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Junipero Serra Boulevard loop from West Menlo Park
50.1km
02:58
930m
930m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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By Fede from komoot
·
Updated May 29, 2026
If you’ve ever tried to plan road cycling around Portola Valley, you know how many options pop up, making it tough to figure out which routes are genuinely worth your time and effort. It’s easy to get lost in a sea of choices, wondering which climbs deliver the best views or which loops offer the smoothest ride. That’s where we come in. Our komoot community has ridden, mapped, and reviewed countless routes here, so we’ve done the legwork to bring you a curated shortlist of the ones that truly earn their place.
Road cycling around Portola Valley is defined by its rolling hills, tree-lined roads, and open vistas, offering everything from moderate hills to longer, challenging ascents. You’ll find varied terrain that sweeps past residential areas and natural preserves, often with stunning views of the Crystal Springs reservoir and the San Francisco Bay from elevated points. While the riding is great year-round, keep an eye out for "Bicycle Sundays" on Cañada Road, when a section is closed to cars for a truly peaceful experience.
If you only have time for one ride, we’d point you straight to the Old La Honda Road – Old La Honda Road loop from Portola Valley. This moderate 9.4 miles (15.1 km) route is a local favorite for a reason, offering a consistent workout and a real taste of the area's character. For something a bit longer with varied terrain, the Rossotti's Alpine Inn – Dwight Crowder Path loop from Los Trancos Open Space Preserve is a fantastic moderate option at 14.9 miles (24.0 km), leading through wooded areas and open vistas. With over 10,000 road cyclists having explored Portola Valley with komoot, you’re in good company.
Trail | Distance | Elevation | Difficulty |
|---|---|---|---|
| Junipero Serra Boulevard loop from West Menlo Park | 50.1 km | 930 m | Hard |
| Old La Honda Road – Old La Honda Road loop from Portola Valley | 21.4 km | 510 m | Moderate |
| Rossotti's Alpine Inn – Dwight Crowder Path loop from Los Trancos Open Space Preserve | 24.0 km | 470 m | Moderate |
| Portola Road – Old La Honda Road loop from Portola Valley | 14.7 km | 260 m | Easy |
| Alpine Road loop from Portola Valley | 14.5 km | 200 m | Easy |
50.1km
02:58
930m
930m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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21.4km
01:15
510m
510m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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24.0km
01:26
470m
470m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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14.7km
00:47
260m
260m
The Portola Road – Old La Honda Road loop is a classic road cycling route that takes you through some of the Bay Area's most picturesque landscapes. You'll start with a gentle roll on Portola Road before tackling the renowned Old La Honda Road climb, a sustained ascent through oak woodlands that gradually gives way to tranquil redwood groves. This 9.1-mile (14.7 km) loop, with 838 feet (255 metres) of elevation gain, offers a rewarding challenge for cyclists, despite its overall easy rating, and can be completed in about 46 minutes.
Planning your ride is straightforward, as the route is well-known and easily accessible from Portola Valley. While the climb up Old La Honda Road is a highlight, its narrow, twisty nature means descending it is generally discouraged; many cyclists opt for alternative routes like Highway 84. Parking can be found in Portola Valley, though it's wise to arrive early on busy days to ensure a spot. The consistent grade and shaded sections of the climb make it enjoyable even during warmer periods.
Old La Honda Road is famous among local cyclists as a
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14.5km
00:44
200m
200m
The Alpine Road loop from Portola Valley offers a delightful, quick escape for road cyclists, winding through the scenic Portola Valley community. You'll experience a consistent climb on the paved road, rewarded by stunning mountain views before a narrow, twisty descent under moderate tree cover. It's a perfect ride for those seeking a manageable workout and beautiful surroundings without an all-day commitment.
This easy racebike route covers 9.0 miles (14.5 km) with 668 feet (203 metres) of elevation gain, typically taking about 44 minutes to complete. Parking is usually accessible in Portola Valley, making it convenient to start your ride. While the paved road is generally good, be mindful that shoulders are often absent, and light car traffic can be present.
Historically, parts of Alpine Road were open to vehicular traffic before being repurposed into trails, highlighting the area's evolution for cyclists. This particular loop provides a taste of the region's natural beauty and challenging terrain, distinct from the much steeper unpaved sections like Joaquin Road, which are better suited for mountain or gravel bikes.
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The Northern part of Alpine Road is a paved and curvy descent through wooded areas and runs parallel to Coal Mine Ridge Preserve, eventually connecting with the trailhead there.
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This mostly paved bike trail alongside Alpine Road is great for bike commuting — just don't run over any slower trail users! The trail runs all the way from Portola Valley to Stanford, offering some nice shade along the way. The brief moments of unpaved trail are near the Portola Valley end.
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Didn’t OLR used to turn into Dirt before reaching Skyline? Is it all pavement now?? Scott
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A sculpture made by Augustin Rodnin
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Page Mill Road is a classic route for cyclists looking for a challenge, with its steep climbs, sharp switchbacks, and stunning views of Silicon Valley. Starting near Palo Alto and climbing into the Santa Cruz Mountains, the ride tests your legs but rewards you with breathtaking scenery. Be prepared for varying gradients, especially in the lower sections, and pack plenty of water—the climb can be intense, especially on warmer days.
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This fantastic tavern, founded in 1852, is the second oldest in the state. It features a large, beer garden-style outdoor area with plenty of shade. An extensive beer and food menu makes it a perfect stop to enjoy a brew and some great food after a ride.
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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
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There are over 170 road cycling routes around Portola Valley, offering a wide range of options for different skill levels. You'll find everything from easy, leisurely rides to more challenging ascents.
Yes, Portola Valley offers several easy road cycling routes. A great option for a relaxed ride is the Portola Valley – Rossotti's Alpine Inn loop from Enid Pearson-Arastradero Preserve, which is about 11.9 miles (19.2 km) long and features less strenuous terrain. Another easy route is the Manzanita Way – Tree Tunnel on Portola Road loop from Portola Valley.
For experienced road cyclists seeking a challenge, the Old La Honda Road – Manzanita Way loop from Portola Valley is highly recommended. This 20.1-mile (32.4 km) route includes significant elevation gain, providing a demanding workout. Another challenging option is the Old La Honda Road loop from Stanford Linear Accelerator Center National Accelerator Laboratory, known for its substantial climbs.
Portola Valley is well-suited for loop routes, allowing you to start and end your ride in the same location. Popular options include the Old La Honda Road – Manzanita Way loop and the Rossotti's Alpine Inn – Junipero Serra Boulevard loop, both offering varied terrain and scenic views.
Road cycling routes around Portola Valley are characterized by rolling hills, tree-lined roads, and scenic valleys. You'll encounter a mix of challenging climbs and more gentle sections, often passing through residential areas and natural preserves. Elevations range from moderate hills to longer ascents, providing diverse terrain.
The best time for road biking in Portola Valley is generally during the spring and fall months when temperatures are mild and the weather is pleasant. Summers can be warm, especially inland, while winters are typically mild but can bring occasional rain. Always check the local forecast before heading out.
Many road cycling routes in Portola Valley offer access to scenic viewpoints and natural attractions. You might pass by the unique Tafoni Sandstone Formation, enjoy panoramic views from Windy Hill Summit, or discover the Byrne Preserve Lookout. The region's natural beauty is a highlight of any ride.
Beyond the natural beauty, you can find interesting landmarks such as Black Mountain, which offers impressive vistas. Many routes also pass through charming residential areas with unique architecture and mature trees, adding to the scenic appeal.
The area is highly rated by the komoot community, with an average score of 4.6 stars from over 280 reviews. Reviewers often praise the diverse terrain, the beautiful tree-lined roads, and the challenging climbs that make for a rewarding cycling experience. The well-maintained roads and scenic vistas are frequently highlighted.
Parking is generally available at various access points and trailheads around Portola Valley. Many routes start from or pass through areas with public parking facilities, including local parks or designated roadside spots. It's advisable to check specific route details for recommended starting points with parking.
Yes, several routes pass by or are in close proximity to local cafes and eateries, particularly in the more developed areas of Portola Valley and neighboring towns. For example, the Portola Valley – Rossotti's Alpine Inn loop includes Rossotti's Alpine Inn, a popular stop for cyclists.


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