Around Mt Hood. (Mt. Hood Vettes did this a few months ago)
Start in Troutdale, go east on Old Columbia River Highway, join 84, continue east to Hood River. South on Hwy 35. West on 26 (stop at Timberline Lodge). Continue back to Gresham (couple of interesting back roads too).
Soft-serve ice cream in Cascade Locks, Lots of restaurants in Hood River (and Full Sail Brewery). Fruit stand near O'dell. Food and drink at Timberline.
Drive - not including stops - is about 3.5 hours.
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Attitude - The difference between ordeal and adventure.