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Whether you’re a biking novice or just looking for some new paths to follow this summer, there are plenty of cycling routes to explore in the 650.
We asked local bikers and outdoor experts for their favorite road and trail rides in San Mateo and Santa Clara counties. Their tips are below.
To look up other rides, check out the Trail Explorer web app, which allows users to filter biking trails and gives information on the slope, sun exposure, trail material and width, among other information. There’s also Bay Area Mountain Bike Rides, a website with a comprehensive guide to biking the region. Peninsula Open Space Trust also keeps a list of its favorite bike trails within its 93,000 acres of protected open spaces.
Mount Umunhum Trail, Los Gatos
Distance and difficulty: 3.9 miles, 1,150 feet elevation gain, easy to moderate
Description: This trail, located within the Sierra Azul Open Space Preserve, extends from the Bald Mountain parking area to the summit, crossing through the varied habitats. Riding the trail offers stunning views of the valley below, the neighboring ridgelines and the other great peaks of the Bay Area, including Mount Hamilton, Mount Diablo and Mount Tamalpais on a clear day. The trail is mostly shaded, winding through oaks and bay trees and generally flat/general slope (0%-8% grade).
Why it’s special: At the top of Mount Umunhum, visitors can immerse themselves in the history of the area. Interpretive signage guides visitors through the history of Indigenous peoples and their relationship to Mount Umunhum, how the U.S. Air Force set up a base atop the mountain to monitor for unfriendly aircraft during the Cold War and how the Midpeninsula Regional Open Space District reshaped the peak and has taken efforts to revegetate the summit with native species. The summit also features a Native American ceremonial circle, which was developed in partnership with the Amah Mutsun Tribal Band, as well as the remnants of an old radar tower.
Know before you go: At the summit is the highest point on the Bay Area Ridge Trail. The temperature at the summit fluctuates widely, so riders should be prepared for varied weather conditions. On especially cold days in the winter the summit can get covered in a blanket of snow.
— Nathan Grieg, Midpeninsula Regional Open Space District senior technologist
Cowell-Purisima Coastal Trail, Half Moon Bay
Distance and difficulty: 7 miles out and back, 400 feet elevation gain, easy
Description: This gently graded gravel path winds along bluffs where farmland (artichokes, Brussel sprouts, pumpkins, peas and beans are common plants along the way) meets the Pacific Ocean. It’s part of the California Coastal Trail, which will one day span the entire length of the state. This area contains both beach and coastal scrub ecosystems. Most of this trail is double-wide and has a compacted granite surface with the exception of some steep terrain in the middle, where the trail crosses Purisima Creek.
What makes it special: It is less crowded than other trails. It is scenic, with views of harbor seals, pelicans, towhees, hawks, bunnies and wildflowers along the way.
Know before you go: The trail is mostly gentle, but it has one gully area so riders don’t have to mind a little gravel. Wear a hat and sunscreen since there is no shade along the trail. It is closed when farms are spraying. There is one tricky spot when you have to go into a gully, so walk your bike or if you are agile go slow. There is parking at both ends of the trail but it is limited.
— Kathleen Ferenz, Half Moon Bay Bicycle/Pedestrian Advisory Committee member
Waterdog Lake Open Space, Belmont
Distance and difficulty: 7.5 miles, 1,450 feet elevation gain, difficult
Description: The ride starts by entering the park from the trailhead on Lyall Way. What comes first is a very gradual fire road climb. After a sharp left at the crease of the ravine, a series of steeper fire road drops and climbs come next. Then the route enters the main network of single-track trails of the park, in its southeastern half.
What makes it special: This is a small park and the trail mileage doesn’t add up to a whole lot, but what trails there are are fun and challenging, at least for a quickie ride. Meanwhile, they are tough enough to discourage inexperienced riders. Waterdog is an urban park that provides a surprisingly high amount of fun single-track trails for mountain bikers.
Know before you go: Waterdog has a tight mesh of short trails that interconnect in many places, so a single route doesn’t stand out as the obviously preferred one. There is a long series of steep and very tight switchbacks.
— Ergin Guney, who runs the Bay Area Mountain Bike Rides website
Old La Honda Road, Woodside/Portola Valley
Distance and difficulty: 19-mile loop, 2,600 feet elevation gain, moderate
Description: A world-renowned road bike ride, the classic route is to bike up Old La Honda Road from Portola Road and then descend down Highway 84. Start at the Woodside Town Center, around Woodside Road and Cañada Road.
What makes it special: It’s a great climb. It takes you through rugged terrain with greenery and redwood groves.
Know before you go: Parking is limited at the Woodside Town Center. One thing many cyclists do during this ride is extend the ride onto the other side of Skyline Boulevard.
— Fred Leach, Portola Valley Trails and Paths Committee chair
Coastside Ride, Pescadero
Distance and difficulty: 41.3 miles, 3,467 feet elevation change, difficult
Description: Start at Gazos Creek State Beach and head east on Gazos Creek Road. Ride north through Cloverdale Road until you pass Pescadero through Stage Road. At this point, you could have a snack stop and turn around at San Gregorio, or continue through Tunitas Creek Road and visit the legendary Bike Hut. Come back via Lobitos Creek Road and Highway 1 back to the beginning.
What makes it special: This ride provides a unique look at the rural side of San Mateo County, away from the tech giants of Silicon Valley. Feel the ocean breeze cool you down as you ride past fields of grazing cattle, crop fields and working ranches. These roads are classic climbs with reasonable grades that take you through rural Coastside landscapes. Any time is a good time to go since the weather is temperate near the coast, but the best time to ride is spring for the wildflowers that you can spot along Stage Road.
This route takes you along the borders of several Midpen open spaces, including Cloverdale Ranch, Midpen’s newest preserve. This ecological jewel features several unique species of both flora and fauna and is managed through a conservation grazing program.
Know before you go: Bring a wind shell layer and expect cross and head winds along Highway 1, or else go back through the inland routes. Reward yourself for a ride well done with a sandwich from Archangeli Grocery Co. in Pescadero or drop by Pie Ranch.
— Ivana Yeung, Midpeninsula Regional Open Space District capital project manager III
Sawyer Camp Trail at Crystal Springs Reservoir, San Mateo to Millbrae
Distance and difficulty: 11.6 miles out and back, 456 feet elevation gain, easy
Description: Starting from the south, the trail begins in a parking lot located just north of the Crystal Springs Dam in San Mateo. The path finally ends on Hillcrest Boulevard off of Highway 280 in Millbrae.
What makes it special: What stands out is that it’s relatively safe and easy for the average person or family. There are great views of the reservoir, and you’re likely to see a good variety of birds and other wildlife. If you want to extend your ride, you can even ride to the south end of the reservoir on Cañada Road and visit the Pulgas Water Temple, a stone structure inspired by classical Greek and Roman architecture beside a tree-lined reflecting pool. Midway along the Sawyer Camp segment is where one will find the more than 600-year-old Jepson Laurel, the oldest and largest known laurel in the state.
Know before you go: Typically more parking is available at the northern trailhead. It can be crowded. There is a speed limit of 15 mph.
— Mark Medeiros, Peninsula Open Space Trust director of community engagement
Old Haul Road, Loma Mar
Distance and difficulty: 5.7 miles, 369 feet elevation gain, moderate
Description: This fire-road ride is deep in the redwood forests of the Santa Cruz Mountains and is located within Pescadero Creek County Park. This route starts in Memorial Park and brings you to Portola Redwoods State Park. You’ll ride on trails surrounded by dense foliage.
What makes it special: Much of this ride follows the route of a narrow gauge railroad line that hauled logs to the various mills that once flourished in the Santa Cruz Mountains. Even today you can find rusty chocker cables used to skid and lift logs onto flatcars. Many of the trails within Pescadero Creek County Park intersect with Old Haul Road.
Know before you go: Recreational users should remain aware that this is the main access road for maintenance crews and should expect to meet the occasional heavy truck and tractors along the way. This fire road is unique among such easy rides because of its remoteness.
— Hannah Ormshaw, San Mateo County Parks assistant parks director
Fifield-Cahill Ridge Trail, San Bruno to San Mateo
Distance and difficulty: 13 miles, elevation gain/loss: 1,725 feet/1,490 feet, difficult
Description: On this guided tour, you will start at the Cemetery Gate in San Bruno and end at the Pacific Ocean Overlook.
What makes it special: Local nature lovers can enjoy the rare opportunity to bike through pristine stands of old growth Douglas fir, evergreen and fragrant coastal scrub while enjoying ridge-top vistas of the San Francisco Peninsula watershed lands, reservoirs, the Pacific Ocean and San Francisco Bay.
Know before you go: Small groups can make reservations for guided excursions along the Fifield-Cahill Ridge Trail. Because of environmental restrictions within our fragile ecosystem, groups must be accompanied by a volunteer trail leader and are limited to approximately 20 people, scheduled no more than three times a day on Wednesdays, Saturdays and Sundays. You can reserve spaces for as many as five people for any one event.
— Jim Sullivan, Half Moon Bay Bicycle/Pedestrian Advisory Committee member
Editor’s note: This article has been updated to reflect that Peninsula Open Space Trust has 93,000 acres of protected open spaces, not 76,000 acres.
