Bay Area driving guide · Hills above the city

East Bay ridge run: Skyline, Redwood and Pinehurst

Three short roads that link into one good hour without leaving the East Bay. Skyline runs the ridge above Oakland, Redwood drops through the regional parks, and Pinehurst threads the redwoods at Canyon.

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Skyline Boulevard
Redwood Road
Pinehurst Road

Start: Golf Links Road, Oakland
Finish: Moraga
Return: Optional loop below

Why this drive

Convenience is the point — this is minutes from the city rather than a day out. The trade is traffic: Redwood is heavily used by cyclists, Skyline has driveways along most of its length, and Pinehurst is narrow enough that pace stays low whatever you drive.

The route

Skyline Boulevard north
Start at Golf Links Road and follow Skyline along the ridge, with the bay below on the left.
Road details & map →
Redwood Road
Drop east on Redwood Road through the park. Expect cyclists at almost any hour.
Road details & map →
Pinehurst Road through Canyon
Turn onto Pinehurst for the narrow, shaded run down through Canyon toward Moraga.
Road details & map →

Good places to stop

Redwood Regional Park ↗
Parking and trailheads along Redwood Road if you want to stop.
Canyon
A one-room post office and not much else, halfway down Pinehurst.

Make it a loop

From Moraga, take Moraga Way and Highway 24 back through the tunnel, or reverse the route and drive Pinehurst uphill.

Weekends & road conditions

Police sometimes patrol Highway 9 and Skyline, including weekends. Local riders have reported enforcement on both roads. Follow posted limits throughout the drive.

Expect other drivers, motorcycles and cyclists around these popular roads and junctions. Before heading out, check Caltrans QuickMap for state-highway conditions and San Mateo County road closures for local roads.