I have only done it north to south, clockwise around Diablo. The steep sections are hard. My epic ride was doing it with a friend who years before raced for the Athena School. It was an ill fated ride. Early on, my tube fell from my saddlebag and became toast. Up Morgan Territory, my friend did not have it. We made it over with me pushing him as best I could. (He couldn't ride steady enough for me to always stay in contact and this 150 pounder riding one handed pushing a 200 pounder was a little much. We got to the top. Coming down, he misjudged a corner and crashed. Down on the final flat 4 miles IIRC I flatted. We were running out of light. I borrowed his wheel, got his car and picked him up riding slowly along on my tire which he patched.

One of our epic adventures, Not the most epic. That goes to having the 24' sailboat we were running down the coast knocked over and pinned at 90 degrees 16 miles offshore at midnight in a lot of wind.

Ben