68
riders
15
rides
Road cycling around Woodside offers diverse landscapes and challenging terrain within the Santa Cruz Mountains. The region features redwood forests, open ridgelines, and scenic valleys, providing varied cycling experiences. Cyclists encounter steady climbs through shaded oak canopies and second-growth redwoods, with higher elevations offering views of the Bay. The area is characterized by a mix of forested roads and open pastures.
Last updated: May 13, 2026
7
riders
40.2km
01:42
260m
260m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
126km
06:28
1,180m
1,180m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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14
riders
85.5km
03:42
630m
630m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
10
riders
56.3km
02:36
480m
470m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
73.0km
03:14
650m
650m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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The "Let the Dance Begin" sculptures are an imposing tribute to peace and culture on the border of Lifford and Strabane. These five giant steel figures β musicians and dancers β symbolize the connection between North and South. Locally, they are known as The Tinnies and form an indispensable modern landmark for any cyclist crossing the River Foyle.
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Situated on a site adjacent to the Strabane bypass, the 'Let the Dance Begin' sculpture by Maurice Harron is an ensemble of five stainless steel and bronze figures. Commissioned by the former Strabane District Council in collaboration with the Strabane Lifford Development Commission, this artwork symbolises the transition to the new millennium. The statues, standing at an impressive height of approximately 30 foot (10 m) have affectionately been named "The Tinnies" by the locals.
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There is plenty to see in Castlederg for history lovers. On the pilgrim's route to Station Island on Lough Derg, it boasts monastic ruins as well as the impressive Castlederg Castle which is set in beautiful parklands accompanied by a sculpture trail.
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Newtownstewart is a historic village with Baronscourt Castle as a notable attraction. Nestled in the scenic Sperrin Mountains, it offers outdoor activities like hiking and boasts a heritage-rich atmosphere with well-preserved architecture.
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Gortin Glen Forest Park is full of good trails and beautiful trees. There is a 5 mile scenic forest drive which is signposted and takes in all of the best views. With waterfalls, resident sika deer and a cafe at the centre of the park it makes an ideal detour from the road.
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There is plenty to see in Castlederg for history lovers. On the pilgrim's route to Station Island on Lough Derg, it boasts monastic ruins as well as the impressive Castlederg Castle which is set in beautiful parklands accompanied by a sculpture trail.
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Newtownstewart Bridge spans the Strule River on its way north to meet Fairy Water and Owenkillew.
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Road cycling routes around Woodside offer a diverse range of terrain, from challenging climbs through dense redwood forests and shaded oak canopies to open ridgelines with expansive views of the Santa Cruz Mountains and the San Francisco Bay. You'll also find scenic valleys, open pastures, and routes alongside natural features like the Crystal Springs Reservoir.
Yes, while Woodside is known for its challenging climbs, there are routes with more moderate profiles. For instance, sections of CaΓ±ada Road offer scenic views of horse farms and the Crystal Springs Reservoir, with a segment often closed to vehicle traffic on weekends, making it ideal for a more relaxed ride. The region has 2 easy routes and 12 moderate routes available.
Many routes in Woodside are incredibly scenic. Skyline Boulevard is renowned for its broad views of the surrounding hills and the Bay. CaΓ±ada Road provides picturesque views of horse farms and the Crystal Springs Reservoir. Routes through redwood forests, such as Kings Mountain Road and Tunitas Creek Road, offer contemplative solitude amidst towering trees.
Yes, for cyclists seeking longer rides with significant climbing, the Pescadero Creek Road loop offers an extensive route through forests, farmland, and coastal areas. This loop provides a substantial challenge and a full day's adventure.
Woodside is cyclist-friendly, with popular stops like Alice's Restaurant, which is a well-known gathering spot for riders. Additionally, The Bike Hut offers water, snacks, and tools, providing essential support for passing cyclists.
Woodside is famous for its challenging ascents. Kings Mountain Road features multiple switchbacks through redwoods, making it popular for fitness training. Old La Honda Road is another classic climb that tests cyclists early in their rides. Tunitas Creek Road is considered a Bay Area 'bucket list' climb, offering a demanding yet rewarding experience.
Woodside generally offers excellent cycling conditions for much of the year. The best seasons are typically spring and fall, when temperatures are mild and the scenery is vibrant. Winter cycling is possible, but riders should be prepared for cooler temperatures, potential rain, and shaded sections that might remain damp. Always check local weather forecasts before heading out.
Generally, no specific permits are required for road cycling on public roads in Woodside. However, if your route includes sections that enter county parks or open space preserves, it's always a good idea to check their specific regulations regarding cycling, as some multi-use trails within these areas may have restrictions or require permits for certain activities. For example, parks like Wunderlich County Park and Huddart Park are primarily for hiking and equestrian use, so road cyclists should stick to designated roads.
For families, the segment of CaΓ±ada Road that closes to vehicle traffic on weekends offers a safer and more relaxed environment for cycling alongside the Crystal Springs Reservoir. This car-free zone is ideal for families or those looking for a less strenuous ride without traffic concerns.
Beyond cycling, Woodside offers numerous outdoor attractions. You can explore the wooded hillsides and redwood groves of Wunderlich County Park or Huddart Park. Edgewood Park and Natural Preserve is known for its wildflowers and native plant diversity. For a blend of history and nature, Filoli Historic House & Gardens features beautiful gardens and an estate trail. These locations provide great opportunities for hiking or nature walks.
While Woodside is primarily accessed by car, some public transport options in the wider San Mateo County area may accommodate bikes. However, direct public transport links specifically designed for cyclists to reach the start of many popular road cycling routes in Woodside are limited. It's advisable to check local transit authority websites for current bike policies and route accessibility if you plan to use public transport.
Parking for road cycling routes in Woodside is often available at various points along popular routes or near trailheads. Specific parking areas can be found near the start of well-known climbs like Kings Mountain Road or along Skyline Boulevard. It's recommended to check specific route details on komoot or local park websites for designated parking facilities.
Woodside's unique appeal for road cyclists lies in its combination of diverse landscapes, challenging climbs, and natural beauty. It offers everything from serene redwood forests and open ridgelines with panoramic views to iconic climbs like Old La Honda Road and Tunitas Creek Road. The cycling-friendly community, with stops like Alice's Restaurant, further enhances the experience, making it a premier destination in the Bay Area.


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