Willamette Tier - Sawtooth Struggle

Bite off as much as you want to chew on this lush, rolling river trail. (less)

A long gravel climb with jaw dropping views with a raw and rugged singletrack descent. (less)

A great introduction to high-desert riding—the trail takes you through prairies, aspen groves, giant ponderosas, and views in every direction.
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One of Mount Hood's funnest backcountry rides traversing through ponderosa and oak forests on the mountain's dry east side. (less)

This ride has it all - a big gravel climb and a raw descent through a spectacular burn with big views of The Sisters and Broken Top. (less)

A great route for multiple skill levels on relatively flat terrain traveling past three inviting lakes. (less)

Tie the mighty Columbia River to Mt. Hood through Wasco County’s hill country and the verdant Hood River Valley along ribbons of backcountry singletrack. The mountain, the forest, the prairie, and the river all converge here, creating a varied splendor of geology, flora, fauna, and many layers of human history. (less)

Trappers Butte offers a little of everything for riders of all skill levels. (less)

The 14.5.-mile route along Crescent Mountain’s ridgelines isn’t for the faint of heart—it gains more than 2,600 feet—but rewards riders with up-close looks at the unique topography of the Old Cascades. (less)

Ask any seasoned rider for their favorite outing in the Old Cascade Crest, and chances are good they’ll wax poetically about the South Pyramid Creek Ride. (less)

Pack portable lights for this all-day ride. The 27-mile Pyramids Epic Loop incorporates elements of several other rides in this article while heading further into the Cascades and circling the entire Middle Santiam River drainage. (less)

Finally: some relief! We’re taking a break from increasingly more difficult rides to shout out the much easier Old Santiam Wagon Road, a jaunt at the southernmost regions of the Old Cascades Crest region.
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Aug 25, 2025 (less)

This is the best hot-day ride with plenty of opportunities to take a dip in the river to cool off. Better still, it starts from downtown Oakridge so you can easily eat lunch, cruise the trail, and be back in time for a pre-dinner beverage. It can also be made more challenging by crossing the river at NF-207 and returning on the south side, which is more technical and just as beautiful. (less)

A high-elevation ride across the state line to the highest point on the Oregon Timber Trail. (less)

This is a great ride to sample one of the most scenic legs of the Oregon Timber Trail. (less)

Knebal Springs may perhaps be THE classic ride in the 44 Trails system. It’s a great, classic old school singletrack ride that seems to have a bit of interest for everyone at every skill level. (less)

A great backcountry ride that samples a bit of the Oregon Timber Trail terrain around remote lakes. (less)

Pedal your way through massive old growth, past bubbling blue pools, around alpine lakes, and along a indigenous explorer’s route on the Oregon Timber Trail. The Anaxshat Passage embodies the trails and backcountry landscapes of the Hood Tier, all easily accessible over a long weekend from the Portland metro area and geared towards a less-experienced mountain biker. (less)

The Scar Mountain Traverse is one of the shortest rides in the area—but riders will be rewarded with solitude and views of several cascade peaks. (less)

Can’t decide between Scar Mountain and Trappers Butte? With this ride, you don’t have to. (less)

Ready to really test yourself on Crescent Mountain? The Crescent Mountain loop traverses 18.4 miles while climbing nearly 3,000 feet, challenging even the heartiest of riders. But the rewards are some of the most gratifying views anywhere in Oregon. (less)

So far, our rides have skirted around the Old Cascades Crest—but the Three Pyramids Ride heads into the heart of the region for a challenging ride that thrills with speedy descents and offers an opportunity for a mid-ride dip in the Middle Santiam River. (less)

There’s no getting around it: The Pyramids Popsicle Loop is, far and away, the most difficult ride on this list. (less)

The Oregon Timber Trail is a world-class bikepacking destination and North America’s premiere long-distance mountain bike route. It runs south to north and travels through a variety of landscapes, communities, ecosystems, terrain, and, most importantly, mountain bike trails.

Divided into four unique tiers, the Oregon Timber Trail is approachable by a wide variety of cyclists. If it sounds familiar, you’re not mistaken: the Oregon Timber Trail is inspired by the Pacific Crest Trail and other trails in the National Scenic Trail system. What sets it apart is that it’s designed with mountain biking in mind and consists of more than 60 percent singletrack. (less)