Hitchin’ a ride

by Jessie O’Brien

U.S. Highway 550 between Durango and Hermosa is one of the few places in America where it’s still normal to see hitchhikers. For the past two months, I’ve driven that stretch of highway to and from work, and at least once a week I’ll see someone with a large pack, sun-kissed cheeks, and uncombed hair under a sweat-stained hat with a thumb in the air. Every time I pass these mysterious travelers, I think to myself, “One of these days I’m going to pull over.” That day came in early April. I had forgotten a camera for work, and was driving back to get it when I saw two guys on the side of the road. They looked to be in their mid-20s, were hauling a lot of gear, and appeared not to be the steal-your-skin types.

They were headed to Ouray, and my mind was miles away from an office chair. I felt anxious as I pulled off onto the shoulder. It’s exhilarating to do something that most people would consider dangerous.

As they were walking up, I leaned over my seat to throw a yoga mat, towel, backpack (holding my precious, pawnable MacBook), sun shield, and random volleyball into the back of the car. I immediately regretted my decision not to keep the volleyball at arm’s length. I could use the desirable Wilson as bargaining leverage for my life, or as a weapon that I would Karch Kiraly spike into my passengers’ eyes if they made any wrong moves. Now I would have to murder them with my bare hands if it came to it. In retrospect, I realize it would have been wise to scope them out before letting them pile in, but at that point, I was committed.

They opened the trunk and threw in their packs, which were carrying hammocks, a tent, high-end sleeping bags, a backpacking stove, cooking gear, seven days worth of canned food and, though they are beer guys, pints of alcohol because they were easier to carry.


Kyle sat in front. He was initially far more chatty than Caleb, who took the backseat. Both had beards, hats, and sunglasses, and I was immediately disarmed by their lack of creepiness, and Kyle’s eagerness to talk. Plus, they were the ones who should have been worried; they had just hopped into a smashed up 2009 Chevrolet HHR with poor alignment and massive blind spots – worse than macular degeneration – with a barely-competent driver to take them through the treacherous twists and turns of Red Mountain Pass.

Standard small talk ensued. Before I was able to turn on my phone to record our conversation (and collect clues in case I were to go missing), Kyle filled me in on what they were doing on the side of the road.

My two passengers were from Grand Junction. They had taken a week off from work at Fun Junction, a liquor store that used to be an amusement park of the same name. The purpose of the trip was to hitchhike. They were making a giant loop, and had camped at Capitol Reef National Park, Stout Canyon, by the dam at Lake Powell, Cortez, and Durango.

Both of them have cars, money, and the means to travel, but this was Kyle’s baptism into the world of “only the essentials.” Caleb was more seasoned. Originally from Bay City, Texas, he would hitchhike after floating the river to get a ride back up. He’s hitched thousands of miles, including a trip from Junction to Alaska.

I turned the volume down on Parquet Courts to record while we made small talk about traveling, school loans, and their boss at the liquor store. Caleb silently sipped on a Monster Energy drink in the back seat until Kyle nudged him to talk.

“Caleb is moving to Panama,” Kyle said. “You can speak for yourself.”

“I’m ex-patting,” Caleb said.

I’ve never met anyone who’s traveled as much as Caleb. He takes a week off every month to go somewhere – most recently Colombia, the Gateway in Mesa County with friends, and a solo hitching trip to the Grand Canyon. Hearing how much Caleb has hitched squashed any subconscious stereotypes about hitchhikers I had – people on the sexual offender’s list with a half-empty flask of Old Crow in their back pocket and a missing toe. People who are forced to rely on others. It’s not a choice.

The reality is though, that Caleb is more disciplined than the majority of Americans. He has a degree. He paid off his motorcycle. He doesn’t have Netflix. He doesn’t buy Starbucks.

“I converted a retired U-Haul truck into a house. I virtually live bill-free,” he said. “When I travel, it ends up being cheaper than when I am at home. Always, I hitchhike. I’m out in nature not spending anything. I can go all over the sickest places in the U.S. for free.”

Most of his income goes to savings, which is why he can take a week off from work to travel. He could work as little as two shifts per week, but he is saving up enough money to live off of for five years to fund a solo bike trip to Panama.

“I’ve always wanted to do (the)Pan-American Highway. Panama’s economy is really booming so (cycling) is a good way to travel, and see a lot of the world on the way,” Caleb said.


Kyle’s roadmap looks much different. “I don’t have any big future plans,” he said. “I am more or less winging it right now.”

Luckily, winging it is an essential skill for hitching. Two powerful factors – weather and time – are out of your control. At one point, my passengers got caught in a deluge and had to camp next to a dog park. It was a low point, but Kyle said it was a good lesson.

“That night, for me, to an extent, was miserable,” Kyle said. “I still got to sleep though, so it could have been a lot worse. I am glad that happened, because up until that point, it was smooth sailing.”

Another factor is the drivers. Caleb and Kyle say it’s never who you expect to be behind the wheel. As vanning has grown in popularity, one would think that a Volkswagen bus would be a hitcher’s best friend, since the cultures share the same ethos of freedom, traveling, and the road. But that’s not always the case.

“People with van conversions, young dudes in Chacos driving a Subaru (never pick you up). It’s hardly ever – not like it never happens – a young, liberal, new-age hippy dude,” Caleb said. “I think it’s because those people are not living the lifestyle of fully embracing that people are just people. They are judgier than the old dude who picks you up and understands, ‘I’ve done too much hitchhiking to pass up on a hitchhiker.’”

Kyle was surprised at the unpredictability of their chauffeurs. He said there isn’t a specific demographic, other than people who are open-minded.

“We got picked up by two Korean ladies and only one could speak a little bit of English, but not well enough to continue to talk to,” Kyle said.

It was around this time that we saw two bighorn sheep grazing on the side of the road. “If you haven’t driven this yet, be careful, too, because every deer in Colorado lives on Red Mountain Pass,” Caleb said.


“The other random ride we got was from a state trooper who took us, I want to say 70 miles, from Bryce Canyon to Stout Canyon,” Kyle said. They camped out with a couple who gave them a ride and smoked them up. The currency of hitchhiking is beer and weed, Caleb said.

“We met this dude from Germany who had six months off this year (and is) traveling to the hotspots of the U.S.,” Kyle said. They went for a swim in the San Juan River near the Arizona-Utah border. The German man, Mole, took them on a scenic loop through the Valley of the Gods. They also hitched through a few Indian reservations. Kyle said he was uncomfortable with the idea at first.

“When Caleb went to (the) Grand Canyon – Navajo natives live there –the way he explained (his experience) sounded kind of sketchy to me. He got picked up by people who were drinking and driving. Some kid picked him up in a raggedy car and went off-roading.”

But hitching through the reservations were some of the most relaxed parts of the trip. They were picked up by women with children in the car. (Caleb said he has gotten many rides from women. His mom boils it down to women being more nurturing and sympathetic.)

“Everyone has these interpretations and stories of how they understand how reservations work and how the Native people are now,” Caleb said. “Most people assume – there are issues and stereotypes that come from the truth – but overall hitchhiking through a reservation is more chill than going through public land. It’s more of a relaxed culture, more open-minded people. It is honestly common to hitchhike on reservations. Natives hitchhike through reservations all the time.”

Throughout his hitching career, Caleb said there was only one time he asked to get out. A big rig trucker was incessantly asking him to hang out to the point it made him uncomfortable. He simply asked to get out and that was that. The strangest people they encountered this trip were, unsurprisingly, from Utah.

“The dude was 36, but he looked young. He was dating this girl who was 23. She was saying she had a baby, but the feds came and took it from her,” Kyle said.

“In reality, they were a little eccentric, a little weird, but so harmless. The guy bought us scratch tickets,” Caleb said. Kyle won three bucks.

Joey has so far been the most memorable person they’ve met on the trip. He had been living in his van for five years.

“Street smarts was why he was wise,” Kyle said. “He was book smart, but it was through all his experiences.”

Joey backpacks 200 days a year and supports himself with temp jobs and writing about his experiences. He told them to always do things for their own personal experience. How many mountains you climbed and how many miles you’ve traveled isn’t a competition.

Not much later, I turned the corner into Ouray. By the time I parked the car, I fully understood the appeal of hitchhiking.

“You are relying on the unknown,” Kyle said. “That’s what makes it adventurous.”

“This is (Kyle’s) first trip, and I’m sure he’s hooked,” Caleb said.

“Oh, I’ll admit, I am,” Kyle said.”

We had a beer before we parted ways. On the way to the car, Caleb told me that traveling with a friend is far more silly than his introspective solo trips, and left me with a word of advice: If I’m ever in Ridgway, go to Taco Del Gnar.


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