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: September 26, 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

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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 …

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27.4 km

Bol Park Path

Highlight (Segment) • Trail

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

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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 …

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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. …

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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 …

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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 …

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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 …

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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.

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