California: Dipsea Trail
Beginning in Mill Valley, the 7-mile-long Dipsea Trail runs up and over Mount Tamalapais, with more than 2,300 feet of steep, often slippery, uphills and downhills. (This is also where the Dipsea Race unfolds, the oldest trail race in America.) The first mile climbs up 676 steps—three flights of stairs as tall as a 50-story building. It then maneuvers through oak and redwood forest to reach the highest point with views of San Francisco
, the Golden Gate Bridge, and the Pacific Ocean. Continue along coastal hills with chaparral and scrub and through a band of gnarled live oak until you reach the trail’s end in Stinson Beach. It’s also, conveniently, where you’ll find the Sand Dollar (built in 1921 by fusing three barges together). Do as the locals do, and order a Lagunitas IPA with oysters on the half shell.