Historic Hwy. Take Stark St east through Gresham. It'll T with the historic Hwy at Dabney Park. I've only been as far as Cascade Locks, but it goes all the way through HR and ends near the Dalles, I think. There are, however, some sections that no longer exist where you have no choice but to ride on the shoulder of I-84 for a bit. Not fun, but the rest is pretty nice. It's a little hilly, but doable on a fixed gear. Probably right in the neighborhood of 100 miles.
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