The guy with the shotgun showed up just as we were setting up the tent. Dave and I had been halfway up Wauconda Pass when one of us broke a spoke, and with darkness only 30 minutes away, we decided to call it a day. That little grassy patch next to a horse pasture, without a house in sight, seemed like the perfect place to crash until dawn — but the limping bearded vet who lived at the end of the driveway thought otherwise.

“You boys horse wrasslers?” he demanded, shining a Maglight in our eyes. We were standing there in spandex shorts with tent poles in our hands; our fully loaded touring bikes leaned against the pasture fence.

The situation deescalated quickly. He lowered the shotgun, and 15 minutes later we were standing in his living room swapping stories as we sipped coffee and whiskey. He told us about the leg injury he brought home from Vietnam, and his one-man war against horse thieves. Dave and I described the first week of our summer adventure — a cross-country bike ride from Seattle that had brought us to the eastern Cascades and hopefully would bring us to New York.

When our 3,000-mile bike tour had begun, we had foreseen a procession of long mountain passes, but perhaps we had underestimated how many conversations with strangers the trip would demand. I have a photograph of me and Dave right before the trip began. We’re sitting on a curb outside the Bellingham airport, where we’d just dumped a rental car. In the picture, our Cannondale T400s are shiny and our panniers are neatly stuffed to the gills and our faces look free of worry. It was July 1, 1992 — 25 years ago.

I am writing this sentence the day before my 50th birthday, which means I’m recalling an adventure that took place half a lifetime ago. Certain memories from that trip are still vivid and sharp, but the truth is that the whole thing seems like a dream about a play I was in long ago.

Contemplations about how the experience would age over the decades were the farthest thing from my mind as we pointed our bikes eastward into the Cascades. We were as rooted in the present tense as I’d ever been in my life.

Geographically and temporally, the trip could be broken down into three parts — the journey from the Pacific to the Rockies, with a daily pattern of one or two big mountain passes a day; the 1,000-mile-plus trip across Montana and North Dakota, with endless vistas and blustery winds; and the slow but steady reentry into civilization that came after that.

My memories of riding across Washington State are impressionistic — rain storms and fully loaded logging trucks and sore quads. I had spent the week before the trip began on the floor of a friend’s apartment with a fever, too sick to ride and barely well enough to pack. I started the journey in poor shape and bogged down with too much stuff (including a heavy SLR with multiple lenses). In short, I suffered. I would guess my fully loaded bike weighed at least 75 pounds (34 kilos), and riding up an endless parade of Cascades passes was demoralizing.

Our Cannondales had triple chainrings and we spent a lot of time in the 26. We quickly coined a nickname for our 26×28 granny gear: home.

“You home?” Dave would call out as we churned up some densely forested 15-mile (24km) climb.

“Yup,” I would reply. “I’m definitely home.”

I considered Dave Otto to be my best friend. We had gone to grade school together and been tight since seventh grade. We ran track together in high school and drank a million beers together and shared 15 years of quality hijinks. In the years after college, we lived together in San Diego and rode together all the time. We’d stay tight for years down the road — we shared a flat in San Francisco the following year and he would be my best man at my wedding a decade later — but in retrospect our big adventure would be an inflection point, the moment in which we started drifting apart in subtle but persistent ways.

Fortunately, we didn’t perceive that shift in our relationship at the time. It felt like we were sharing infinite hours of solo riding time punctuated by occasional funny moments. But we both were serious about girlfriends who were waiting at the end of the ride, about plans for new jobs or graduate school, and that 3,000-mile (4,830km) ride would wind up being the end of one chapter and the start of another. In my case, the cross-country ride would further catalyze my passion for cycling as a central element in my life, while for Dave if would seem more like the end of an era. He would spend the next 15 years seriously training for marathons.

More than anything on our grand adventure, Dave and I shared food. We were in our 20s, active and thin, and now we were riding eight or ten hours a day. Most small towns along the northern edge of America had establishments called cafés that were like miniature New York diners, with equally bad coffee and comically lower prices. I remember that I brought $1,000 in travelers checks — neither of us had a credit card — and I didn’t come close to spending it in seven weeks of travel. Our only significant expense was food.

We typically slept in one town and then rode to the next one for breakfast. We would amble into these cafés, looking like scraggly beatniks, and order what most folks would consider three breakfasts — a big stack of pancakes, eggs, toast, bacon, cereal, muffins. A lot of these cafés had a fat trucker selection that offered the kitchen sink for $6. Waitresses would snicker when we ordered and then offer apologies when we asked for extra toast 15 minutes later.

Once you truly settle into a real adventure, strange and wondrous things start to happen. You see the randomness in the universe, you open yourself completely to strangers, you lose a sense of anything beyond the present moment. Things that otherwise would seem bizarre seem normal.

We ate lunch two or three times every day. I was craving fat and started living on grilled cheese sandwiches and vanilla milkshakes. Sometimes, in the empty rural midsection of the country a grilled cheese sandwich cost about a dollar. There were days I ate seven or eight grilled cheese sandwiches and gulped down three milkshakes. This was the era before convenience stores sold energy bars, and I typically ate a couple of Hostess fruit pies as snacks along the way. I’d lose 10 pounds (about five kilos) before we reached New York.

We had a camp stove and a cookery set and most nights we boiled up and slammed a couple pounds of pasta for dinner. In retrospect, we drank oddly few beers along the way — I’d guess I had maybe three or four beers a week — but we still had this odd habit of staying up late and getting started late the next day. I think this is because our bodies were fucked up. It’s hard to remember the pain in detail, but I think I felt like I’d lost a street fight — sore all over, continually wondering when the trauma would subside. It felt fine to sit on a bike and pedal, but excruciating to do anything else. Walking hurt. Sitting in a chair hurt. Sleeping on the ground hurt a ton. I started pounding aspirin in quantities that surely can’t be healthy (sometimes 20 or 25 a day).

But the constant pain didn’t really slow down the fun. One night as we neared the Washington-Idaho border, we had dinner and beers at a bar that had a large sign posted making it clear that environmentalists were not welcome. We were in logging country. Some women belted out Prince and Bon Jovi songs in a karaoke sideshow as we sat at the bar and ate burgers and split a pitcher of Olympia.

We spent a couple of hours talking with a group of guys our age who worked at a mill. Our lives could not have been more different — we were young college grads who had quit jobs to seek adventure and they already had families and dead-end jobs. Everyone called one guy T-Bone and he mentioned that he had never visited Glacier National Park, even though it was only a few hours away in a car.

At some point we asked him why everyone called him T-Bone. He explained how he lived up in a cabin in the woods and for years had fed and watched over a clan of half-wolves and wolves who now slept on his floor. He was running through the names of all these creatures when one of his buddies cut him off — “Anyway, we always say that the wolves just look at him and think that one day he’ll be a good T-bone.”

We laughed about that and then set up our tent on a grassy patch right next to the bar. I presume that drunk people walked past us all night but we slept through everything. Near each of the coasts we stayed in official campgrounds, but everywhere else we just slept right in town. Most downtowns had these wonderful grassy squares adjacent to Main Street, with a gazebo and picnic tables and maybe even a bathroom, and we would just crash there. We tried to wait until dark before we threw down our sleeping bags, but nobody seemed to care.

For the first half of the trip we traced a route recommended by the nonprofit group known then as Bikecentennial (it would soon rebrand itself as the less-interesting sounding Adventure Cycling Association). We had purchased these awesome laminated maps that were perfectly sized and folded to fit into the clear sleeve on a handlebar bag. The routes guided riders onto scenic and quiet roads wherever possible, and they were so popular that you’d run into other touring cyclists every day. Nobody had coined the term bikepacking yet.

We parted ways with Bikecentennial’s northern route in Fargo — we wanted to ride from Michigan into Canada and cross back to the States at Niagara — so from there we navigated off roadway maps that we bought at gas stations. Other than a few miserable days riding alongside Lake Huron amid constant truck traffic on the Trans-Canada Highway, our bushwacking went great.

Despite how big and overstuffed our panniers were, we had shockingly little kit to wear on hot summer days. I had two pairs of Descente bike shorts, one blue Cannondale cycling jersey, and two T-shirts (one from a Pixies gig and the other from the Black Dog Bakery on Martha’s Vineyard). We took showers and did laundry about once a week. I can only presume that we smelled like trash heaps.

The last big pass we rode was the legendary Going-to-the Sun Road in Glacier National Park. We did most of that climb in the dark, on purpose. With so much heavy RV traffic on that famously scenic byway, the National Park Service prohibited cyclists from using the road between 11am and 4pm. But there was a full moon scheduled that night, and a bike-shop guy in Whitefish, the ski town on the west side of the park, told us that some riders finish the climb in the dark, guerrilla camp by the visitor center atop Logan Pass, and tackle the 15-mile descent in the morning. Dave and I — along with four other cyclists we’d hooked up with — decided to go for it.

We started the 24-mile climb an hour before dark but wasted most of the day’s remaining daylight trying to shoo away a momma black bear and two cubs who were warming their rumps on the pavement. Then the sun went down, and we pedaled above the treeline into a moonlit landscape of soaring cliff faces. We could hear the thunder of waterfalls and feel the mist without being able to see the cataracts themselves.

I think the climb took about three hours, and when we got to the top of the 6,646-foot pass, the temperature was close to freezing. The parking lot was jammed with folks who had driven up to take in the moonscape — a surreal panorama of jagged peaks glowing in the darkness. We found a quiet corner of pavement near the back of the visitor center and threw down our sleeping bags. We were cold and exhausted.

Just as we settled into our bags, someone appeared and shined a bright light in our faces. It was a park ranger — an angry park ranger who said that no one was allowed up camp out up there because of grizzly bear activity. He didn’t care what the bike shop guy in Whitefish had told us or how wasted we were or how the only lights we had were dinky backpacking headlamps. We had to descend.

We rode together in a shivering cluster. The moon had slid westward and now the sky was black. A descent that would have been 45 minutes of awesomeness in daylight was instead two hours of dark comedy. Someone got a flat after hitting a chunk of ice in the road. Someone else swerved to avoid a porcupine that was crossing the road. We all complained bitterly and laughed, already sensing that our misadventure would seem worthwhile in the morning and forever after.

Once you truly settle into a real adventure, strange and wondrous things start to happen. You see the randomness in the universe, you open yourself completely to strangers, you lose a sense of anything beyond the present moment. Things that otherwise would seem bizarre seem normal.

One day in North Dakota, we rolled into a town called Fort Totten about an hour before dark. Throughout most of rural interior America, communities are dotted along state routes every 15 to 20 miles — in other words, about an hour of riding apart. This meant that Dave and I wouldn’t decide where to crash until we were nearly out of light or energy. In this case, however, we were in the middle of an Indian reservation at least 25 miles (40km) from the next sizable town. We asked a few people — all of them members of the Spirit Lake Tribe who eyed us cautiously — to point us to the nearest town park and they all told us we weren’t welcome. That was something we’d not heard before.

Someone directed us to the local police station and that’s how we wound up spending a night in a jail cell. The office was an outpost of the Bureau of Indian Affairs— an island of the U.S. federal government in a sovereign nation — and officers there explained that it wasn’t safe or legal for outsiders to camp out, and urged us to get off the reservation. But the sun was setting and we explained our limitations and that’s when they offered to put us up for the night. We took showers in a spartan concrete room with eight nozzles and an armored door. We made jokes about dropping the soap. The BIA officers gave us pizza for dinner. We watched Bull Durham with two Sioux convicts, who didn’t really believe that we were biking cross country and visiting the prison voluntarily. It felt less weird than it sounds now.

Throughout the month of July, we tried to follow the Tour de France as best we could. This was not exactly easy to do in 1992, especially if you were pedaling a bike across Montana and North Dakota. That summer, the only option was a one-hour packaged highlight show that aired every afternoon on ESPN. On weekdays, that show aired at 3pm, and when the Tour hit the mountains we tried to find a bar or restaurant that would change the channel for us.

The highlight of this strange ritual came on July 17. We were in a small town near Rugby, North Dakota, and clattered into this bar that had once been the local bank — there was still a big safe filled with empty safety-deposit boxes in the back. The patrons were a mix of cowboy types and a group of guys who’d just gotten off a shift doing road construction. We explained the situation to the bartender and he reluctantly flipped the TV to ESPN. No one else in the room had ever watched a bike race on TV or knew who the hell Greg LeMond was. This, it turned out, was the day LeMond’s Tour came to an end, as he labored to dismount his bike on the Galibier and climbed into a team car.

But another American would carry the day on a hard mountain stage that concluded on l’Alpe d’Huez. Back in the select GC group, Miguel Indurain was absorbing whatever Claudio Chiappucci was throwing at him to solidify his hold on the yellow jersey. But in the break, a lanky rider on the Motorola squad with short hair and downtube shifters was lighting it up. It turns out you do not need to have special knowledge to appreciate the athleticism and grace of Andy Hampsten riding everyone off his wheel to solo for the win. Phil Liggett and Paul Sherwen, not yet well known to American viewers, were in trademark form. Dave and I were shouting and high-fiving. The cowboys and road-crew guys were cheering for a racer they’d just learned had grown up in North Dakota. We finished our lagers and shook hands with our new friends and got back on the road.

During our 50-day journey we only stayed in motels twice. Once was in the Upper Peninsula of Michigan after we’d been battered by heavy rain for two days. The other time was on Dave’s birthday, on August 2. We were somewhere in northern Wisconsin, a tourist town with a lake (in other words, northern Wisconsin). We ate dinner in a steakhouse and split a bottle of wine and destroyed the salad bar.

The Tour had ended a week or two earlier and now the Barcelona Olympics were going on. We hadn’t intentionally timed it this way, but the men’s road race was televised that night. We sprawled out on our beds, our bellies full of prime rib and Cabernet, hoping that the young American phenom named Lance Armstrong would prevail. Though the 20-year-old Texan rode hung tough with the 70-rider lead pack, he never really factored in the finale, which was won out of a three man breakaway by a 21-year-old Italian named Fabio Casartelli. I remember thinking, who the hell is that?

I spent 15 years chasing fitness and camaraderie, increasingly choosing the weekly world championship over the solo ramble. And now, I’m oversaturated in exploring the utility of the bicycle. I honestly can’t tell you the last time I just got on a bike and spent the better part of a day wandering the countryside, not using my bike as functional transportation or thinking about holding a wheel. This is something I want back.

As we slogged our way eastward, the gravitational pull of the lives that awaited us at home started to exert greater force. We started to grow more excited to see our girlfriends and find an apartment in San Francisco and otherwise get going with our lives. From Ontario onward, the landscape and human interactions seemed to get more familiar.

Even though our bodies were a mess — I did my best sleeping on concrete floors or on top of picnic benches because of back and shoulder pain that only subsided on the bike — we were fit as hell. We rode 1,300 miles (2,100km) in two weeks. When we crossed back onto American soil at Niagara, we took funny pictures of ourselves riding naked.

The trip ended without great drama. The last couple of days took us through familiar terrain as we got closer to our childhood homes in suburban New York. The roads were more crowded and everyone seemed busy with something. Now when we went into restaurants, few strangers would approach us to ask questions (though our unkempt beards and general aroma might have been a factor, too). The price of grilled cheese and milkshakes skyrocketed.

We spent our final night only 40 miles from home, in Bear Mountain State Park. We stumbled onto a cluster of unoccupied cabins that surrounded a small meadow and one of them was unlocked. We cooked spaghetti on the deck and then slept on the saggy cots inside.

In the middle of the night I woke up and crept outside to pee. I stared at my feet as I shuffled to the edge of meadow. And then, when I finally looked up, the meadow was alit with moonlight and full of deer who were staring at me. It was like a dream. I went back inside so I could wake Dave. He saw the dreamy deers, too.

Looking back now, it all feels like a dream. I am writing the last few paragraphs of this story the day after my 50th birthday. I am flipping through old photographs and remembering the greatest bike adventure of my life and trying to sort through my feelings.

I think I could learn something from the young me who is smiling in all those pictures. My life is of course different now — I have a family and a career and have an existence defined by obligations — but I think my riding life could really use more unstructured randomness. I don’t get on my bike and fart around the way I used to. I spent 15 years chasing fitness and camaraderie, increasingly choosing the weekly world championship over the solo ramble. And now, I’m oversaturated in exploring the utility of the bicycle. I honestly can’t tell you the last time I just got on a bike and spent the better part of a day wandering the countryside, not using my bike as functional transportation or thinking about holding a wheel. This is something I want back.

I also want to reclaim my friendship with Dave. It’s been at least four years since we talked; we’ve both spent the past decade changing jobs, raising kids, moving great distances. I’ve spent years focused almost entirely on three things — my family, my career, and riding my bike — that I’ve let a lot of other things slip through my fingers. Life doesn’t give you many best friends and yet, as I look at photos of my 1992 adventure, it’s painfully clear what I’ve lost to time. I have work to do.

I’m struck with nostalgia for simpler times. I can’t stop thinking about one night Dave and I shared in North Dakota. It’s one of those spotty recollections from half a lifetime ago where I can picture the campsite in detail without really having a clue where we rode that day. Anyway, we were in the tent and I woke up and had to pee and found the fortitude to leave my warm bag and take care of business.

This time, I looked up and there was the starriest sky I’ve ever seen. It was as though there was more light in the sky than darkness. It was one of the most beautiful things I’ve ever seen.

I roused Dave from his deep sleep — he initially was not happy about it — but he staggered out to see that wondrous sky. We stood there, two young men with bare feet in wet grass beneath a sparkling tableau of starlight, and took it in together.