Actions

Work Header

Dean Winchester's Guide to the Appalachian Trail

Summary:

On the heels of his father’s sudden death, Dean makes the impulsive decision to hike the Appalachian Trail in hopes that it will disconnect him from the world and his grief. However, soon after Dean meets the mysterious Castiel on the trail, hikers begin to disappear, and as Dean hikes more and more miles, it becomes clear that something lurks deep in the woods—an evil whose true nature Dean and Castiel must unravel before it’s too late.

Notes:

I'm so excited to be posting this for the second year of AURBB!!
The story has been on my mind ever since I saw Hawk's gorgeous prompt, and researching for it/writing the draft has been a THRILL and a journey. I've always been an avid hiker (nothing so far as the Appalachian Trail, but one day), so it was really fun to inflict some of my personal experiences onto Dean. Hawk, you've been a wonderful partner to work with, thank you for making the experience so lovely and for sharing the brainstorming on Appalachian Trail facts and experiences! Thank you also to FriendofCarlotta and Tiffany, both who beta read this for me and corrected all of my silly mistakes and, as always, had thoughtful suggestions to make the fic really make some sense. Thank you also to cosmicjuliet for reading this in the preliminary stages and offering advice, and for prosopopeya for your unhinged reactions as well as incredibly helpful mentions about the Virginian landscape and weather. Clearly, this fic took a village, and I'm grateful to all of you!

And please, for the love that ALL IS HOLY, you must you MUST look at the each piece of art that Hawk created for at least 5 minutes and not even BLINK. It's all so gorgeous and brings the fic to life in ways I never could!

Chapter 1: Tip #1: Don't Do It

Chapter Text

 

 

DAY 1
0 Miles/2,190


 

The quarter goes into the payphone, clinking on its way down into the abyss. A flat dial tone blares in Dean’s ear. Punching in the number, he listens to the ringing until the voicemail picks up.

Hey, it’s Sam. Can’t come to the phone right now, but I’ll call back as soon as I can. 

Chewing at the skin around his left thumb, Dean clears his throat and waits impatiently for the voicemail greeting to end. Not like he expected Sam to pick up, but—still. His eyes dart to the lobby of the lodge, where tall, grand windows display the mountain range. He’s not even sure what the mountain he’s supposed to be climbing today is called. Springer? No, that can’t be right. The grueling, godforsaken walk up the hill to this lodge had a sign at the beginning that said Amicalola Falls State Park. 

Maybe Springer Mountain is later in the hike. Maybe he’s already on the mountain, since yesterday it seemed like he walked up a steep enough hill to get to the freakin’ moon. 

Maybe Dean should actually read the map.

Beep. 

“Hey, Sammy, me again,” Dean says into the phone. “Not sure if you got my first message, I know it was kind of out of the blue, but… yeah. Just callin’ to tell you I made it to the lodge. It’s where all the ‘northbound’ hikers start, apparently, or at least that’s what the trail guide I bought told me. It was a buck fifty at Savers, so I dunno, maybe it’s not even accurate. But there’s a lot of people here, and a lot of them look like they just stepped out of an L.L. Bean catalogue, so I guess I’m in the right place. Did you know how much freakin’ equipment you need for a hike like this? I sure as hell didn’t. Rufus—you remember him, Bobby’s buddy, has that cabin in Montana and is a little rough around the edges, but a heart of gold that he’d sooner kill you than let you see—well, he lent me a lot of the hiking gear I needed. But I guess if you’re a, uh, thru-hiker or whatever, then you need special stuff? Like a camp stove. That folds up. Yeah, I know, I’m thinking it too: that thing’s gonna be trouble. Even after Rufus’s gear, though, I was still lacking in a few things, so I used some phony credit cards to buy that kind of stuff from a fancy camp store. Right out of the old John Winchester playbook.” 

He’s rambling. He knows he’s rambling. But he’s not even sure what else to say. What do you say to an estranged brother you haven’t talked to in months? And before that, years?

His time is probably almost up. Drumming his fingers against his leg, Dean sucks in a breath through his teeth. Happy, nervous chatter suddenly floods the lobby, and when he turns, he sees people coming down the stairs en masse, a collection of giant backpacks and wide-brimmed hats and jackets in shades of Patagonia blue and green. Dean, meanwhile, isn’t even completely sure that the boots he’s wearing are hiking-proof. 

“All right, well, the Happy Campers are here. Next payphone after this is twenty miles away, so I’ll update you then.” 

If you even answer. 

Hanging up the phone, he stares down at his pack. It lies on its side, burdened by the forty pounds of junk inside. He’s not even fully confident he packed enough food in there. Seems like his life has been full of impulsive choices lately: hiking a trail he knows nothing about, calling a little brother who probably wants nothing to do with him—just a couple of small examples.

“What the hell are you doing, Winchester?” he mutters, rubbing at his forehead with shaky fingers.

“Hey there pal, you okay?”

Dean nearly jumps at the voice. Two women have suddenly materialized next to him, weighed down by their heavy packs. The one who asked Dean the question is wearing a wide-brimmed hat, her blonde hair falling in her face, cheeks rosy and eyes bright like she’s already been on a hike for hours.

“You need some trail mix or something?” she continues. “Breakfast is the most important meal out here. If you’re already looking pale and green around the gills like you are, well, that’s no good start, I’ll tell ya that.”

“Donna,” the other woman says, a hand on her shoulder, “I think you’re scaring him.”

Donna laughs, the sound echoing across the lobby. “Sweetie, the only thing scary around here is low blood sugar.” She reaches into her khaki hiking pants, digs out a small Nutri-Grain trail mix package, and holds it out to Dean. “Take it, then thank me later.”

“I’m good,” Dean assures her, “seriously.” 

Donna doesn’t retract her hand, though. The woman next to her sighs and tells Dean, “I would take it. Don’t think she’s gonna back down.”

Desperate to end the interaction, Dean grimaces and takes the crinkly bag. “Thanks.” 

“First time on the trail?” the other woman asks. She tips her head. “Name’s Jody, by the way.”

“Dean,” he offers. “And, yeah. First time.” 

Donna smiles at him expectantly, and Jody waits with raised eyebrows. He realizes, with a sinking feeling, that they’re waiting for him to chug the small talk train along. 

“How about… you guys?” he asks with a tight smile.

“We’re section hikers,” Donna says. “We’ve done the trail southbound from Katahdin to around Goose Eye Mountain, and boy, oh boy, was that a doozy for us,” she adds, laughing in Jody’s direction. 

“Definitely not seasoned hikers at that point,” Jody adds.

“And then we tried to do a section in Connecticut, but started when it was way too cold, got stuck in a blizzard, and said nooo thank you,” Donna continues, rolling her eyes. “But in our defense, there were record cold temperatures that year. Kinda like this year—good thing we missed all those crazy tornadoes last week, right? We were worried that we wouldn’t be able to get up here this weekend.” 

“Yeah,” Dean says lamely, because he definitely didn’t check any kind of weather before coming here. Finding that Appalachian Trail guide at Savers, flipping through it, and reading that most northbound hikers start in early March was as far as he got.

“You guys talking about the tornadoes last week?” A lanky man with a toothy smile ambles up to them, his large pack practically swallowing him whole. “We got some crazy ones down in Tennessee in February, too. My girlfriend thought I was missing a few Cheerios in my cereal bowl for wanting to come out here after all the bad weather we’ve been having this year.”

“We were called crazy, too,” Donna says with a good-natured roll of her eyes. “My lovely mother asked us if we wanted the nice men in the white suits to come pick us up after we inevitably quit at mile 20.” 

“To be fair, we haven’t given her a lot of good history to work with,” Jody says. “Our longest hike hasn’t been more than fifteen miles. And there was that time you called her from a payphone begging for an airlift out of the Rockies because you got that nasty blister.” 

“I’ve hiked only fourteen consecutively myself,” the man says. “Garth Fitzgerald IV, nice to meet you.” He merrily shakes Donna, Jody, and Dean’s hands, one after the other. “Y’all hiking together?” 

“Me and Jody are,” Donna says. “Dean, are you hiking solo?”

Something twists in Dean’s stomach. He smiles. “Just me, myself, and I.”

“Hey, me too!” Garth says. He raises his hand in an expectant high-five. “Solo buddies, you and me!” 

Dean’s pretty sure that having buddies paired with solo cancels each other out, but Dean gives Garth a reluctant slap against his palm anyway. 

“Oh, hey! We’re gonna pop over to the dining hall and have some breakfast if you want to join us!” Donna says. “Heard that they’re serving pancakes.”

“Hell to the yes on that, my new friend,” Garth says with a hearty pat to his stomach. “Need all the fuel I can get before getting out there. Solo buddy, you comin’ too?”

Even though Dean’s stomach is traitorously growling at the mention of food, he shakes his head. “Thanks for the invite, but I already ate. Gonna break a leg, hit the trail. Or whatever.”

“Sounds good to us,” Jody says, giving Donna a knowing look as she starts to protest. “Maybe we’ll see you out there.”

“Yeah. Maybe.” 

“Happy hiking!” Donna says with a wave. 

“Solo buddies!” are Garth’s departing words, with a pair of thumbs up held high over his head. 

Dean watches them walk toward the dining hall with a sense of relief. The best lesson John ever taught him was to keep his distance and not to pull other people into your bullshit, since there’s always the danger that they might pull you into theirs. Dean intends to keep that philosophy close to the chest and hike this trail alone, his forklift’s worth of bullshit and all. 

“Guess going incognito on this hike from hell was a pipe dream,” he mutters to his still-fallen pack on the floor. Hauling it off its side and zipping open one of the hundreds of pockets to stuff Donna’s trail mix in, he pats it. “At least you’ll stay quiet the whole time.” 

The pack, of course, doesn’t respond, because it’s a pack and doesn’t have a mouth or ears or a brain. Dean hauls it up onto his shoulders with a grunt, then stumbles backwards into the payphone from the sudden weight. Several people turn at the crashing sound, mouths open. 

“Oh, yeah,” he mutters, avoiding their eyes, “this is gonna be fuckin’ peachy.”


Dean’s the only one out on the trail. It’s barely six in the morning, and everyone’s still chowing down on their pancakes in the dining hall, so it makes sense. And because no one is out there, he can stand in front of the stone arch with a red sign that announces in white, blocky lettering: Appalachian Trail Approach. The path is paved, but Dean’s wise enough to know that it’ll soon turn to dirt and stone. 

He stands there for a long moment, breathing in the nauseatingly fresh mountain air. Past the arch, the trees stand still and proud. Birds chirp somewhere in their bare branches. Dean’s breath makes clouds in the cold air. 

“This is stupid,” he tells the arch. “You know how many miles I’ve walked, compared to Donna and Jody and whatever the hell that Energizer Bunny’s name was? Zero. A big old goose egg. Can’t even remember the last time I walked a fucking mile—probably high school, because they wouldn’t let me graduate otherwise. Not that I graduated anyway, but that’s not the point. Point is—high school. Last time I even bothered walking anywhere for anything. Ten years and a lot fewer creaky joints ago.”

He’s not sure who he’s talking to. All he knows is that if he doesn’t get a move on, he’s destined to be part of a pancake-stuffed, chatty herd of happy hikers. 

Adjusting his pack on his already sore shoulders, he walks through the arch. 

At first, walking isn’t so bad. Sure, his boots are kind of pinching his toes, and his hands are getting stiff from how cold it is, despite how warm he is under his jacket, but it’s fine. It’s manageable. He’s definitely had worse. Working for a roofing company right out of high school that wasn’t even insured—that was worse. That whole fiasco ended when he fell off a roof and broke his leg, one of his coworkers dumping him at the front of a hospital and the company refusing to pay a dime. John chewed him out pretty bad for that. 

Just as the walking begins to feel boring, things get more vertical. Each step feels a little more labored, his pack a little heavier. The trees begin to thicken around him, pressing in on the trail, as the elevation takes him further up the mountain. Just when he gets to a plateau, heart soaring—maybe this is the peak—he’s faced with another stretch of trail going up, up, up. 

Breathing heavily, sweat pooling in the collar of his jacket, he checks his watch. One hour. It’s been… one hour. 

“Fuck,” he says plainly and leans against a tree. Next to him, painted on the bark, is a white blaze that marks the trail. 

When he starts walking again, he follows those white blazes through sweat-dripped eyes. They’re on tree trunks, cairns, even a random post or two. It makes the trail easy enough to find at first, but when it starts to wind around bends and his breath starts to get harder to find again, the trail becomes a blurred, fuzzy thing.

Dean wants to take a break, but he knows that as soon as he puts down his pack, he won’t be able to pick it back up again. Step by step, he trudges forward. Salt is rubbed in the wound when small packs of hikers from the lodge start passing him, full of pancakes and syrup and happy chatter. When a group of what seem to be college students—wearing barely any clothes at all, despite it being at least twenty degrees outside—pass by while he’s catching his breath against a tree, Dean decides that's the last fucking straw.

“Okay,” he tells himself, unparking himself from the tree. “You never played any sports. You’ve never been to a gym. And you indulge in pie a little too much, sometimes—sure! But you are going to climb,” he pants, trudging forward, “this fucking,” he trips a little over a cluster of rocks, rights himself, “mountain!”

Another hour passes. A bear could attack him, and he probably wouldn’t even notice—hell, would probably welcome it at this point. At least he’d get to lie down.

Donna and Jody eventually pass by with cheerful smiles and waves, Garth—whose name Dean only remembers now since Garth graciously reintroduced himself while passing—not long behind them.

“See you at the summit, solo buddy! Only six more miles!”

Six? That can’t be right. That means Dean's only been hiking for... He digs out his map of the trail, tucked safely into a laminated pocket that hangs around his neck. Yup. It’s only been two and a half miles. Awesome.

There’s nothing to turn back for. Nothing is waiting for him if he quits and goes home—wherever the hell home is now. 

So, he keeps going.

Everyone’s passed him. He’s about damn sure of it. He can’t hear anything but the woods—the crunching of his boots, the occasional screech of a hawk above, the relentless birdsong. When he stops to take a shaky sip from his water, a confused squirrel fresh out of hibernation streaks across the trail.

His surroundings would seem pretty if he didn’t feel like hell. Tucking his water back into his pack, he continues.

The sun is high in the sky, warm and bright despite the cold air of early spring, causing a confusing combination of cold and sweat under his jacket. His feet throb, his head aches. He’s suddenly very aware of his knees. Every step is agony, and this might be what death feels like. 

He stops to dig Donna’s bag of trail mix out of his pack. The salty and sweet taste gives him some distraction as he goes on, and, unfortunately, some clarity about the whole situation. He failed to take into account how much time there would be to think out here. He’s hiking this trail to escape his life, not turn it over and over in his mind. Whenever he gets any sort of reprieve from the elevation, flashes of memory slam at him: Sam as a baby being put in his arms. The Impala wrapped around a tree. The very faint memory of his mom's smile. His childhood home engulfed in flames. His dad’s shoulders shaking with silent sobs, his back to Dean. The way the walls shook when John screamed at Sammy after finding his acceptance letter from Stanford.

Dean’s toe finds a patch of moss. This time, he’s too tired to catch himself. With a grunt, he falls forward, facedown onto the moss. The pack is a dead weight against his back, pushing him firmly into the dirt. 

Weirdly enough, the fall doesn’t hurt. If anything, it’s nice to finally lie down. Turning his head, he looks at the dirt and moss and pebbles by his head. This close, he can see the finer details in them—the granules and grooves of the rock. The little ants that march across the dirt. The way that moss almost looks like hills belonging to a micro universe that the human eye can’t fully behold.

He lies there for a while because it feels nice. He’s not sure how long. But it feels better than walking.

At some point, he knows he needs to get up. But maybe he could just...melt into the ground. Be one with nature, in the most literal sense. Maybe he could feed a nice bear family without daddy issues or a brother who won't answer his phone.

Maybe he could be good for something. For once.

“Are you all right?”

Dean slowly looks up. Someone is standing above him, his face shadowed by the sun that’s just behind the crown of his head.

“Oh, yeah,” Dean says, half his face still in the moss, “fucking peachy.”

For a moment, the man stands there, seeming to be at a loss. “I can help you up,” he offers, but the words sound unsure. Like he can’t tell what Dean even needs. Come to think of it, actually, his voice is nice—deep like the gravel that Dean’s face-first in.

“Nah,” Dean says. “I’m just gonna lie here.”

“It’ll be dark soon.”

Dean grunts an affirmative into the moss.

The man sighs. “I assume you’re trying to summit the mountain.”

“No shit, Sherlock.” 

One hand grips his arm, the other his backpack. With a yelp, Dean’s hauled up to his knees in one fell swoop. “Hey!” he snaps. 

The man, unruffled, takes a step back. “You can’t keep lying there. You need to make camp on the summit before it gets dark. The temperatures are too cold for you to be out here without any sort of shelter.”

Dean rubs his arm and glares. Now that he’s out of the sunlight, he can see that the man’s face is about as nice as his voice: a cut jaw, bright blue eyes, dark tousled hair. He’s not wearing hiking clothes and is in a trench coat, of all things. And... dress shoes. This guy is even less prepared than Dean, which is saying something. 

“You work at the lodge or something?” Dean asks.

“No,” the man says. He offers no other explanation.

“Okay, well, thanks for the help, but I think I’m just gonna turn around.”

The man tilts his head, ear almost touching his shoulder. “Why?”

“Because I’m not cut out for this, that’s why. I probably don’t even have enough shit in this backpack to keep me alive. Plus, everyone passed me, even a freaking twelve-year-old and his dad, and—I’m done. Okay?”

Looking up the trail and then back at Dean, the man hums. “This is a record. Most people don’t quit until the first payphone.”

“Huh?”

“There’s a payphone, twenty-one miles from here, at Woody Gap. In my experience, that’s where people normally quit. They call the shuttle that took them from the airport to the trailhead, begging to be picked up.” His eyes trail up and down Dean, assessing him. “Not many people turn around after merely four miles.”

“Is this some kind of reverse psychology?” Dean growls.

“No. I’m stating facts. It’s not of import what you decide to do.”

“Oh, great,” Dean says with a strangled laugh, throwing up his hands. “If it’s not of import—”

“However, I did witness an 80-year-old woman finish the trail last year. When she hiked this portion of the trail, she didn’t complain nearly as much as you are.” 

Dean grinds his teeth together. “You just assume my masculinity is so fragile that I’m gonna get my feathers ruffled by a grandma doing the trail when I can’t even make it up this mountain?”

The man shrugs a shoulder. “I’m not assuming anything.”

Dean narrows his eyes. “You said I’m four miles from the summit?”

The man nods. 

“Great.” Dean pushes past the man, who easily steps aside. “And don’t go thinking that your crappy motivational speech actually worked on me!” he yells over his shoulder.  

The man doesn’t reply. When Dean turns, the trail is empty. He must have gone back down the mountain and walked fast enough to be out of view. With a frown, Dean slowly keeps walking forward.


Five more hours and a lot of swearing later, he finally reaches the peak. 

The sun is heavy, dipping down past the horizon. There are already tents clustered together on the campsite, which is tucked into the basin of trees just off the main part of the trail. Groups of people chatter over fires and campfire stoves and food. Dean could fall to his knees, he’s so relieved to see flat ground and open space.

He stumbles through people and avoids their gazes in a desperate search for a free space in the army of tents. There’s a shelter, a little A-frame with an actual floor and roof, but it’s littered with 20-somethings who probably summited the mountain first, all armed with harmonicas and guitars and loud laughs—leaving Dean to wonder why in the world—and cheerfully passing steaming, hot food between them. He has nothing against the younger generation, but in that moment, he does kind of hate what they represent: youthful strength, hope, and the ability to scale a steep mountainside in what was probably four hours flat.

Finally, he finds a free corner at the very edge of the trees. He’s nearly bumper-to-bumper with a tree trunk, and there’s a hell of a lot of deep, morphless darkness at his back. He’s too tired to care what that darkness might hold. With shaking, cold hands, he pitches his tent, unrolls his sleeping bag (not even bothering with the inflatable sleeping pad, since Rufus mentioned that there may or may not be a leak in it), and curls into a ball. Jacket and hat still on, shivering against the cold, Dean pulls out what’s left of Donna’s trail mix—that’s starting to feel like literal magic in his pocket—and eats a handful.  

He barely finishes chewing before sleep pulls him under.


Four months ago, on an unseasonably warm winter night, John Winchester, going a boozy one hundred miles per hour, crashed his car into a huge oak tree on the side of the highway. Dean should have followed the slow ambulance to the morgue, to fill out the paperwork for the body lying on a cold slab—it’d have been the right, decent thing to do—but instead he followed the tow truck that pulled the Impala to the nearest junkyard.

She was ruined. There was no gentler way to put it. The side punched through, the grill buckled in, the windows shattered. It would take months, maybe years, for Dean to fix her. Maybe she was even beyond saving. Dean paid the owner of the junkyard to tow her to Bobby’s salvage yard a few states away before making his way to the morgue.

Looking at his dead father, cold and pale, somehow didn’t make him sad at all. Like he’d spent all his tears on the car instead. Dean knows this makes him seem like a monster who didn’t love his father, but he did. For all his complications, for all his vices, Dean loved him. Respected him, at the very least—which is probably what John would want to hear more.

There was no funeral. No wake. Sam wouldn’t have shown up to anything like that anyway. 

Done and dusted with no fuss, as John would have wanted.

He sold their trailer to pay off John’s debts. Bobby took him in and chafed Dean with constant worried glances. After staring at Baby’s corpse rotting in Bobby’s junkyard for a few months, and waiting for Sam to call and acknowledge the news that their dad was dead, Dean decided it was time for a change. 

He set out in one of Bobby’s clunker cars, waving off his well-meaning concerns, to drive east. When he ran into the Blue Ridge Mountains, snow still on the peaks that poked through the clouds, he knew, deep in his bones, that he was going to climb to the top of that ridge. That he was going to go up so high that nothing could touch him again. 

In fact, all things considered, deciding to hike the Appalachian Trail felt like the most sane decision Dean’s ever made. 


When Dean wakes up, the sun’s barely risen. He has that foggy feeling like he was dreaming, but can’t remember about what. There’s condensation all around his tent from his heavy snores. Untangling himself from the sleeping bag and unzipping the tent, he squints at his surroundings—and the breath punches out of his chest.

The sky is a burst of bright yellow. It glides over the blue mountains in the distance, just atop a dense fog. The grass is greener than Dean’s ever seen, pearls of early morning dew perfectly dropped on each blade. Everything’s motionless, a moment frozen in time, still untouched by the day. Through the valley of tents, Dean sees the trail, sprawling towards the distant mountain range. 

Something stirs in his bones. Something primal, something that makes him want to move. Move forward. He can’t explain it—whether it’s the human condition of wanting to explore, the same madness that made someone want to construct the trail from scratch in the first place, or the very real desire to keep walking forward, tired and delirious, until he forgets his own name. 

Whatever it is, it’s making him pack up his tent and fish out a granola bar from his backpack to wash down with a swig of water. It’s making him lace up his boots and put on his pack, passing the tents and the shelter with snoring college students, and step onto the trail before anyone else has stirred. 

Step by step, he walks. It’s all he can think to do, after all.