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United States
California
San Mateo County
Woodside

Woodside – Cañada Road & Woodside Road loop from Woodside

Routes
Running trails & routes
United States
California
San Mateo County
Woodside

Woodside – Cañada Road & Woodside Road loop from Woodside

Moderate

2.8

(28)

81

runners

Woodside – Cañada Road & Woodside Road loop from Woodside

01:08

10.4km

80m

Running

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels. The starting point of the route is right next to a parking lot.

Last updated: June 1, 2026

Waypoints

A

Start point

Parking

Get Directions

1

280 m

Woodside

Highlight • Settlement

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 …

Tip by

2

374 m

Cañada Road & Woodside Road

Highlight (Segment) • Cycleway

Sundays Cañada Road is closed to cars, biker-heaven toward Crystal Springs bike path.

Tip by

B

10.4 km

End point

Parking

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Way Types & Surfaces

Way Types

5.01 km

2.28 km

2.13 km

676 m

329 m

Surfaces

5.18 km

2.62 km

1.40 km

888 m

336 m

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Elevation

Elevation

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

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Weather

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Thursday 9 July

29°C

11°C

-- %

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Description

If you're looking for a scenic and accessible jogging route in the Bay Area, the Woodside – Cañada Road & Woodside Road loop from Woodside is definitely worth your time. This moderate 6.5-mile (10.4 km) jogging trail, with a gentle 264 feet (80 metres) of elevation gain, can be completed in about 1 hour and 8 minutes. It’s an ideal choice for anyone seeking a smooth, mostly paved surface with beautiful views, especially if you prefer a car-free experience on Sundays.

What to expect on Woodside – Cañada Road & Woodside Road loop from Woodside

This Woodside Cañada Road Woodside Road loop offers a journey through picturesque landscapes, primarily on paved surfaces that are perfect for road jogging. You'll enjoy stunning lake views of the Upper and Lower Crystal Springs Reservoir, which are particularly poetic on a misty morning. While generally flat, expect some long, gentle grades and a few short, steeper sections, especially where Cañada Road meets Highway 92. The route also takes you past the historic Filoli Estate and the unique Pulgas Water Temple, adding architectural interest to your run. This trail is well-suited for beginners looking for a longer distance or experienced joggers wanting a relaxed, scenic outing.

Planning your visit

A major highlight for this Woodside jogging trail is "Bicycle Sunday," when a nearly 4-mile segment of Cañada Road is closed to motor vehicles every Sunday from 9 AM to 3 PM, offering a safe and enjoyable experience. Parking is available at various points, including along Woodside Road, near Whiskey Hill Road, and close to the intersection of I-280 and CA-84. Restrooms are conveniently located at the Pulgas Water Temple. Remember to keep an eye out for local wildlife like turkeys and deer, but also be aware that rattlesnakes have been sighted in natural areas along Cañada Road.

Trail details

  • Distance: 6.5 miles (10.4 km)
  • Elevation gain: 264 feet (80 metres)
  • Difficulty: moderate
  • Estimated time: 1 hours and 8 minutes

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