Grab a breakfast sandwich and a drink to power you up the hills. Start by climbing up Tunnel Road, a benchmark climb in the Oakland hills. At the top of the climb head into Sibley and take the dirt down Skyline Trail, which is steep in parts but has a nice flow to it. When you hit the gate at the bottom, hang a right and begin the long climb up the paved switchbacks through Sibley Volcanic Regional Park. You’ll go back onto some gravel and probably have to hike a bit, pass (or ride) by the labyrinth, and then descend again back to the parking lot on swoopy dirt trails.
Finish the swoopies, then ride the pavement on Grizzly Peak Boulevard up to the top of the hill just below Vollmer Peak. Continue on dirt by bombing down the Seaview trail, where you’ll find excellent views of San Francisco (and even the Farallon Islands on a clear day). Seaview is wide, loose, and fast, with a few little uphill sections mixed in. At the bottom, continue North on the paved Nimitz Way trail along the ridge toward Wildcat Peak. There are plenty of dirt cuts to ride parallel to the paved path - these are likely trails made by cows, so don’t get your wheel caught in a hoof track.
Make a U-turn, then descend into the woods down some singletrack on Havey Canyon Trail. Enjoy some of the mini jumps and lazy berms. Beware the pits. It’s a fun one!
At the bottom you’ll turn left onto Wildcat Creek Trail, climbing a bit and pedaling over some dirt rollers on Meadows Canyon Trail. Top out at Wildcat Canyon Road. Well, sort of, because you have one more climb, and it’s South Park Drive - saving the best for last. The road can be closed to car traffic for 6 months out of the year, so you’ll want to check for other riders flying down the hill, and people walking their dogs off-leash in the middle of the road! The climb is strenuous but the descent down Claremont Avenue to the bottom of the hill is joyful bliss on two wheels. End the day with a tasty beverage, you deserve it.