It seems to me that one of Boulder's big advantages/draws is that it's a college town close to a big city (Denver). There's no arrangement quite like that in Oregon. Bend is hours away from Eugene or Portland.

Having lived in Eugene for a while, I'd say it's pretty nice, but you might get bored pretty quickly, even as a runner. It's just to small (for me).

I think Portland is better for outdoorsy stuff in general. There's Forest Park, Mt Tabor, etc in the city and lots of camping, hiking, snowboarding nearby.