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Running Trails
United States
California
San Mateo County

Woodside

The best running trails around Woodside

4.7

(32)

2,307

runners

16

runs

Jogging around Woodside offers access to a diverse network of trails set amidst redwood forests, open ridgelines, and scenic valleys. The region is characterized by towering redwood groves, mixed evergreen forests, and drier chaparral at higher elevations. Many running routes provide panoramic views of the San Francisco Peninsula and the Santa Cruz Mountains. This varied terrain ensures a range of experiences for runners of all levels.

Best jogging routes around Woodside

  • The most popular jogging route is Woodside Trail Loop…

Last updated: August 17, 2026

2

runners

#1.

Woodside Trail Loop

5.29km

00:36

30m

30m

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

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Moderate

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

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

Moderate

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

Hard
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Popular around Woodside

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Tips from the Community

mtm05005
June 29, 2025, Richards Road Trail

Richards Road Trail is a popular trail through the redwoods in Huddart County Park. The trail is actually a fire road and is not a particularly challenging hike.

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Once upon a time this was the only general store in this area, serving not only as a general-purpose retailer but also the post office, bank, and informal dentist's office. Nowadays it's a museum, staffed by docents ready to offer drop-in history lessons.

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Zachary
January 23, 2025, Woodside

Woodside is a historic town-turned upscale community along the old wagon path from San Francisco to Santa Clara. The downtown is a great place to take a break from your ride and features a few quaint shops, a market, bakery, and outdoor seating.

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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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Alex
September 23, 2024, Purisima Creek Trailhead

Purisima Creek Trailhead features a fence separating the trail from the road and a small pit toilet at the base. Parking is available just 250 feet southeast along Skyline Boulevard. This trail offers everything, from stunning views to towering redwoods, fern-filled canyons, and creeks. Riding through the redwoods is a unique experience.

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Skyline Boulevard, also known as State Route 35, offers a scenic drive through the majestic redwoods of the Santa Cruz Mountains and Bay Area. Winding through forests, open spaces, and mountains, this section passes by the Purisima Creek Redwoods. It's a breathtaking ride through where the redwoods meet the road.

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The Woodside Store, also known as Tripp Store, is located at 3300 Tripp Road at Kings Mountain Road in Woodside, San Mateo County, California. It has been listed on the National Register of Historic Places since 1985 and was designated a California Historical Landmark in 1949. The store's history dates back to October 1849 when Matthias Alfred Parkhurst purchased land in the area and began a shingle-making and lumber business with his partners, including Robert Orville Tripp. The store was established in 1853, originally serving the needs of lumbermen and settlers during the Gold Rush era. Dr. Tripp became the sole operator of the store after Parkhurst's death in 1863, running it until his own death in 1909. He was a well-known figure in Woodside, holding various public offices. The San Mateo County Historical Association acquired the store in the 1940s, and it was restored to its 1880s condition by 1994.

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51m
December 7, 2023, Kings Mountain Road

An awesome descent or ascent following the pretty, tree lined mountain road. There aren't many cars, but it's not a wide road so do watch out and enjoy the road rather than race it.

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Frequently Asked Questions

How many running routes are available in Woodside?

Woodside offers a vast network of trails, with over 200 running routes documented on komoot. These routes cater to all levels, from easy jogs to challenging long-distance runs through diverse landscapes.

Are there easy running trails suitable for beginners or a quick jog?

Yes, Woodside has several easy running options. For a relatively flat and accessible run, consider the Woodside Trail Loop, which is about 3.3 miles long. The region features 29 easy routes, many of which are found in parks like Huddart Park, offering shaded paths through redwood and oak canopies.

What do other runners enjoy most about the trails in Woodside?

The running trails in Woodside are highly rated by the komoot community, with an average score of 4.3 stars from over 27 reviews. Runners frequently praise the diverse terrain, from towering redwood groves to open ridgelines with panoramic views, and the well-maintained paths that offer both challenging workouts and serene natural beauty.

Are there any running routes that offer scenic viewpoints?

Absolutely. Many trails in Woodside provide breathtaking vistas. For expansive views of the San Francisco Peninsula and the Santa Cruz Mountains, you might enjoy routes that traverse open ridgelines, such as the Windy Hill Summit loop from Portola Valley. The Windy Hill Summit itself is a notable viewpoint.

Can I find circular running routes in Woodside?

Yes, Woodside is rich in circular running routes. Many parks, including Huddart Park and Wunderlich County Park, feature interconnected trail systems that allow for various loop configurations. The Woodside Store (Historic Site) – Purisima Creek Trailhead loop from Woodside is an example of a longer, challenging loop.

Are there any historical or natural landmarks to see along the running trails?

Woodside's trails offer access to several interesting landmarks. You can encounter the Pulgas Water Temple, a beautiful man-made monument, or the unique Tafoni Sandstone Formation. The Methuselah Tree – Sierra Morena Trail Access also offers a glimpse of ancient redwoods.

What kind of terrain can I expect on Woodside's running trails?

Woodside's running trails feature a diverse range of terrain. You'll find shaded dirt paths winding through towering redwood forests, mixed evergreen woodlands, and oak canopies. Higher elevations often transition to drier chaparral and manzanita-covered ridgelines. Many routes include significant elevation gains, providing both challenging climbs and rewarding descents.

Are there any challenging running routes for experienced runners?

For experienced runners seeking a challenge, Woodside offers 35 difficult routes. Trails like the Bear Gulch Trail (Meadow) loop from Wunderlich County Park or the Purisima Creek Trailhead – Huddart County Park loop from Huddart County Park provide substantial elevation changes and longer distances through varied terrain, including redwood groves and open hillsides.

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

Woodside is an excellent destination for running year-round. The towering redwood groves provide cool, shaded paths, making summer runs enjoyable. In spring, the region's wildflower-covered slopes, particularly in areas like Edgewood Park, are a beautiful sight. Fall and winter offer crisp air and often clear views, though some trails may be muddy after rain.

Are there running routes suitable for families with children?

While many trails offer varied terrain, families can find suitable options, especially among the easier routes. Huddart Park is known for its numerous interconnected trails through native woodland, providing varied paths that can be adapted for shorter, family-friendly outings. Look for routes with minimal elevation gain and well-maintained surfaces.

Where can I find parking for the running trails in Woodside?

Many of Woodside's popular parks and preserves, such as Huddart Park and Wunderlich County Park, offer designated parking areas at their trailheads. It's advisable to check specific park websites or komoot route details for precise parking information, especially during peak times.

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