Bike the Oakland Hills via Pinehurst and Skyline

14.6 Miles Round Trip - 1441 ft gain - Loop Trail

Valle Vista Staging Area - Search Nearby - 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.

Tags

Cycling
Bathrooms
Forest
Scenic

Details

14.6 Miles
1441 ft elevation gain
Loop Trail

Stay Nearby

San Francisco, California

Aquatic Park Cove San Francisco Maritime Nhp

From $10/night

Sausalito, California

Bicentennial Campground

From $20/night

Petaluma, California

San Francisco North / Petaluma KOA

Point Reyes Station, California

Point Reyes National Seashore Campground

From $20/night

Nearby Adventures

Bike Pinehurst Road to Grizzly Peak

25 Miles Round Trip - 2294 ft gain

Hike the Sequoia Bayview Trail

2.9 Miles Round Trip - 429 ft gain

Hike the Skyline Gate Staging Area

4 Miles Round Trip - 692 ft gain

More Nearby Adventures

Tours

More Tours

Reviews

Leave a Review

Overall rating:  Rate this Adventure

Have you done this adventure? Be the first to leave a review!

Win a Vacation Getaway to Santa Cruz!

Experience all Santa Cruz County has to offer this season! Enter to win a customized “Let’s Cruz” vacation getaway and choose from an array of activities to enhance your visit. 

Grand prize includes a 2-night stay at a three-bedroom condo at Pajaro Dunes Resort, a $150 “Capitola Dine & Shop Experience” gift certificate in Capitola Village, a Craftbar Experience at Annieglass Studios for four guests, four tickets to the Santa Cruz Beach Boardwalk, and four tickets to Roaring Camp Railroads.

Customize your “Let’s Cruz” vacation package entry by selecting four activities below to include outdoor adventure, dining, beer and wine tasting, family fun, spa treatments, and relaxation.