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, 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, who fuel up at places like the Elusive Trout (503/668-7884), at 39333 Proctor Boulevard, a pub/restaurant serving gourmet hamburgers and homemade soup. After 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 Inn Between (503/622-5400) in Wemme, one of the little wide spots clustered at the base of Mt. Hood, has affordable eats varying from teriyaki chicken to macho nachos.
The other suggested stop is the Mount Hood Visitor Center (daily; 503/622-4822), in Welches at 65000 E. US-26, operated by the USFS and loaded with maps, brochures, and other information on the mountain and surrounding recreational hotspots.