Let's start with the stag. It bursts from a deep and brambly creek bed and bounds across the crushed granite trail. This is one of my regular rides, along the Colorado River near my home in Austin, Texas, and though I've come across plenty of critters here, I've never seen a beast—an animal this majestic, this wild. Benedict and I skid to a stop. We stare at the stag as it saunters through the field of knee-high grass beside the trail then comes to a standstill. His muscular chest is pronounced. His multipronged horns stretch high and wide. His tan fur is thick with a midwinter coat. As he breathes, steam wafts from his nostrils. When I reach for my phone to snap a photo, the stag vanishes as quickly as he appeared. I wonder, aloud, why things such as this tend to happen while riding with Benedict.

I met the man who is also known as Poppi, Bolty, J.B., and a variety of other names (but who, for the purpose of telling this story and out of respect for what he says are "tax reasons," we'll refer to as Benedict) in Austin in 2006. He was a bike messenger and a Cat 5 road racer with the persona of a vain Euro pro: his bike accented with gold parts, his muscular body rippling under white spandex. Despite holding a license that classified him as belonging to the lowest, most inexperienced level of amateur bike racing, he regularly dropped everyone, including me (a former pro), on the weekend hammer ride. He was dating a female bike racer from San Antonio, a woman with soft green eyes and long dark hair, and the words Fuck and Y'all tattooed on the back of either thigh. They fell in love and moved to Benedict's boyhood home on the mouth of the Connecticut River, and I never heard much about him after that, never really thought about him except during those occasional times some of us would swap stories about the characters who'd passed through our local cycling scene.

In the years after he left and I more or less forgot about him, my friends and I transitioned from aimless twentysomethings into semi-responsible adults, working full time, building families, and coming to rely on social media to keep in touch. In the course of one three-year period, I got married, wrote a book, bought a house. I stopped racing so much. Built an office in my backyard. Had a son. Started another book. I woke early each morning to write, and as I watched the sun rise from my office window, I often thought about how lucky I was, how happy to have both found my way toward and built this successful, grown-up life, and how thankful I was. This kind of accounting occasionally, but inevitably, also leads you to think about all that you've given up, as well.

Thousands of devoted Instagram followers track his adventures. He blasts berms and bathes nude in steaming hot springs. Brian Vernor

It was during one such reverie that I found Benedict again. I stumbled across him on Instagram after clicking onto the pictures of a character calling himself Ultra Romance. The fully shaven roadie I'd known was thickly bearded and bedecked in wool. He rode vintage mountain bikes outfitted with racks and baskets and canvas bags through deep woods and rugged alpine wildernesses. He blasted berms and bathed in the nude in steaming hot springs.

Thousands of devoted followers—similarly office bound, I assumed—tracked his adventures. In the comments, people wrote things like, "I just told my wife that if, god forbid, she ever left this world before me, this is what I would look like, and this is exactly what I would be doing." I felt the same way: I resolutely loved my life, but I kind of wanted his life, too.

Curious, envious, doubtful—was Benedict as romantic as he seemed online, and had he actually become this simple being who foraged for food and lived off of 10 dollars a day, or was this just one more of those overly curated facades hiding a day-to-day existence that was not much different from mine or anyone else's—I sent him an email. He responded immediately. He told me he'd broken up with the dark-haired woman and after that had found himself gradually following his passions more and more, just seeing where the pursuits might take him. Those passions, he wrote, include rusty bicycles, camping, history, women (he's fielded marriage proposals on Instagram), and tanning. (If possible, Benedict forgoes a shirt.)

Before I could think too much about the reasons or potential outcomes, I asked Benedict if I could maybe join him on one of his adventures.

Benedict was a bike messenger and a Cat 5 road racer with the persona of a vain Euro pro. Brian Vernor

Planning, it's not Benedict's forte. He's frequently in the wild, out of cell phone range, and he's regularly without service on his hand-me-down iPhone, anyhow. So communication can be spotty. And he prefers to work off a rough outline—there's a point A and a point B, and everything in between should occur organically.

I make my best attempt to adopt his laidback confidence. I don't let on that I had gone bike touring only once, credit-card style, and had never actually camped in the backcountry. When I send Benedict a photo of my proposed vehicle for the trip, an old cyclocross bike I primarily use as a townie and to tow a baby trailer, he simply responds, "What're the biggest tires yer frame can handle?" Then, he describes our proposed route as a mix of "forest service roads and mystery goat paths." In regard to gear, Benedict suggests a modest assortment of wool garments and recommends I bring a bivy sack. When I wonder why, he explains, "It will help keep out the scorpions." Upon which I stop asking him questions.

After a number of stomach-twisting credit-card swipes at the camping store and local bike shop, and a very late night turning my townie into an adventure touring machine, I fly to California and on a Monday afternoon in early December meet Benedict at the Whole Foods Market in San Luis Obispo, near a nature preserve where he's been camping. We meet up with the photographer and adventurer, Brian Vernor, and his close friend Chris McNally, an illustrator from San Francisco, who are also along for the ride, and with Chris Ellefson, who is part of a local bike company, Stinner Frameworks, and has agreed to shuttle us south up into the hills. The rough plan is to ride from there along the ridgeline of the Sierra Madre Mountains, then turn toward the coast, summit a succession of steep and treacherous peaks, and arrive in Santa Barbara by Thursday evening.

Later, when our bikes are unloaded and we're cramming our bags with foodstuffs—pesto sauce and corn tortillas and goat cheese and a small fortune in gourmet chocolate bars, bulk nuts, grains, and dried fruits—I sidle up to Ellefson.

"This doesn't seem like a National Forest," I say, waving my hand toward the golden hills, dotted with intermittent groves of oak trees.

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"Yeah, it's pretty much a desert," says Ellefson.

"Oh," I say. "What about water?"

"Water?" Ellefson chuckles, almost as a disclaimer that although he drove us here, he isn't liable for anything that happens next. "You might manage to find a spring. But with this drought, that's pretty unlikely."

I tilt back a jug of water and gulp until my belly aches. Then we each throw a leg over our beastly, bag-laden bikes and start the long, slow, dirt-road ascent into the mountains.

He's 35. He can't live this way forever. Or can he? Brian Vernor

The next morning, after a sleepless, wind-whipped night atop an exposed ridge, I rise to find that a puddle of precious water has leaked from one of my plastic bladders. I eye Benedict's impenetrable stainless-steel canteen, and transfer my store to a spare bladder.

The evening prior, we'd climbed until the sun slipped well below the horizon, then set camp with headlamps. This morning, as we embark on our first full day of riding, the road continues up. We climb and climb and climb. It's 15 miles uphill in total from where we'd started to the knife's edge of the mountain range, at which point the dirt road rolls from peak to pointed peak for another 30 miles. I spend much of the day in my lowest gear, and beside Benedict.

He tells me it's taken about six years to figure out how to fund his lifestyle. Summers find him in his hometown of Clinton, on the mouth of the Connecticut River, one of the East Coast's most pristine watersheds and finest fisheries. For decades, his father has operated a charter fishing boat and Benedict has acted as his first mate, casting lines, charming customers, and filleting trophy-size stripers, sea bass, and black fish. He makes good money, though he says he's not sure exactly how much. He seals his earnings in plastic bags that he buries in the backyard of a family member. He tells me that he does know he's able to subsist off roughly $10,000 a year. When November comes and the boat gets docked, Benedict begins wandering.

The West Coast calls to him first, San Francisco to LA by bike and train, then Austin, where he spends Christmas visiting old friends. In January, he's on an Amtrak to Sedona, Arizona, where he builds a remote base camp out among the singletrack. In the spring, he returns to one of the world's best locales for mountain biking, Durango, Colorado, where he once raced for the Fort Lewis College cycling team and earned a bachelor's degree in exercise science. Recently, he's taken to touring the dirt roads that cut across some of Colorado's highest mountain passes.

Predictably, the adventures don't always go smoothly. In California's Gold Country, Benedict and a group of friends attempted to re-create the route of the historic Donner Party. Just as in that ill-fated expedition, which ultimately led to cannibalism, a blizzard blew in. Benedict and his friends made it through by stoking a survival fire and digging snow caves. On a tour in Norway, where he traveled to try to connect with his Viking heritage, he rode for days just to reach a fjord. Instead, he found a seaside wasteland inhabited by Somali refugees—then, in the night, a fox stole his titanium spork. In New Zealand, a helicopter rescued him from a raging river. On more than a couple occasions, in the absence of fresh water sources, he's resorted to drinking his own urine.

As Benedict pedals along and recounts these misadventures, my appreciation for the scenery and the sense of adventure I'd been relishing morphs into a mild terror. The views span every direction, row upon row of ragged green ridgelines to the west, and far below to the east, an arid valley painted in crimson desert hues. Two more full days of riding, and many thousands of feet in elevation gain, remain between us and our destination on the coast. I pray my bike and body hold up. I suddenly can't stop fixating on the scarcity of water and the amount I'd already let drip to waste.

Only the sheer beauty surrounding us saves me from a sudden panic attack. With the setting sun comes a thick purple haze, drenching the landscape. As we start our descent from the ridgeline, rattling and shaking down switchbacks, a herd of spooked cows scrambles onto the road in front of us. When one of them suddenly trips, Benedict gasps. He's an animal lover and a vegetarian, and moreover, an incredibly kind, compassionate person. He commands us to stop and walk.

When we finally reach a grassy valley at the bottom of the hill, we lay out our bags beneath a giant rock bearing ancient petroglyphs. Before I go to sleep, I suck the last ounces of water from my hydration pack. As he walks toward his tarp, Benedict carries his similarly empty canteen. "I'm going to save my pee tonight," he says. "You might want to do the same."

Brian Vernor

In the morning, down a narrow trail cutting across the slope, we find a spring. Benedict proclaims, "These are times of plenty," and it really feels that way. We cook heaping bowls of hot cereal and brew coffee and eat until our bowels begin to grumble. Then Benedict comes running from a brushy ravine, holding a bundle of leafy green ferns wrapped tightly in his trusty bandana.

"Nettles!" he screams, as if he were holding a wad of hundred-dollar bills.

In a pot with condensed coconut butter, he sautes the foraged stinging nettles—"Nature's most nutrient-dense green," he says when he can see that I'm wary. And they're delicious. Much of Benedict's diet comes from food he finds along the way—nuts he grinds and cooks into pancakes with harvested berries, and fresh herbs like wild onion that he uses as toppings for pizzas cooked on a plate over glowing coals.

We linger, because it is just what we should be doing right now. We enjoy the breakfast, then a brunch, then a hearty snack. When we hit the road, our bellies and bags are sloshing. But for as content and refreshed as I feel, I can't ignore a painful, grating feeling in my Achilles, like the tendon is encased in sand paper. Up ahead, I know, is a crossroad where I can continue with our planned route up and over the mountains to the coast or take a bail-out down into the valley. When Brian rides up beside me, I confide to him that I'm hurting.

He encourages me to suck it up. Then he shows me some tough love, surging to the front of our group and setting a lung-heaving pace. I'm on the cusp of cracking, my trip about to crumble, and I might leave without any of my questions about Benedict really answered. Did he choose this life freely, or is he running from something, someone? Does how it started matter? Does he truly find this fulfilling?

I grimace and catch up with Benedict. As we ride, I outright ask him the deep, personal shit.

He begins with the dark-haired woman and her difficult past. An absent father, and a younger brother and sister she essentially raised. A child of her own, whom she gave birth to as a teenager. He tells me that the woman had demons that neither she nor he could slay. Long periods of darkness. But, Benedict says, despite these problems, they grew as a couple. He became close with the woman's son, who was then 14 years old. Summers, he woke the boy at 4 a.m. every day, and they rode 18 miles to the boat, where they worked until the sun set. The woman started an organic garden, and they sold the produce at the local farmers' market.

Then Benedict becomes a little vague. He says that the woman saw her darkness wearing on him and she couldn't bear it. He says he began to feel an urge to roam. That the path they'd been on together, toward marriage, began to divide. One day, he tells me, he just let go of internal and societal pressures such as finding a partner, building a family, making a home. "The moment I did that," he says, "I felt totally free. I decided that from then on, I was going to live the rest of my life exactly the way I wanted."

We reach the cutoff, the turning point where I can bail if I need to. Or want to. We've been riding hard, and we stop to catch our breath. All that morning's caffeine, combined with our flowing endorphins and the thin mountain air and everything else, makes a potent cocktail, and we straddle our bikes like a bunch of stoners, laughing heartily. Brian gives me a look. I nod, and we roll on, riding toward the trip's high point, Big Pine Mountain.

Above us, gray clouds hang over the mountains like a giant bucket of dirty mop water, staining the morning's blue sky. The previous evening, in fading light, we'd successfully summited Big Pine Mountain, climbing through a towering forest and weaving around pinecones the size of footballs. After a circuitous descent across the windward face of the mountain, we'd found a shelter with running water at its base. Knowing that all we faced in the morning was a mostly downhill ride back into Santa Barbara, we'd partied hard, eating up most of our remaining food and enjoying satisfying puffs from Benedict's long wooden pipe, a wizardly implement he carved himself.

But now, it seems, the party is over. We roll out into a dense mist, on the soft dirt road that snakes along the mountainsides. If this turns into a downpour, we could be facing miles and miles of hiking through mud—as Benedict puts it, we're in danger of being "fudge fracked." But we keep rolling, down, down, down, and soon we ride our way out of the fog and below the clouds. The Pacific Ocean emerges before us. Benedict leads us toward the Santa Cruz trail, a ribbon of mostly smooth singletrack that drops more than 3,000 feet over four miles. We launch down the descent, handling our loaded bikes like semi drivers racing down a series of switchback turns. By the time we hit the bottom, my arms are shaking and my hands have cramped from pumping my brake levers. We holler and high five and bask in a luxuriant overflow of adrenaline.

Only a handful of paved miles remain between us and our destination, Stinner Frameworks, just outside of Santa Barbara. We spin through a manicured park and begin a gradual climb up Stagecoach Road. Halfway up the hill, we stumble across the historic Cold Spring Tavern. We order bomber bottles of a local porter and plates of French fries and onion rings. As we eat and drink, the sky continues to darken, the fine mist turns into a light rain, then it pours.

Back home, weeks later, I stare over my computer screen as the sun rises above the horizon. The trip still lingers, powerful, talismanic in my life now, though I'm unsure what I learned, what it all meant. To anyone who'll share a beer with me, I eagerly recount the details. I order new bike parts for my commuting/baby-trailer-towing/now-trail-shredding machine, in preparation for future adventures I haven't even planned yet.

More than ever in my life, I'm inspired to explore. Yet, I also worry that this newly born desire conflicts with my life as a husband, a father, and a provider—the life I chose and cherish. In my quiet moments, when my mind wanders, I turn the question over in my head, how I might square these two lives—the one I love and the other one, the one I lust for.

One day Benedict visits Austin, and he gets in touch with me. We go out for a ride, and I try to talk with him about his future. Not his future trips but his future-future. He's 35, I point out. He can't live this way forever, or can he? Perhaps he could find a way to monetize his growing popularity, somehow turn his wandering into a stable livelihood?

"Yeah," he says, and it seems for once I will get a concrete answer from Benedict. "If I could get a new custom-built bike, that would be incredible."

And so let's end with the stag.

Mysterious and magnificent, seeming to come from nowhere but in reality right there at home all along, then gone the moment I tried too hard to capture it. Had my ride really required Benedict's presence to summon the stag? Some answers, I decide, maybe are better left as questions. That way, you see, you have to keep trying to find them.

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