The Hitchhiker’s Guide to the (Oregon) Galaxy

When Santi Elijah Holley, writer and author of An Amerikan Family: The Shakurs and the Nation They Created, was 25, he took the ultimate travel leap of faith: He hitchhiked 400 miles from Northern California to Portland through small-town Oregon.

But for Holley—who had just moved to Portland from Michigan—it wasn’t just about getting a ride. After a year of feeling like an outsider as a person of color in one of America’s whitest states, this journey would test whether Oregon would accept him or leave him standing on the side of the road.

Transcript

Aislyn Greene, host: Hitchhiking is the ultimate act of faith—faith that strangers will stop, that they’ll be kind, and, frankly, that they won’t do anything creepy slash weird slash murdery. When writer Santi Elijah Holley found himself needing to get home to Portland from Northern California, he chose faith over a bus ticket. But this wasn’t just about getting from point A to point B.

As a broke 25-year-old from Michigan, Santi had been living in Portland for a year, but Oregon still felt like an exclusive club he’d never be invited to join. As a person of color in one of the whitest states in America, he was ready to give up and move back home. So when a friend offered him a ride to California but left him to figure out his own way back, Santi saw it as more than just a transportation challenge; it was a test of whether Oregon would accept him.

What he discovered during those 400 miles changed everything. I’m Aislyn Greene, and this is Travel Tales by Afar. Let’s hit the road with Santi.

Santi Elijah Holley: It began with a very straightforward invitation. My friend, Sasha, asked if I’d wanted to tag along with her as she drove from Portland to California. I said I’d be happy to. Sasha would be in California for at least a few weeks, however, so she asked me how I’d get back up to Portland.

“No problem,” I said. “I’ll hitchhike.”

A year into my new life in Portland, Oregon, I wasn’t in a great place. I was broke, underemployed, and lonely, far from my hometown of Ann Arbor, Michigan. As a person of color in one of the whitest cities in the country, I felt especially ill at ease. The whole state of Oregon gave me the impression of an exclusive country club for white people.

I was considering calling it quits and moving back to Michigan. Sasha’s offer felt like a lifeline, a distraction—and a chance to become much more familiar with Oregon and the people who live here.

This wouldn’t be my first time hitchhiking. As a teenager in Michigan, I’d hitched rides to visit friends, enjoying the freedom and adventure of placing my life in strangers’ hands for short drives. I thought of myself as a teenage, brown-skinned Kerouac. I never had any frightening encounters with anyone, and I didn’t worry that I would.

This trip would be different. I’d be traveling slowly over multiple days through small Oregon towns. I wanted to feel that same sense of freedom and adventure, but I also wanted to learn if my newly adopted state—lily-white Oregon—would accept and look after a young, anonymous, brown-skinned man far from home.

Sasha dropped me off in Arcata, a small town 100 miles south of the Oregon border. Early the next morning, she wished me luck and drove off, leaving me with a backpack, sleeping bag, snacks, and water. I didn’t own a cellphone. All I had to guide me on my 400-plus-mile journey was a paper road map of the Pacific Coast.

After two cups of coffee at a café called Muddy Waters, I walked to the Highway 101 entrance ramp. Now, as I stood on the side of the road, faced the oncoming cars, [and] stuck my thumb out, I tried to tell myself that I hadn’t made a terrible mistake.

Before long, a pickup truck pulled to a stop, and a man in his early 30s rolled down the passenger side window and asked where I was headed.

“North,” I replied, which seemed to me like the simplest answer.

“I’m goin’ to McKinleyville,” the man said. “I can drop you off there.”

After a quick, mostly silent 10-minute drive, the man let me off near a gas station in the nondescript town of McKinleyville. Soon after, I went back to the road and stuck out my thumb, [and] another truck stopped.

“I just seen you get out of Brad’s truck,” the man explained. “He’s a buddy of mine.”

This man drove me another 10 minutes up to Westhaven, where I soon got picked up by another driver, who dropped me off 5 minutes later, in the seaside town of Trinidad. At this rate, I thought to myself, it would take me all day just to get out of California. But though it had been years since I’d last hitchhiked, I remembered that the most important thing is to be patient.

After 20 minutes of standing on the side of the road with my thumb out, watching drivers rubberneck as they whizzed past me, I was relieved when an elderly couple in a rusted old station wagon pulled over and told me they were heading to Crescent City, about 60 miles north. They didn’t speak much during the drive, and I didn’t get the impression that they cared at all about who I was or why I was hitchhiking alone on the highway. I assumed they’d just felt some kind of moral obligation to stop for me and bring me a little closer to my destination. We drove silently up the coast until the 101 turned east and snaked through the Redwood National Park, with its towering, primeval trees reaching into the clouds. They dropped me off in Crescent City, gave me a little wave, and continued on.

I didn’t have to wait long before I was picked up by a man in his mid-30s. He had silver-streaked hair, a navy-blue sports coat, an expensive watch—and he was driving a bright-red convertible. His name was Peter. He told me he lived in New York and this was his first trip to the West Coast. He’d rented this car in San Francisco to drive up the 101 and see the sights. After about 20 minutes, we crossed the state line, with its large “Welcome to Oregon” sign, which Peter earnestly said aloud, like a flight attendant.

He soon became distracted while looking out of the window at the Pacific Ocean, gleaming in the afternoon light. The car swerved toward the shoulder once, then swerved again a moment later over the yellow line.

“Hey, so, do you want to pull over?” I asked.

“Actually, yeah,” he said. “Do you mind?”

We turned into the small parking area of Harris Beach State Park, then followed the trail to the beach, eating wild blackberries off the vine. When we got to the beach, we slipped off our shoes, letting our toes sink into the cool sand. He pulled a flip phone from his pocket and began snapping photos of the ocean, and I reflected for a moment on the peculiarity of this sight: the broke, brown-skinned hitchhiker and the white, affluent New Yorker, walking barefoot together on the beach. Despite Peter’s obvious wealth and success, I didn’t envy him. Though I didn’t own a car or a fancy watch, and I probably had at that moment $100 total in my checking account, I didn’t want to be at a place in life where I felt compelled to snap tiny cell phone photos of the ocean.

Eventually we returned to his car and continued north. We reached the small town of Gold Beach as dusk was approaching. Peter told me he was going to look for a hotel for the night before continuing in the morning up to Seattle, where he’d return the car and fly back to New York. I didn’t have money for a hotel, so I told him he could drop me off anywhere.

“Suit yourself,” he said.

He dropped me off at Gold Beach Books and Art Gallery, where I whiled away the rest of the day. I bought a cup of coffee, browsed the bookshelves, and looked at the collection of amateur art on the walls, killing time until I’d have to go out and find a place to sleep for the night.

I wasn’t entirely new to sleeping on the street—or “urban camping,” as I thought of it. I’d spent a handful of uncomfortable nights on park benches or in the backseats of cars on previous road trips, so I knew how to find relatively safe and inconspicuous places to camp out. It’s a helpful survival skill to have when you’re poor.

When the store closed for the night, I discovered that Gold Beach was as dark and quiet as a ghost town. I wasn’t especially concerned about being discovered during the night, but I didn’t want to wake in the light of the morning, staring up into a cop’s face. After exploring for a little less than 30 minutes, I came upon a small church with a low roof that I could easily climb up onto. From my divine perch, I drifted off to sleep with the bright stars above. It was cold, damp, and exhilarating.

The first day of my hitchhiking road trip had not helped me become any more acquainted with Oregon or Oregonians. I’d spent most of the day, in fact, just getting out of California. Aside from Peter—who, like me, was only traveling through—I’d hardly shared two words with anyone. On this second day, I was prepared for anything to happen, but I hoped that people would at least be more conversational.

Early the next morning, I returned to Gold Beach Books for a cup of coffee, then walked back to the highway. I was still about 300 miles from Portland, if I took the most direct route on I-5, but I wanted to remain on the more scenic 101, at least until Newport, which would add almost 200 miles to the trip. I was in no hurry to return to Portland since there wasn’t anything waiting for me there but an empty fridge and a twin bed with threadbare sheets.

I stood on the side of the road and stuck out my thumb. In a short time, a minivan pulled over, and a woman rolled the window down and asked where I was headed.

“North,” I said.

“OK,” she said and opened the door.

She told me her name was Deborah, and she was on her way to Port Orford—a fishing town, one of the oldest and smallest towns in Oregon—where she lived with her teenage son. Her son considered enlisting in the Navy, but he was disheartened by his early experience and recently returned home.

“He doesn’t like it in Port Orford,” Deborah told me. “It isn’t easy for young people here, and I feel bad for them. There should be more things for young people to do. This area is nice, but it’s just a bunch of old folks and retirees, mostly, and they don’t care about the younger generation. They would rather ignore them or treat them like delinquents.”

Deborah and her son used to live in Bend, but at that time, it didn’t have much going for it. “Now Bend has gotten to be a nice city and so expensive we can’t even afford to move back,” she said with a bitter laugh.

Deborah told me about a building in Port Orford that served as a center for high school bands to play shows and practice and hold events that they couldn’t hold anywhere else. This building, however, was dilapidated, decaying, and unsafe. Asbestos drifted from the ceiling, pipes were rusted, and paint curled from the walls. There was a threat of it being condemned and boarded up, shutting down the one and only place in town for teens to put on events.

“So I started showing up with paint brushes and brooms and mop buckets,” Deborah told me. “I’ve put in a whole lot of hours trying to clean that place up. A few other women have started helping out, and it’s starting to look a little better, but we need much more. It costs a lot of money, and I’ve been paying out of my pocket for cleaning supplies. I’ve been trying to get the city to recognize the need to fund more places where kids can go and put together events and shows and things, but nothing ever happens.”

I wondered why Deborah was sharing all of this with me. Perhaps I reminded her of her wayward son? Or perhaps she’d only needed to vent to someone neutral, an outsider, who would listen impartially to her concerns and anxieties. When she dropped me off, 30 minutes later, outside a Port Orford supermarket, she thanked me, as though I were the one who had done her a favor by riding with her and listening to her story.

Feeling encouraged by my first ride of the day, I walked a short distance to the 101, stuck out my thumb, and looked forward to who I’d meet next. I waited only 10 minutes before a young man in a pickup truck pulled over. He didn’t ask where I was going and didn’t introduce himself. He drove his truck at breakneck speed, like he was either in a hurry to get somewhere or a hurry to get away from somewhere.

“I’ve got a court appearance in Reedsport,” he explained. “DUI. They pulled me over for speeding, then gave me a breath test. I’m not even supposed to be driving right now. Matter of fact, I’ve got another speeding violation up in another county, which I hope they don’t find out about, and this vehicle is registered in Washington, and my girlfriend—well, my ex-girlfriend—works at this bar in Eugene, so that’s why I was drinking. Fuck ’em, it don’t matter.”

I wanted to know more about his story, but I had trouble concentrating on anything else but the blur of the road and the squeal of the tires as we whipped around the curves. Seventy harrowing miles later—which we covered in less than 40 minutes—he dropped me off at a Reedsport convenience store and sped away to his court appearance. I took a few minutes to myself to catch my breath, then went inside the convenience store and bought an apple and a loaf of bread to eat later.

When I returned to the highway, I had to stand at the head of the Umpqua River Bridge, which I knew wasn’t a good place to try to get a ride, since there was hardly any room on the shoulder for cars to pull over, but I didn’t see any other options. Sure enough, I stood there with my thumb out for over three hours, until an older man in a dirty pickup truck finally pulled over, practically blocking traffic in one lane.

“I only picked you up cuz you’re standin’ in a terrible spot,” the man told me as I jumped into his truck. “I’m gonna take you crost that bridge and drop you there, cuz that’s where I’m turnin’ off. I’m goin’ off to work down there. You should have better luck gettin’ a ride, but if you’re still there by the time I come back up, when it starts gettin’ dark out, you’d be welcome to come over to the house. Me an’ my wife’ll cook you up some dinner, and you could stay there till mornin.’”

I was heartened by the man’s hospitality. I’d only been in his truck for a few minutes. We hadn’t had enough time to get acquainted, and yet his concern for this strange young man’s well-being evidently took priority over any suspicions or misgivings he’d had. I wondered if he, too, had an errant son somewhere. I might’ve taken him up on his offer if it had come to it, but almost as soon as we’d crossed the bridge and he dropped me off, an old Chevy pulled over to the side of the road.

“I’m going to Florence,” the man told me. “I can take you as far as that.”

He wore a button-up shirt with a National Park Service badge. His name was Howard (“folks call me How”). His car was a mess of fast-food wrappers. There were cigarette burns in the upholstery. As we were driving north of the town of Gardiner, Howard nodded toward a large, dilapidated structure. “That over there is the old paper mill,” he said. “Hundreds of men worked there, a lot of them just out of the Army or out of school. The pay wasn’t hardly anything, but it was steady, reliable work. I was 18 years old when I came there, and I stayed for 15 years before they went out of business and shut their doors for good. I’ve been working up at the park since then—maintenance and what have you.”

Howard spoke softly but quickly, as though he knew we only had a short time for him to tell me everything he wanted about himself.

“Another park offered me a little more money, but all I’d be doing is cleaning toilets,” he continued. “At this park I still have to clean toilets, but not all the time. Still, it’s not the best work. I’ve been living with my mother in Florence and I’ll eventually move out, but I’d like to stay in this area . . .”

When I was a teenager hitchhiker, my conversations with drivers were surface-level—if that. When I’d set out on this road trip, I wasn’t sure what to expect, though I’d hoped for more. And today, three different people had opened up to me in different ways. Now, I’d never considered myself an especially gifted listener. I’d just thought of myself as a curious person—someone who goes on adventures and takes risks for the opportunity to learn something. But I was now discovering that I was apparently someone who people—strangers—felt free to confide in. I was apparently someone who could be trusted with sensitive stories.

I didn’t realize it at the time, but I now believe that here—on this stretch of Highway 101 in Southern Oregon—was where I started out on the path that would lead to my present career as a journalist and author. All of us want to share our stories. We want others to be interested in our lives, no matter how unremarkable they might seem. All we need is a receptive audience—and there’s no better audience than a complete stranger sitting beside you in your car for 40 to 50 minutes.

Howard dropped me off north of Florence, just south of Yachats, near Cape Perpetua in the Siuslaw National Forest. I had a few hours of daylight left, so, upon Howard’s recommendation, I decided to hike the nearby St. Perpetua trail, an uphill trek through sword ferns and spruce trees, ending at a small, stone lookout point, with an astonishing view of the Pacific Ocean. I sat at the top of the trail, ate my apple and the loaf of bread I’d bought in Reedsport, and watched the sun sink into the Pacific. I then spread out my sleeping bag and slept there, hidden inside that stone shelter, with the moon shining down on the ocean like a spotlight illuminating a giant stage.

In the morning I hiked down the trail, returned to the 101, and quickly caught a ride with a nurse on her way home to Yachats, after working the graveyard shift in Florence. She dropped me off in town, where I bought snacks and coffee at the C&K Market. I rode in the bed of a pickup truck from Yachats to Newport, and from Newport to Toledo I sat in a minivan with a mother and her daughter. I was surprised that the mother would stop for a hitchhiker with her young daughter in the car, but both of them were open and friendly, as though this were a completely normal situation, as though picking up hitchhikers was something mother and daughter did all the time.

They dropped me off in Toledo, where a young couple picked me up and drove me 40 miles east along Route 20, to the college town of Corvallis. I spent the rest of the day in Corvallis, drinking coffee at the Sunnyside Up café, and treating myself to my first hot meal in days, at the Evergreen Indian restaurant.

When night came, I wandered around town, scouting a place to sleep, but I couldn’t find anywhere sufficiently out of sight. I finally climbed up to the corrugated tin roof of an automatic car wash on a dark street and tried to make myself comfortable enough to sleep. I awoke early in the morning, cold and with all my limbs aching, and I longed for my twin bed with the threadbare sheets.

I got a ride out of Corvallis by yet another man in a pickup truck, who told me he would take me as far as Wilsonville. “You shouldn’t have any problem gettin’ the rest of the way to Portland from there,” he said.

He was on his way to work and he was already late and would be even later on account of picking me up, but he stopped for me because, he said, “You don’t look like your normal hitchhiker,” which I wasn’t sure if I was supposed to take as a compliment.

I noticed a cassette tape of Willie Nelson’s Stardust on the floor of the truck. “Great album,” I said.

The man turned and looked at me. “Yessir, it is,” he said. “I was stationed in Georgia for a good long while, and they’d play that album every chance they could. Especially that song, ‘Georgia on My Mind.’”

We drove up the bustling I-5—passing outlet malls, truck stops, the Enchanted Forest Theme Park, vineyards and wineries, more outlet malls, more truck stops—listening to country music and talking philosophically about the road.

“I’ve done my fair share of traveling,” the man said. “I was stationed in Japan for a while before being transferred to Georgia, and, from what I’ve seen, ain’t nothin’ wrong with people. The world’s one large place and sometimes we just have a hard time gettin’ along, you know what I mean? It’s all about experience. Anything we know comes from our direct experiences and nothin’ else.”

He dropped me off in Wilsonville, just across the Boone Bridge over the Willamette River, and from there I was picked up by a young man in a rickety old Jeep, who took me all the way back into Portland, where I walked through the front door of my house, shucked off my backpack, and collapsed on my bed. I thought about all the things I’d seen—the redwood trees, open beaches, verdant trails, wide rivers—but mostly I thought of the people who’d stopped for me, welcomed me into their cars and trucks, invited me to dinner, or shared their stories with me—an unfamiliar, brown-skinned young man on the side of the road—and I thought, Maybe I’ll be OK here. Maybe I’ll be accepted in Oregon after all.

Aislyn: And that was Santi Elijah Holley. Santi was OK, in fact he went on to live in Oregon for the next 18 years, and while he now lives in Los Angeles, he says that Oregon still feels like home and probably always will.

And no, he hasn’t hitched since that trip, and while he says he “misses the freedom and adventure of hitchhikinging, he has no inclination to ever again stand on the highway with my thumb out.”

You can learn more about Santi on his website, santielijahholley.com—I’ve included that link in the show notes, as well as a link to his excellent book,  An Amerikan Family: The Shakurs and the Nation They Created.

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