People Told Us Their Weirdest Road Trip Stories

It’s almost May long weekend in Canada, which means some of us are already optimistically throwing swimsuits into duffel bags, buying tanks of gas that cost more than an entire MALM bedroom set (in BC at least), and forgetting that mosquitoes are still a thing.

But while some of us will enjoy open roads, blue skies, cold beer and feel like we finally understand country music, others won’t have such easy rides. Because embarking on a road trip ill-prepared, then banking on the kindness of strangers to see you through the storm, can be a bit like jumping into a ball pit with a bunch of wild animals: you might have the time of your life with some unlikely new friends, or you might get your ass kicked by a combination of nature and society as the adults of the world nod and say, “told you so.”

When VICE asked people for their weirdest road trip stories, we weren’t exactly surprised that the reality of The Road can be even stranger and more far-fetched than the (slightly stupid) metaphor above. For example, you might befriend a pathological liar and end up in jail, be conned into selling your vehicle for a loonie (only in Canada), or encounter a steely-eyed border patrolman named Gomez who won’t rest until justice is done on a certain dope-smoking young man hoping to attend a music festival.

In the words of Carrie Bradshaw, who has nothing to do with this article but everything to do with life: “So many roads. So many detours. So many choices. So many mistakes.”

I was 18 and working at Sunshine Village. I had a kitchen job with this guy, Ace*, who was always talking about how rich he was, saying he was the CEO of this company I’d never heard of. He said he liked to take time off to work as a cook because it was less stressful. I guess he wanted to get to know me better, and so he moved all his stuff into my room and we started living together. Then Ace found out I had a car and said that we should drive down into Banff for a pub crawl. When we got there he started buying tons of drinks—really throwing money around—and so I started to believe he actually was rich. When the bars closed, he insisted we take an impromptu road trip to Calgary because he was hungry and Calgary had a Denny’s. My memory pretty much stops there.

The next memory I have is opening my eyes, looking at a steel toilet, and seeing Ace peeing into it. He’s like, “Hey buddy,” and I’m like, “Where are we?” He says, “We’re in jail,” then tells me we got in a bad car accident and that I had been driving—which I really don’t think I had, because I didn’t even have my license at the time. Then he gets down on the floor, grabs me, and says, “Look, there’s cameras and microphones in here, so watch what you say, but last night I told the cops that we met two guys named Hugo and Maximillion from Montreal. They wanted to go to Calgary, and since they needed a car and we needed a sober driver, we decided to team up. But on the way we hit a patch of black ice and rolled the car. Then Maximillion and Hugo ran away.” Then Ace told me that, to back up the story, he and I had gotten out of the car and ran around the woods and made footprints to make Max and Hugo’s escape believable. He said, “Just tell the cops that you don’t remember anything except for picking up these two guys and that neither of us was driving. Now, they’re going to come in and separate us, but don’t crack and neither will I.”

Neither of us did. They suspected I was driving and said they’d take my prints off the wheel as evidence, but at this time I was kind of pissed because I really didn’t think I’d been driving. I told them obviously they’d find my prints on the wheel because it was my car. They kept saying, “We think you were driving, and if you don’t tell us the truth, you’re going to be here for a very long time.” I said something like, “I hope you’re cooking burgers for lunch because I’m hungry.” And then one of them slammed his hand on the table, ushered me outside to the street, and let me go. Ace was already outside having a cigarette, waiting for me.

We went to wash our clothes because, during the accident, the front windshield had broken and a bunch of dirt and stuff had flown in the car. We were sitting outside the laundromat and that’s when he told me the “true story,” which was that I had been driving while “Ghetto Supastar” was playing in the car. When the song ended, I apparently shouted “one more time!” and hit the back button, and that’s when we hit the ice and rolled into the ditch. He also claimed he saved me by pulling me out of the car before we ran into the forest to fake Hugo and Maximillion’s running away.

The weirdest part was the way he left. He was like, “Ah man, this accident made me realize that I’ve got a girlfriend and a good job and so I’m just going to go home.” I said, “So you’re not going to come back to finish the work week or get your stuff?” He said, “Nope, I’m gonna go.” And so I went with him to buy a bus ticket, and then he was gone.

After a few days back at work, I decided to see what he’d left behind. He had a garbage bag full of stuff, and there wasn’t even that much in it—just some weird track suits, a wig, sunglasses, a toy gun that looked super real, and a Russian passport that he had glued his own picture to. I never heard from him again.

For awhile I worked on the midway—the carnival, essentially—and so I spent two summers roadtripping between major cities. The first summer, I was in Edmonton and got into a really stupid car accident. I was turning left on a green light, but the car on the other side of the intersection suddenly accelerated and hit the passenger’s side of my car. There was no physical damage to the car except for it started making a weird noise. I was like 20 years old, and brought the car to a mechanic. He was like, “Nope, I absolutely can’t fix it. This car is too unsafe to drive, and I can’t let you leave the property in it. You can either pay for a tow truck or you can sell it to me for one dollar.” I was freaking out because I thought he’d call the cops on me if I left the lot in this car, and I didn’t want to get a tow. So I sold him my car for a dollar. Literally a loonie. I still have it.

I ended up taking the bus back to Vancouver, but once I got home I realized I left my radio in the car, which was worth some money. When I called the mechanic, he was like, “Well, the car is in the shop right now and I won’t be able to reach the shop until tomorrow.” So this asshole totally cheated me out of my car for a dollar.

When I was a teenager, my friend and I went on a two-month trip across Canada and back. We decided to hitchhike. On day two, we were just outside Lloydminster, Alberta, standing in the pouring rain. Then about 30 yards down the road, a pick-up truck glides off onto the shoulder and flashes its lights at us. We walk over to it, and inside the truck is this ageless old man—you know, he could have been anywhere from 50 to 80 with this leathery old quality to him. Hands wrapped around a leather steering wheel, he’s wearing these large wrap-around sunglasses and staring straight ahead. He rolls down the passenger window, and without looking at us he mumbles: “I don’t normally pick up hitchhikers, but you boys were looking so pathetic out there that I decided to relax my own rules.”

So I hop in the front, my friend gets in the back, and this man pulls off the road and starts driving ahead. He doesn’t say anything, just keeps driving in silence. I’m getting progressively more unnerved, and I can’t put my finger on why until I realize that, this whole time, the radio of the cab of this very expensive pick-up is set to a dead air channel. Just plain air static as we drive through a thunderstorm. And just as I’m starting to get pretty creeped out, he peels off the highway onto a dirt road and heads into the middle of the forest. He says, “I hope you don’t mind if I take a little detour”—again, totally monotone and with no eye contact. So I’m thinking, Well this is the beginning of the end.

He drives through these progressively darkening woods for about ten minutes until we come to a clearing. And in the centre of the clearing is an old, beaten-down, white, abandoned church. The shutters are hanging off the windows and it probably hasn’t been painted in 40 years. I’m thinking, This is his kill site. This is where he does the business.

He pulls up to the front of the church, peels his hands off the steering wheel and, still looking straight ahead, says, “I like to make charitable donations sometimes.” Then he gets out of the vehicle, walks around to the back of the pick-up, and grabs four huge trash bags that I think have to contain human body parts. He walks up to the front of the church, opens the door, and throws it all inside. This whole time my friend and I are looking back and forth at each other thinking, how do we get out of this?

Then all of a sudden he gets back in the truck, turns it around and drives back towards the road. We drive for about 15 more minutes in silence before we reach the top of a hill near North Battleford. He says, “I think I’ve driven you two about far enough for today” and we get out of that car faster than we’ve ever moved, even forgetting our raincoats.

My friend and I were on a cross-mountain bike trip that we’d started on a whim. We didn't even have tools or a patch kit or anything like that. Around day eight, my friend’s tube popped and it was a literal Band-Aid fix—we wrapped extra strength Band-Aids around the hole. He could get about two kilometres at a time before the tube needed to be inflated again. He did this for about 30 kilometres. By the time we arrived in Blue River he just threw his bike down in the parking lot, completely over the trip.

We went to a restaurant, sat down, and asked our server if anyone in town knew how to fix a bike tire. She went to go call "Nick, the helicopter pilot” because apparently we had arrived in a resort town known for its world-class heli-skiing. Our plan was to tent, but there were bears everywhere so the server let us stay with her and her roommate for the night.

When we got to the house we were staying at—after biking 120 km that day—a house party was already in full swing. The workers of the town—who all worked for the owner of the mountain and town, a guy called Mike Wiegele—fed us and got us drunk and gave us this whole incredible night. By the morning, apparently the story of these two idiots with Craigslist bikes heading across the mountains had reached Mike Wiegele. Wiegele, who turned out to be an avid biker, descended down from his mountain and gave my friend a new set of tires that were easily worth more than his bike. We were back on the road.

My girlfriend, her brother, my friend, and I were driving from Canada down to Bonnaroo, a music festival in Tennessee. When we were in line for the US border, my girlfriend asked, “Does anybody have anything in their bag that we need to know about?” We were all like, “Nope, nope, we’re fine.”

When we got to the border, the agent asked if we had anything worth over $10,000 in the car, and my buddy made some cheap joke about how he wished he was richer but, sadly, no, he didn’t have any money in the car. Right away the agent was like, “Pull up here,” and we knew we were getting searched. As we pulled into the parking stall, I had this feeling like, “oh my god,” because my backpack had a secret pocket and I was pretty sure there were some crumbs of weed and rolling papers in there. The weed was from a snowboarding trip years ago—dry and old and shitty—but I was still like, “Oh no, what if they find it?”

After they searched our car, they brought us back individually into rooms for questioning. When they asked me if I’d ever smoked weed, I lied and said, “No, I’ve never really tried, never been into that kind of stuff.” So then they brought us all together again, made us wait, and then asked who owned the grey backpack. I was like “Oh fuck.”

Two officers—Gomez and Gunderson—took me to a back room for more questioning. Gomez was clearly the bad cop and was like, “So, you’ve never tried any marijuana, ecstasy, or cocaine?” and I was like, “No, never.” And then he was like, “Oh, so what’s this then?” and pulled out this little bag of papers and three little lint-sized pieces of pot. I stood up and said, “oh my god I did not know that was in there!” and started pacing around. Gomez yelled, “Sit down!” and then asked me a few more questions. At one point I couldn’t help but stand up with my hands on my head, because this was the USA and I was probably going to go to jail for smuggling drugs. Anyway, Gomez kept pointing to a sign on the wall, which listed a $10,000 fine for deceiving an agent. So I said, “Honestly, I know exactly where the weed is from. It’s from a ski trip years ago. Sorry, I wasn’t trying to deceive you.” Then the good cop—Gunderson—was like, “Yeah, you could probably get that at the music festival anyway!” But I said, “Sir, I wouldn’t even dream of it.”

The officers started getting looser after that, but they wanted me to sign this paper that said I had 0.5 grams of marijuana. I don’t know if that’s the smallest amount you can charge a person for or something, but I definitely didn’t have 0.5 grams, and so I said, “I don’t mean to be disrespectful but I can’t sign that piece of paper unless you show me on a scale that it weighs that much.” Eventually they said, “You can sign this, pay a $500 fine and we’ll let you and your friends into the country, or else we won’t let you in.” And so I signed it.

It only took a couple of days for the fear to wear off. I bought some pot at the music festival, stored it in the tent, then forgot about it when we rolled up the tent to leave. Fortunately I remembered to take the pot out of the tent before we got to the border, but the smell was still pretty bad. At the Canadian border, they pulled us in for questioning again—probably because we were on some list—and had us all stand in a line while a dog sniffed our bodies and our stuff. When the dog got to the tent he started nodding like “Yes!” The border guy was like, “My dog likes your tent. Why would he like your tent?” I told him that, at one point, I’d had some weed in there from a camping trip. The border guy said, “That’s good enough for me,” and let us go.

It was 1975, and my best friend and I drove to Tucson to visit another friend. When we got down to Tucson, we decided we wanted to go to Mexico because it was closeby. We’d just planned to go for a week or something. But when we got there it was so much fun, we had a great place to stay—like I think our hotel was 60 cents a night or something—and so we decided to stay for a couple more weeks. We sent a postcard to our friend in Tucson right away (because she was expecting us back) but I guess it didn’t arrive. In those days in Mexico, I heard it was common to take the back off postcards and sell them again. But I’m not sure if that’s true, or if that’s what happened.

So of course our friend is expecting us back but we don’t show. She pushed the panic button and phoned my friend’s dad, who decided to come down to Mexico and look for us himself. But he ended up arriving in Tucson the same day we arrived in Tucson, and so he decided to drive back with us towards Regina. On the way, we stopped in Vegas and he took us to see Elvis Presley. It was pretty fun. Of course, when we got home there were all sorts of rumours that we’d been in jail and that. Back then, we didn’t have cell phones. It was a different world when you traveled because you just couldn’t stay in touch.

I used to be a performer as part of this cast of 12 people. In the summer of 2012, we had a van full of people and a car full of people, all driving from Toronto to Edmonton. We stopped at this rest stop and gas station in Schreiber, Ontario—really in the middle of nowhere, blink and you miss it kind of thing. So we go into this rest stop, and there’s a gentleman behind the counter. It really feels like we’re walking into the past because this place is very vintagey—like a ma and pop shop. And there’s a bunch of photos on the wall of this guy who looks like some 60s or 70s crooner. There’s also a record player.

Then the guy behind the counter starts chatting with us and tells us his name is Cosimo Filane. Apparently he’s a Canadian-Italian crooner from the 70s. He’s got all these commemorative water bottles with his name on it and we’re like, “What the hell is this?” Then all of a sudden he puts on a record, whips out a microphone and starts singing to us—I think it was “When the moon hits your eye like a big pizza pie, that’s amore.” After a while, we had to leave because it was late and we had to get to our hotel or something. But he gave us all commemorative water bottles. I felt like I was in a David Lynch movie. Follow Mica Lemiski on Twitter.

Sign up for the VICE Canada Newsletter to get the best of VICE Canada delivered to your inbox daily.