I worked as a courier in Southern Oregon between 1998 and 2001. I've seen a few strange sights in my time but the night I saw the Grinning Man, I'll never forget. You see, there's a nearly derelict old highway that connects Interstate 5 to Highway 101 between California and Oregon. It winds through the mountains and over a couple rivers across a three hour drive. It connects a few small towns and communities together and is an easy moneymaker for someone who runs packages through these areas that have no one else to rely on. These small towns can't put much trust into the postal service because they only shipped out mail twice a week, if they were lucky; So they were stuck with me. I would start near central Oregon, pick up packages to be delivered near Coastal Northern California on the 101 and then vice versa. One night I was running late, four hours or so, and was just making my winds through the 199 going east towards the 5 as the sun was setting in the distance. Darkness quickly consumed the forested highway and the only light was coming from the front of my truck. As I turned one of the sharp ridges, I nearly skid off a cliff as I maneuvered to dodge a person. I didn't get much more than a quick glimpse at him but I just barely missed him. It was far too dark on such a thin and dangerous highway to be hitchhiking but nevertheless I'm sure I saw his thumb in the air as I barely glided past him. I honked my horn in anger as I cursed to myself. Probably “Stupid shithead” or something to that effect.

A few minutes in, the silent darkness went by and I was able to calm myself. I was on part of the highway that was generally stressless, pretty much a twenty minutes straight away, when I say another person. I didn't get a good glimpse at the last one so I couldn't be sure but It almost looked like this guy was wearing the same clothes as the last one. I let off the gas just enough to get a decent look at the guy. Black slacks, suspenders and a nice pinstriped shirt. Was he smiling at me? I wasn't sure but something about the whole situation creeped me out. I pushed back down on the pedal and sped away. I'm pretty sure I passed the same man yet again, near the fifty mile mark. Just standing near the speed sign, face towards it. Just staring at it, with less than an inch between it and his face. As I turned that corner he raised his hand, like he was waving at me but was somehow aimed the wrong direction.

The next twenty minutes were entirely uneventful, except a dead deer near a turnoff for a rest spot. I had convinced myself that I allowed the darkness to scare me. As the drive went on the road began to twist and turn in ways I wasn’t familiar with. I looked at the clock again and then once more. It had felt like ten, maybe fifteen, minutes of driving and the little digital clock on my dashboard never clicked past 10:41. I began to panic, I tried harder and harder to convince myself that I was tired and the night was scaring me. That the incident with the hitchhiker had frazzled me. As I turned another corner I saw the same man again on the other side of the street. I slowed down enough to look at him, to see his dark eyes in the light of my head beams and for him to meet my gaze. He just continued staring at me, waving and smiling. Smiling with a mouth so wide that it just seemed so unnatural. I drove on.

Minutes later he was there again. Waving and smiling. The twisting road now turned into a thin road heavily forested with sickly looking pines. I was now sure, for whatever reason, I was no longer on route 199. In the distance, just beyond the lights of my truck, I could see the figure again. Already waving, probably already smiling. I lifted my foot from the pedal and my truck began to slow. It creeped to a stop a few feet from the man and I saw him walk. Still smiling. He approached the passenger side window and I rolled it down.

“Who are you?” I asked

“A Hitchhiker.” He responded with a strange and metallic voice, almost like he wasn't used to speaking. I could hear the light clicking or the man trying to open the passenger’s side door but it was locked.

“Okay,” I responded nervously, “But what's your name?”

There was silence as the man's dark eyes stared into mine, still smiling with his yellow teeth proudly displayed “I'm a Hitchhiker.”

For some reason this response creeped me out even more than the last time he said it

“Okay. Well, where are you headed?” I asked.

Without looking away from me, without allowing me one moment free from his gaze and haunting smile, he pointed ahead.

“That way.” He said.

“And what's that way?” His jaw twitched, just slightly for just a moment.

“Darkness. Nothingness. Endless nothing.” He began to gargle and his lower jaw dislodged and began to hang loosely as the man's mouth began to grow into a larger and larger gape in his face. I slammed my foot onto the gas pedal and floored it. I could hear the screech of my back tires. In my rear view mirrors I could still see him in the darkness, just barely. I could see that he was waving.

Minutes later, the forested cleared and the road looked familiar again. I was finally nearing one of the small towns on my route. As I passed the small minimart and the second hand store, both dark and lifeless. I approached a turn and a highway patrol car was rested at the side of the road. I pulled up next to the car, he rolled down his window and I rolled down mine. He gave me a bewildered look, like he had been awoken by my approach.

“You okay son?” He asked and I responded by telling him about the man. I decided to leave out some of the more fantastically parts of my story for fear that the officer would drag me away for intoxication. I told him the man tried forcing his way into my truck. The officer nodded, reversed his car and I watched him make his way back down the way I came.

I made it home that night and quit my job the next day. Decided I'd find a nice office job, one where I wouldn't have to travel. That weekend the highlight of the local news was a missing highway patrol officer. Harold Kline went missing during a shift on Route 199.