Adventure Cycling Association

There’s something alluring about a long-distance adventure. Maybe it’s the chance to disengage from the complications of daily life. Maybe it’s to do with the way long trips distill life to the basics, like where to sleep and where to find water. Maybe it’s simply the chance to immerse yourself in nature and new places. Whatever the appeal is, it definitely has its hold on me. I’ve spent many a work day dreaming about riding the Great Divide or hiking the Pacific Crest Trail.

Planning a Short Trip

But for Matt, Nick, and I, all thirty-somethings with fairly hectic lives and full-time jobs, a months-long adventure wasn’t in the cards. The specific long trail we wished we could tackle was the Oregon Timber Trail, which my circle of bikepacking friends talked about in hushed, reverent tones. One of the only long-distance trails created with mountain bikes in mind, the OTT is nearly 700 miles of jeep roads and singletrack that trace the spine of the Oregon Cascades from the California border to Washington. Without the time to spare to ride the trail in its entirety, our next best idea was a quick weekend getaway that would at least capture a few of the highlights on that epic route. 

I know we aren’t alone in seeking out long-distance trails for weekend trips. Though long trails are often completed in one go, it’s also a non-starter for many of us with what we begrudgingly refer to as “real lives.” According to the Oregon Timber Trail Association, about half of the users on the Timber Trail are out on day rides or weekend trips. As it turns out, a short trip on a long trail is a great way to connect with the experience of a grand adventure while holding down a 9-5.

Bicycle Camping for the Time Challenged

The route we chose, just outside Hood River, Oregon, was a point-to-point ride heavy on flowing singletrack and alpine vistas, and one specifically recommended by OTT trail builders. At 33 miles, serious riders could accomplish it in a day; we planned to smell the proverbial flowers and make it an overnighter. For us, coming from Boise, Idaho, it was a fairly long drive. But for riders in Portland or the surrounding area, it clocks in about two hours away — a perfect weekend escape. Since we were short on time, we opted to shuttle the ride from Parkdale. If time allows, a loop is possible — the ride from Parkdale to Bennett Pass trailhead is 19 miles, on a busy but wide road with good shoulders.

Snowpack in June

Having chosen a weekend in mid-June, we were prepared for spring conditions, but we still weren’t entirely sure what that would entail. We knew temperatures were unlikely to dip very low overnight, so we could keep our camp setup fairly light with 30 degree sleeping bags and ultralight tarp and tent setups. However, ski resorts on nearby Mount Hood are famous for staying open well into summer, thanks to snow that just won’t melt. Our main concern was lingering snowpack, not cold weather. Still, we had high hopes that the trails would be in passable condition. After all, Mt. Hood is 11,279 feet tall; our trip maxed out below 6,000 feet.

Ultralight Packing List

We were wrong. After just a few miles of climbing on gentle double track, we took a sharp left-hander onto Gunsight Trail and before long, we were walking our bikes across snowfields. On a steel hardtail complete with frame bag, bar bag, a mini rear rack, and 29+ tires, this was no easy task. Later on, the Tumbleweed Prospector I rode would prove about perfect for the trail conditions, but as we traversed seemingly endless snowfields, it felt like it weighed a ton.

The going was, of course, slow. The snow — sheltered from the sun by towering fir trees and the north-facing aspect of the ridge — hid the trail many times. Since we were only a few miles into our trip, our bikes were fully laden with all the water and all of the food we thought needed for the weekend. Since we were passing water sources every few miles and had a filter, we realized there was no reason to carry more than a liter or two. I had opted for hot meals, so a stove and fuel added to the weight. (In retrospect, the trip was short enough that I could have left the stove at home and brought only cold food.)

We crossed several blowdowns which required all three of us to carry each bike over the downed logs, all the while fighting to keep ourselves upright on slippery, melting hardpack. Our hopes were to knock out about 10 miles of the trip on our first day, leaving us plenty of time to savor the trails the following day. But as the sun began to set, we had only traveled about half that distance, hadn’t yet escaped the snow, and were close to exhaustion. Unsure of how much more snow we would encounter, we began to discuss our options — including scrapping the trip altogether — before we came across a welcome sight: an idyllic campsite in a saddle of the ridge with flat ground, room for several tents, and enough tree cover to block the wind. To the west, the sun was setting behind Mt. Hood, and to the north, an unobscured trail lay before us, promising better luck for the next day.

Dispersed Camping for Cyclists

We made camp for the night, debating the merits of the different shelters we had brought along: my trekking pole tent, Matt’s pyramid tent, and Nick’s 9x5 tarp. In the end, the clear and quiet night meant all three performed just fine. After dinner, we scaled up a rocky outcropping to take in 360-degree views of the Cascades before settling in for the night. 

Setting off in the morning, our good luck held out. As we slowly dropped in elevation along Gunsight Ridge, the snow became more and more sparse and soon disappeared altogether. Still, we had learned our lesson. Even in the lower reaches of the Cascades, we were in the high country. A weekend in July would have been a better choice.

Timber Trail Takeaways

In total, the route is made up of three distinctive parts. First, there’s Gunsight Ridge, which winds through dense, dark pine forests and generally trends downhill. At least a few miles of this section are hard for me to describe because they were entirely snow-covered. The trail miles we did experience were primarily soft and tacky, interrupted by a few demanding traverses across talus fields. Next, a steep climb on a double-track road brings you to High Prairie Trailhead, where you’ll take Eightmile Trail through meadows of wildflowers and mostly travel along smooth, winding singletrack. Last is Surveyor’s Ridge, where you’ll find the most technically demanding terrain, with short punchy climbs, sandier surfaces, and hair-raising, rock-strewn descents.

With so many miles of ridgeline riding, the views on this trip are immense. Mt. Hood dominates the landscape and is never out of sight for long. The peak has a classic, postcard-worthy silhouette. It stands proud and alone, the only monolith that breaks through the endless pine forests for many miles, its flanks streaked by glaciers and snowfields that defied the hot summer sun. We often wound our way through miles of forest, eventually reaching a meadow or vista where the peak was once again visible from a slowly changing vantage point as we traveled north. 

Though the mileage may sound easy, we found this route plenty challenging for a short weekend. Even experienced mountain bikers and bikepackers will likely agree with this assessment — 30 miles of tough singletrack is nothing like 30 miles on the road or smooth gravel. By the time we wrapped up the sandy, switchback-filled descent off of Surveyor’s Ridge on Oak Ridge Trail, we were happy to be back on pavement and only a few miles from Parkdale, where our car and a burger at Solera Brewing were waiting for us. 

The weekend hadn’t been a massive undertaking. In fact, we were out for less than 24 hours. But despite the quick turnaround and leisurely pace, it did feel like an adventure. I bottomed out my 150mm fork often enough that my front tire wore a small hole in my handlebar bag, which I regard as a casualty of a fun weekend and proof that the singletrack was pretty technical. We didn’t experience all the highs and lows of an epic, 700-mile trip. We didn’t ascend the Oregon Timber Trail’s hardest climbs, explore its most remote stretches, or ride our brakes down the toughest descents. But for one weekend, we saw a small slice of it — a beautiful slice, I might add — and that’s good enough for me.

Oregon's Volcanoes