Bend sits on the dry east side of the Cascades, where the rain shadow of the volcanoes gives way to ponderosa pine, juniper and sagebrush. The Deschutes River runs through the middle of town, and on one side of the city rises Pilot Butte, a cinder cone you can drive up for a view of the Three Sisters and the rest of the range to the west. The elevation is around 3,600 feet, so the air is thin and clear, and the sun is strong even in winter.
The town began as a timber and milling center, and the old mill smokestacks still stand in the Old Mill District, where shops and restaurants now line the riverbank. It has since grown into one of the great outdoor towns of the Northwest, with more than eighty thousand people, a famous craft beer scene and a population that skis in the morning and rafts in the afternoon. Mt. Bachelor, the nearby ski mountain, draws snow lovers for much of the year. For a rider, that means good breakfasts, gear shops and every kind of fuel station.
The Cascade Lakes Scenic Byway, Highway 46, is the reason to start here. It heads southwest out of Bend, climbing past Mt. Bachelor and then winding through a string of alpine lakes including Sparks, Elk and Devils Lake, with views of the volcanoes at nearly every bend. The road is smooth and well graded, with gentle curves and good sight lines, and it passes through lodgepole forest and old lava flows. The Lava Butte area south of town has a cinder cone and a lava flow you can walk across, and the Lava Lands visitor center is a useful stop.
Timing is crucial. The byway is closed in winter beyond the Mt. Bachelor turnoff, usually from around November until late spring or early summer, depending on snow. Summer is the best season, though mosquitoes can be thick near the lakes in June and July, and weekend traffic is heavy at the trailheads. Mornings are chilly even in August, so bring a warm layer.
Fuel stations thin out as you leave town, so top up before you climb. Sunriver has services, but there is little along the lakes beyond a handful of lodges and small stores.