Going from Silicon Valley across the Santa Cruz Mountains to the Pacific Ocean and back is one of the finest experiences a cyclist can have in the San Francisco Bay Area. Despite being so close to major population centers, the route focuses on mostly low-traffic country roads, winding either up or down the mountain range, traversing various flora and fauna, paired with picturesque views and, likely, some temperature differences.

There are a few possible variations to this loop, which can be lengthened or shortened to your personal desire. The first test of your stamina is the climb on Page Mill Road, past Foothills, Los Trancos, and Monte Bello Open Space Preserves up to Skyline Boulevard.

After a quick pause at the junction, the road descends to the other side, twisting and turning Alpine Road and through Redwood groves, whizzing past the occasional house. San Mateo County Memorial Park provides a convenient stop to fill up on water, use the restroom, and marvel at the giant trees, hundreds of years old. A little further down, the Loma Mar Store provides an opportunity for a (late) breakfast or lunch.

The temperature difference between the San Francisco Bay and your current location should have become noticeable. The area closer to the Pacific can often be up to ten degrees Fahrenheit cooler than in the Valley.

Pescadero is a small hamlet of 349 people with a rather charming/inviting main street. It invites a stop, either at Downtown Local for a coffee and pastry or at the Arcangeli Grocery Market a little further down. The town can get surprisingly busy on good weather weekends, popular with locals and non-local folks out for a drive or motorcycle ride along the coast.

Stage Road takes one north through open farmland, yet again with a change in vegetation. Redwood trees are replaced by open fields, farms, and ranches, and the hardy brushes are adapted to a harsh coastal environment.

Despite some climbing, this section will be over in no time, and one will reach San Gregorio General Store, a charmingly preserved relic from a different time. Truly a general store, selling everything from clothing to books to tourist curiosities, as well as a full bar and live music on weekends. The local post office is located in the same building, same as it has been since the first settlement. The store is another popular stop, just off Hwy 1, and at the end of a descent on La Honda Road, another alternative downhill option from Skyline Boulevard.

A short climb and swift descent on Hwy 1 brings me to Tunitas Creek Road, the path that leads back up to the ridge. Before all that though, The Bike Hut is another must-stop and its existence warms my heart every time I am on this road.

If you feel so inclined, there is a detour via Tunita and Lobitos, but it is optional. And what a climb it is. At a length of 9.4 miles, climbing roughly 2000 feet in the process, it is almost exclusively winding its way through a redwood forest. Combined with very little automotive traffic (you’ll likely encounter more cyclists than cars) and in the shadow of massive trees, this always puts me in awe, peacefulness, and reverence.

Towards the top, the climb seems neverending. Eventually, it levels out just before returning me to Skyline Boulevard for a swift descent down Kings Mountain Road and downtown Woodside. Firmly back in affluent Silicon Valley areas, the route goes back to the starting point via Portola Valley, through Pearson-Arastradero Preserve and Palo Alto Hills.