Summary: Sam and Dean are on the road again, this time heading to Mystic Falls, Virginia. What seems like a simple milk run vampire hunt, turns one Winchester's life upside down.

This is mid Season 4 of Supernatural and Post Season 8 of Vampire Diaries with a few changes. Elena is still under the sleeping spell and Damon never had the cure. Let's assume Dean and Bonnie are in their early thirties. Some timelines and details will be fudged to fit the plot.

AN: Well guys! This is my first multi chapter SPN fanfic and I'm really excited about it. I just finished watching all 15 seasons, and I'm not even ashamed by how quickly I blew through it, but of course, it left me wanting more. So I thought, what better way to pay homage than to bring my two favorite shows together. We'll see after this if I end up doing more crossovers, but I definitely feel like there will be more SPN stories. Please enjoy! – Vanessa

…

Chapter One: The Past Comes Knocking

The ring on Dean's finger tapped rhythmically on the steering wheel to Lynyrd Skynyrd as they passed the Welcome sign into Mystic Falls. When he stumbled along this case, his first instinct was to pass it over to another hunter, but the more he thought about it, the more he knew it had to be them.

"So, where did you hear about this case again?" Sam piped up from the passenger seat, flipping through the pages of his father's journal.

"Ellen. Turns out a hunter's gone missing and the last place anyone heard from him was here. Dug a little deeper and this place is a hub for supernatural activity; I'm talking a long history of missing persons, bodies drained of blood, animal attacks. I figured we had a case." He answered tightly, keeping his eyes on the road.

Sam frowned. "Mystic Falls…that name sound familiar to you?"

Dean's mouth turned down. "Nope."

He eyed his brother questionably. "Really? I could have sworn we'd been here before." He turned his gaze out the window, watching the trees as they passed. "You jumped on this one pretty quick. Given everything that's going on…"

"It's a hunter, Sammy. One of our own."

"Yeah, but we also need to focus on finding Lilith and stopping her from breaking the seals."

Dean finally swung a look in his brother's direction. "We need a distraction Sam. Lilith has been one step ahead of us and I need something to kill…" He nodded resolutely. "So let's find Asa, find this vamp, waste it, and then we can go back to saving the world, okay?"

Sam shrugged before something in the journal caught his eye. "Hey…you know what, I think we have been here before. Dad wrote about tracking a werewolf here years ago."

Dean's jaw clenched. "Really."

"Yeah, we were here for a few months. I remember because you and dad got in this huge fight over leaving. You liked it here…" Sam realized, watching his brother. His knuckles were white, and his knee was bouncing anxiously. "You do remember."

Letting out an annoyed huff, Dean pinned Sam with a glare. "Yeah, Sam, I remember Dad letting us make friends and feel normal for a while before pulling us out of school to go hunt a Rugaru in Dallas. But that's ancient history, okay." He finished brusquely.

Sam held up his hands in defense, closing the journal. "Okay…"

"I'm starving. Burgers?" He nodded at the sign as he pulled into the parking lot.

"Sure." Sam agreed absentmindedly. He was still hung up over his brother's reaction, and wasn't ready to let it go. As they walked in the doors of the Bar and Grill and found a booth, he brought it up again. "Wasn't there a girl here you liked?" He knew he was right when he caught Dean subtly scanning the room. "She was the mayor's daughter, right?"

Dean snapped a glare at him again. "Sam…" he warned.

With a chuckle, he pried further. "Yeah…cute little thing, dark hair, a gift for turning you into a bumbling idiot."

"You done?" He wasn't use to being on the receiving end of the merciless taunting, Dean was always the one dishing it out.

"Oh God no, this is too much fun. What was her name? Bianca? No…Brittney?"

"Bonnie Bennett." Dean mumbled; his gaze locked on something across the room.

Sam snapped his fingers. "Yeah, that's it. Man…she sure had you bent out of shape back then." He commented looking over the menu. "Is that why you were so eager to come here?"

"Not eager…curious." He took a moment to watch her, greeting the bartender as she sat down on the far end. The years had done her good, and her once shy innocence was replaced with a radiant confidence. Sam was right, she was the one girl that got under his skin and stayed there.

He was seventeen, solely focused on protecting Sammy and helping his dad any way he could in the fight. At first, he wasn't thrilled about sticking around anywhere too long; Dean knew not to let himself get too attached anywhere…or to anyone. That pretty much went out the window when he met Bonnie. She wasn't like the other girls he'd met along the way; shamelessly flirty, desperate for his attention, swooning over his boyish charm and mysterious bad boy attitude. She gave him a run for his money, rolled her eyes at him and gave him the brush off and it only made him like her more. But of course, product of his own demise, he ruined it.

As if she felt the holes his stare was burning into her, Bonnie's eyes shifted up from the bar, looking at him stunned for a moment. Dean tried to look away, but he was trapped in her gaze. Her lips cracked in a smile and he let out a breath he didn't know he was holding, smiling back. She remembered him.

Sam frowned. "You good?"

"Yeah." Dean snapped out of it. "Yeah…I'm good. Oh God, she's coming over." He panicked, straightening up. "How do I look?"

"Seriously?" Sam laughed, thoroughly enjoying this flustered version of his brother. Dean shot him a dead eye glare. "You look how you always look." Sam went back to looking at his menu. "Like a giant douche."

"Bitch." Dean grumbled back.

"Jerk."

"Dean...?" Both of them snapped their heads up to look at the woman who just approached their table.

He swallowed. "Hey Bonnie." It came out raspier than he intended. He stood, unsure whether it was appropriate to hug her or shake her hand, but she leaned in, wrapping her arms around him. He did the same, catching the scent of her hair just below his chin. It brought back memories long since passed. "How've you been? Good? You look…real good." Fuck, dude shut up. He didn't have to look at Sam to know he was laughing at him.

She pulled back still stunned by the blast from the past. "Yeah, I'm great, I just got back in town actually." She gaped at him for a moment again, shaking herself out of it. "Sorry, I'm just-I'm floored…What's it been…fifteen years?" He changed a lot. She could feel it when she hugged him; he'd led a dark life, a lot of loss, a lot of pain. She could relate.

"Give or take." He quirked a smirk before pointing at Sam. "You remember my brother, don't you?" Yes Dean. Deflect.

Bonnie's eyes widened. "No way…Sammy? You're so tall, I barely recognized you." She laughed, still seeing the scrawny kid he used to be.

He cleared his throat when Dean snickered. "It's just Sam now. Its good to see you, Bonnie. You haven't changed at all."

She laughed at the irony with a loose shrug. "I wouldn't say that." In the last ten years, she'd changed a lot too. She'd been a witch, a ghost, an anchor, a hunter; lost more than her fair share of family and friends…and lovers. Her eyes drifted back to Dean. "So what brings you guys to town?"

"Sort of a brother bonding road trip." Dean offered, shoving his hands in his jacket pockets, rocking back on his heels. "We'll be here for a few days."

She smiled. "Good." The bell at the door rang, and she watched Damon walk in, nodding that he'd be at the bar. "Look, I kind of have this thing I have to do, but hopefully we can talk sometime…before you go?"

He knew there was a lot to talk about. The day he left for starters. "Yeah…of course."

Bonnie texted him her number and left with a little wave in Dean's direction before meeting the man at the bar.

When Dean settled back into his seat, Sam broke out into a chuckle. "It is so entertaining to see you get rattled like that. What's that about?"

Dean ignored his brother, keeping a watchful eye on Bonnie with this other man. He was tall, noticeably attractive and judging by the tight hug he gave her; they were close. "Who do you think that is with her?"

Sam glanced back over his shoulder. "Why does it matter? We'll be gone in a few days, right?" he threw back at him.

Dean nodded, snapping his attention to the menu. "Right."

…

Damon eyed the two men in the back corner of the Grill, as Bonnie ordered two more shots. "So how do you know the Hardy boys over there?" He snarked. "The pretty one keeps staring at you."

She rolled her eyes at his nickname. "Just some old friends."

"Old friends? Bon, I'm the oldest friend you got." He teased with a lopsided grin.

Bonnie let out a laugh, playfully shoving his shoulder. "You know, I did have a life before you and Stefan blew into town." She downed her shot, making a face.

Damon followed suit, unbothered like he was drinking water. "Sure. But I highly doubt it was as thrilling."

Bonnie smiled to herself. "No…but it was normal."

Damon's tone turned serious. "So…who is he?" Naturally, he needed to know everything about this person. It wasn't that he was jealous, he was just protective…or that's what he told himself.

"Dean was this mysterious bad boy; new to town, had this sort of hot loner vibe." She remembered the way he walked into campus, leather jacket, popped collar, stepping out of his dad's '67 Impala.

Damon scoffed. "Well, you sure do have a type." He said with a flash of his eyes.

"He was only in town for a few months but, I don't know…we connected, I guess. Then just when I thought something might actually happen, he was gone." Bonnie pinned him with a look. "I guess I do have a type, don't I?" Things had been tense between them lately, and no one was addressing it, which obviously meant at some point one of them would end up exploding this unresolved tension in a very destructive way. And at this rate it was going to be her.

Damon deflated, reaching for her. "Bonnie…"

She held up a hand to stop him, shutting her eyes against the wounded puppy eyes he was about to give her. She remembered how this went. "It's fine, I get it. We're good." When she opened her eyes, she forced a smile. "Besides, we're here for Caroline. Where is she anyways?" Bonnie glanced at her phone. "She's never late."

Minutes later, the doors opened, and Caroline rushed in, blonde hair bouncing around her. She located them quickly and made her way over. "Sorry I'm late. Raising two teenage witches…not as sitcom-y as it sounds." She threw her arms around Bonnie, squeezing tightly. "You're back!" She sang out excitedly, pulling away. "I missed you."

"I missed you too. I came as soon as I heard. How are the girls?"

Caroline sighed, shrugging out of her coat. "As good as they can be, all things considered." Damon's brows pulled together. "They found a body in the woods a few nights ago. We think it was a camper, but by the condition he was left in, it was kind of hard to tell who it was."

"Any leads on the attacker?" Damon asked.

She glanced at him. "I have my suspicions, but there's no solid evidence."

"Have you talked to Matt?" Bonnie questioned lowly.

The blonde shook her head. "Ric and I handled it. Kinda wanted to keep the law out of this one. You know the rules…" Matt would always be a friend, but years of losing those he loved to vampires, he wasn't keen on saving any. To say he was disappointed when he found out about their school for the 'gifted' would be an understatement, but together, they had made rules…rules that were just broken. "It could be anyone, but if it's one of my kids…" she trailed off dejectedly. "I can't save them from whatever happens next." She whispered in a conflicted tone. "I need a little outside help."

Damon scoffed. "And by help do you mean…" He dragged his thumb across his neck.

Caroline balked at him. "No! We can't just kill them, Damon. My job is to help them, teach them how to exist as a supernatural thing in this world. I'd be failing them all if I didn't at least try."

Bonnie nodded. "I'll do a little recon tonight. Check out where they found the body; see if I can sense anything."

Damon snapped his head to hers with a worried brow. "I don't want you out there all by yourself, Bon. Especially not if something is out there killing people."

She shot him a reassuring smile. "I can handle my own." He wasn't convinced. "Really, I'm fine." The truth was, she needed the time alone. There were a lot of emotions coming back home, and for her it was something that was always best handled alone.

"So then what am I expected to do here?" Damon drawled. "Babysit?"

"Well you two are all I got now, so…" It had been hard for all of them. With Stefan dead, Elena still slumbering and her strained relationship with Matt, she didn't have many friends left. Her and Rick had been passing ships; the only thing keeping them in contact was the kids and the school. "Actually…do you mind staying at the boarding house for a few days? In case something happens?"

"Do I get my old room back?" Caroline canted her head with a pointed look. "I guess that's a no." He turned serious, giving his sister-in-law a nod. "I'll be there."

Bonnie squeezed her friend's hand. "We'll do whatever we can to help."

…

Dean cleaned and organized their weapon's that night, laying them out on the bed while Sam tapped away on the laptop, looking further into the missing person cases. "So how do you want to play this?" Dean started looking over his shoulder. "Fish and wildlife? Park Ranger? FBI?"

Sam sighed seemingly not registering his brother's question. "Look at these reports, Dean. It's all animal attacks, but with significant blood loss and puncture wounds. These are vampire attacks, and for some reason the police in this town are covering it up." He finished pushing the laptop away and leaning back in his chair in frustration.

Dean nodded once, pulling out their badges from the box. "FBI it is then. I think we should lay low tonight, get our bearings, hit up the Sherriff in the morning and see what the hell is going on."

…

Bonnie followed Caroline's directions into the woods, but mostly let her senses guide her. Her powers had evolved over the years, and her time as a hunter made her hunting skills more attuned. When she reached the area where Lizzie and Josie found the camper, you wouldn't have guessed that anything sinister had happened by the look of it; the downpour of rain this week had washed away any blood or evidence, but the feeling she got, shook her to her core.

This person suffered…horribly. It nearly staggered her and it made her stomach roll. Bonnie followed the energy further into the woods, and stopped when she reached a tent trailer in a small clearing. With a mournful sigh, she entered it and was shocked by what she found. Weapons, maps, symbols and sigils painted on the inside of the small trailer and something she recognized as a devil's trap on the ground beneath her. This wasn't just a camper…this was a hunter. She collected what she could shoving the hunter's belongings in his duffel bag and hoisting it over her shoulder. It was just as she was leaving when something shiny caught her eye in the moonlight. A necklace. She picked it up, holding the pendant in her hand and her eyes closed in disappointment.

She got out of the trailer and pulled her phone out of her back pocket to call Caroline. "Hey…I think I know who did this. And you're not going to like it."

…

AN: Hey everyone! I hope you are interested in this one! In the next chapter, we'll have some more Dean/Bonnie interactions possibly a Dean and Damon interaction. Looking forward to getting a little Dean/Bonnie/Damon triangle going.

Please leave a review and let me know what you think and if I should continue! Thanks - Vanessa