Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Places to see
North America
United States
California
San Mateo County

Portola Valley

Attractions and Places To See around Portola Valley - Top 20

Best attractions and places to see around Portola Valley are situated in the scenic Santa Cruz Mountains of San Mateo County, California. This area is characterized by its natural beauty, rural ambiance, and extensive outdoor recreational opportunities. Visitors can explore a blend of natural features and historical sites. The region offers a variety of experiences for those interested in outdoor activities and local heritage.

Best attractions and places to see around Portola Valley

  • The most popular attractions is Old La…

Last updated: April 24, 2026

Old La Honda Road

Highlight (Segment) β€’ Climb

Once the "real" climb on Old La Honda starts (roughly at the first hairpin curve), it lasts for almost exactly three miles until you meet with Skyline Boulevard, and averages …

Tip by

See rides here

Send to Phone

Save

Kings Mountain Road

Highlight (Segment) β€’ Cycleway

Kings Mountain Road arrives about one mile into the descent portion of your loop. This is a narrow and very twisty road that descends for a little over four miles …

Tip by

Save

Sign up now to discover places like this

Get recommendations on the best single tracks, peaks, & plenty of other exciting outdoor places.

Sign up for free

Junipero Serra Boulevard

Highlight (Segment) β€’ Cycleway

Junipero Serra Boulevard has a generous, paved bike lane in both directions for the entire length of the ride.
Car traffic is everpresent on this route, and it can get …

Tip by

Save

Woodside Store (Historic Site)

Highlight β€’ Historical Site

Trails looping around and through the open air pioneer settlement museum. Even if inside displays should be closed it's interesting and some buildings have windows to peek through

Tip by

Save

Tafoni Sandstone Formation

Highlight β€’ Natural Monument

The Tafoni sandstone consists of sand from ancient dunes cemented by water-soluble calcite. Due to calcite, water easily passes through the porous rock, thereby dissolving the calcite and then depositing …

Tip by

Save

Sign up for free to discover even more attractions around Portola Valley.

Sign up for free

Already have an account?

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Portola Valley

Bay Area Ridge Trail β€” 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

Running Trails around Portola Valley

Cycling around Portola Valley

Gravel biking around Portola Valley

Other adventures around Portola Valley

Bay Area Ridge Trail β€” Hiking the backbone of The Bay

Hiking Collection by

Andrus

Tips from the Community

Scott Pierson
March 3, 2025, Old La Honda Road

Didn’t OLR used to turn into Dirt before reaching Skyline? Is it all pavement now?? Scott

0

0

good

0

0

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.

0

0

Tim
November 4, 2024, Junipero Serra Boulevard

While this is an expressway, there is good room for safe riding and most of the day it isn't too heavily trafficked which makes for a great, rolling straight run

1

0

Old La Honda Rd downhill video: https://youtu.be/icnBpBZQ8gE?si=xYovaH-Nr8llwLEM

0

0

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.

0

0

Quiet and beautiful climb

0

0

Nico
October 9, 2022, Old La Honda Road

The road has just been resurfaced. Smooth ride

0

0

Frequently Asked Questions

What unique natural features can I explore in Portola Valley?

Portola Valley is home to the fascinating Tafoni Sandstone Formation. These unique rock structures are formed by natural weathering over thousands of years, creating intricate, cave-like shapes. You can observe these formations from a dedicated platform, and the area is part of a lightly trafficked loop trail near Redwood City.

Are there historical sites to visit in Portola Valley?

Yes, Portola Valley offers several historical sites. A notable one is the Woodside Store (Historic Site), also known as Tripp Store. Dating back to 1853, it served as a vital stagecoach stop and general store during the Gold Rush era. The store has been restored to its 1880s condition, offering a glimpse into the region's pioneer past. Other historical landmarks include Our Lady of the Wayside Church (1912) and the historic Portola Valley School (1909).

What cycling routes are popular in Portola Valley?

Portola Valley is renowned for its cycling opportunities. Cyclists frequently tackle Old La Honda Road, a challenging climb spanning nearly three miles with an average grade just under 8%. For an exhilarating descent, Kings Mountain Road offers a fast, twisty ride through moderate tree cover. Additionally, Junipero Serra Boulevard provides a generous, paved bike lane for safe riding, mostly independent of car traffic.

Where can I find trails for hiking and mountain biking in Portola Valley?

The region boasts an extensive network of trails. Windy Hill Open Space Preserve offers trails for hikers and mountain bikers with diverse terrain and views of the San Francisco Bay. Coal Mine Ridge Nature Preserve provides tranquil paths through oak woodlands, ideal for birdwatching. For more challenging hikes, the El Corte de Madera Creek Trail winds through redwood groves and sandstone canyons. Many of these trails are maintained by the town and the Midpeninsula Regional Open Space District.

Are there any family-friendly attractions or activities in Portola Valley?

The Woodside Store (Historic Site) is considered family-friendly, offering a historical experience with looping trails around an open-air pioneer settlement museum. Beyond specific attractions, the Portola Valley Town Center features landscaped gardens, meadows, and creeks, providing pleasant outdoor spaces. Many of the easier trails in preserves like Windy Hill also cater to families looking for a gentle outdoor experience.

What are the best places for scenic views in Portola Valley?

For breathtaking vistas, Windy Hill Open Space Preserve offers expansive views of the San Francisco Bay and surrounding valleys. The Tafoni Sandstone Formation area also provides unique natural scenery. Additionally, cycling routes like Old La Honda Road and Kings Mountain Road offer scenic stretches through forests and along mountain ridges.

What kind of outdoor activities can I do near Portola Valley attractions?

Beyond the attractions themselves, Portola Valley is a hub for outdoor sports. You can find numerous cycling routes, including challenging climbs and scenic descents. For road cycling, explore options like the "Old La Honda Road – Manzanita Way loop from Portola Valley" or the "Portola Valley – Rossotti's Alpine Inn loop." Mountain bikers can find gravel biking routes such as the "San Francisco Bay and Ravenswood Trail Loop." For more details on routes, check the Cycling around Portola Valley or Road Cycling Routes around Portola Valley guides.

Where can I experience local culture and arts in Portola Valley?

The Portola Valley Town Center serves as a cultural hub, housing a library, community hall, and an art gallery that features works by local artists. The Portola Valley Theatre Conservatory is a community-based group that offers theatrical productions and workshops, enriching the local arts scene. Additionally, the Ohlone Ranch provides insights into the indigenous heritage of the Bay Area through its living museum.

What is the best time of year to visit Portola Valley for outdoor activities?

Portola Valley generally offers pleasant conditions for outdoor activities throughout much of the year. Spring brings wildflowers to the trails, while fall provides comfortable temperatures and beautiful foliage. Summers are typically warm and dry, ideal for hiking and cycling, though it's wise to start early to avoid midday heat. Winters are mild, and popular spots like Windy Hill Open Space Preserve are known for paragliding and hang gliding during this season.

Are there any historic drinking establishments in Portola Valley?

Yes, Portola Valley is home to The Alpine Inn (also known as Casa de Tableta, Rossotti's, or Zott's). This establishment dates back to around 1852 and is recognized as one of California's oldest existing drinking establishments, originally built as a gambling house. It offers a unique historical atmosphere for visitors.

What are some lesser-known natural spots or 'hidden gems' in Portola Valley?

While not entirely hidden, the Coal Mine Ridge Nature Preserve offers a tranquil escape with wide trails through oak woodlands, providing a peaceful environment away from more crowded spots. The unique geological formations of the Tafoni Sandstone Formation, though accessible, are a distinctive natural wonder that many visitors might overlook.

What kind of terrain can I expect on Portola Valley trails?

The terrain in Portola Valley varies significantly. You'll find wide trails through oak woodlands and chaparral at places like Coal Mine Ridge, while Windy Hill Open Space Preserve features a mix of lush forests and open grasslands. More challenging trails, such as El Corte de Madera Creek, navigate through redwood groves and sandstone canyons. Cycling routes like Old La Honda Road are known for consistent grades, and Kings Mountain Road offers twisty descents.

Most popular routes around Portola Valley

Easy hikes around Portola Valley

Most popular attractions around Portola Valley

Lakes

Store rating

Get inspired with the komoot mobile app

With aΒ free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Still not found the Highlight you’re looking for? See guides of the top attractions in other regions:

AthertonRedwood CityDaly CityMenlo ParkLaderaWest Menlo ParkLa HondaNorth Fair OaksMillbraeSan BrunoSouth San FranciscoBurlingameBrisbaneBaywood ParkSan MateoWoodsideHighlandsHillsboroughMontaraEmerald Lake HillsSan CarlosPacificaEast Palo AltoHalf Moon BayFoster CityEl GranadaMoss BeachBelmontColmaBroadmoorLoma MarPescaderoEl Corte De Madera Creek Open Space PreservePurisima Creek Redwoods Open Space PreserveSkyline Ridge Open Space PreserveAΓ±o Nuevo State ParkPescadero Creek County ParkSan Bruno Mountain State ParkRussian Ridge Open Space PreserveSan Pedro Valley County ParkHuddart County ParkWindy Hill Open Space PreserveRavenswood Open Space PreservePortola Redwoods State Park

Nearby adventure guides

Things to Do in Windy Hill Open Space Preserve (Closed Areas)

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

Β© komoot GmbH

Privacy Policy