Get this: Yet another local hiker named Tom who has a hiking site. Weekly Walker is old-school, without many of the doo-dads some of us are prone to play with, but it has in-depth descriptions of hikes across the Bay Area, with category pages hikes according to interest (one for Grandads and Grandkids) and location (no Santa Clara County page just yet, but there are some South Bay hikes in the site.)
The Footnotes page has a ton of hiking-related info.
The entries are columns Tom Davids wrote for some newspapers on the Peninsula. I liked the ones I saw. (No new ones since spring of 2007, though).