With so many twists and turns on the way to Mt. Madonna's 1,309-foot peak, driving up sloping Hecker Pass Highway (State 152) is invigorating. The views up top are equally thrilling, looking east over Santa Clara Valley and west to Monterey Bay. But don't rush: This drive is best enjoyed by taking your time, stopping along the way at pretty parks and boutique wineries.
Just west of Gilroy, wineries beckon before the road begins to climb. After passing the colorful 17-acre flower gardens at Goldsmith Seeds (2280 Hecker Pass Hwy.; 408/847-7333), you can check out the rides and botanical marvels at Bonfante Gardens Family Theme Park ($32; 10-6 Sat-Sun; 3050 Hecker Pass Hwy.; 408/840-7100). Or head straight to Hecker Pass Winery (10-5 daily; 4605 Hecker Pass Hwy.; 408/842-8755) and Solis Winery (11-5 daily; 3920 Hecker Pass Hwy.; 408/847-6306).
A detour north leads to Chitactac-Adams Heritage County Park (10001 Watsonville Rd.), where a 1-mile loop trail follows Uvas Creek. Rocks here are pocked with grinding holes, and interpretive signs describe life long before the Spanish planted wine grapes.
One mile farther north, Kirigin Cellars (10-5 daily; 11550 Watsonville Rd.; 408/847-8827) offers samples of Cabernet and Pinot, and, surprisingly, weekend cricket matches in the field behind the tasting room.
The real payoff is at the mountain's peak: At Mt. Madonna County Park ($4 per car; 7850 Pole Line Rd., at summit of State 152), you can explore cattle baron Henry Miller's crumbling estate, savor shade under the redwood trees, and hunt for wildflowers on the park's 20 miles of trails.
A deviled egg sandwich and iced tea at the Mt. Madonna Inn Restaurant ($$$; 1285 Hecker Pass Rd.; 831/724-2275) are a nice cap for the day. The dining room offers magnificent views looking west to the ocean over the fields of Watsonville ― a preview in case you're itching to continue the long, winding road to the sea.
From Gilroy, State 152 heads west 18 miles to Watsonville, crossing Hecker Pass. For area information, contact the Gilroy Visitors Bureau (408/842-6436). For information on all parks listed, contact Santa Clara County Parks and Recreation (408/355-2200).