; the cut that marred the basket would take more work to hide. Cherry decided it was a good time to start training Scootaloo on repairs as well as flying.

Not that she was in any hurry; the scratch was a little unsightly, but Cherry wasn’t as angry about it as she thought she would be. In fact, she thought, it lent the balloon a little bit of character.

With Cherry steering it once again, the balloon ride back home was much smoother than Scootaloo’s brave but rocky flight to school. Cherry floated low over the thatched roofs of Ponyville, admiring the fallen leaves as they danced on the cold autumn wind. The Running of the Leaves had kicked autumn into full swing, but Cherry knew it wouldn’t be long before even autumn faded, just like the summer had, and winter settled over the land.

Winter would be a slow season with little work. She would almost certainly have to pick up a job on the ground to cover the shortfalls in her budget. But the prospect didn’t trouble her the way it had before; whatever it took, whichever compromises she needed to make, she would still fly. Her obligation was no longer just to herself — she owed it to Scootaloo to keep flying, no matter which way the winds of her life were blowing.

And even if Scootaloo never rode the winds the same way Cherry did, it didn’t matter: there was room enough the big sky above them for each and every way to fly.

Author's Note

Hey, if you read through to this point, big thanks for reading my humble (first) fic. I’ve been a fan of MLP for years and was always keen to try my hand at writing fanfiction but it never really happened for a variety of reasons.

Anyways, I finally decided to get off my butt and scratch it off the ol’ bucket list. I had no idea what I was doing writing this and there are certainly a few sections that could use some refinement but for what it’s worth it was a lot of fun getting lost in my own little world for a time. I hope you got something out of your time with this fic as well.