The plan was to ride 50 miles. I went from to Castro Valley to San Ramon to Danville to Livermore. I thought that would easily cover it. Instead I was about 5 miles short as I rode into Pleasanton. I ended up zig zagging through the neighborhood in an effort to round it off. I finally just got bored and finished at 49 miles.
Looking at the map, it looks like I covered significantly more area than my odometer would indicate. If you were to overlay this same route in say Chicago, I feel like it would have been 100 miles. The Bay Area is deceivingly smaller than it looks.