Oakland Hills

109 mi · 2,700 ft of climbing · high point 1,470 ft · start/finish downtown Napa (First St & Main St)

Ridden Mar 23, 2026 · Delta & Valley

The ride

Close to home and full of curves. South on 29 through American Canyon to Vallejo, over the Carquinez Strait and down San Pablo Avenue into Crockett, where Cummings Skyway climbs up into the hills.

From there the route goes through the back roads of Contra Costa: McHarry Ranch Road and Alhambra Valley Road to Martinez, Reliez Valley Road down to Lafayette, then CA-24 through Orinda. Skyline Boulevard and Grizzly Peak Boulevard run along the ridge above Oakland and Berkeley, the route's 1,470 ft high point with the Bay spread out below, and Tunnel Road takes you down into Berkeley.

Home is I-80 north along the bay through Albany, Richmond and Pinole, San Pablo Avenue through Hercules, Rodeo and Crockett, then back over the Carquinez Bridge to Vallejo and up through American Canyon to Napa. About 109 mi with ~2,700 ft of climbing, an easy half day. Fuel is everywhere on this one. Skyline and Grizzly Peak are narrow and busy on weekends, and the hill roads get closures for slides and roadwork, so check conditions first.

[Steve: add your full write-up here]

Key roads and highlights

  • CA-29 through American Canyon, Vallejo

  • Carquinez Bridge, San Pablo Avenue to Crockett

  • Cummings Skyway

  • McHarry Ranch Road and Franklin Canyon area

  • Alhambra Valley Road to Martinez

  • Reliez Valley Road to Lafayette

  • CA-24 through Orinda

  • Skyline Boulevard and Grizzly Peak Boulevard, high point ~1,470 ft

  • Tunnel Road into Berkeley

  • I-80 / San Pablo Avenue through Richmond, Pinole, Hercules, Rodeo

Gallery

Ride photos coming soon

Not starting in Napa? No problem. Every Two Wheel Touring GPX is a loop that begins and ends at First & Main in downtown Napa, but you don't have to. Join the line wherever it's closest to you, ride any section you like, or flip the whole thing and run it the other way. For step-by-step help in Garmin, REVER, Calimoto, Scenic, Google My Maps, and a free GPX editor, see Riding a route from your own start.

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