Ken's favorite Silicon Valley road bicycle rides

The year round pleasant weather, interesting terrain, and beautiful scenery make the San Francisco peninsula a great place for road bicycle riding. Here are some of my favorite bicycle routes. Click on each link for a street map and detailed route description. These maps were generated by a mapping program that assumes a constant 15mph speed. Since you probably won't ride at the same speed both up and down hills, you can ignore the route time stamps. Click your browser's BACK button to return here from the map pages.

Rolling Loops

These rides travel through the rolling foothills of San Mateo County. Except for the last ride, the hills are not long and these are great rides for the winter when days are shorter and weather is less predictable. The hilly loops in the next section all travel up to Skyline Blvd., which is sometimes cold and wet during the winter.
  1. Portola Valley Loop (17 miles, 840 feet of climbing) - the classic Stanford area ride
  2. Lakeview Loop (28 miles, 1300 feet of climbing) - continue from Portola Valley through Woodside to the scenic hills of Redwood City
  3. Canada and Crystal Springs Loop (41 miles, 2200 feet of climbing) - north along scenic Canada Road to the Crystal Springs reservoirs, return via suburban Alameda de las Pulgas
  4. Local hill training (33 miles, 3200 feet of climbing) - you don't need to go all the way to Skyline to find 15% grades; this is a tour of some monsters in Los Altos Hills and Portola Valley. This route goes by the Alpine Inn twice; if you're tired when you get there the first time, stop for a beer and do the second (much harder) half of the ride another day.

Hilly Loops

These hilly rides all climb up to Skyline Blvd. (sometimes twice) for great views of both the San Francisco Bay and the Pacific Ocean. Note that Skyline and the coast can be cool and foggy during the summer. I recommend bringing at least a wind vest, especially for early morning rides. During the winter, tights and long sleeves are usually a good idea.
  1. East and West Old La Honda (35 miles, 3300 feet of climbing) - east Old La Honda Rd. is the easiest climb to Skyline; this route also climbs scenic west Old La Honda Rd. in a figure 8
  2. Page Mill and Kings Mountain (38 miles, 3800 feet of climbing) - this scenic route can be done in either direction for two very different (but both very fun) experiences. Kings Mountain is more shaded and has an constant grade. Page Mill is more sunny with mixed steeper and flatter sections.
  3. West Alpine Road (38 miles, 4100 feet of climbing) - a very beautiful (and sometimes very warm) climb on the west side of Skyline
  4. Pescadero and Alpine Road (68 miles, 5700 feet of climbing) - a longer version of the previous ride, including the Pacific coast and the towns of San Gregario and Pescadero
  5. Tunitas Creek (54 miles, 4700 feet of climbing) - have lunch at the beach, then climb back to Skyline through a dark cool canyon
  6. Page Mill, Pescadero, and Half Moon Bay (84 miles, 8000 feet of climbing) - two great climbs (Page Mill and Tunitas Creek), plus a tour of the old stage coach route connecting the rural coast-side towns of Pescadero, San Gregorio, and Half Moon Bay
  7. Long Skyline Loop (64 miles, 5200 feet of climbing) - take the (in)famous Redwood Gulch route up to Skyline, then head north along the ridge for great views of the bay and ocean. The Highway 92 descent can have a lot of traffic, but a skilled rider can usually keep up. For a shorter route, descend via Page Mill Road or Kings Mountain Road instead.
  8. Big Basin Loop (82 miles, 7400 feet of climbing) - climb Redwood Gulch like the previous loop, but head south to the beautiful Big Basin Redwoods State Park near Santa Cruz. The return climb up Highway 9 is long, but not too steep.


These routes all start at Peers Park in Palo Alto, mostly because that is near where I live. Peers Park is at the corner of Stanford Ave. and Park Ave. a few blocks east of Stanford University. If you live elsewhere, you can reach Peers Park via Caltrain to the California Avenue station which is a couple of blocks south of the park. Bicycles are free on Caltrain, though space can be tight during commute hours. For bicycle routes to Peers Park, see the bike routes map on the City of Palo Alto web site. Park Ave. is a major bike route running from Stanford University to downtown Mountain View. You can also cross under the Caltrain tracks at the train station to access Palo Alto's Bryant Street bicycle boulevard to downtown Palo Alto and Menlo Park.

California Avenue has a grocery store for snacks and several moderately priced restaurants for post-ride meals. For last minute equipment purchases or repairs, try Bike Connection at the corner of Stanford Ave. and El Camino Real.

There are rest rooms, water fountains, and grocery stores along all these routes. Here are some of the more useful ones:


If you've lived in the San Francisco area for a while, you know that weather conditions can vary considerably between "microclimates". The TV and newspaper weather forecasts focus on the major cities, but are may not be very accurate for the rural areas where cyclists like to ride. I generally check the Internet weather sites like the National Weather Service and Accuweather before riding, especially for morning and evening rides when fog and wind are more likely to affect your ride. When the La Honda weather forecast is cool or foggy, you would be wise to bring at least a wind vest on your Skyline rides.


Of course, bicycling on public streets involves sharing the road with motor vehicles. Bicycling is generally safe if you follow the state vehicle code and also apply your common sense. Ride in a predictable fashion, wear visible colors, and watch carefully for cars to your sides (intersections, driveways, parking spaces). In California, bicycle helmets are required for children and are a good idea for adults.

The City of Palo Alto offers a bicycle Street Skills course which I recommend for cyclists of all experience levels. The course is free to Palo Alto residents and inexpensive for non-residents. You can find more information on the City of Palo Alto web site. There is also a good on-line introduction to bicycle safety called Bicycling Street Smarts.

I tried to find routes that generally avoid heavy traffic, though traffic still happens, especially during commute hours. Most of the routes do involve freeway interchanges, which are often poorly designed for bicycles. Take care to merge carefully, but quickly, away from on-ramp areas. This is especially important at the I-280 and (westbound) Page Mill Road interchange where there are 3 on-ramps and a bike lane on the left side of the road. Children, please ask your parents to show you the correct way to navigate through these areas.


Bike clubs are a great way to ride with other people, learn new routes, learn about bikes, and generally have fun. There are two big recreational bike clubs in the Silicon Valley area. Both lead a dozen or more rides every week at several different ability levels. Guest are welcome on rides, but membership is pretty cheap as well. The Western Wheelers start most of their rides in the northern half of Santa Clara county and southern end of San Mateo county (Palo Alto, Los Altos, Sunnyvale, Menlo Park, etc.). The Almaden Cycle Touring Club starts most of their rides in the southern half of Santa Clara county (San Jose, Cupertino, Saratoga, Los Gatos, etc.). The club web sites have more info on the clubs, as well as ride schedules (guests are welcome) and route descriptions for many of their rides.

There are also several racing clubs in the area. As a non-racer, I don't know much about them, but many seem to be associated with local bike shops or universities. There is a list of California bike racing clubs on the Northern California/Nevada Cycling Association web site.

There are a number of bicycle advocacy organizations that lobby for improved bicycle saftey. The main local organizations are the Silicon Valley Bicycle Coalition (for Santa Clara County) and the Peninsula Bicycle & Pedestrian Coalition (for San Mateo County).

There are dozens of good bike shops in the area. I haven't tried them all, so won't recommend anyone in particular here (except for the ones near the ride starting point that I listed above). A couple of local shops with good web sites, however, are Chain Reaction and Palo Alto Bicycles. The web sites have maps and route descriptions for many good rides. Local bike shops also sell books and maps describing local bike rides.

If you're interested in Silicon Valley mountain biking, check out my mountain bike page.

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