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Running Trails
United States
California
San Mateo County

Portola Valley

The best running trails around Portola Valley

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.

Best jogging routes around Portola Valley

  • The most popular jogging route is Windy Hill Summit loop from Portola Valley, a 14.5 miles (23.4 km) trail that takes 3 hours 8 minutes to complete. This route offers panoramic vistas from its summit, encompassing the San Francisco Bay and beyond.
  • Another top favourite among local runners is Alpine Pond – Borel Hill loop from Portola Valley, a difficult 18.0 miles (29.0 km) path. This challenging route leads through varied landscapes, including open spaces and forested sections.
  • Local runners also love the Running loop from Portola Valley, a 5.1 miles (8.2 km) trail leading through oak woodlands and grasslands, often completed in about 1 hour 2 minutes.
  • Jogging around Portola Valley is defined by open grassland ridges, redwood and oak forests, and an extensive network of trails. The region's routes offer options for easy, moderate, and difficult running, catering to various ability levels.
  • The routes in Portola Valley are highly rated by the komoot community with an average score of 4.5 stars from more than 30 reviews. More than 2,900 runners have used komoot to explore Portola Valley's varied terrain.

Last updated: April 27, 2026

#1.

Meadowlark Trail to Woodland Star Trail via View Point Trail loop

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.

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Easy

4.0

(1)

66

runners

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

5.0

(1)

10

runners

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

9

runners

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Popular around Portola Valley

Bay Area Ridge Trail — Hiking the backbone of The Bay

Classy road bike rides on the SF peninsula

Hiking around Portola Valley

Road Cycling Routes around Portola Valley

MTB Trails around Portola Valley

Cycling around Portola Valley

Gravel biking around Portola Valley

Other adventures around Portola Valley

Bay Area Ridge Trail — Hiking the backbone of The Bay

Hiking Collection by

Andrus

Tips from the Community

Rama
June 30, 2025, Windy Hill Summit

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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Alex
September 15, 2024, Windy Hill Summit

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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Matthew
November 20, 2023, Arastradero Overlook

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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Frequently Asked Questions

How many running routes are available in Portola Valley?

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.

Are there easy running trails suitable for beginners in Portola Valley?

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.

Where can I find challenging running routes in Portola Valley?

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.

Are there any running trails with great views in Portola Valley?

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.

What kind of natural features or landmarks can I see while running in Portola Valley?

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.

Are there loop running routes available in Portola Valley?

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.

What do other runners enjoy most about jogging in Portola Valley?

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.

Are there any hidden gem running trails in Portola Valley?

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.

What are the typical trail conditions for running in Portola Valley?

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.

Can I find running routes near coffee shops in Portola Valley?

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.

What is the best time of year to go running in Portola Valley?

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.

Most popular routes around Portola Valley

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