Road Bike Rides

This is the classic Oakland Hills full loop. From the top of Tunnel, you turn right on Skyline and follow it along the ridge and down to the corner of Joaquin Miller Road. At this corner, you turn left on Skyline, and then left onto Redwood. Redwood is a fun descent down to the valley floor - it’s smooth and doesn’t turn too sharply - a great descent to lay off the brakes.  

From the bottom of Redwood road, past the regional park turnoff and fire station, is the left turn for Pinehurst Road.  

Pinehurst is broken up into three sections. Little Pinehurst comes first, a moderate climb up to the trailhead with East Ridge. This can be very hot on a summer day, as it’s pretty exposed. From there, the road enters the trees and descends into the small town of Canyon, one stoplight and all. The descent is twisty and fast, so watch your speed into the corners.

At the bottom it flattens out and begins a slow climb (one may call it a false flat) through Canyon and up towards the main part of the Pinehurst climb. Once you pass the Wilcox Staging area and Huckleberry parking lot, the climb fully begins with a steep left hand switchback.

From there, the road narrows and climbs steeply up the hill, reaching its hardest part after the right hairpin turn. You’ll know it when you see it. The remainder of the climb is manageable, but difficult for even a strong rider. You reach the top when you hit Skyline - it’s all downhill from there.

The Fairmont/Redwood loop is a Team Alameda favorite. Taking streets through Bay Farm Island and San Leandro, the ride begins in earnest with a climb up Fairmont Drive, just above 580. It’s wide and exposed, but a good challenge of a climb in either direction. From the top of Fairmont, you descend down to Lake Chabot and head out towards Redwood Road in Castro Valley.

Fairmont turns into Lake Chabot road here. You’ll turn left onto Seven Hills Road. The most common way to reach Redwood from here is to take a quick left on Walnut and then a right on Proctor. Seven Hills Road also takes you all the way through, but, you know, the name.

At the end of Proctor, you’ll turn left onto Redwood. Redwood Road will take you all the way back to Oakland - it’s gorgeous and windy, with multiple climbs and descents on the way back up to Skyline Boulevard. Of course, you can add Pinehurst Road onto this loop if you’re feeling extra strong.

This is a great loop if you’re shorter on time - it never goes over the hill, just up to the top. It’s also a great climb for someone looking to start riding in the Oakland hills. Once you’re up at the corner of Lincoln Avenue and Highway 13, you climb through the bucolic Butters Canyon on Burdeck Drive, Butters Drive, and Robinson - three winding, narrow streets through a quiet neighborhood, tree-lined and very low traffic.  

There is an access path to the bottom of Burdeck across the street from Woodminster Market, just above the freeway off ramp. Climb up Burdeck and merge onto Butters, continuing up the hill. There are a couple switchback turns that make you feel like you’re riding in the Alps somewhere, truly legendary Oakland hills riding. The steepest part is where the road narrows parallel to the canyon below. When you reach the four way intersection with Robinson, turn left and take that to Joaquin Miller Road.

Turn right onto Joaquin Miller Road - take that for a bit and enjoy the views of Oakland below. You’ll soon turn left onto Skyline and climb up to the ridge. It’s about a mile up to Roberts Regional Park (there’s water here) before it flattens out and rolls along the ridge, twisting and turning past Skyline Gate and Sibley Regional Park.  

Turn right onto Grizzly Peak Boulevard and ride along the ridge of the Berkeley hills, heading down towards the four way intersection of Grizzly Peak and Claremont/Fish Ranch Road. Turn left on Claremont and bomb down into the canyon - be careful here, there are steep corners and the road is fast! You’ll eventually pass the Claremont hotel and descent Claremont Avenue into Rockridge.