They are actually very different
I've done a couple of Sandy's rides (Oregon Bike Ride). These rides are <400 people, the support is excellent, the rider level I can keep up with.
cycle Oregon is huge - bigger everything including #s of people, generally has more hills and, I think, more miles. I have been afraid to try a Cycle Oregon, I have friends that can't wait to do Cycle Oregon every year.
I can recommend the former with some petty little reservations. I've also ridden Bike Idaho with Sandy. Simply, Bike Oregon is smaller, more intimate, and easier. I've been told that Cycle Oregon is a giant rolling party.



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