This list simply wouldn’t be complete without the notorious Dipsea. Attached to a century-long annual event, the Dipsea Race, this trail is as connected to the local community and culture as it could be. The trail (including quite a few stairs) stretches from Mill Valley to Stinson Beach with over 2,000 feet of climbing. Starting at Old Mill Park in downtown Mill Valley, three flights of stairs — as tall as a 50-story building — meet up with Panoramic Highway where the trail dips and begins to weave through Muir Woods. On the Stinson end, rolling hills lead into the lush, shaded groves of Steep Ravine. Treat yourself to something refreshing in Stinson — lunch, drinks, a dip in the Pacific, whatever suits your fancy. Pro tip: Unless you want to head back on the trail for another 7.4 miles (the Double Dipsea), plan to leave a car at Stinson or take the Marin Transit shuttle #61 back to Mill Valley. Relive Link — View the Trail