Death of the American Hobo

When walking through a city, or a suburb, or a section of forest, I feel an enormous sense of relief when I come upon a set of railroad tracks. It is as if the fears and doubts and anxieties of daily life abruptly vanish. The vise grip that civilization and this world have on my head loosens, and for a moment I can breathe freely. The train tracks persist in the shadows of our stark, digitized 2001: A Space Odyssey future, relics of the time when iron behemoths and Pullman passenger cars cut through the inky-black primeval wilderness on their diesel-stained voyage through the night.

In this endless matrix of streets, cars, cell-phone towers, businesses, houses, jobs, and families, the train tracks are a trapdoor exit, a gap, an exception where silence and lawlessness still reign.

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If highways and roads are America’s veins, the hundreds of thousands of miles of tracks are like those chakra diagrams in acupuncturists’ offices, the hidden flows of energy that affect the body as a whole. It’s as if the vapor of several hundred years of America’s daring and rugged spirit is contained within the wafting, intoxicating smell of hot railroad tar. It is the last truly American place, untainted by the regrets of modern progress.

Most people know that in the mid-1800s, Henry David Thoreau moved to a cabin off the banks of a little pond outside his hometown of Concord, Massachusetts, to live there for two years while writing a book called Walden. What is less widely known is that his cabin was no more than 300 feet from a set of railroad tracks leading into Concord, and that it was only a 30-minute walk down the line to get to his mother’s house.

On a recent visit to Walden Pond, while I was awed by the pristine site Henry David had chosen for his experiment, I saw that without the tracks—that lifeline, that trail of bread crumbs that could be followed back to civilization—his long hermitage could have been an unending hell. Thoreau had found the best of both worlds, the thing we all want—nature and civilization together in one tidy package.

I can only imagine that on some lonely, cold nights in his little cabin, when he was missing his friends in Boston, wondering why he had moved back to his birthplace to grow string beans, the sound of the train whistle echoing through the woods in the dead of night steeled his will to the task at hand and reminded him that while he was alone, he was still a part of humanity.

I grew up in the suburbs of central North Carolina, a gentle and compassionate eastern wood, where the freight train was a vital part of the texture of the landscape. In high school, on late autumn nights as multicolored leaves fell in my neighborhood, I listened for the din of the high school marching band in the distance and the whistle of the train as it chugged through dense deciduous forests and my spirit surged with excitement for the future and all that was left to be done.

I spent my formative years on the tracks. There was something magical about the way you could part the foliage or walk down a clay gully behind the CVS parking lot and suddenly enter a hidden world.

Just after I turned 18, on a crisp fall afternoon, I hopped my first freight train out from downtown Raleigh with my friend Doug MacPherson. Those pleasurable hours spent lying around on tarry pieces of lumber, trying to figure out the mysterious shuffling of cars and locomotives in the yard, are seared into the marrow of my bones—like a puzzle you don’t understand that begins to make sense the longer you look at it. My friend Cricket, a veteran train-hopper, gave us a little hand-drawn map to help us navigate our way once we got into the Linwood yard in western North Carolina. His advice was the stern warning given to most first-time riders: “Stay down and don’t let anyone see you.”

As our train creaked out of Raleigh, we promptly ignored Cricket’s advice and sat up on our grainer porch, visible to all the cars stopped at the railroad crossings. There was something incredible about waving to all the drivers as we passed—when they saw us, their faces lit up and they pointed, mouthing, “Look, hobos!” It was almost as if by riding on the porch of the train we had made them believe in mystery again, the contemplation of the unknown.

The scenery along the tracks is completely different from that seen through the window of a speeding car—there are no gas stations, billboard advertisements, bars, sidewalks, or pedestrians. It is a world of disused lots and shadows cast from backyard floodlights, stray dogs howling, underpass bums drinking, concrete monoliths, and telephone poles engulfed by kudzu. Once you get out there into the open country and away from the roads, you see pristine nature, untouched by the withering hand of civilization.

With our ragged map, heading on to a strange place, Doug and I felt as if we were a pair of early Americans—pioneers far from home on a great adventure. And so began my contorted, largely unfulfilled love of riding freight trains.

Be wary of any enterprise that requires new clothes,” Thoreau warned. The great New England radical and nonconformist could be described as the proto-hobo, with his emphasis on self-sufficiency, living outdoors, and aimlessly wandering the still-virginal American landscape. Historians agree that the modern American hobo emerged after the Civil War. The nation’s young men had returned to devastation at home. Some, already accustomed to sleeping outside and foraging for food, became transients, setting off across the country in search of work. In the mid- to late 1800s, the growth of the hobo followed the westward sprawl of track.

In the early days, hobos were migrant workers who jumped train cars rather than paying to ride in passenger class. One estimate put about 1 million hobos on the rails between 1890 and 1930. Ben Reitman, a peripatetic anarchist of the 1920s, famous for being the lover of Emma Goldman, subdivided the transient taxonomy as such: “Hobos [were] the unattached men and women traveling around looking for work; tramps the unattached penniless ones tramping around for excitement and adventure like myself, and bums, who make up the third and smallest but the most troublesome type of vagrant, the type addicted to drugs and to drink and who have lost all sense of respectability [italics mine].”

The turn of the century was a perilous time to be a hobo. Between 1898 and 1908, the Interstate Commerce Commission recorded an estimated 48,000 tramps killed on freight trains and an equal number maimed. It was common for migrants to “ride the rods,” lying across the skeletal steel bars under the train, extended like Superman. They also rode the “blinds,” crouching on the platforms of fast-moving passenger trains. Boxcars and lumber cars would often be so packed with riders that it was hard to find room inside. Life was cheap on the rails—some hobos fell off or under trains, others were murdered, while the least fortunate froze to death in refrigerator cars or suffocated in long tunnels unequipped with modern ventilation. Railroad expert Lee Wheelbarger told me a story that well illustrated these perils—the steam trains at the time sprayed boiling oil and hot effluent onto a little platform behind the second locomotive, called the “monkey porch.” On cold nights, hobos who didn’t know any better would move up the cars toward the warmth radiating from the locomotive’s furnace; when the crew found them, they were scalded so badly that they looked like burned monkeys.

Today, if caught trespassing in a train yard by a railroad bull (rail police), you are given a polite warning, cited, or at worst thrown in jail for a couple of days. At the turn of the century, however, a low-grade guerrilla war raged between the rail companies and the hobos. Bulls would wantonly kill hobos, and the hobos would avenge the fallen by shooting bulls. This saga is best dramatized in the movie Emperor of the North Pole, in which a ruthless, hobo-murdering bull named “Shack” is challenged by the heroic hobo “A Number One.” A Number One is determined to jump Shack’s unridable train. The Shack character was probably loosely based on Jeff Carr, a turn-of-the-century bull with a terrifying reputation among itinerants.

In his 1926 underworld autobiography You Can’t Win, outlaw author Jack Black wrote, “[Jeff Carr is] ‘bum simple’—simple-minded on the subject of killing bums. If you run, he’ll shoot you; if you stand, he’ll get you six months [in prison]. And he’d rather have you run.” Jack London also wrote about Carr in The Road, his 1907 book about train-hopping: “Fortunately, I never encountered Jeff Carr. I passed through Cheyenne in a blizzard. There were 84 hoboes [sic] with me at the time. The strength of numbers made us pretty nonchalant on most things, but not on Jeff Carr. The connotation of Jeff Carr stunned our imagination, numbed our virility and the whole gang was mortally scared of meeting him.”

In addition to murder, extortion was rampant. Railroad workers would barge into boxcars and shake down riders for the small amounts of cash they had, threatening to kick them off or have them arrested if they didn’t pay up. In the late 1800s, a group of hobos formed a union of unemployed and itinerant workers called Tourist Union #63 to protect themselves against the railroad workers and bulls. Some of these hobos went on to found the American Civil Liberties Union. More than 50 years later, in 1972, they won their long fight to repeal outdated and repressive vagrancy laws.

Around the turn of the century, Tourist Union #63 held their annual Hobo Convention in Chicago, then the nexus of American hobo life. Chicago had the biggest freight yards in the country and was a natural way station for the nation’s outlaws, criminals, radicals, and itinerants. After riots and police violence marred a couple of the conventions, the organizers put out word that they were looking to relocate. The founders of a small, newly incorporated farming community in Iowa called Britt got in touch to offer their humble lot as host.

Unlike so many towns with draconian vagrancy laws, Britt actually wanted the hobos around—they needed temporary farmworkers. They shrewdly saw that inviting hobos to their town was a way to distinguish themselves from other developing communities. So the founders bought the hobos first-class Pullman tickets from Chicago to check the place out. The hobos liked Britt—there was plenty of space in the little town to hold their large gatherings. A deal was made, and the National Hobo Convention has been held there for the past 112 years.

Today, the hobos still descend on the quiet little town for one weekend a year in August to reconnect with their kin, honor their dead, eat mulligan stew, and elect a Hobo King and Queen. Britt has a Hobo Museum, a Hobo Graveyard, a Hobo Jungle, and even a shrine to the Unknown Hobo.

I’d always wanted to attend the convention, so a scheme was hatched to ride trains from Oakland to Britt with three people I barely knew in just under five days. One should really have an open schedule when riding trains, allowing plenty of time for detours of fate and luck. Due to other obligations, more time was not possible, but we set off on the race anyway. As Tennessee Williams said, “Make voyages! Attempt them! There’s nothing else.”

Our train trip began inauspiciously. The four of us rendezvoused at Heinold’s First and Last Chance Saloon, a century-old dive bar and Jack London’s old haunt, which sits on the Oakland waterfront: There was Jackson, the photographer; Ben, his friend who had a couple of weeks off work and wanted an adventure; and Chris, an itinerant train rider whom I had corresponded with but had never met in person. Chris had ridden extensively, I had ridden a decent amount, and it was Jackson and Ben’s first trip. We camped out on a culvert in the Oakland train yard, downwind from a noxious, throat-burning wastewater-treatment plant. The next morning we were kicked out of the yard by a bull, who threatened to throw us in jail, “and you do not want to go to jail in Oakland.”

Heeding the bull’s warning, we went to the Amtrak station with our tails between our legs and bought tickets to Roseville, the next stop down the line on the Union Pacific Overland Route. Once there, we jumped a slow-moving junk train and got about five miles out of town before it screeched to a halt. We were pulled off by three friendly cops who told us a conductor had seen us hop on. That night, after spending hours wandering around the suburban edges of Roseville so I could replace my ripped backpack, we slept on some high school bleachers just outside the train yard. In the morning, Chris took off on his own, and Ben, Jackson, and I walked across town to catch the $15 casino bus to Reno, Nevada.

The Union Pacific yard in Reno is in the shadow of the towering Nugget Casino. As soon as we arrived, we ventured into the casino. After we’d lived outside for two days, the low-pile carpet and mirrored walls offered a hallucinatory experience, like being inside a fun house.

We walked out of the casino past the sprinklers and neon-green Astroturf and ducked into the first gap in the ornamental bushes. Just behind the hedge was a scrubby hobo jungle (an encampment or catch-out spot by the tracks) beside a chain-link fence, littered with beer cans and trash.

For most of the 20th century, train riders learned the rail system through trial and error and by swapping information with other riders. In the 20s, the jungles were full of people doing laundry and cooking up big meals. You could stumble into one and ask the old-timers when the next hotshot was leaving. The old-timers knew the schedules, yard layouts, and catch-out spots by heart through years of repetition and experience.

In 1997, an anonymous train enthusiast catalogued this folk knowledge in a single codex, a guide of how to hop out of every city, town, and suburb in North America. The thick photocopied pamphlet is updated every year with information submitted by contributors from around the nation. This modern-day sextant for the explorer out on the iron sea is then discreetly passed from hand to hand among freight riders. All 50 states and the Canadian territories are covered, rendered in nine-point Times New Roman font, with an elaborate system of acronyms. An excerpt from the section about Reno:

Reno (UP): YD is 3ME of Reno CH in Sparks… For WBS, you will need to be down at the McCarren overpass at E end, or maybe further E of there. This is fenced off now, but there are access points… Best at night, there is a bull who sporadically scans pig and GM trains, most often daytime.

An eastbound double-stack train headed to Chicago pulled up around midday. We hoisted ourselves over the chain-link fence and ran along the side, looking for a ridable car. Not finding any, we settled for the rear unit—an unmanned locomotive at the back of the train—pulling open the metal door and scurrying inside.

The inside of a locomotive cab resembles a pilot’s cockpit—it’s temperature-controlled, filled with buttons, knobs, and captains’ chairs. There’s bottled water in a minifridge and a bathroom. Jackson and Ben looked around hesitantly. They’d expected to be riding outside, in an open boxcar or in the convertible of a ridable freight car, a 48-foot well—a five-foot-deep cubbyhole beside the double stacks of shipping containers.

On board, a train is like a living creature, a primordial dragon. It creaks and groans and releases air and beeps—it even farts. With each strange noise, Ben and Jackson jumped, thinking something had gone wrong. After I explained that the sounds were completely normal, they relaxed. Once our train lumbered out of Reno, we came out from hiding and sat up on the pneumatic captains’ chairs. The tracks veered away from the highway, and soon enough we were in the open country, scrubby bushes and white desert as far as the eye could see. We opened the windows and smoked and sat out on the platform, just to feel the hot desert wind whipping against our faces. We traveled farther and farther from civilization, away from roads, water, and other people, where cell phones don’t work and you have to rely on context clues or rail maps to decipher your location. As the locomotive cabin grew dark across Nevada, we unrolled our sleeping bags and went to sleep.

When I awoke, it was the middle of the night, and we were in the Elko, Nevada, train yard. Headlights shone outside on either side of our locomotive. I peeked out the window and saw a refueling truck on one side and a golf cart on the other. I shook Ben and Jackson awake and told them we needed to go. Rear locomotives are typically inspected every 24 hours. When you’re riding alone, you can just hide in the bathroom and keep quiet, but with three of us we had nowhere to run. Sensing that a worker was about to burst in on us, I went up to the big steel door and put my weight against it, holding the handle. I heard footsteps on the other side and someone pushed down the handle from the outside. He tried three or four more times, but I held the door until he gave up and walked away.

As soon as he left, we bolted out through the open desert into some scrub bushes near the yard office. As we huddled there in the prickly desert sage with our heavy backpacks, train-hopping felt like some DIY version of boot camp.

The menacing headlights of worker trucks circled around us, boxing us in. We watched as our train pulled away. Just as we were about to give up and walk to the highway, a long grain train pulled into the yard, headed east.

All of a sudden, the trucks disappeared and left us a clear path. We jogged alongside the train as it picked up speed, then pulled ourselves up on a perfect grainer car, wide enough for us all to lie down. The train accelerated and entered a desert canyon, bathed in the soft light of the full moon. The freight train, dark taskmaster that it was, had made us suffer before we earned its grand rewards. The grainer car swayed and creaked across the endless desert; the cool night air was invigorating. I crawled into my sleeping bag and slept more soundly than I have in years.

When I awoke, the horizon was pink, and we were crossing a jetty stretching over the Great Salt Lake. Red tabletop mountains were reflected in the stagnant, mirrorlike water. The smell of sulfur wafted off the water, and gulls flitted about overhead. In the distance a single anchored boat looked like an ancient Phoenician ship. Ben, Jackson, and I gasped, feeling blessed to be among the few given an opportunity to see such splendor. It was almost like time traveling. We passed pure white salt beaches, ruinous old power lines, and beached tugboats entirely eaten by rust.

Though we were running out of water, we decided to stay on through Ogden, Utah, to Green River, Wyoming. In Green River, once the train stopped, we moseyed over a bridge into town like cowboys in a spaghetti western.

Green River is a major freight stopover in the West. Union Pacific logos are plastered on all the overpasses, and the substantial freight yard occupies the spot where downtown should be. A gorgeous Greek Revival building that looks like it should be City Hall is in fact the local train-company headquarters. Rail workers constantly circulate in white trucks.

Transients seemed to be an accepted part of daily life in Green River. Residents smiled at us on the street and asked us whether we were hopping out. Cops crept slowly by, eyeing us with their windows rolled down. A cop we met estimated that the town received 1,000 transients a year. Half starved and dangerously dehydrated, we gorged ourselves at a wood-paneled restaurant called the Crazy Moose, then stocked up on cigarettes, water, and beer and tromped back to the catch-out spot by the river.

We waited under the bridge like trolls, passing the empty hours drinking beer and throwing rocks, trying to break 40-ounce bottles suspended in a brine of mud. Waiting for freight trains has a rhythm similar to warfare or big-game hunting—long stretches of monotony are punctuated by moments of high-adrenaline action.

The tracks were strangely quiet, so we decided to call it a night and try to get a cheap hotel. This proved difficult. Three in a row turned us away, claiming they had no vacancies. Seeing the empty parking lots, we realized we had been denied because we were transients. After hiding our backpacks in some bushes and cleaning up a bit, we had no problem checking in at the Super 8. The next morning, feeling like our catch-out spot might be a dud, we ventured into the main train yard. A worker promptly called the cops, and we spent an hour hiding behind train wheels, trying to not be seen by a prowling cop car. We managed to jump over a couple strings of cars and get out of the yard and were wandering past suburban houses when two cop cars rolled out of nowhere. A bald, angry-looking officer swaggered over to us. “Cat-and-mouse game, huh? Looks like we win,” he scoffed. The other, a soft-spoken “good cop,” asked us a lot of questions about ourselves, and we managed to build up a friendly rapport. The bald one narrowed his eyes and glared at Jackson: “You’ve got a wedding ring on and a nice-ass camera around your neck. So what are you doing out here?”

They let us go with a warning that they would throw us in jail if they caught us again. Tempting fate, we went right back to the river and waited under the rail bridge. In no time, an eastbound junk train came along, and we jumped into the rear unit. It stopped in the middle of the Green River yard, and we spent a nerve-racking hour hiding, imagining the inside of the Green River jail. Our train finally departed, but it was running so slow we decided to get off in Rawlins, Wyoming.

By the tracks in Rawlins we met a 17-year-old rapper named Whytesmoke, who freestyled for us, surrounded by his entourage of BMX bikers. We ate some very good Thai food, and the owners of Rawlins’ only coffee shop let us fill our water bottles. A young father walking with his family stopped us on the street and told us that he had ridden trains in the 80s. “I remember it being a physically grueling experience,” he recalled wistfully. It was a strange moment, realizing that riding trains inevitably becomes just another exciting story of something you did when you were young.

At sunset, we walked down the tracks and crawled up into an old jungle in the jagged cliffs. It looked like a medieval grotto—we started a fire in a rusty barrel. After a while, an eastbound train made up of refrigerated cars came along in the darkness, and we hopped into the rear unit.

Each train is a roll of the die, a unique and unpredictable experience. Perhaps that’s why we do it—to gamble, to relinquish control completely and give ourselves over to fate and luck. The train out of Rawlins gave all the appearances that it would blaze across Wyoming. But instead it puttered along miserably, stopping for higher-priority trains every hour. Frustrated, we jumped off in Laramie, Wyoming.

We were now in a race against time. We had 12 hours to make it to the National Hobo Convention, and were already late. We rented the cheapest one-way vehicle we could find—a U-Haul truck—and got on the road, resolving to pick up every hitchhiker we saw along the way.

Just outside Laramie, we spotted a lone figure on the side of the highway. He had a bushy gray Walt Whitman beard and was pushing a heavy, tanklike bicycle up a Sisyphean hill. We made a U-turn and pulled over, startling the man. He was sitting in the dirt, smoking a rolled cigarette and staring into the trees. His face was deeply lined and his clothes were filthy. He had starkly expressive blue eyes and looked like Tom Hanks in Cast Away. He introduced himself as Joe. With his missing teeth and calloused skin he looked ancient; he told us he was only 55.

After five minutes of chatting, I could tell that he was one of the last of a dying breed. Joe said he had been camping out in Oregon for a couple of years and was now biking to Arkansas, where he planned to set up camp for “three or four years” and pan for gold. He had ridden to Montana but had been forced to make a 1,000-mile detour on account of wildfires. After Arkansas, Joe planned to get a couple of horses and ride west across the American backcountry. “I’ve seen the country by car and will have seen it by bike and foot; I figured I wanted to see it by horse, the way the old-timers saw it.”

In his long hermitage, Joe befriended the fauna. “You wouldn’t believe the kind of animals I’ve seen up close.” He said he talked to badgers. Joe’s bike was more of a two-wheeled shopping cart than a form of transportation. It was about 200 pounds, weighted down with pickaxes, shovels, tents, tarps, and cookware. We helped Joe and his belongings into the back of the U-Haul and told him we could take him as far as Des Moines. He was exceedingly grateful and said that we were probably saving him “one or two months” of biking.

Down the road we stopped for another hitchhiker, a young, handsome guy with frizzy long hair, sunglasses, and a dog. He introduced himself as Alex and said he was a travel writer.

His dog was a red-nosed pit bull named Batman. Alex explained that, in 2010, he had left his job at Google and set off on the road hitchhiking, using couchsurfing.org to arrange for places to stay. In his entire two years of peripatetic travel he had only been forced to sleep outdoors for two or three nights.

After a couple of hours, we stopped for gas and opened up the U-Haul to find our human cargo crumpled in the back, squinty-eyed and soaked with sweat. With a length of rope, we rigged open the cargo door to give them a breeze while we drove onward.

Two hours later, in Nebraska, blue lights flashed and we were pulled over. An officer sidled up to the window, explaining that someone had called us in: “They said it looked like you were trafficking Mexicans.” He checked on Alex and Joe in the back and then let us go with the warning that I-80 was a major vein for human trafficking and that we would likely get called in again.

Our next stop was Omaha, where we soaked up the enlivening Friday-night vibe of the city—everyone was dressed up in their best, the midwestern girls startlingly gorgeous (reaffirming Jack Kerouac’s 50-year-old observation that “the prettiest girls in the world live in Des Moines”). Alex stayed sober and drove us through the night. We stopped to catch a few hours of sleep in the parking lot of an Embassy Suites, waking up at dawn to drive the remaining two hours through the Iowa cornfields into Britt, just in time to watch the high school marching band parade down a placid residential street. Senior citizens and middle-aged women threw candy and magnets from convertibles and floats. A chunky preteen boy on a colossal John Deere tractor struck poses and waved.

Britt was overrun with tourists but there was a conspicuous absence of people who looked like real hobos who had spent any considerable amount of time on the tracks. Rural families ambled down the main street past dunking booths and food stalls and tents blasting top-40 hits. Pubescent girls bought pink hobo girly tees from the Hobo Museum and then went to eat breakfast across the street at Mary Jo’s Hobo House.

We walked over to Britt’s makeshift Hobo Jungle, a well-mowed stretch of grass by the railroad tracks. There, clustered around a disused boxcar, were about 20 people milling about, mostly gray-haired and wearing leather vests or coonskin caps. Ten or 15 tents dotted the green, along with a little village of RVs and vans. There couldn’t have been more than 60 people in all camped out. It had more of the ambience of a hippie craft fair than a Depression-era Hooverville. To put things into perspective, 1,800 hobos had attended the 1949 convention in Britt.

Across town in City Park, Britt residents served up vats of mulligan stew, the traditional improvised gumbo of the hobos, to a mixed crowd of transients and tourists. The ceremony to elect this year’s Hobo King and Queen began with an older woman singing all three refrains of “The Star-Spangled Banner.” As the anthem droned on, attendees looked off into the distance glaze-eyed. They didn’t know the words.

The candidates for Hobo King, a collection of scruffy elderly gentlemen with names like Adman and Minnesota Jim, took to the stage to give their stump speeches. There’s been a Hobo King crowned every year since 1900, and to keep interlopers out, the Hobo King has to have lived considerable portions of his life on freight trains. Adman and Minnesota Jim’s two-minute speeches were moving. Both men talked about their health problems, and Adman announced his retirement from riding the rails. Old-timers who had “caught the westbound” (the hobo term for dying) were canonized and lauded.

The crowd went wild when a friendly-looking older hobo with one leg rolled his wheelchair up to the microphone. “Hi, I’m Frog,” he said in a croaking, high-pitched voice. He announced that he had taken a bad spill off one of the floats that morning, but that he was fine. While Adman’s speech had been laden with morose self-pity, Frog seemed full of gratitude to his hobo family.

The nominees for Hobo Queen were all senior citizens—Angel, Minnesota Jewel, and a woman named Empress Vagabond Lump, the only black hobo at the event. The winners were decided by applause. In the end, Minnesota Jim, who looked like a cadaverous Woody Guthrie, won, alongside Angel, a woman from Britt. They were crowned with tin Folgers-can hats.

After the proceedings wrapped up, I found Frog sitting off by himself, smoking. Frog lived alone out in Helena, Montana. He had gotten his name in a California immigration jail, “because my traveling partner told them I hopped the trains like a frog.” I assumed he had lost his leg on the freights, but he said that a gang of teenagers had jumped him in the early 2000s. “Just some kids coming home from a ballgame. It happens a lot these days,” he said, upbeat and smiling. He had ridden trains for 31 years before his accident. “My wanderlust spirit started at eight years old, and it’s still there. Though I’m not riding trains anymore, I still want to ride. I have one final ride, and that’s my westbound journey.”

I asked Frog why there were so few young riders at the Convention. “The young anarchist brothers and sisters are out there, still riding trains, just not calling themselves hobos. I honestly feel like, give it another 25 years and the Hobo Convention will be a thing of the past.”

He explained that, over the previous two decades, Britt had clamped down hard on the convention. It had become county-fair mainstream, completely sanitized—little kids milled around the Hobo Jungle collecting autographs and gawking, as if it were a circus. The city started enforcing leash laws and instituted a hard line on fights, drug use, and drunkenness. A final insult was the installation of a railroad bull on the tracks during the convention, preventing hobos from hopping into or out of Britt. As I took a stroll on the tracks in the late afternoon, the clean-cut, sharklike bull stopped me and demanded my driver’s-license number with a smile.

In Jack Black’s You Can’t Win he described a turn-of-the-century iteration of the National Hobo Convention: “There was a grand jungle by a small, clean river where they boiled up their vermined clothes, or ‘rags’ as they are always called, cooked their mulligans, or if enough bums got together, held their ‘conventions.’ These conventions, like many others, were an excuse for a big drunk. Sometimes they would end in a killing or some drunken bum would fall in the fire and get burned to death, after which they would silently steal away.”

In 1998, a sect of hobo attendees got fed up with the convention’s increasingly restrictive rules and regulations and started their own roving event called Trampfest, meant to run closer to the original outlaw spirit of Britt’s Hobo Convention. “They decided, if they’re going to bring in all these cops and railroad dicks and the media, they didn’t need that,” Frog explained. The stories I’ve heard about Trampfest give the impression it is the younger, drunker, stabbier version of Britt’s convention.

Darkness fell, the campfire was lit, and Styrofoam plates of beans and hot dogs were served; the whole thing took on the ambience of a Ren fair or a Wes Anderson movie. A terrifying Amish-looking guy with a neckbeard danced around and performed a flute version of “Call Me Maybe.” One of the crusty punk kids who had shown up, who looked half-human, half-pig, breathed fire while standing inside the boxcar. There was a lot of Kiwanis-style talk of patriotism, and the evening was moderated by a 66-year-old MC named Medicine Man, who was not even a hobo, but rather a kind of hobo enthusiast who traveled the country with his wife in an RV.

These “hobos at heart” (a euphemism faux hobos invoke to describe themselves) seemed to have commandeered the convention—the authentic hobos, ailing and tired, tried to sit back and appreciate the time with their family. Empress Vagabond Lump told me, “When I first came here in ’81, it was different. It wasn’t policed then like it is now. Now it’s like a history thing, people learning the history of the hobo. This is just like weekend stuff.”

Hanging around the Hobo Jungle as the sun went down, I met the enfant terrible of the National Hobo Convention, camped under the wheels of a parked boxcar with a scrap of ragged blanket, nursing a 12-pack of Beast Ice. He wore a filthy tie-dyed T-shirt, and his skin was the color of boiled hot dog. He moonwalked out from his hole, shouting, “I’m the Tan Man, baby!” and singing Lady Gaga—”Lemme take a ride on your disco stick!”

In his early 40s, filthy, and deranged, Tan Man came off like a caricature of a crackpot bum. He explained that he had spent his life living on the streets, and that he was proud to be “king of the thumb bums.” He said he felt safer in a gutter than in a warm bed. He raged against what the Hobo Convention had become. “A lot of these people here are credit-card hobos, hobo millionaires,” he seethed. Tan Man showed up, even though it had become a parody of itself, out of respect for the elderly hobos. “One thing the old-timers taught me: Always respect, always offer a cigarette, always offer something to eat and a beer if you’ve got it. That’s old hobo rules. You’ve got to give respect to get respect.”

Tan Man said that after the convention he was heading to Clinton, Iowa, to get sober and become a youth pastor in an evangelical program for homeless youth. “Instead of running butt-naked down the beach with the police coming after me asking, ‘Who’s that guy?’ ‘I don’t know, they call him the Tan Man,’ I’d like to just do one thing good. If I could just help one person, one punk kid, it’s worth my whole journey, my whole life.”

After I left Tan Man, Medicine Man, the “hobo at heart,” came over to me with a worried look on his face. “I saw you were over there talking to Tan Man. We’ve had a lot of problems with him over the years, so I don’t know what he told you. But I just want you to know that if you print any of the things he said, you all won’t be welcomed back here.” After going back and forth with him a bit and a couple more open-mic acts, it was time to call it a night.

The next day, I learned that Tan Man had been arrested for pissing on a fence. The most basic primal human need, barely an affront to lawful society, singled out in a town that was once the hobo’s sanctuary. I’d had enough. Disgusted by the petty paternalism of Britt and with the convention, it was time to leave. We flew back to New York.

When I got back home, I called Frog to continue a conversation we had been having in Britt. He had told me that he had been one of the founding members of an infamous transient gang called the FTRA, which is the freight-train equivalent of the Crips. Frog laughed off the reputation of the much-feared cabal. “It stands for Fuck the Reagan Administration—we started it when Reagan cut our food stamps—but somehow it became Freight Train Riders of America. To this day, sometimes people ask me to rag-and-tag ’em.” He laughed.

A warm and generous man, Frog had told me that plenty of train riders and hobos stopped through to visit him in Helena. I had imagined him living in a rickety, paint-peeling cabin with a woodstove, surrounded by sunflowers and a collection of rusted railroad spikes stacked on the porch. In my mind, he was living out his sunset years in a cheerful sanctuary, with tramps, bums, and outlaws with names like Minneapolis Minnie, Pasco Slim, and Salt Chunk Mary constantly passing through, cooking up big meals together, getting drunk, and disappearing back out into the night. So I was caught off guard when during the course of our conversation he mentioned that he lived in a senior center. My fantasy idea of his life crumbled, replaced by gray reality—fiberboard walls, fresh-cut grass, welcome centers, and parking lots.

The thought of Frog in his wheelchair, all alone in a Montana senior center, was too much. Sensing my malaise, he began describing his surroundings. “I’m overlooking the Sleeping Giant Mountains. I watch the trains go by my house, and they zoom right by my window,” he said wistfully. “There’s two sets of tracks—one going west and the other going east. And directly behind the tracks is an airport, so I can sit and watch the planes going in and out of here.” I imagined the rumble of the trains, the lonesome horn waking him in the middle of the night from persistent dreams of riding once again. I promised to write him a letter and come visit sometime before saying goodbye.

Sitting at my desk after hanging up with Frog, I found myself crying for all the gone people and gone ways of life, and the great American hobo, disappearing down the westbound track, never to return again.