Adventure Cycling Association

The road into Bend was the icing on the cake. My eyes were sunken from exhaustion, my legs felt like lead, and I had a half-empty pizza box strapped to my front rack for emergency snacking. Two weeks of riding and skiing through Oregon’s backcountry had taken its toll on all of us. But the final miles were among the finest. A scenic gravel bypass gave way to serpentine pavement through the central Oregon countryside, and in spite of being physically exhausted, we were happy as could be.

It started last winter as three friends and I carved out an ambitious itinerary to keep ourselves busy for two weeks in May. Oregon’s central Cascades, some of the most appealing ski mountaineering volcanoes in the western U.S., were calling our names. Our first objective was Mt. Hood, 60 miles east of Portland. After summiting we would continue south to Mt. Jefferson, then to Three Fingered Jack, finally culminating in the Sisters Wilderness west of Bend, Oregon.

Our route wound some 300 miles through the sinuous paved and gravel forest roads of Oregon’s backcountry. The mountains there jut skyward in a wide arc of peaks that cradles the coastal Northwest. The roads that connect the dots between them are worthy of a bike tour on their own merits, but we approached the tour mostly as an interesting way to move from ski objective to ski objective. On the first day, we left our cars in Bend and rented a U-Haul truck for a user-friendly one-way shuttle to Portland, where we started pedaling.

Oregon in general, but specifically Portland, sits on a pedestal in my mind as a cycling utopia. Even for Portland, the veritable mecca of eccentric bicycle culture in the U.S., our quartet was something of a spectacle. Each bike was laden with four full panniers and an overloaded B.O.B. trailer, from which skis jutted four feet astern. Each vessel was about 15 feet long altogether, and the four of us in single file were about the same length as a school bus. In addition to the regular bicycle-touring and camping gear, we carried ski boots, climbing equipment, cold-weather clothing, and the endless minutiae of backcountry ski gear. Our loads weighed somewhere around 150 pounds each.

In spite of the unwieldy nature of our steeds, a gentle breeze pressed against our backs and the miles ticked away with relative ease. We rode a few blocks through neighborhoods and on side roads before emerging onto a smoothly paved, two-lane bicycle path that would take us east and more than halfway to Government Camp on the slopes of Mt. Hood. The sky was a shallow kind of blue that stood as a blank canvas for the bold green undergrowth that insulated the bike path and made it feel much more remote than a bicycle-friendly alternative to arterial streets.

In spite of sunshine and a tailwind that kept our spirits high, several hours on these bicycles forced us to confront in real terms what we had only known in a nebulous, conceptual way before: the next two weeks were going to be extremely difficult. Mt. Hood loomed in the distance and gave a menacing air to an otherwise pleasant, blue-skied day. We hadn’t ridden more than 45 or 50 mellow miles, but there was no conversation about pushing on toward the higher town when we rolled into Welches in the late afternoon.

For the first day of riding, we still had in our minds that this was primarily a ski trip — that the bicycle-touring component was an added perk but ultimately a means to an end. Over coffee and maps on the second morning, we found a dirt road that skirted the highway miles we’d been counting on, but we made the right choice — this little forest road changed the tenor of the trip.

We found ourselves on a wisp of pavement nestled along the lower banks of a trickle of water called Still Creek. We climbed along the stream on smooth, mossy asphalt until the grade kicked a little steeper and became a well-graded gravel road. In planning the trip, we had thought that at least some of the riding would be on forest roads, and so we were outfitted with high-volume, aggressively treaded tires to handle their weight and unpredictable surfaces. The road deteriorated slowly, and we climbed past the reasonable expectations of smaller tires.

The road was less than 15 miles, but it took us nearly four hours. The climbing was steep and difficult, and our skis dragged along the uneven road, feeling more like boat anchors than assets. But we had all day and the canopy of trees kept us cool against the sun. Clear, cold water rolled over dark igneous stones, rounded by the permanence of the creek and the patience of time.

It was quiet there, and pretty. We joked that the highway would have been easier, but there wasn’t another place that we would rather have been. We climbed slowly enough to watch the lush, dense understory of Oregon’s rain forest give way to a drier, coniferous climate one tree at a time, and with every breath the air seemed to thin. On only the second day of the tour, our ski trip with bikes began to morph into a bike trip with skis.

Of course, we were still there to ski, and our day on Mt. Hood was about as pleasant as our plan allowed. We groaned as we got out of bed before 5:00 AM, ate a quick breakfast of oats and coffee, and got back onto our bikes. We had the benefit of leaving everything but the bare essentials behind in a locked garage, but climbing 2,000 feet to snowline in the predawn grey still stung my tired legs. It was only the third day of the trip and our first day skiing, but I was tired.

The parking lot was all but abandoned as we transitioned to skis. We left the bikes locked to a light post, hiked up to the snow, and strapped the sticky climbing skins to the bottoms of our skis. The grade was gradual at first but steepened all the way to the summit. By 10:00 AM the slope was too steep for skinning and we strapped the skis to our backs, ascended steadily with crampons and ice axes, and shielded any bare skin from the already-hot sun.

We stood on the summit well before noon and snapped a few photos. The traverse to the ski descent required walking gingerly along a narrow ridge. After a few icy, patient turns near the top, the snow softened to the spring corn conditions that we’d come looking for. It took us 20 minutes to descend what we had spent nearly five hours climbing. By noon we had celebrated with beer in the base lodge and were negotiating the parking lots, which had become crammed with hikers and skiers. We coasted back down the winding 2,000-foot mountain road to naps and an early dinner in Government Camp.
After Hood the ride to Mount Jefferson took us two days. It seemed fair to budget that much time for 100 miles of riding, given that we had never been there before, that the roads we had in mind were dubiously labeled on various maps, and that much of the route was scheduled to be closed due to low-elevation snowpack. The winter of 2014-15 was historically mild in the Pacific Northwest, and before we left we were skeptical of how good the skiing would be, but we had felt safe anticipating clear roads for bike touring. The maps were sketchy, and we weren’t quite sure what we would find. It could have been rough, steep logging roads, or gnarled washboard for 100 miles. In fact we found one of Oregon’s hidden gems.

National Forest Road 42, where it’s drawn at all, appears innocuously on the maps. Other maps call it Oregon Skyline Road and hint that it’s closed during the winter months. We only know it now as we found it then, a narrow ribbon of silky smooth pavement, only a lane wide, that rolls down the distal flank of Hood and toward the Clackamas River. We spent the first several miles in silence, basking in smooth corner after smooth corner. “Did you know it would be like this?” Mike asked at one point, unable to control his beaming smile. “I had no idea,” I laughed. Before we left, I had thought it would be a hellish, character-building kind of experience.

By evening we had ridden 70 miles and found an idyllic campsite in the hills above Detroit, Oregon.
Over the first several days, the route finding was deceptively easy. Even the relatively tricky route from Mt. Hood toward Jefferson only required a couple of turns, and through the maps were lacking, the roads themselves turned out to be intuitive. Things changed slightly when we made it to Jefferson.

The mountain itself offers a much more remote backcountry experience than Hood, which is home to multiple year-round ski resorts, hotels, lodges, restaurants, and a paved road that winds much of the way toward the summit. Jefferson, by contrast, is reached by relatively few and steep dirt roads. The nearest grocery store is 20 miles from the trailhead, and the skiing is more exposed and more difficult. The approach to the trailhead, too, was more arduous than on Hood.

After the turn from the highway, the first mile or two of the dirt road to the trailhead was level and smooth. As we climbed, the grade pitched steeper and the exposed rocks began to bounce even the heavy bikes around. By the top of the climb, the rain had turned to sleet and the clouds hovered only a few stories above our heads. We were cold and hungry and couldn’t even tell where the mountain was from where we were standing.

We didn’t know it at the time, but the sun wouldn’t show its face for another week. The clouds continued to hang low in the canyons, and our gear slowly got more and more damp. The air was cool and humid, and drying anything was out of the question. We stood around a campfire and steeped our clothes and gear in the unshakable, pungent smell of pine smoke but never managed to dry anything out.

Rain, snow, and low visibility kept us off the summit of Mt. Jefferson. We burned several days waiting for the skies to clear before skiing from near the top between storm cycles. Our time on the mountain felt unfinished. While planning the trip, Jefferson had emerged as the crown jewel of the itinerary, so turning away without standing on its summit left a hole. Our enthusiasm to keep going was low as we rolled wet tents and clothes into our drybags, but as soon as we loaded the bikes again our moods improved. Through every disappointment on skis, climbing back on the bikes refreshed the simple joy of making progress on two wheels.

It’s always a pleasure to start the day with a descent. That’s even more true when the bikes weigh more than 150 pounds. We didn’t say much when we left our campsite, but we smiled and laughed quietly through chattering teeth at the bottom. It was cold in the mornings, and we were tired and wet, but it felt good to make progress again. We were only 30 miles from Sisters, Oregon.

When you’re living outside, the weather has a tremendous impact on your mood. The road to Sisters took us over Santiam Pass and to the east side of the Cascade divide, where the air was palpably drier. At the top of the climb was the turn to McKenzie Pass. It’s a road that’s not maintained in the winter, and in the spring finds itself available only to bikes. It’s a beautiful, winding, narrow, smooth mountain road that a Bend local described to me as “the most baller ride in Oregon.” We’d looked forward to riding McKenzie Highway since January, but when the time came we didn’t make the turn. It would have added considerable mileage and climbing, and after 10 days without rest we were just too tired, too ready for the hot showers, soft beds, and pizza and beer that waited for us in town.

From Sisters we had the best skiing of the spring. We left at dawn and made it back to the hotel after dark. We spent the day approaching, climbing, and skiing two of the mountains there. It was a huge day, and our legs were finally cooked. All that was left was a lazy morning and a short cruise to Bend.

In a car, the cities in Oregon are easily linked by an efficient network of bustling two-lane highways. They tend to have wide shoulders and drivers are aware of cyclists, but it’s also the land of lifted pickups and aftermarket exhaust, and touring on those roads has drawbacks. The state is also home to a huge collection of meandering side roads. Sometimes they’re dirt. Sometimes they’re glassy ribbons of pavement that feel like they were created with only cyclists in mind.

Exhausted, we found our way winding across gravel and perfect pavement into Bend. In the beginning, this had been a ski trip. We had planned the route around ski lines, packed accordingly, and brought bikes as an amusing means of getting from point to point. But we spent 12 days on the road and only skied for four. We had high expectations for the spring skiing, but Oregon surprised even our veteran bike tourists with the quality and style of its roads. Even though we had only stood on top of two of the six peaks we’d had in mind, the trip felt a lot like a success. In the end, riding bikes with friends is about as good as it gets. And if you manage to squeeze in a few turns? That’s a bonus.

Nuts & Bolts

We spent two weeks on a difficult tour that included some challenging skiing. We had a great time riding bikes with skis, but it probably isn’t for everyone. That said, there’s no reason not to consider a multi-sport aspect to just about any bike tour. We timed the trip in May so that we could ski, but by waiting a few months, this exact itinerary would make an excellent bike tour with stops for day hikes along the way. Mt. Hood and Three Fingered Jack offer relatively accessible hiking right from the road, while Mt. Jefferson, Mt. Washington, and the Three Sisters Wilderness are all veritable playgrounds for a backcountry experience. On your next tour, think about bringing along hiking shoes, climbing gear, or even a packraft to explore your destination beyond the pavement.

We planned for a mix of camping, hotels, and vacation rentals over the course of two weeks. We found that free, dispersed camping was usually easy to come by along the way and at trailheads where we would ski. We wound up leaving our bikes locked but unattended and never had any issues. Every once in a while, though, we needed a hot shower. We had great success along the way with these groups:

Mt. Hood Area

Mt. Hood Vacation Rentals: These folks are great. We stayed in their places in both Welches and Government Camp around Mt. Hood, and they’re a great option for lodging in that area.

Sisters, Oregon

Sisters Motor Lodge: This old-school motor inn is right on the outskirts of town from the west. They have clean rooms, a friendly staff, and a secure garage for bikes so you don’t have to cram everything into your room. We also took advantage of their large courtyard to dry out wet gear.

Bend, Oregon

Wall Street Suites: These hip hotel suites are a revitalized boon to what used to be a seedy part of Bend. The suites have plenty of space for bikes and gear shuffling, soft beds, and a communal fire pit. They’ve also got kitchenettes that are plenty capable for cooking in the room if you can pull yourself away from the great restaurants and breweries that are just walking distance from the hotel.