One lump or two?
So it’s too late in the season to ride over the Cascades, then turn around and ride back over them again before sunset? There might be enough time to at least make it around Mount Hood before this part of the planet inconveniently rotates away from the nearest star.
So there is the teeny problem of the 4600 foot climb up over Bennett Pass, but that’s simply a matter of sitting on the bicycle and grinding on uphill for 40 or so miles out of Hood River (and none of that at a grade much worse than 4%, which is better than certain other brevets I can think of) and then stopping, putting on many layers of windproof clothing and screaming down the mountain to Sandy, Orient, and 282nd into Gresham.
Shoot, The sun probably might not even go down until I reached Orient. Or home, if I could sell enough junk on eBay to pay for the remaining parts of the hypothetical midlife crisis mobile and ride that instead of the 50 pound luxury yacht I’m currently using for everything.
All I’d have to worry about would be the possibility of snow on the ground. And finding other crazy people who’d want to do it with me.