Daydreaming about a ride through one of Southern California’s most magnificent expanses of roadway? Well, you must be thinking of the 60-mile stretch of the famous highway known as Skyline Boulevard, which showcases can’t-miss sights from The Golden City of San Fran all the way across the Santa Cruz Mountain range. This ride is one for the bucket list, from twisty roads that will have your adrenaline pumping to large expanses of awe-inspiring natural sights. If you’ve always envisioned yourself riding through Silicon Valley and taking in all the exciting sights in between, you’ll want to put this ride at the front of the line. So, fire up those Thirsty Biker apps because we’re going on one of the most popular Southern California rides ever created. In episode 38 of the Thirsty Biker Chronicles, we’re zigzagging through Ben Lomond and Silicon Valley for a ride you’ll never forget.

Must-See Stops

Alice's Restaurant

We start our trip out in Ben Lomond at one of the most well-known establishments in the area for over 75 years. One step into Henflings of Ben Lomond, and you’ll be captivated by the electric atmosphere and comradery inside. Not only does Henflings serve outstanding food and ice-cold beverages, but there’s plenty of entertainment for everyone. With 12 craft beers on tap, plus talented bartenders who know a thing or two about slingin’ drinks, you can’t go wrong at Henflings. Next up, we have a stop at Alice’s Restaurant in Woodside, right on Skyline Boulevard at the heart of it all. With a motto like “You can get anything you want at Alice’s Restaurant,” you know you’ve struck gold here. Known as “a little slice of bliss among the redwoods,” you’ll find that Alice’s offers it all—good food, rich history, and plenty of friendly faces to talk to throughout your visit.

Finally, we end our trip at Upper Crystal Spring Reservoir Vista Point, a 2.9-mile-long trail and historical landmark near San Carlos. Ideal for hiking, biking, and running, this natural setting showcases beautiful sights and tranquility that can’t be beaten. Open year-round and ready for visitors, this area is the perfect way to end your epic trip through the Santa Cruz Mountains.

The Ride

ride map

Stay alert on this exciting California ride, as these roads are filled with twists and turns, plus loads of sights to take in mile after mile. With tall trees and vineyards on both sides, you’ll feel like you’re cascading alone through nature with only your bike as your guide. This short ride doesn’t take up much of your day, but it will leave a lasting impression, with iconic views of San Francisco Bay, Silicon Valley, and the Santa Cruz Mountains. It’s recommended to take your time and stay cautious on these roads, as there are many sharp turns and tight corners to navigate. Novice riders, especially, are advised to be accompanied by riders with more experience to help lead them through. This Southern California trip is a must-see when you’re looking for an engaging ride. Open up your Thirsty Biker apps, and let’s get ready to rock.

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