AS ONE MIGHT GUESS, there are simpler ways to hop a freight train than the way a gutter punk does. For instance, you could wait outside a rail yard for a train to stop, find an open boxcar, climb in, and remain inside until the train gets where it’s going. Then, presumably, at that final destination you’d step from the train with a new view of yourself. You’d have shaken free of the confines of schedules and even concrete time. You’d have tweaked the system, gotten something for nothing, and accomplished a feat few dare to attempt, having seen the country by a means of travel that most folks classify, in terms of desirability, somewhere between hitchhiking and getting kidnapped. But that would be boring compared with the gutter punk way, or so I learned from a nineteen-year-old Houston street kid, a hopped-up thrill seeker with multiple lip rings, a taste for WWII-era military attire, and a home in a tattoo parlor doorway near the intersection of Westheimer and Montrose.

Already I need to back up. It was a year ago April, in a Marfa art gallery, of all places, that I met “Dennis,” a made-up name that will hide the kid’s identity and make him sound significantly less disaffected than does the nickname he actually goes by. It was opening night for an exhibit loosely billed as an installation/performance piece: The gallery had moved an Austin music lover’s living room and 10,000-volume record collection out west for a ten-day listening party and lecture series. Among the usual crowd of 75 or so ranchers, writers, artists, and tourists was a handful of gutter punks who’d swept in with Dennis. He had just jumped off a train in Alpine, a tall, wiry, engaging kid, with eyes the color of the sky on the first day of spring break and a slack-jawed grin that softened his sharp cheekbones into a look of perpetual amazement. When he laughed, he looked as if he couldn’t believe just how wonderful and funny life could be, and when he told a story—like the one about how his heroin-addict mother had been sent to prison for killing a liquor store clerk when Dennis was ten—he looked surprised that you might think such a thing was unthinkable. He was an upbeat kid and handsome enough that you could actually forget the foot-long, cherry-red mohawk that, left unattended that night, fell to one side of his head.

When the record collector played something by the Ramones, Dennis approached the turntables with a request. He knew that the punk forefathers had once covered “Do You Want to Dance?” but it was not their 90-mile-an-hour version he wanted to hear. He asked for the original 1958 recording, by a one-hit wonder from San Francisco named Bobby Freeman. Dennis said he used to listen to it with his parents when he was little, before his mom was locked up and his dad, a homeless guy who preferred thievery to begging, booted him from the nest at fourteen.

But his father gave him one great gift before casting him into the world. To Dennis’s utter enchantment—not to mention that of the Marfa art lovers who now sat enrapt at his feet—his father had told him stories about how he used to ride freight trains. And thus began Dennis’s hoboing existence of the past four and a half years. As he rolled through the story, his wonderment transferred to his audience, and his chest puffed up as he fielded dumbfounded queries. Isn’t it dangerous? Hell no, it’s fun. Where do you sleep? Wherever I am. How do you know where you’re going? I always wind up wherever the train takes me.

He didn’t just describe total freedom, he personified it, and when he returned to the gallery the next night, I was waiting with more questions. This time he was ready for the spotlight, his mohawk waxed into long red spikes. Even though he was barely coherent—a ghost-faced attendee said he’d seen some of Dennis’s cronies huffing what looked to be Sterno—he did manage to string together a couple of sentences about having tutored novice train hoppers. And he said he was willing to do the same for me. I almost jumped out of my shoes.

ON AN ALARMINGLY COLD NIGHT eleven months later I was learning at the hand of the master. We were lying in a field of tall, wet weeds in a particularly sketchy part of Houston’s Fifth Ward, across the street from the rail yard. Dennis was dressed for the weather, with a long, olive-green U.S. Army greatcoat cinched at the waist with a brown leather belt, his mohawk now forsaken for a warmer full head of light-brown hair. The hour was nearing midnight, and we’d been hiding since five, first for a couple of hours under a bridge, then for four or five more amid the chiggers and stray-dog turds collected in the weeds. Earlier, a railroad cop, known as a “bull,” had thrown us out of the yard, following in his pickup as we walked from the tracks. Here Dennis turned to me and the two friends he’d brought along for the trip, “Dave” and “Rich,” and explained a rule that all train hoppers know: If you’re caught in a train yard in the Northeast, the bull will likely beat you. But in the genteel South, you get a second try. So we would wait in the weeds until night fell and the bull’s shift ended. And there we waited. And waited. And the boys smoked bowl after bowl of pot while I itched at the chiggers. While we waited.

I must have been dozing when Dave whispered to Dennis that open boxcars were rolling through the yard. “Let’s go!” said Dennis, as he threw on his backpack and ran across the road. My first step was somewhat slower than the kids’, and they got to the train fifty feet ahead of me. I was still shaking sleep out of my head when Dave and Rich bounced up and into a boxcar. Dennis looked back and yelled, “Come on! Get on the train!” I tried to catch up to their car, but the train was thundering by at about 15 miles per hour. Running on loose rocks at the side of the tracks with a forty-pound pack on my back, I was losing ground.

“Just jump on the train!” yelled Dennis. I looked at the boxcar in front of me. Its floor was at my shoulders. Its wheels looked much closer. There was simply no way.

“Goddammit!” yelled Dennis at me, and then to Dave and Rich, “He can’t get on! Peel off!” They jumped off the train, and we ran back to the weeds.

“What’s wrong with you?” asked Dennis when we were back on our bellies.

“I couldn’t catch up with y’all’s car, and I wasn’t going to be able to jump into anything with this pack on my back.”

“My God!” he said in frustration. “You never jump in with your pack on! You always throw it in first!”

“And we don’t have to all get in the same car,” spat Dave. “We’ll hook up again when the train makes a stop. My God!” Those seemed like good points to have made before we ran to the train, but I let that slide.

Two hours later a second chance came, but with no open boxcars. Again we ran into the yard, and this time I grabbed the ladder of a passing grain car, or “grainer.” There was a small platform at the front of the car where I could lie down and hide, and Dennis hid next to me. Rich and Dave found similar spots on the grainer in front of us. We were all on. And we were rolling, at least for ten minutes. At the edge of the rail yard, our train stopped.

Now came a rule unique to the gutter punk way: Always be moving. Whether that was to avoid being discovered or merely a function of Dennis’s attention span never became clear. Either way, we jumped from our spots and crept up to an empty engine at the front of the train and crawled inside. In the cramped cockpit, Dave looked out one front window and Rich the other, while I watched the back door. Dennis used what room was left to pace around. We stayed like that for an hour, the boys whispering play-by-plays for drug deals they could see outside the yard.

When the train finally started moving, sometime around three in the morning, Dennis ordered everybody out of the engine. We found a stacker, an open car with four-foot-tall sides and no floor, just two-by-four steel crossbeams on which freight containers sit. Jutting from the inner walls of the car was a six-inch-wide metal shelf, and that’s where we stood, in a four-by-seven-foot space in front of a container, hanging on to the sides as the train crawled by downtown Houston. The view was stunning, although my attention was split between the bright skyline and the exposed tracks passing just inches beneath my feet. When the train stopped thirty minutes later, on the other side of downtown, Dennis directed us off again.

“Back to those grainers!” he barked as we jogged down the tracks. The ladder was harder to climb than it had been the first time, but I pulled myself up.

Finally Dennis announced he was going to sleep. I moved my backpack under my head to do the same. It was four-thirty, below freezing, and as the train picked up speed, pushing itself to 50, then 60 miles an hour, a light drizzle started to fall. It grew into a cold, heavy rain. Such were the joys of being a gutter punk.

DENNIS IS NOT BIG on explaining himself. The charm he radiates in large groups gets turned off quickly. I spent time with him in Houston in the months before our trip, and there he was different, sullen. He’d go long stretches without talking, piping up only to describe some graffiti he’d recently painted or to say he wanted some pot or to complain about “actual people”—folks with houses and jobs, what he called “actual lives.” He repeatedly asked me how much he’d be paid for our trip, although I had told him that that was not part of the deal. Our plan was to take a freight train to San Francisco, just the two of us, except for a short first stretch when we’d be joined by his girlfriend, a journalism student at a Houston college whose well-to-do family had been kept deep in the dark about Dennis. She hoped to take some photos to sell to texas monthly, and Dennis wanted the article to make him a star. I wanted to ride a freight train. That was the exchange.

But plans change. The girlfriend backed out, and Dennis brought along his two buddies, announcing that the destination was now San Diego. He said he didn’t have time for a longer trip: “I want to get back to Houston, get a job, and start a family with my gal.” There was no negotiation. With such little control over the rest of his life, he was intent on running the show.

We woke up just after dawn with the train stopped somewhere west of Houston. The rain was done, but the wind blew hard. Dennis directed us back to the empty engine, where we manned our previous lookout positions. While the boys talked about which rap styles sounded best on which prescription meds, I largely stayed quiet, thinking instead about the difference between being 19, like Dennis, and 38, like me. Rich tried to bring me into the conversation.

“Hey, man, do you have any tattoos?”

“No. Those weren’t quite cool yet when I was y’all’s age,” I said. “Then all of a sudden there’s Dennis Rodman, just covered in them.”

“Yeah,” said Dennis sarcastically. “Dennis Rodman invented tattoos.” Dave and Rich laughed.

Then the front door, which Dave was supposed to be watching, opened, and a mildly startled conductor walked in.

“I didn’t know anybody was riding in here,” he said. “It’s just us,” offered Dennis.

“Where are y’all going?” he asked.

“To California,” said Dennis.

“Y’all are on the wrong train,” said the conductor. “We’re fixing to switch tracks and head to Laredo. But I tell you what. I’ll slow the train down when it makes its turn south. Then you can hop off.”

“Will that be somewhere that we can catch another train?” asked Dennis.

“It could be,” the conductor said, raising an eyebrow. “Let me show you something. But remember, you didn’t hear it from me.” He pulled up a cushion on the seat Rich had been sitting on and revealed a big box of flares. They looked like sticks of dynamite. “Take some of these with you. Then wait in the woods, and when you see a train coming, light two of them and leave them in the middle of the tracks. Any train has to stop when they see these flares. Then you can get on any car you want.” Dennis eyeballed a flare.

“Have you been riding all night?” the conductor asked. We shook our heads yes. “Man, you kids must be freezing. This engine you’re in doesn’t get any juice. Let me go up to the next engine and turn on the heater. That should be a little warmer for you.”

I was thrilled, and not just because I hadn’t been called a kid in fifteen years. This was unexpected generosity. Dennis said that 99 percent of train crewmen would have done us the same favor, at least in the South. Now I felt good. I had a comfortable seat, and I saw no chance of jail. I asked Dennis why we didn’t reroute our trip to Mexico and just stay in the engine.

He didn’t acknowledge the question. A train rolled slowly by on the tracks beside us, and he yelled, “That’s our train west. Come on!” Again we ran along the tracks until Dennis found a stacker and pulled himself over the side. It’s a tricky move; if you miss the frame, you’ve got an instant on the ground and then the rest of your life—a very brief rest of your life—under the train. But I made it in and held the side of the stacker as the train picked up speed. We got up to 70 miles an hour, the tracks passing below so fast you couldn’t distinguish the ties. The ground was a gray blur, and I knew that one bump would send me under the car. Of course, given the twenty-ton weight of our stacker, the chance of a bump was small. But thinking of the stacker’s weight, its big iron wheels grinding two feet from my hip, did not put me at ease. I looked at Dennis. He was focused on lighting another bowl as the train barreled on.

AN HOUR LATER, I didn’t really mind when Dennis ordered us to the ground. He said we were headed to the engines. But then he grabbed a ladder between two freight cars and said to climb up. We lay down on a platform above where the cars connected as the train rolled out again. Once it was up to about 30 miles an hour, we moved to a bench on the platform and sat up. Dave and Rich were nowhere in sight. Dennis said, “Follow me!” and scaled the side of the freight car, then headed across the top of it to the engine. I stayed where I was.

A few minutes later he jumped back down. He was furious. “What’s wrong with you?” he yelled.

“Dennis, I’m not walking on top of any freight cars on a train going forty miles an hour.”

He put his face in his hands and cussed into fingerless gloves. Then he started screaming. “You’re ruining everything! I’m tired of being homeless, but I couldn’t get a job and get off the streets because I knew I wouldn’t be able to take two weeks off to take your ass on this trip!”

“Hey, Dennis, you know what?” I asked, knowing I’d sound like some middle-aged jerk. “I’m not the reason you live on the streets. And you know what else? I’m not getting on top of any moving freight cars.”

He crossed his arms and stewed for five silent minutes. Then he hopped on top of the freight car and walked to the engines. I stood and watched his greatcoat flap as he jumped to the next car, and I finally understood the philosophy of the kid and his method. A train’s just something to mess with, a playground, a chance to show a world that doesn’t care about him that he doesn’t care about it. To me, on the other hand, a train was something eminently capable of messing with me.

I sat back down. South Central Texas farmland was on both sides of the train. Trees and creeks and cows and fields. This was the view I’d been waiting for. I waved at kids in cars when the highway got close to the tracks. And when the train stopped just west of Luling, I climbed down of my own accord. Three freight trains, fifteen hours, and 150 miles into it, my train-hopping days—make that “day”—were over.