Starting out along Powell Boulevard east from Portland, US-26—now dubbed the Mount Hood Highway—follows, albeit in reverse, the final leg of the historic Oregon Trail. Passing first through the comically named photo-stop town of Boring, the road some 20 miles east of Portland reaches Sandy (pop. 10,644), a boisterous gateway to the mountains. Nestled in berry-farm country, Sandy is full of ski shops, pizza parlors, and other enterprises geared for outdoor enthusiasts, but east of Sandy’s lively commerce the road ambles through pastureland and into the foothills of the Cascades.

East of Sandy, oddly named towns along US-26 hold good places to eat and drink before or after a day out in the mountains. The Barlow Trail Roadhouse (69580 US-26, 503/622-1662), housed in an old log cabin in Welches, is one of the many little wide spots clustered at the base of Mt. Hood, drawing day-tripping Portlanders for serious carbo-loading.

If you’re planning to get out of your car and explore Mt. Hood, make sure you stop beforehand at the Mount Hood National Forest ZigZag Ranger Station (70220 E. US-26, 503/622-3191), in Zigzag, operated by the USFS and loaded with maps, brochures, and other information on the mountain and surrounding recreational hot spots.