Thanks for reminding me of Eureka Canyon into the Santa Cruz mountains. I lived one year in Santa Cruz. Loved that climb. Like some cherished valley in Europe. One of my near-epic days started there, then I followed the ridge north, crossing the highway to San Jose (17?) then dropping into Big Basin Redwood State Park. Then I climbed back toward Ben Lomond but before dropping down to the town, I turned right and went up a bear of steep climb.
And Joaquin Miller in Oakland; my crazy years (doing work I knew I would pay the consequences for the rest of my life and riding the roller coaster that is post TBI. For sanity, I would ride up it on my beater fix gear, an ancient UO-8 in a 42-17, get to Skyline, turn around and do the just as crazy descent.
Crater Lake - did it with Cycle Oregon 2012 on my brand new road fix gear (with a dropout long enough to use any cog mad without messing with chain length). The big climbing days I brought 3 cogs. 17, 23 and 12. We went up the south entrance. The climb didn't impress me. For the rim, I took off the 17 and put the 12 on. (There's only 1 mile of the 23 that is sorta flat.) All good so far, Went over the first hill and as I came down I came upon a fork. Right option had a crowd of riders. Thinking sight seeing pull-off, I went left. Spectacular descent (like on my all-time list), at least until the road leveled out a bit and I was riding though a weird "meadow" of volcanic rocks, not shrubs. I'd just descended to almost Diamond lake, more than a 1000', and the ride was back up that hill.
In my racing days two climbs stood out. Smuggler's Notch; a climb I was built for and thrived on. And the climb out of Skowhegan, Maine 15 miles from the finish. The race split apart. I had moved up until I felt every rider ahead of me was solid. That hill was the hardest thing I have ever done, just trying to stay 2' back from the wheel in front of me in a long line of single file riders, all at their limit. Halfway up I was so desperate I looked over my shoulder to see how many places I could drop back and still be in it (assuming me pulling out didn't cause a permanent split which it probably would have). Next rider was 25' back. I knew instantly that the wheel I was on was going to beat him by 10 minutes and I had a choice. Hung on, was in survival mode the rest of the race, crested the final hill dead last, managed to pick off 5 riders and finished in the money (barely) and under the previous course record.
Ben