It wasn't his place to tell Winchester how to raise his kids, but there were just some things children were supposed to do as far as Bobby was concerned, and Halloween was one of them. It wasn't about ghosts and ghouls; it wasn't about religion. It was about every red-blooded American kid's right to go door to door and get free candy. It was that simple. Or it would've been simple if Winchester hadn't blown a gasket when Bobby mentioned taking Sam and Dean out trick or treating.
It had all started out innocently enough. Bobby had done the leg work investigating a demon John was hunting with Daniel Elkins. The two-man job was going to last the weekend, so Bobby offered to take the boys. John was packed up and headed out the door as dawn broke across the sky; Bobby mentioned taking the boys into town that evening to trick or treat. Damn if the man didn't actually stop dead in his tracks and do a slow-mo turn back toward Bobby.
The long and short of it was a patented Winchester rant that revolved around "knowing what is out there" and "keeping the boys safe". Eventually John laid down an ultimatum – swear to keep the boys in on Halloween or he'd go right back upstairs, get the boys out of bed and drop them off at some motel where they could spend the holiday locked in on their own. Bobby didn't point out to John that leaving a twelve year-old and an eight year-old unattended in a motel was not "keeping them safe" but by that time Dean had been roused by the yelling which meant Sam wouldn't be far behind. Bobby promised not to take the boys trick or treating, and Winchester left with one last, "Look out for Sammy" for Dean. The whole thing left a bitter taste in Bobby's mouth that couldn't be washed away with even the strongest cup of coffee.
Halloween day passed uneventfully. Early on in the day Sam bonded with Bobby's dogs. Those poor animals got more of a workout trying to keep up with the energetic boy than they ever did walking the perimeter of the yard with Bobby. Dean had adopted a sadly neglected lawnmower motor as his project, and kept half an eye on Sam while he worked. If Bobby had simply suggested renting some horror movies and pigging out on junk food the boys would have been more than satisfied; it was more of a treat than they usually got. But it wouldn't have satisfied Bobby; not on Halloween.
A trip into town for lunch gave Bobby all the time he needed to pick up supplies. He set the boys to sorting a huge pile of nails, screws, nuts and bolts. It was really just supposed to me a make-work kind of task, but damn if those boys didn't have every last item neatly organized by the time he was ready to go. He tucked that piece of information in the back of his mind for the next time the boys might visit.
"Alright boys," Bobby began. "I'm glad to see you finished this up. I've got one more job for you to do." He led the boys to the far left corner of the yard. There was no obvious job for them to do, so they looked at him curiously. Bobby suppressed the ghost of a grin that crossed his face, then put a "serious" face into place. "This is a big job, boys…with some serious consequences at the end." That got Sam's wandering attention.
Bobby pointed. "Do you see that trail of oil?" Dean squinted and nodded; Sam actually walked over to point at it. His small face wrinkled in concern. "Do we have to clean it up, Mr. Singer?"
"No sir. You're going to follow it all the way through the yard. Don't let anything get in your way." Dean and Sam exchanged looks – they were beginning to get the idea that this was no ordinary job. "There's only one rule…" Dean's focus snapped back to Bobby; he was definitely one for following rules set down by an authority. "You've got to stick together."
"That's the one rule?" Dean asked.
Bobby nodded. "That's it. Stick together and see what you find in the end."
Sam and Dean exchanged another look. Something silent passed between them, and suddenly things shifted. Sam was poised to move, but he was waiting for a cue from Dean. Dean was working through everything Bobby said; he could see it on the boy's face. But once it was clear in Dean's head that he understood the limited rules of this engagement, he was ready to move forward.
"Okay. Let's go, Sam." Sam broke out into a wide grin that brought his dimples out in full force. With a whoop, Sam rushed forward. Even before the boys were out of sight, Dean had to remind Sam to stick together.
The first part of the trail was easy enough to follow. But it wasn't long before the boys came to the first obstacle. Sam got there first, and then paused, waiting for Dean. Bobby was interested to see what they would do. He deliberately wove the trail of oil through the shell of a car near the far wall. Bobby knew that John had laid down the law – the boys were never allowed to play in the junkers around the yard. It was one rule Bobby always backed fully. But this was different; the boys weren't playing, they were on a mission, and he was right there.
Dean turned to look at Bobby. "Follow the trail all the way through the yard. Don't let anything get in our way." It wasn't a question, Dean was looking for confirmation. Bobby nodded; he was more than a little surprised when there was no, "But Dad says…" from Dean. Then again, Dean was a boy who understood the chain of command. Right now, Bobby was the one giving the orders. Dean turned back to Sam. "Stay right behind me, Sammy."
With the first step Dean took to climb through the old car, the energy of the game changed. They were out of bounds, and both boys knew it. It gave the task an edge of excitement and made it feel a little dangerous. Once the boys were through the car they were out of Bobby's line of sight. But he could follow their progress by listening to them.
"Here's the trail, Sammy."
"Dean! We climbed through that old car!" Sam was gleeful with enthusiasm.
"We're hunting, Sammy. Can't let some old car get in our way." Dean tried to sound off-hand about it, but Bobby could hear the excitement in his voice as well.
"Hey! What's this?" Sam exclaimed. Bobby knew that the boys had come across the empty treat bag he left on the trail. "Should we take it?"
There was a pause. Because Bobby was out of sight, Dean could no longer look to him for visual confirmation. "I think we should, Sammy. Mr. Singer put it there on the trail."
A rustling of the bag indicated that it had been picked up. There was no further discussion, and the boys moved forward.
The winding oil trail led the boys through a maze of old appliances. Sporadic exclamations from Sam when they came across various stashes of candy let Bobby track the boys' progress. The biggest reaction came from Dean when they discovered the bag of peanut M&Ms. By the time they reached the next obstacle, Bobby had the boys back in his line of sight though he stayed out of their field of vision. The trail of oil led the Winchesters to a tall section of chain link fence in the back corner of the "old" yard. There was not a lot of traffic in this section of the yard anymore, so Bobby had padlocked the back gate. It was clear to Sam and Dean that the trail extended outside the yard.
The fence wasn't all that high, and Bobby knew that both boys could climb. He fully expected them to jump the fence. So he watched with no small amount of amusement as Dean pulled some small tools out of his back pocket and handed them to Sam. Wordlessly, Sam passed the loot bag he'd been carrying over to Dean in exchange for the tools. With a look of intense concentration, Sam bent to the task of picking the padlock on the gate. Dean stood by, at ease, nodding with approval.
"Way to go, Sammy!" he praised with a slap to his younger brother's shoulder. Bobby shook his head and stifled a snort - Dean sounded uncannily like John when praising Sam. It was downright scary.
Spurred on by their success, the boys surged forward. "Do you think we're close, Dean?" Sam inquired as they walked along the perimeter of the fence.
"I'm pretty sure, Sam. We're not far from the front of the yard now." Dean tossed a glance over his shoulder, aware of Bobby shadowing them although Sam was not.
Sam stopped short causing Dean to stumble into him. Sam let out a breathless, "Whoa." as he stared at their last obstacle. "Dean…" he whispered as he sucked in his breath. "The tires…"
There it was – the tempting, enticing, heretofore forbidden wall of tires. This time, Dean didn't look back at Bobby. With a war-cry he ran forward; Sam was hot on his heels. There was a mad scramble to reach the top. Dean reached the summit first, but he was not inclined to play King of the Mountain. Instead he reached down and offered Sam a hand up. There the two of them sat - perched on the highest tire with the bag of candy between them - looking happier than pigs in shit. It almost made up for the lack of trick-or-treating.
"Alright now, boys," Bobby called out from below. "Y'all made it to the end of the trail. Climb on down here and let's open up some of that candy that you found."
Planted in front of the TV running a marathon of horror movies playing on the local station, the three shared two pizzas, a six-pack of soda and at least half of the chocolate from the loot bag, including the pound of peanut M&Ms. When the sugar induced comas hit the boys, Bobby leaned back in his recliner and started planning the festivities for next year.