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Portola Valley – Old La Honda Road loop from Winchester

Portola Valley – Old La Honda Road loop from Winchester

Hard

4.7

(2304)

5,074

riders

Portola Valley – Old La Honda Road loop from Winchester

04:48

104km

1,090m

Road cycling

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is accessible with public transport.

Last updated: June 28, 2026

Tips

The surface for a segment of your route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 27.4 km for 290 m

Waypoints

Start point

Train Station

Get Directions

26.1 km

Palo Alto-Los Altos Bike Path

Highlight (Segment) • Cycleway

The Palo Alto-Los Altos Bike and Pedestrian Path, also known as the Hetch Hetchy Trail, is a well-maintained multi-use route that connects Los Altos Avenue to Arastradero Road. It’s popular for biking, running, and hiking, offering scenic views and access to parks like Terman Park, Bol Park, and Barron Park Donkeys. The trail includes a mini library and is part of Henry M. Gunn High School's recommended walking routes.

Tip by

27.4 km

Bol Park Path

Highlight (Segment) • Trail

Excellent paved north-south dedicated car-free bike trail between Palo Alto and Los Altos.

Tip by

38.4 km

Dwight Crowder Path

Highlight (Segment) • Cycleway

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.

Tip by

41.7 km

Portola Valley

Highlight (Segment) • Settlement

The ride takes you through the (very) well-to-do town of Portola Valley, which usually ranks as one of the top 10 in the US in terms of average household income. You may have heard that Portola Valley has a higher population of horses than of people. While that seems to have been true only in much earlier years, this is still a town with a very high rate of horse ownership and, just like in the neighboring Woodside, you shouldn't be surprised if you encounter residents heading to the corner store on horseback.

Tip by

51.3 km

Old La Honda Road

Highlight (Segment) • 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 a grade that is a touch under 8%. Naturally, there are brief spots where it's considerably steeper than that, but all such spots recorded by my GPS receiver had a grade less than 14%. The climb will not feel like any special challenge to anyone who is used to doing road climbs, but it's a good workout. The road is very narrow but its traffic is extremely light. There is a double yellow dividing line along the middle in the earliest stretches of the climb, but it soon disappears and doesn't re-emerge until you reach Skyline.

Tip by

60.6 km

Manzanita Way

Highlight (Segment) • Cycleway

Most boiler-template routes for this immediate area use Whisky Hill Rd. to get back and forth. Manzanita is several levels better (which includes a brief stretch of Mountain Home). Almost no cars, canopied and bucolic, it's perfect on a bike. So, substitute this for any Whiskey Rd routes!

Tip by

67.7 km

Junipero Serra Boulevard

Highlight (Segment) • 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 particularly busy during commute hours on weekdays, though this shouldn't concern you much because (other than having to switch to the left-hand side of the right-turn lane at some intersections) you will be mostly independent of the traffic lanes in your own bike lane during this ride. Meanwhile, weekends with good weather will result in heavy bicycle traffic, in which case it would be worthwhile to pay extra attention to fast riders that might be approaching from behind, at least when you're stopping or resuming after a stop.

Tip by

82.6 km

Mora Trail - Rancho San Antonio

Highlight (Segment) • Viewpoint

Quite steep on the south side but a really nice outlook over the south bay. Was a great little spot to stop in the shade in the afternoon and take in the view and the breeze.

Tip by

85.8 km

Rancho San Antonio County Park

Nature Reserve

104 km

End point

Train Station

Way Types & Surfaces

Way Types

69.3 km

19.7 km

9.73 km

3.57 km

1.09 km

414 m

320 m

Surfaces

95.8 km

7.91 km

280 m

< 100 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (510 m)

Lowest point (10 m)

Weather

Today

Friday 10 July

25°C

14°C

0 %

Additional weather tips

Max wind speed: 24.0 km/h

to get more detailed weather forecasts along your route

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Portola Valley – Old La Honda Road loop from Winchester

Palo Alto-Los Altos Bike Path

Bol Park Path

Dwight Crowder Path

Portola Valley

Old La Honda Road

Manzanita Way

Junipero Serra Boulevard

Mora Trail - Rancho San Antonio

Nearby routes

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