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Road Trip Along Skyline Boulevard

Just south of San Francisco, balancing on the ridge of the Santa Cruz Mountains, lies a highway of great roadside stops and vistas.

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  • Alice's Restaurant along Skyline Boulevard in Woodside, California, picture
    Photo credit
    Photo: Erin Klenow
    Photo caption
    The front deck at Alice’s Restaurant in Wooside, Calif., has long been a popular spot for locals and visitors looking for locally sourced eats.
  • Penelope's Den along Skyline Boulevard in Woodside, California, picture
    Photo credit
    Photo: Leah Lee
    Photo caption
    Among the artworks for sale and show inside Penelope’s Den in Woodside, Calif., are armillary spheres by Mark Chase.
  • Thomas Fogarty Winery along Skyline Boulevard in Woodside, California, picture
    Photo credit
    Photo: Anne Krolczyk
    Photo caption
    Chardonnay vines flourish under broad skies at Thomas Fogarty Winery in Woodside, Calif., founded in 1978.
  • Unusual rock formations in Castle Rock State Park in Woodside, California, picture
    Photo credit
    Photo: Erin Klenow
    Photo caption
    The unusual rock formations of Castle Rock State Park are popular with climbers.
  • Wildflowers in the Russian Ridge Open Space Preserve in Woodside, California, picture
    Photo credit
    Photo: Vaibhav Tripathi
    Photo caption
    In the spring and summer, wildflowers such as yellow madia elegans bloom along the 8 miles of trails at the Russian Ridge Open Space Preserve.

Every day a hundred thousand drivers on Interstate 280, south of San Francisco, look west to a lofty Santa Cruz Mountain ridge, then zip past the easy access to it at Highway 92. Here's what they miss: redwoods and stunning roadside vistas on Skyline Boulevard, or Highway 35, as it follows the ridge top south to Saratoga. To best enjoy the sights, allow four hours.

  • EL CORTE DE MADERA CREEK OPEN SPACE PRESERVE After a winding nine-mile drive from Highway 92, stretch out under the 1,800-year-old redwood locals call Methuselah, then take the Tafoni Trail to rare honeycomb sandstone formations. Explore some 35 miles of trails; check their Web site ahead of time for any trail closures. (650) 691-1200, openspace.org.
  • ALICE’S RESTAURANT This roadhouse diner is a popular lunch spot for hungry hikers, battered mountain cyclists, and tattooed bikers. Fuel up on omelets, biscuit breakfast sandwiches, or specialty burgers such as the Harley (smoked bacon, sausage, grilled onions, and cheese) or the BMW (bacon, mushroom, and Worcestershire). (650) 851-0303, alicesrestaurant.com.
  • PENELOPE’S DEN Just across the road from Alice’s, Woodside resident and textile designer Jolan Bogdan silkscreens Highway 35 T-shirts, weaves scarves, and curates a collection of gifts made by local artists. Think ceramic tableware, spherical brass sculptures, and steampunk jewelry. (408) 309-8206, facebook.com/pages/penelopes-den/338115256236674.
  • THOMAS FOGARTY WINERY For $8 you can sip three of winemaker Michael Martella’s creations, including including Santa Cruz Mountain pinot noir and chardonnay. Then soak up the sweeping views of San Francisco Bay. (650) 851-6777, fogartywinery.com.
  • RUSSIAN RIDGE OPEN SPACE PRESERVE Ready to get wild? In spring, look for patches of buttercups, Johnny-jump-ups, and loads of other wildflowers at this 3,137-acre tract. Throughout the year, hike and bike the trails. Keep an eye to the sky; red-tailed hawks and golden eagles are known to soar here. (650) 851-0303, openspace.org.
  • CASTLE ROCK STATE PARK A small canyon full of mossy boulders, ancient oaks, and dusky firs hugs Saratoga Gap Trail as it passes 100-foot-high Castle Rock Falls. Call the park for operating hours. (408) 867-2952, www.parks.ca.gov.

This article was first published in May 2006 and updated in September 2013. Some facts may have aged gracelessly. Please call ahead to verify information.