Northern California’s San Francisco Peninsula separates San Francisco Bay from the Pacific Ocean, with San Francisco at the northern tip and the Santa Cruz mountains extending south. Think giant redwoods, beautiful scenery, great roads, a rich history, tremendous wealth and awesome riding. This magnificent destination is but a short hop south from San Francisco. It is an amazing loop through the Santa Cruz Mountains and along the Pacific Coast. The area is surprisingly rural for a location so close to San Francisco and Silicon Valley. Take I-280 south from San Francisco for 30 miles and exit at the sign for Woodside. The loop consists of SR 84 west to Woodside, SR 35 north, SR 92 west, SR 1 south (the Pacific Coast Highway, or PCH), and then SR 84 east again to complete the loop.
Woodside, one of the wealthiest towns in America, comes up quickly once you leave the freeway. It’s rustic appearance is belied by current and former residents, including Charles Schwab, Steve Jobs, Michelle Pfeiffer, Joan Baez, Carl Djerassi (the guy who developed the birth control pill), Larry Ellison (CEO of Oracle Corporation), James Folger (need a cup of coffee?), Kazuo Hirai (Sony’s CEO), Gordon Moore (Intel’s co-founder and originator of Moore’s Law), Prince Vasili Alexandrovich (the nephew of Tsar Nicholas II of Russia), Shirley Temple, John Thompson (Symantec’s CEO), and Nick Woodman (the GoPro guy).
Alice’s Restaurant is at the intersection of SR 35 and SR 84. It’s not the Alice’s Restaurant made famous by Arlo Guthrie, but the founder is named Alice, and hey, why not ride that coattail? SR 35 is called Skyline Boulevard through this stretch for good reason: It’s a twisting 13 miles along the Santa Cruz Mountains ridgeline and the views are stunning (you can see San Francisco Bay on the right and the Pacific on the left).
SR 92 turns west to drop down to the Pacific Coast Highway and Half Moon Bay. It’s a touristy place, but one in which you can’t find a bad restaurant (my favorite is the Greek Taverna as you enter town). Bring money; things are expensive in Half Moon Bay. The major employer is the Ritz Carlton Hotel (it’s that kind of place). Until recently, Half Moon Bay hosted big wave surfing competitions; the area sees 60-foot waves when conditions are right.
Point your front wheel south on the fabulous PCH toward San Gregorio State Beach, but not without a stop to first visit a ghost town and a beautiful old cemetery four miles south of Half Moon Bay. The town of Purissima is long gone, but the cemetery and its photo ops are still there (they’re about a half mile east on Verde Road). After Purissima, seven miles farther south on the PCH brings us to San Gregorio State Beach. Spaniards were the first Europeans to explore this region in 1769 while expanding the Alta California missions; they named San Gregorio after Pope Gregory I. San Gregorio was a favored 1850s destination when wealthy San Franciscans visited for swimming, fishing, and hunting (grizzly bears roamed these hills; mountain lion and deer still do).
At San Gregorio, it’s another left on SR 84 to climb back into the Santa Cruz Mountains and the tiny town of La Honda (Spanish for “the sling”) to complete the loop. SR 84 nominally runs east, but it’s really more like east, north, west, and south (and every direction in between) as the twisties and 15mph hairpins follow the topo map contours. A sparsely populated wide spot in the road, La Honda has a colorful history. When not robbing banks, Cole Younger and his brothers lived here, as did Ken Kesey (One Flew Over The Cuckoo’s Nest), and at times, famed writers Hunter S. Thompson and Tom Wolfe. La Honda is a cool place made even cooler by giant redwoods and eucalyptus trees that form a leafy tunnel through the area.
Allow two hours for a relaxed ride during the week, and maybe throw in another hour or two if you want to stop to eat or take a few photos. The loop described here (after exiting I-280) is just under 60 miles. — Joe Berk
What: The Santa Cruz Mountains.
How to Get There: From either the north or south, take I-280 to the Woodside exit. Go west and follow the route outlined above.
Best Kept Secret: The La Honda Country Market deli bar (try the pastrami on toasted marbled rye).
Avoid: The weekends and tinted visors. Weekends see heavy traffic, and the giant trees bathe the roads in alternating patches of bright sunlight and deep shade.
More Info:Santa Cruz Mountains Bioregional Council
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