Sonoma and Napa Valleys
California
Two parallel valleys north of San Francisco Bay, divided by the Mayacamas Mountains: the Napa Valley, with its Cabernet vineyards, stone wineries and restaurant towns along Highway 29, and the Sonoma Valley, Jack London's Valley of the Moon, where California's mission era and its first commercial winery began. Most tasting rooms charge a fee and many need a booking, so these challenges keep mostly to plazas, old towns, parks and summits.
5 challenges · 23 stops
STARTERThe Plaza, the Mission and the General
≈ 1,700 steps0.8 mi · about 2 hoursStarter · 3 stops · 500 credStart where you live.Three stops on foot around the old town of Sonoma, from the stone city hall in the middle of the plaza to the last mission built in California and on to General Vallejo's Gothic farmhouse. About two miles in all, two unhurried hours, best on a weekday morning.
STANDARDDown by the Napa River
≈ 1,600 steps0.8 mi · about 3.5 hoursStandard · 4 stops · 600 credOne trip earns it.Four stops on foot through downtown Napa as the afternoon turns to evening: a food hall on the river, an 1880 opera house, the courthouse that survived the 2014 earthquake, and the old mill on the water. About two miles, three to four hours with dinner along the way.
STANDARDUp Highway 29, Yountville to St. Helena
≈ 2,000 steps + 8.4 mi by car1.1 mi on foot · about 4 hoursStandard · 4 stops · 600 credOne trip earns it.A morning drive up the spine of the Napa Valley with four stops: the grave of the valley's first American settler, the carved redwood welcome sign, a country store from the 1870s, and a century-old cinema on St. Helena's Main Street. About fifteen miles and half a day.
ADVANCEDMills, Geysers and Stevenson's Mountain
18 mi by cara full dayAdvanced · 6 stops · 800 credGetting there is not the hard part.A full day with a car through the northern valley: a stone winery turned cooking school, a water-powered grist mill, the old spa town of Calistoga, a geyser that erupts every few minutes, and a mile climb to where Robert Louis Stevenson spent his honeymoon. Two stops charge admission; the mill opens on weekends only.
ADVANCEDValley of the Moon, from the Press House to Bald Mountain
≈ 1,600 steps + 21 mi by car0.8 mi on foot · a full day · + the walk in to 1 stopAdvanced · 6 stops · 800 credGetting there is not the hard part.A long day up the Sonoma Valley by car and on foot: California's oldest commercial winery, Jack London's ranch and the ruins of the house he never lived in, a seasonal waterfall and a summit that looks over both valleys. Most stops sit inside parks or a winery that charge admission; a six-mile round trip hike ends the day.
Counted between stops; you'll walk more at each one.
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