Title: Highway To Hell

Author: Hadlee May

Disclaimer: Don't own anything. The show, the game, the movie - whatever. Everything is owned by their respective owners.

Summary: Beginning a month after Gilmore Girls' series finale and Supernatural's season one finale, the lives of Sam and Dean Winchester and Rory Gilmore have crossed and intertwined in an event that none of them were to prevent. Now tagging along on their dangerous, other worldly mission, the three of them journey into the dark world of the unexplained to find and destroy the demon who's wreaked havoc on their lives…and killed Sam and Dean's mother. Crisscrossing the lonely and mysterious back roads of the country in a '67 Chevy Impala (all fixed up and everything) Rory and the Winchester's encounter creatures the most people believe only exist in folklore, superstition and nightmares. Following the clues in John Winchester's journal, the crusade to hunt down the evil that preys upon the innocent in the darkest corners of America continues.

AN: You can kill me if you want, or torture me a bit, I know I have to be getting a tad bit annoying with my indecisiveness. Once more, I'm beginning to re write this fiction - hopefully on a path way that I can follow and not loose interest. So as of this post - officially - this is a Supernatural/Gilmore Girls/Silent Hill crossover with a few Carnivalé implications thrown in (more like a huge chunk of the plot is based off of the brilliant series, Carnivalé )

Before I jump right into my re write, I wanted to mention a few things.

First off, I'd like to think Simple Tirade d'Aujourd'Hui for your comment. I'm glad you alike it. I work so hard on this, many times putting people's opinions over my own and your comment made my day. Also, I thank PadfootCc, Ghostwriter, purpleribbions, cl06,

Therayynfire, magic skittles, neko-in-tears, truebeliever517, -jaycat-, midnigh893, scary-girly, and maze2010. I love getting reviews. They make my day. Really. So thank you.

Another thing is - someone mentioned something about a comment made by Rory in the first chapter - about her actually liking Metalica…Remember. This is fan fiction and anything is possible…even the characters being slightly OOC. I was using the phrase merely as a tool to show how closer she'd become with the guys in such a short time (ie: teasing dean about his music).

In finishing, I'm hoping that this story will be able to follow a plot line - a nice story that follows from beginning to end.

With that…to quote NSYNC - "Here we go".

PREFACE

Unto each generation was born a creature of light and a creature of darkness

And great armies clashed by night in the ancient war between good and evil.

There was magic then.

Nobility.

And unimaginable cruelty.

And so it was until the day that a false sun exploded over trinity

And man forever traded wonder for reason

"Morning." Rory Gilmore yawned, plopping herself into the empty yellow booth, sitting across her equally tired traveling companion. Sam looked like death warmed over, his skin slightly pale, bags harboring under his eyes, hair unkempt. His whole demeanor seemed to be off. Mornings seemed to be Sam's favorite part of the day. He was more then likely the first one up, enjoying the torturous process of waking her and Dean up so that they could start their day. This morning, though, he was slouched haphazardly over the table, heavy head resting on a lazy palm, elbow slowly sliding against the smooth surface of the table.

Dean, on the other hand, sat happily in the corner, munching on a muffin and sipping coffee. Rory felt incredibly annoyed at his content nature.

"Looks like someone had a rough night." Dean commented, a wily smile situated on his handsome face. Rory rolled her eyes at him, ignoring his cocky gesture and pretending she didn't notice the flirty smile he sent her next. As usually, she was amused with Dean Winchester's antics. Especially ones that kept her up all hours of the night. She felt more then positive that most people at the hotel last night got as much sleep as she did. Every fiber in her being wished that she hadn't forgotten her headphones at the last run down hotel they'd stayed in a few states over. In fact, after all this, she was more then willing to walk back just to retain them for future occurrences.

The oldest of the two brother's night time excursion was something she preferred not to think about. She definitely didn't want to hear about them either. She answered his cheeky response, finally, with a glare and, "Shut it, Dean." She tried her best to sound menacing, though it came out only a weary mumble.

Dean responded the only way Dean knew how to respond. He blew her a teasing kiss, handsome face turned up in a smirking grin, green eyes glowing with something akin to delight. Rory, on reflex, batted away the kiss and attempted to turn her attention to her drowsy companion.

"Sam, how the hell did you put up with him for so long." She asked before dropping her head on the table, a loud thump sounding through the empty diner. She winced. She whispered an 'ow', which Dean snickered to. She hadn't meant to do it that hard.

"I just ignore him." Sam laughed quietly, trying to sit up long enough to grab a bit of bacon to shove into his mouth before returning to his relaxed half asleep state.

Rory watched Dean for his reaction and smiled when the grin dropped. A sparkle formed in those hazel green eyes which widened with surprise. His mouth formed a mocking O, hand flying to his breast. "So that's what you've been doing" He teased, his lip in a prominent pout. Sam avoided his question.

"You know what you want to eat?" Sam's focused attention on her made her giggle quietly. Especially when Dean's mock shocked face turned into something that seemed more real. Rory lifted her head from the table and responded with a mutter about something involving thirty pots of coffee.

She peered at Sam through a curtain of dark hair, then smiled, nodding her head excitedly. Sam returned her grin, and for a moment she was reminded of her past. It was uncanny the resemblance between Sam Winchester and Dean Forester. Same hair, Same caring eyes, both impossibly tall. Though taking a moment, there were obvious differences that were hard to miss. Sam wasn't Dean and Dean definitely wasn't Sam. Sam Winchester possessed many important things that Dean never had. The spark of fire that resonated in her traveling companions eyes spoke of ambition. This man had a goal. And even though that goal was some what on the odd side (killing a demon just wasn't an ordinary goal), it was a goal. Something Dean Forester never had. Sam was smart and it added volumes to the conversations they had. A student at one time of an Ivy League college himself, he understood the pressure of succeeding. He was out there to better himself; to get away from the mess of a life that was his family. Rory was sure he would have made it too, had he not been dragged back into the full time job of hunting.

Sam wasn't unhappy, though. In the two weeks that she'd joined them on their adventure, she'd gotten to know both brothers on some level. Sam, of course, more then Dean.

Dean. Well, Dean was an enigma. A mystery. The loyal soldier willing to do anything and everything to follow his father's orders. The protector that would go above and beyond to make sure that she and Sam were safe from a world that seemed to want them all dead. He never had much to say about himself, but it was a rarity of him shutting up. He was always there, sly grin on his face, eyes enticing as they looked at you. He'd seemed to have rising above the evils of the world while existing in the lowest level of hell at the same time.

The there was her, the unlikely companion. The good girl who'd ended up in a bad situation and was now stuck up the proverbial creek without a proverbial paddle. She was beginning to understand the sort of limbo that had plagued the Winchester's since Sam was six months old. The kind of never ending nightmare where you spent all your time running and always ending back in the same place your started. Sam had escaped, been the normal boy. College. A girlfriend. A life. Look at him now, playing shot gun to his brother in their hunt for the one thing that seemed almost illusive in nature.

She was the lucky one of the three. She'd had a semi normal life filled with laughter, love, and coffee. She'd gone to a good school, had good friends, and had attended Yale. Her dream had been on the path to realization when her life had crossed over into theirs. Now, she, like them, was trapped in the same limbo, experiencing the same nightmares. Hoping against hope she made it to the next stop. In one week, she'd discovered the underside of America, seeing things that everyone else had the luxury of passing it off as a cheesy plot to a SCI FI move of the week.

She assumed that in some ways, though, Sam enjoyed his life. He enjoyed time spent with his brother, no matter how aggravated with him he became. In some ways, she was beginning to enjoy his life too. She might be on the run from some evil demon out to get her, but for once, she was apart of something. She was helping people. That and this whole experience would make a great story. If she ever got home in order to write it. That was if she could go home. Her mother was more or less this close to disowning her after this one. Lorelai had been upset enough when she informed her that she had a job covering the barak obama campaign. That meant weeks or months on the road with no physical contact. Two weeks into the gig, she'd all but disappeared. She called her mother once to let her know she was okay and almost immediately after, Dean had thrown her cell phone out the window.

"The usual." She finally responded. Sam grinned wide, a laugh threatening to come out.

"Should've known." Dean teased, ignoring the fact that they were ignoring him. Sam closed the menu and set it towards the end of the tale while looking at Dean. "What?" He asked, "You know the girl eats just as much as we do…" He paused to wink at Rory, "Put together." He snickered at his own remark and took another sip of his coffee.

"Shut up, Dean." Rory spoke, glaring at him. She was meaning to be mean, but it must have come out looking playful, "I've heard enough of you in the past twelve hours to last me a lifetime." Dean chuckled, shaking his head while flipping through the worn pages of

"Shut up, Dean. I've heard enough of you in the past twelve hours to last me a life time." She remarked. Dean chuckled, shaking his head while flipping through the worn pages of his dad's journal. "Anyways, where to next?" She asked. Dean didn't reply, flipping another page, seemingly engrossed in the content that he'd read hundreds of times. She waited a moment, then, "Dean?" She asked. She turned to Sam. "Is he ignoring me?"

The taller man shrugged, a small smile forming on his face. "Ugh." She groaned, "Explain to me why I'm the only girl on this trip?" She asked. "Neither of you are exactly chatty. Dean listens to the greatest hits of mullet rock and you…you're all with the research…not much a journalist can do here." She rambled.

"You know," Dean cut her off, "journalists occasionally allow their subjects to talk." He said it so casually that it was infuriating.

"Dean-" She warned.

"Yeah, yeah. I know." Dean laughed, " 'Shut up, Dean'" He mimicked her before returning to the journal.

"You are so whipped, Dean." Sam teased, "and the two of you aren't even dating." Rory glared, throwing a balled up napkin at his head, while Dean punched him in the shoulder.

"I think it's time for you to do the shutting up thing." Dean spoke evenly to his brother. Sam just chuckled, completely unfazed by the two's abuse.

"You ready to order?" A pretty blonde waitress approached their table. Rory noticed Dean's eyes begin to scrutinize the blonde and she felt it her civic duty to surreptitiously kicked him in the shin. Dean barely reacted, only a wince passing across his face before it morphed into a flirtatious smile. Rory grinned at the girl and nodded, proceeding to recite her order, the waitress hardly keeping up with her fast paced talking. Dean ordered next before sending Rory a glare. Sam smiled again as he handed the waitress their menus. The waitress, who's name was Candy, popped a bubble in farewell, promising to bring them more coffee as soon as she could.

"Why'd you kick me in the shin?" Dean asked once Candy was out of ear shot.

"She was checking you out." Rory commented as if it were nothing. Sam leaned his head on the table laughing. "We are not staying another night just because some waitress has the hots for you." Dean gave a wide grin, shrugging his shoulders as though the occurrence was an everyday thing. Sam's laughs became louder and once more he became the subject of their abuse. Breakfast flew by quickly, occasionally a few snippy remarks were exchanged, but it was relatively peaceful.

By the time they got up to leave, Rory had nursed down at least six cups of coffee before Dean decided that it was time to go. They'd spent an extra day in town to relax (and for Dean to get his jollies) before beginning their way onto the next stop. A stop Dean had failed to mention, as of yet. It'd been a waist. Only Dean seemed to be in a perpetually good mood. Rory and Sam followed behind Dean sluggishly. No doubt Dean's '67 Chevy Impala was going to be a makeshift bed for the next few hours. Chasing after the demon took a lot out of him, and even she had protested the extra day. Especially when the demon was always one step ahead of them. It was getting harder to do the whole saving people's lives thing when they were constantly having to watch their backs. It'd been a group decision that she stay out of the grand fight against evil. Or at least fight in the most subtle way possible. So far, she'd opted to stay in the hotel room, cross legged on the bed, surrounded in a ring of salt, a string of garlic near the door, and a small pistol waiting for use on the bed side table. She could barely walk without falling, she could hardly imagine herself throwing any form of decent punch. Chances were, she'd more then likely injure herself more then she'd hurt her opponent. She endured a small bit of teasing from Dean, but she'd learned not to care about anything he said anyways.

"Can we listen to the radio for once?" Rory asked as she laid down in the back seat. Dean turned around, fixing her eyes on her as he started the engine. He raised an eyebrow.

"You remember the house rules?" Dean asked.

"Yeah. Driver chooses the music, and the passengers shut their cake holes." She recited it like it like it was poetry.

"Exactly." He exclaimed as he pushed a Metalica tape into the tape player.

"Well, can you at least tell us where we're going." She said, pouting.

Dean sighed, then, "you remember when you asked about why you were the only girl on the trip.." He asked. Her eyes widened, and she groaned.

"Not the roadhouse." She whined.

"Yes the roadhouse." He nodded as 'Enter Sandman' began to stream throuogh the speakers as the tape caught. Dean turned up the music, playfully singing along to the track as he pulled out of the rock laden parking lot. Rory growled.

This was going to be a long trip.

AN: I'm going to try to stop putting two author's notes in the story. I read somewhere that it was almost as unprofessional as putting an author's note in the middle of the story. None the less, hope you guys like the re write. Just FYI, this episode definitely takes place after 'In My Time Of Dying'…mainly because Dean isn't in a hospital bed. I liked the series finale of GG, so I decided to move the beginning to just after she begins working as a journalist on the campaign tour. That way I don't have to deal with any extra turmoil when she finally gets back to Stars Hollow.

Of course, I wasn't fond of Logan's exit. I figured if he liked her enough to ask her to marry him, he wouldn't let her go that easily. He'll have an important part to play in this story, as will another rich bastard from Rory's past…only one guess as to who. Starting next chap I'll start involving the whole Carnivale and Silent Hill stuff.

Thanks for reading. Please Review!