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…
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.…
32
riders
43.1km
03:00
730m
730m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
17
riders
49.9km
03:20
780m
780m
This difficult 31.0-mile (49.9 km) touring cycling route, with its 2545 feet (776 metres) of elevation gain, offers a dynamic ride that typically takes around 3 hours and 20 minutes.…
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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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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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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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Moody Road is a short route for cyclists connected to nearby trails or longer climbs like Page Mill Road. It offers a mix of rolling hills and quiet, scenic vibes. The last km is tough, but in the end it is always worth it.
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Gerona Road area is quiet and residential; it is also flat, well-paved and surrounded by some cool trees. Perfect for an easy ride.
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This fantastic tavern, founded in 1852, is the second oldest in the state. It features a large, beer garden-style outdoor area with plenty of shade. An extensive beer and food menu makes it a perfect stop to enjoy a brew and some great food after a ride.
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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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