I've been able to do this once every year so far. I took a six mile ride up the hill to the Old Five Mile House. (It's six miles because I didn't take the direct route.)
The green is the elevation profile and the blue is my speed, according to RunKeeper. The Old Five Mile House is 1085 feet above my house. I tried Willow Valley Road all the way this time, and it has a fifty feet or so drop before getting into the climb. When I got to the point on Willow Valley I had ridden before, I dropped to 2 miles per hour because I was stopping at every patch of shade to rest.
I can't make it to the top of this hill, but I think I can make that bit of shade fifteen feet ahead.
This time, Willow Valley was paved all the way, which is nice:
Of course, the really important thing is that I made it:
And they seem to be honoring my mother's passing (Mom lived in New Mexico):
I came back down via Scotts Flat Road/Scotts Valley Road. Scotts Valley Road is steep and graveled -- I'm glad I didn't try to go up it, but coming down was a little scary, too, because of the lack of control I felt in spots. Still, I made it home safely. Runkeeper tells me I hit 32.7 miles per hour at one point. I can assure you that was not on the way up.