Oregon is a big state to ride, and it rewards riders who treat it as several distinct regions rather than one loop. The Cascades split the state cleanly — wet forests and coastal fog on the west side, dry canyon country on the east — and the best rides happen when you cross that divide deliberately.

West Side: Forests, Coast, and the Pass Roads

Start in Portland's Laurelhurst neighborhood at One Moto Cafe, where Stumptown coffee and a community board of local rides will sort out your morning routing. From there, the Historic Columbia River Highway (US-30) runs 74 miles east along the Gorge past five major waterfalls and over the stacked switchbacks at the Rowena Curves. Pull off at Rowena Crest Viewpoint for the wide horseshoe view of the Columbia before dropping down toward The Dalles.

Head south from the Gorge and you reach the McKenzie River corridor. The Aufderheide Scenic Drive (Forest Road 19) threads 58 miles through the Willamette National Forest between OR-126 and OR-58 near Oakridge — smooth pavement, consistent-radius curves, nearly neutral camber, and almost no traffic. It's a good road for finding a rhythm. North of it, McKenzie Pass / Old McKenzie Highway (OR-242) is a different animal: narrow, historic, and built across a 2,000-year-old lava field with a 5,325-foot summit. The Dee Wright Observatory at the top lets you sight named Cascade peaks through stone porthole windows. OR-242 is closed to motor vehicles from around mid-November through mid-June — the earliest opening is the third Monday in June — so confirm current status before planning around it.

For coast riding, the Pacific Coast Scenic Byway (US-101) runs the full 363-mile length of the Oregon coast from Astoria to the California border. It's relaxed, bagger-friendly touring with frequent pull-outs, coastal towns for fuel, and highlights including Cape Perpetua and the Samuel H. Boardman State Scenic Corridor near Brookings. Devil's Churn at Cape Perpetua is worth a short stop — the basalt sea channel is most active at high tide or in swell. If you want to escape US-101's traffic for a stretch, the Three Capes Scenic Route departs from Tillamook west on OR-131, loops 40 miles past Cape Meares, Cape Lookout, and Cape Kiwanda, and reconnects to the highway outside Pacific City — the road is narrower and quieter than 101 with coastal headland character throughout.

The Siuslaw River Road (OR-36) offers a 52-mile valley-to-coast crossing through the Coast Range between Junction City and Mapleton — steady curves, light traffic, and a good alternative to busier corridors.

East Side: Cascades to Canyon Country

East of the Cascades, the Cascade Lakes Scenic Byway (Century Drive) loops 66 miles west and south of Bend through the Deschutes National Forest past a dozen alpine lakes under Mount Bachelor and the Three Sisters. The byway is seasonal — typically open June through November. For high desert, the Outback Scenic Byway (OR-31 / US-395) runs 170 miles of two-lane rural highway through Lake County past Fort Rock State Park and Summer Lake. Plan fuel carefully: gaps between towns are long.

In the northeast, the Hells Canyon Scenic Byway makes a 218-mile loop encircling the Wallowa Mountains and skirting the rim of Hells Canyon. The FR-39 segment between Joseph and Halfway closes in winter. If you ride the byway, the Hells Canyon Overlook at 5,400 feet gives you the full panoramic drop into the deepest river gorge in North America.

In southern Oregon, the Rogue-Umpqua Scenic Byway (OR-138 / OR-230 / OR-62) strings 167 miles of sweeping forest road from Roseburg through Diamond Lake and south to Medford, past Toketee Falls and 272-foot Watson Falls. Pair it with Dead Indian Memorial Road — a county road east of Ashland that climbs into the Rogue River-Siskiyou National Forest with a long serpentine ascent and views over the Rogue Valley. The road connects Ashland and the Rogue River Valley with the Upper Klamath Basin and has a notably different character on the descent than the climb.

For a destination stop, Crater Lake Rim Drive — the 33-mile loop around the caldera at 7,000-plus feet — is worth building a route around. The Cloudcap Overlook sits at nearly 8,000 feet on the eastern rim and is one of the highest paved motor vehicle viewpoints in the Cascades. The full loop is accessible mainly mid-July through October; the West Rim typically clears snow earlier than the East Rim. Check current road status before arrival — late-season snow closures can happen without much notice.

Rally

The Ride Oregon Rally is the BMW Riders of Oregon's annual gathering at the Grant County Fairgrounds in John Day, deep in the Blue Mountains canyon country — now in its 46th year. For a more open-format event, Maupin Madness is a multi-day rally held each June at the Oasis Riverview Campground on the Deschutes River in Maupin, with ride routes for on-road and off-road riders, a poker run, and a small-town atmosphere that keeps it from feeling like a production event.

Plan Your Ride

Oregon's seasonal windows matter more than in most states. OR-242, Crater Lake Rim Drive, the FR-39 segment of the Hells Canyon Byway, and the Cascade Lakes Byway all carry firm seasonal closures — mid-June is a realistic opening for the higher routes. The coast and the Columbia Gorge ride year-round but fog, rain, and debris are routine from October through May. The eastern desert routes (Outback Byway, Hells Canyon loop) are best May through October. Build your trip around one or two anchor roads and use Switchback to string the connecting miles — Oregon's back roads tend to be worth the detour.