Bike the Oakland Hills via Pinehurst and Skyline

Rate this Adventure San Francisco Valle Vista Staging Area

Added by Megan MacKenzie

Challenge yourself with 15 miles of climbs and descents! This is a classic East Bay ride with beautiful views of the San Francisco Bay, the San Leandro Reservoir, redwood forests, and of course the golden California hills.

This 14.6-mile loop starts at the Valle Vista Staging Area in Moraga, CA.  

Take a left out of the parking lot onto Canyon Rd.

At 0.65 mi, turn right onto Pinehurst Rd.  This road will take you through Canyon's redwood tree forest, the beginning of a gradual uphill climb.  At around 3.3 mi you will begin 1.3 mi of switchbacks, the steepest section of this cat-3 climb

At 4.6 mi, you'll reach the top of Pinehurst. Turn left onto Skyline Blvd.  You're still climbing up at this point, but at a much gentler slope.

At 5 mi, you will pass the Skyline Gate Staging Area. There is a bathroom here and a water fountain to fill up water bottles if needed.

Continue along Skyline.  At 6.9 mi, congrats, you've reached the top of the cat-3 climb! You've earned a 4.4-mile "downhill trend."

At 8.1 mi, you'll hit a stoplight.  Turn left to continue on Skyline Blvd.

At 8.8 mi, turn left onto Redwood Rd.

At 11.2 mi, stay left onto Pinehurst Rd.  You'll begin a 1.4-mi cat-5 climb here.  Then at 12.6 mi, enjoy this epic downhill!  But remember to not go too crazy... the turns along here are quite sharp!  

At 14 mi, turn right onto Canyon Rd, and cruise the last half- mile back to the car.

***Most of this ride has no bike lane or shoulder.  Drivers in the East Bay are generally pretty bike-aware, but remember to stay to the right-hand side of the road, especially on the curvy roads through the hills.

Pack List

  • Bike! A road bike is preferred, as the climbs are quite steep!
  • Helmet, sunglasses, and layers (e.g. sleeves and a vest).  It can get quite chilly in the hills if there is fog.
  • Water- 2 24-oz-bottles should be sufficient, and remember you top off at the Skyline Gate Staging Area if needed.
  • Snacks! These are some steep hills so you might want some extra calories.
  • Sunscreen
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Skill Level:



Year Round

Trail Type:



14.6 Miles

Elev. Gain:

1441 Feet



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Added by Megan MacKenzie

san francisco bay area native and maine transplant, living semi-nomadically in wyoming, utah, and idaho for the past year working in outdoor education and wilderness therapy. otherwise you can find me on my road bike, backpacking, or roasting vegetables.

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