Best Overall Hike:
Montara Mountain North Peak hike
World Class views on a clear day of the Pacific Coastline and the Bay Area (if you reach the top).
Best Book on Hiking on the Peninsula:
Peninsula Trails: Outdoor Adventures on the San Francisco Peninsula (Trails)
Lots of detail and decent maps and directions
Best Hiking with a Dog:
Hamms Gulch-Windy Hill Loop
It can get wet during the winter storms, but its a great dog trail
(runner-up) Pulgas Ridge Open Space
A true Dog trail, but a bit bland
Best Trail overrun by bikers:
El Corte De Madera Creek - North
Its a great area and nice trails, but its overrun by mountain bikers on weekends
Best Trail WAY OUT there:
Portola Redwoods Park - Peters Creek Loop
Not only is this park remote, but the trail is very lonely on weekdays -- I did not see anyone the whole 13 miles.
Best Trail for views of San Francisco:
San Bruno Mountain - Summit Loop Trail
On clear day, you can see all around the Bay Area... but on foggy days -- not so much
happy hiking!