Woodside is a region located in San Mateo County, California, characterized by its diverse landscape of redwood forests, open ridgelines, and scenic valleys within the Santa Cruz Mountains. This varied terrain provides a setting for several outdoor activities, including touring cycling, hiking, road cycling, and jogging. The area is known for its commitment to preserving open spaces, offering numerous trails through wooded hillsides and along panoramic viewpoints.
Woodside offers a range of outdoor pursuits for…
59
Routes
4.3
(90)
Average rating
827
People visited

5.0
(14)
164
riders
78.7km
05:17
1,210m
1,210m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

44.6km
03:00
700m
700m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.9
(8)
86
riders
49.7km
02:49
170m
170m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(1)
6
riders
61.6km
03:37
250m
250m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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4.0
(4)
16
hikers
5.69km
01:27
20m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

4.2
(6)
15
hikers
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

3.2
(11)
27
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

4.3
(3)
22
hikers
6.00km
01:44
150m
150m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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4.3
(3)
112
riders
71.5km
03:31
940m
940m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

15
riders
46.2km
02:04
200m
200m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

14
riders
107km
05:13
1,130m
1,130m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

10
riders
25.9km
01:10
90m
90m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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32
runners
11.6km
01:12
70m
70m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

29
runners
11.6km
01:13
60m
60m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

15
runners
5.69km
00:35
30m
30m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

16
runners
4.88km
00:31
30m
30m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Woodside offers a range of outdoor activities, including touring cycling, hiking, road cycling, and jogging. The region features diverse landscapes from redwood forests to open ridgelines within the Santa Cruz Mountains.
More than 5,000 visitors have recorded tours in Woodside on komoot. Routes in the area have an average rating of 4.5 out of 5 stars, indicating high user satisfaction.
Yes, komoot provides several guides for Woodside. These include Cycling around Woodside, Hiking around Woodside, and Road Cycling Routes around Woodside. Guides for easy hikes and running trails are also available.
Popular cycling routes in Woodside include Old La Honda Road, Kings Mountain Road, Cañada Road, and Skyline Boulevard. Cañada Road offers a car-free segment on weekends, ideal for cyclists. Explore more options in the Road Cycling Routes around Woodside guide.
Huddart Park offers numerous trails suitable for families, with picnic areas and playgrounds under a canopy of redwoods and oaks. Edgewood Park & Natural Preserve also provides diverse trails for various skill levels. For easier options, consult the Easy hikes around Woodside guide.
Woodside is home to dense redwood forests and is situated within the Santa Cruz Mountains. Notable parks include Wunderlich County Park, Huddart Park, Thornewood Open Space Preserve, Teague Hill Open Space Preserve, and Edgewood Park & Natural Preserve.
Yes, Teague Hill Open Space Preserve offers challenging trails with panoramic views of the Peninsula and Pacific Ocean from its higher elevations. Skyline Boulevard also provides broad views of the surrounding hills.
Huddart Park features several interconnected dirt trails suitable for trail running, offering longer loops with steady elevation through forested slopes and creek crossings. More options are detailed in the Running Trails around Woodside guide.
Beyond outdoor activities, visitors can explore Filoli Historic House & Gardens, a 654-acre estate. The Woodside Store, a historical structure, now functions as a community center and museum.
The official website for the Town of Woodside, CA is www.woodside.com. It provides information on local services and community details.
Woodside offers diverse terrain, ranging from dense redwood forests and oak woodlands to open meadows and challenging ridgelines. Trails feature steady climbs through second-growth redwoods and shaded canopies.
Cañada Road offers a relatively flat and car-free segment on weekends, making it suitable for beginner cyclists. Other routes may vary in difficulty, with some featuring long, steady climbs.
Woodside is unique for its commitment to preserving open spaces and redwoods, offering year-round access to well-maintained trails. Its strong equestrian culture and diverse terrain also contribute to its distinct character.

