We left Squamish, British Columbia at 2 p.m. on a Wednesday in the middle of September.
The day’s only goal was to make it to Portland, Oregon before our favorite pizza joint in town shuttered for the night. Sadly, only a few hours into the drive, our hopes of making it to Scottie’s Pizza in time for a pie were dashed. Apparently, a trip to secondary inspection is required upon entry to the United States for all UK and Finnish nationals. This was something our crew—two British Columbia- based RV-dwellers, a Toronto 9-to-5er, a quirky Finn and an eager Brit—was unaware of. Two hours, three questions and $12 later, we were finally let through.
The original notion for this trip was conceived back in October 2018, just after my co-conspirator Mark Taylor and I had returned home from our third year at the Trans-Cascadia backcountry mountain bike race. The thrill of this unique experience had given us a renewed thirst for riding—a rare feeling late in the season. The resulting withdrawals from Oregon’s sublime singletrack caused us to plan a harebrained, six-day, 365-mile death march, with roughly 43,000 feet of climbing, as we aspired to ride from Oakridge to Hood River. We originally thought by staying in motels we could minimize the amount of essential equipment, keeping bag weights to an absolute minimum and allowing us to travel the ridiculous daily distances more easily. But once it came down to serious planning, we discovered a few problems with our initial concept.
One: We planned to mostly follow the Oregon Timber Trail route, which is designed to be ridden self-supported. As a result, there were two days when we would either have to put in an 85-mile day or sleep in the woods, the latter being very undesirable given the limited amount of gear we were planning to carry.
Two: Even if we met our daily singletrack goals, we still had to navigate to and from our accommodations, which weren’t located near the trailheads. This would tack on an additional 15 to 45 miles of road riding, truly pushing the boundaries of what we were capable of doing.
When it comes to most things, especially riding, I can be optimistically delusional. I am routinely ambitious and minimally prepared, devising schedules with unrealistic to impossible timelines—drive 10 hours, party all night, sleep for four hours, ride 30 miles, then repeat, is not outside the norm. When combined with Taylor’s willful ignorance and stubborn athletic ability, this can make riding with us difficult for those who prefer to have some semblance of control over their destinies.
This was about the time that Vincent Ready, who brings great entertainment to any ride with his constant banter and reckless riding style, chipped in with a bit of realism. “You guys are masochistic idiots,” he said. “This is a stupid idea.”
After nearly a year of unemployment, Ready had recently picked up a carpentry and construction gig in Vancouver’s film industry. It’s a relentless job: physical, fast-paced, long hours and a looming cloud of employment uncertainty. Riding during the week is unfeasible while he is working, and riding on the weekends rarely happens. The last time Ready worked in film, I didn’t see him for 16 months. We knew these trails would suit his moto background and foot-out-flat-out approach to riding. And the trip itself would be an opportunity to ride with him before he fully immersed himself back into the workforce and vanished again.
Also along for the ride would be Lassi Himanka, a former Finnish Navy man, international heartthrob and a Nordic Chuck Norris crossed with Frank Abagnale Jr. Rounding out the roster was David Kenworthy, whose seemingly soft exterior could be attributed to his posh British accent, emerald green eyes and well-coiffed hair.
We devised a new plan that would maximize riding, minimize climbing and leave a healthy chunk of time in the evenings for hanging out and drinking beers.
Listening to our wise and reasonable friends, we decided to clear the schedule and prioritize fun; after all, this was a “riding vacation” for Ready, Himanka and Kenworthy. So, we devised a new plan that would maximize riding, minimize climbing and leave a healthy chunk of time in the evenings for hanging out and drinking beers.
Taylor and I spent a few days poring over maps of the vast swathes of forest between Oakridge and Hood River, trying to recall the best trails we had ridden during our previous fall pilgrimages. We managed to produce a shortlist of trails that we might want to ride, and that’s where the planning stopped.
We subbed our Portland pizza prospects for burritos in Bellingham, Washington before heading farther south on I-5 with our Google Maps set to a Motel 6 in Portland. Once the truck was unloaded and the room rammed full of gear, the crew set off for a latenight pedal to the closest bar for a nightcap.
The next morning, eager to make it to Westfir with enough light for a ride, we were on the road and jamming to Willie Nelson by 6:30 a.m. After a short pit stop to collect our beer rations for six days, we arrived at our first backwoods destination. We loaded our bikes and headed out on the trail. With 3,200 feet of vertical descent in less than four miles, Eula Ridge was the very definition of Oregon singletrack: smooth and fast, with just enough tight switchbacks to keep us honest. Three hundred feet into the trail and our party train was already moving faster than it had in the last three months at home. We descended with a high paced mixture of fear and excitement, buzzing each other’s tires and roosting every corner possible.
Our stoke levels were high when we returned to the truck and one post-ride beer turned into three. With no cell service at our cabin, no one was able to check in with work, chat with girlfriends or cruise the ’gram. Instead, hanging out, shooting the shit and gazing at the incredible star display was our entertainment. A barbecue dinner capped off the evening before everyone passed out wherever they could find space.
With a predawn start, day three was shaping up to be full of riding, with more than 5,500 feet of descending planned between two trails, Fuji Mountain and Lawler. But partway up our first climb, on a short and steep descent portion of the trail, Taylor managed to wreck himself. He’d been leading at a furious pace and pushed just a bit too hard into a soft corner, tucking the front end and cartwheeling into the bushes. With a nasty thumb injury, he was done riding for the trip, but we gained a shuttle driver.
After an already heavy day, we were hoping for a mellow evening. Instead, we almost joined a cult. My good friend Evan Powell had put us in contact with his younger brother, Matt, who had recently moved onto a communal-style property on the banks of the McKenzie River. The land, with its interesting collection of buildings, including a church, had been purchased from a fringe religious group by a wealthy, old-stock American family nearly 20 years ago.
Despite the eeriness of the place and its diverse residents, our dinner and stay with Powell was incredible. An avid hunter and mushroom picker, Powell had cultivated a garden heaving with fruits and vegetables, and we gorged ourselves on tomatoes, golden raspberries, string beans and greens that redefined our conceptions of organic produce. Our dinner of pizza was topped with ingredients Powell had either grown, picked or caught—a true farm-to-table experience.
When we woke just after 4:30 the next morning in an old church building that smelled of stale patchouli and marijuana smoke, we loaded our half-conscious bodies into the truck with the full moon still high in the sky. The early start was necessary, as we planned to descend nearly 8,000 feet that day, and some seriously complex shuttle logistics were required. An hour later, while trying to navigate the web of Forest Service roads in the dark, we reached a dead end. “Road Closed Landslide,” the sign read. Our sleep-deprived brains hardly knew what to do. But, after consulting two different apps and a paper map, we found a possible alternate route. This new road ascended a narrow ridgeline and rewarded our early morning efforts with spectacular sunrise views.
After climbing for what felt like an eternity—but in reality was barely an hour—the trail turned abruptly downhill. Ready immediately transformed from zombie to beast, sprinting down the wide open grassy ridge. Himanka and I were just passengers on the Ready train, and it was all aboard or get dropped. The final descent, a 3,000-foot straight shot, had our eyes tearing up from the speed and our voices hoarse from the hooting and hollering. And it was barely 10 a.m.
We scarfed a quick breakfast at the only open restaurant within an hour’s drive from the trailhead and rolled out to our second trail of the day. The 17-mile ride turned out to be much more challenging than expected, and complicating matters further, Himanka ripped his derailleur into bits three miles in. His only option was to carry on, scootering when the trail flattened out and hiking up the climbs. With the sun setting before we’d reached the top of the main climb, it was clear we wouldn’t reach the bottom before dark. Despite seriously low energy levels, the looming darkness drove us to the top, where we reassembled a nonstop party train. Instituting a no-pedaling rule to prevent us from dropping Himanka, we turned the trail into a downhill pumptrack, riding by feel, braking less and pumping more. Given how little we could see, we rode the last mile and a half way too fast, reaching the truck well after dark.
We smashed a couple of beers before driving into Oakridge, where our hunger forced us to go straight to dinner, still in our chamois. It was Himanka’s birthday, however, so the evening escalated quickly from parking-lot beers to shotgunned beers and finally to fishbowl margaritas. Most of us were seeing sideways as we stumbled around Oakridge in search of a motel.
It was Himanka’s birthday, however, so the evening escalated quickly from parking-lot beers to shotgunned beers and finally to fishbowl margaritas.
Unfortunately for us, on that rainy September Saturday, 600 other mountain bikers were also looking to enjoy the prime trail conditions, leaving every bed in town full. Our only option was to drive an hour to Eugene in search of a place to sleep. As we pulled into Eugene, however, the aftermath of an Oregon Ducks game was spilling onto the road, so Himanka’s birthday celebrations continued. By the time they’d culminated in shot glasses of tequila aside a dive-bar pool table, we were playing doubles with a local whose drug of choice had him sweating like George Constanza after eating some spicy kung pao chicken.
The next morning, we were grateful to see the Indian Summer we’d been experiencing the past few days was over—perfectly timed for our hangover day. We laid in bed until well after our designated checkout time, the rain putting a damper on any motivation to ride, or even move.
By the following morning, we were ready to wake up early and slip back into our usual routine: Drive until we were out of cell service, then keep driving; pull over at an indistinct, logging-road mile marker, and then pedal several hours to the top of a mountain; take in the stunning vista and vast swathes of wilderness around us, feeling truly lost as we had no real notion of where we were; then turn our bikes downhill and sprint as hard as we could because we knew our friends were doing the same thing behind us. We rode faster than we thought we ever had, on trails we’d never ridden before, blindly popping off every roller and trying to rail each corner brakeless, fearing the chirps from our friends if we didn’t. This was the purest antidote to the end-of-season blues.