I love the sounds of an overnighter to Winthrop. Di and I drove the Highway 20 loop in the summer of 2001 and really had fun. Hot and dry, and staying the evening in "Cowboy Town" Winthrop would be a blast, we may even catch a bar room brawl. Count us in.
Driving the Oregon Coast in a Cobra would be spectacular, especially if we catch the sun for a few of the days. Don’t expect perfect weather, in my estimation a week of sun is very rare on the entire Oregon 101 Coastal Highway (until you pass San Francisco). I think August and September are about the best times. It would be more than on overnighter, almost worthy of a Great Oregon 101 Cobra Ride (GO1CR) 2003 or 2004. You can drive down 101 turn around and come back up and it seems like a whole new drive. Other options would be coming back up (or down) Highway 97 through Eastern Oregon. Lots to do and see every step of the way and especially grrrrreeeat Cobra roads. Count us in.