4.6
(37)
2,403
runners
251
runs
Jogging around Portola Valley offers a diverse landscape for runners, situated on the eastern slopes of the Santa Cruz Mountains. The region features open grassland ridges, redwood, fir, and oak forests, and an extensive network of trails. Runners can explore varied terrain, from tranquil woodlands to areas with panoramic views of the San Francisco Bay. This natural setting provides a serene escape with diverse natural features suitable for outdoor activities.
Last updated: April 27, 2026
3.77km
00:25
80m
70m
Jog this 2.3-mile loop in Enid Pearson Arastradero Preserve, featuring rolling hills, Bay Area views, and abundant wildlife.
4.0
(1)
66
runners
16.9km
02:15
490m
490m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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35
runners
10.2km
01:15
200m
200m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
10
runners
7.66km
01:00
200m
200m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
9
runners
11.8km
01:30
290m
290m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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The hike from Razorback Ridge trailhead to the Windyhill summit is mostly through shaded sections. Sections of it kept cool from the fog rolling in from the Santa Cruz Mountains. The final section, Anniversary Trail is out in the open but has nice views of the bay.
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Along the Old Spanish Trail, there’s a small bench tucked under eucalyptus trees where you get a clear view of Mt. Diablo. It’s a good spot to pause, catch your breath, and take in the landscape.
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On a clear day, you can see up the bay to San Francisco and out across Silicon Valley. The trail follows a packed dirt track which winds above the treetops, granting sweeping views from this northern section.
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Windy Hill Summit, located at an elevation of 1,905 feet within the Windy Hill Open Space Preserve, offers great views of Silicon Valley and the Peninsula. The preserve stretches 1,132 acres along the east side of the Santa Cruz Mountains, coming up from the valley road near Portola Valley to this scenic summit. It’s a great spot to watch the sunset and take in views.
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Windy Hill Open Space Preserve encompasses a little over 1,100 acres of barren land with a few spotty forest areas. The majority of the Peninsula Range (the mountain range in which the park is encompassed) is completely covered in trees, but the Windy Hill Open Space Preserve has a bunch of open meadows and bald hills with expansive views.
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The Vista Point Trail dead ends at a bench and overlook area known as Arastradero Overlook. This lookout area offers a great view of the lower Enid Pearson-Arastradero Preserve.
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What a great place for a break in Arastradero. Relax and enjoy the wonderful view.
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Look for a nice bench tucked beneath eucalyptus trees.
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Komoot features 10 dedicated running routes around Portola Valley. These trails offer a variety of experiences, from easy jogs to challenging long-distance runs, catering to different fitness levels.
Yes, Portola Valley offers routes suitable for beginners. While the guide highlights more challenging options, the region's extensive trail network includes easier sections. For a moderate option, consider the Hector Lake loop from Enid Pearson-Arastradero Preserve, which is 5.5 km long and has minimal elevation gain.
For a more challenging experience, Portola Valley provides several demanding routes. The Alpine Pond – Borel Hill loop from Portola Valley is a difficult 29 km path with significant elevation, leading through varied landscapes. Another challenging option is the Windy Hill Summit loop from Portola Valley, offering panoramic views over 23 km.
Absolutely! Many running trails in Portola Valley offer stunning vistas. The Windy Hill Summit loop from Portola Valley is renowned for its panoramic views of the San Francisco Bay, Stanford University, and even the Pacific Ocean from its summit. You can also find breathtaking views from Skeggs Point and Turtle Rock Viewpoint, which are accessible from various trails.
Portola Valley's trails wind through diverse natural settings. You can expect to see open grassland ridges, redwood, fir, and oak forests. Notable landmarks and natural features include Windy Hill Summit, Black Mountain, and Borel Hill. The area is also rich in wildlife, including California mule deer, coyotes, and various bird species.
Yes, many of the best running experiences in Portola Valley are loop routes. For example, the popular Running loop from Portola Valley is an 8.2 km trail through oak woodlands and grasslands. Other excellent loop options include the Windy Hill Summit loop and the Alpine Pond – Borel Hill loop.
The running routes in Portola Valley are highly rated by the komoot community, with an average score of 4.5 stars from over 30 reviews. Runners frequently praise the serene escape offered by the diverse natural features, the extensive network of trails, and the stunning panoramic views, especially from places like Windy Hill.
While many trails are well-known, exploring areas like Coal Mine Ridge Nature Preserve can feel like a hidden gem. Its tranquil environment, ancient California oak forests, and opportunities for wildlife viewing offer a peaceful running experience away from more crowded spots. The Portola Valley Ranch Trails also offer picturesque landscapes with diverse flora and fauna.
The trails in Portola Valley are generally well-maintained, winding through oak woodlands, grasslands, and forested sections. Conditions can vary with weather; during dry periods, trails are typically firm, while rain can make some sections muddy. It's always advisable to check local conditions before heading out, especially after heavy rainfall.
While many running routes in Portola Valley are nestled within natural preserves, offering a true escape, you can often find coffee shops and amenities in the nearby town centers. Planning your run to start or end near the village of Portola Valley or other local hubs would allow for a post-run coffee or snack.
Portola Valley offers excellent running conditions year-round, but spring and fall are particularly pleasant. Spring brings wildflowers and mild temperatures, while fall offers crisp air and beautiful foliage. Summer mornings are ideal to beat the heat, and winter running can be refreshing, though some trails might be muddy after rain.


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