Our first peak is legendary Mt. Tamalpais. And our tip is: Check out the mountain-side West Point Inn. Back in the day (circa 1910), adventurers often explored the North Bay aboard the Mt. Tamalpais and Muir Woods Railway (known as the "Crookedest Railroad in the World") and stayed at the famed West Point Inn. Today, the railroad's gone, but from Mill Valley you can still bike the "Old Railroad Grade" 6.7 thigh-burning miles to the inn. (Hikers have other route options, including one as short as 45 minutes: more info.) The West Point's signature old-school charm and friendly service welcome hikers, bikers, and campers, even if you're just stopping by for an hour. But take our advice and spend the night. Sure, you've got to bring your own sleeping bags and food—but at $35 a night per head, with incredible ocean views, who's complaining?
TIP: For some serious mountain-bike fun, climb another two miles past the inn. Cross the road, and descend Eldridge Grade, a "rock garden"â€"type trail that will scramble your eggs. Be sure you have a map to navigate your way back home; there are multiple trail offshoots.
The West Point Inn, (415)-388-9955.