4.8
(165)
4,329
riders
13
rides
If you've ever tried to plan touring cycling around Woodside, you know how quickly the options can feel overwhelming. It's tough to tell which routes are genuinely worth your time and effort, and which are just filler. We get it – you want to make the most of your ride without endless guesswork.
That's where we come in. Our komoot community has ridden, mapped, and reviewed countless routes here, so we've done the legwork to bring you a curated shortlist of the very best. This guide cuts through the noise, promising to save your legs for the views, not for figuring out where to go.
Touring cycling in Woodside is defined by its dramatic blend of towering redwood forests, open ridgelines, and scenic valleys. Expect significant elevation changes and varied terrain, from quiet roads winding through shaded woods to challenging climbs that reward you with expansive views of the Santa Cruz Mountains and the Bay Area. While many routes are on the more difficult side, the region offers options for different ability levels. The best time for touring cycling here is generally much of the year, with spring and fall offering particularly pleasant conditions.
If you're looking for a challenging ride with classic Woodside character, we'd start with the Portola Road – Old La Honda Road loop from Cañada College. This 24.0 miles (38.6 km) route features challenging climbs and descents through wooded areas, giving you a real taste of the local terrain. For a slightly longer, equally rewarding journey with beautiful reservoir views, the Old La Honda Road – Portola Road loop from Cañada College, at 33.3 miles (53.6 km), is a fantastic option. With over 3,700 touring cyclists having explored Woodside using komoot, you're in good company.
Last updated: May 29, 2026
4.8
(4)
132
riders
38.6km
02:41
710m
710m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
4.0
(1)
53
riders
53.6km
03:50
1,050m
1,050m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(1)
122
riders
38.0km
02:26
470m
470m
The Arastradero Lake – Portola Road loop from Cañada College offers a demanding touring cycling adventure through a mix of paved roads and the natural beauty of the Arastradero Preserve. You'll pedal through rolling grasslands, dense oak woodlands, and evergreen forests, with the tranquil Arastradero Lake providing a serene focal point. Expect varied terrain, from smooth asphalt to dirt and gravel paths, all set against a backdrop of wooded hills and occasional views of the San Francisco Bay.
This difficult 23.6-mile (38.0 km) route involves a substantial 1531 feet (467 metres) of elevation gain, typically taking around 2 hours and 25 minutes to complete. Cyclists should be prepared for significant climbs and some steep sections, particularly within the preserve. If you plan your ride for a Sunday between 9:00 AM and 3:00 PM, you can enjoy a 3.8-mile stretch of Cañada Road closed to motor traffic, enhancing safety and enjoyment.
This loop is a well-known variant of the popular Cañada Road-Portola cycling network, offering a challenging ride for those with very good fitness. The preserve is home to abundant wildlife, including deer and various bird species, adding an extra layer of interest to your journey. Given the mixed surfaces, a gravel bike or a sturdy road bike with wider tires is recommended for optimal comfort and performance.
42
riders
58.8km
04:30
1,500m
1,500m
This challenging touring cycling route takes you on a demanding journey through the Santa Cruz Mountains, starting from Cañada College. You'll climb through majestic redwood forests, particularly along Kings Mountain Road, and be rewarded with expansive vistas of the Bay Area from open ridgelines. The route also passes the historic Woodside Store, a redwood-built landmark that served as a vital community hub in the mid-1800s.
Planning your ride requires acknowledging the significant effort involved; this is a difficult 36.5-mile (58.8 km) loop with 4911 feet (1497 metres) of elevation gain, taking around 4 hours and 29 minutes. The Kings Mountain Road climb features an average gradient of 7.5% over 4.1 miles, with sections over 10%, so very good fitness is essential. The descent is narrow and twisty, demanding full attention.
Beyond the physical challenge, the route offers a rich historical context with the Woodside Store, once the only general store between San Francisco and Santa Clara. The towering redwood groves provide welcome shade and a unique atmosphere, making this a popular trail for cyclists seeking both a workout and scenic beauty. Keep an eye out for "The Bike Hut" if your route extends to Tunitas Creek Road for a convenient rest stop.
4.5
(2)
119
riders
48.1km
03:20
890m
890m
This touring cycling route offers a compelling mix of urban beauty and mountain challenge, starting with the manicured grounds of the Stanford University campus. You'll pedal past iconic architecture and the peaceful Arizona Garden before heading towards the Santa Cruz Mountains. The highlight is the Old La Honda Road climb, a consistent ascent through dense coastal redwood forests that provide welcome shade, eventually opening up to potential views of Silicon Valley from higher elevations.
To tackle this difficult 29.9 miles (48.1 km) loop with its 2906 feet (886 metres) of elevation gain, plan for about 3 hours and 19 minutes in the saddle. The Stanford campus offers various access points and parking, and its bike-friendly nature makes for an easy start. Old La Honda Road is a popular, low-traffic climb, making it enjoyable for cyclists, but ensure you have the fitness for a sustained effort.
Old La Honda Road is renowned among Bay Area cyclists as a benchmark climb, often used to test fitness and a rite of passage for many. Its consistent 7.5% grade over several miles makes it a unique challenge, and it's frequently incorporated into longer, more demanding cycling routes in the region. This ride is perfect if you want to experience a classic local climb combined with the scenic charm of Stanford.
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This is where La Ronda Road meets Skyline Boulevard. After the climb, it’s the perfect place to recharge and grab something to eat at one of the nearby restaurants or grocery stores. Alise's Restaurant is a popular one.
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The Bike Hut is a small hut with fresh water, organic teas and coffee and a variety of snacks for cyclist passing by. It is self-serve and open 24/7. There is also a small picnic area, a bathroom and a message board for posting road conditions or notes to fellow cyclists.
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Tunitas Creek Road is a popular road climb leading up to Kings Mountain. It is normally low traffic and takes you pass beautiful forest and farms.
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Borel Hill is my favorite place to watch spring flowers. The western slope near ancient oaks (5-10min west of Borel Hill) are covered with orange California Poppies and purple flowers starting in April. Borel Hill itself peaks around mid May and has a wide variety of flowers. The show lasts only a few weeks until end of May. The peak time and flower intensity varies from year to year, so come several times between April and May. There is small summit NW of Borel Hill and a narrow dirt trail leads you to a rock within 2 min. The rock is big enough for 2-3 to sit on. On a sunny day, the rock is nice warm even if the air is cold. Good views on the ocean and the Bay.
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Arizona Garden is also known as the Cactus Garden. The garden features a variety of unique plants, including columnar, barrel, and monstrose cacti, as well as succulents like Aloes, Crassulas, and rosette-forming Agaves.
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Woodside Store was built back in the 1850s by two pioneers who came to California for the gold rush. At the time it was the only stagecoach stop between San Francisco and Santa Clara, and it carried all the essential items that travelers riding between cities might need. The store has been restored, inside and out, to look exactly as it did centuries ago. You can call the museum ahead of your trip to book tours.
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Woodside offers a diverse range of landscapes for touring cyclists. You'll find routes winding through majestic redwood forests, along open ridgelines with expansive views, and through scenic valleys. The area is characterized by wooded hillsides and significant elevation changes, providing both physical challenges and picturesque scenery. Some routes feature paved roads, while others include packed dirt and gravel paths.
There are over 10 touring cycling routes detailed in this guide for Woodside, catering to various skill levels. In total, the region boasts an extensive network of over 210 cycling routes, including options for road and gravel biking.
Yes, Woodside offers several moderate touring cycling routes. A good option is the Pulgas Water Temple – San Andreas Lake loop from Cañada College, which is 28.7 miles (46.2 km) long and offers scenic views of the Crystal Springs Reservoir. Another moderate choice is the Pulgas Water Temple loop from Cañada College, a shorter 13.9 miles (22.3 km) route.
For experienced touring cyclists seeking a challenge, Woodside has several difficult routes. The Portola Road – Old La Honda Road loop from Cañada College is a demanding 24.0 miles (38.6 km) trail with significant climbs and descents. Another difficult option is the Tunitas Creek Road – Kings Mountain Road loop from Cañada College, which covers 35.9 miles (57.8 km) and features over 1,400 meters of elevation gain.
The touring cycling routes in Woodside are highly regarded by the komoot community, holding an average rating of 4.8 stars from over 150 reviews. Cyclists often praise the region's stunning redwood groves, the challenging yet rewarding climbs, and the expansive views of the Santa Cruz Mountains and the Bay Area.
Yes, many of the touring cycling routes in Woodside are designed as loops, allowing you to start and end at the same point. Examples include the Portola Road – Old La Honda Road loop from Cañada College and the Rossotti's Alpine Inn – Portola Road loop from Cañada College, both offering varied terrain and scenic views.
Woodside's touring cycling routes offer access to numerous natural features and landmarks. You can cycle through towering redwood groves in parks like Huddart Park and Wunderlich County Park. The region also features open ridgelines with views of the Santa Cruz Mountains and the Bay Area. Notable nearby attractions include Windy Hill Summit, Borel Hill, and various lakes such as Oracle Lagoon and Alpine Pond.
While Woodside is primarily accessed by car, some routes, particularly those starting from Cañada College, may have limited public transport connections. It's advisable to check local transit schedules and bike-on-bus policies if you plan to use public transport to reach the starting points of your touring cycling adventures.
Many parks and open space preserves in and around Woodside, such as Wunderlich County Park and El Corte de Madera Creek Open Space Preserve, offer designated parking areas. Routes often start from locations like Cañada College, which also provides parking facilities. Always check specific park regulations and parking availability before your ride.
Woodside offers good touring cycling conditions for much of the year. Spring brings beautiful wildflower displays, especially in areas like Edgewood Park & Natural Preserve, and generally mild temperatures. Fall also provides pleasant weather and vibrant foliage. Summers can be warm, particularly in open areas, while winters are typically mild but can bring rain, which might affect trail conditions on unpaved sections.
While many routes in Woodside feature significant elevation changes, some parks offer more gentle paths suitable for families. For easier, less strenuous rides, consider exploring sections of trails within parks like Huddart Park or looking for routes with lower elevation gains. The Pulgas Water Temple loop from Cañada College is a moderate option that might be suitable for families with some cycling experience.
Yes, Woodside and its surrounding areas offer various options for refreshments. The town of Woodside itself has cafes and restaurants. Additionally, some routes, like the Rossotti's Alpine Inn – Portola Road loop from Cañada College, pass by well-known local establishments such as Rossotti's Alpine Inn, providing convenient stops for food and drinks during your ride.


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