Oregon Outback

Travel Time: 7 hrs 30 min by train / Trip Length: 364 miles, 5–7 days / Difficulty: Hard / Best Month: June
Welcome to Oregon’s most hallowed bikepacking route. Stretching from Klamath Falls to just east of The Dalles, the Outback runs the length of the state via little-traveled roads (about 75 percent gravel and dirt). Standard practice is to take Amtrak to Klamath Falls and then ride north, through sagebrush-filled high desert (optional stop for 30-ounce steaks at the Cowboy Dinner Tree), past the volcanic monolith that is Fort Rock, along the scenic Crooked River, through the Ochoco Mountains, and into the ghost town of Shaniko. You’ll end, 364 miles later, at the confluence of the Deschutes and the Columbia. (From The Dalles, take a bus back to Portland, or persuade a friend to pick you up). It’s remote, and water sources can be scarce, but damn if it isn’t bragworthy.

Deschutes River Trail

Travel Time from Portland: 1 hr 30 min by car / Trip Length: 24 miles out-and-back, 2 days / Difficulty: Easy / Best Month: June
There is no better introduction to bikepacking than this easy-peasy overnighter along the Deschutes River. It begins about 100 miles east of Portland, where the Deschutes flows into the Columbia, and boasts mellow gravel terrain alongside dramatic canyon views and bucolic riverside campsites. (Pack a fishing rod if you’re feeling ambitious.) The trail itself is a mostly flat, doubletrack, converted railbed on the eastern side of the Deschutes. A brief down-and-up stretch keeps things interesting, but, really, there’s no shame in pushing your bike up a gravel hill.

Cascade Skyline

Travel Time: 1 hr 45 min by bus / Trip Length: 173 miles, 3–4 days / Difficulty: Hard / Best Month: July
Big trees, big mountains, big views—western Oregon at its finest. This horseshoe-shaped route (75 percent gravel and dirt) follows stunning ridgelines through forests between Mount Hood and Mount Jefferson, edging past high-alpine lakes and racking up some serious climbs—and screaming descents—along the way. From Estacada (take TriMet), you’ll bike southeast to Timothy Lake, then south through the Olallie Lake Scenic Area before shimmying west to Detroit along the Breitenbush River and finally into Salem, where you can catch a bus or train back to Portland.