Skyline Boulevard (or California State Route 35) runs from highway 17 in the Santa Cruz Mountains to Daly City, just south of San Francisco. I’ve always felt inspired while driving along Skyline: the views are breathtaking, and you pass countless trailheads along the way… it feels like a trail runner’s paradise.
I’ve had some epic adventures from Skyline trails, yet I still feel I haven’t scratched the surface of what’s out there.
In time, I’d love to run from each of these trailheads, and I’m holding myself accountable (and getting organized) by creating a list of them here. So this is my “Skyline Project”, mapping out and running the best Santa Cruz Mountain trails along SR 35/Skyline Bvld.
One of the very first trailheads on Skyline is John Nicholas Trail in Los Gatos. It seems fitting that I’d start with my namesake trail.
I will update this post with links to each activity as I cross them off the list, as well as any notable trails / discoveries along the way!
Trailheads on Skyline Blvd SR-35 (from south to north):
- Bear Creek Redwoods Open Space Preserve
- Sanborn-Skyline County Park
- Castle Rock State Park
- Saratoga Gap Open Space Preserve
- Long Ridge Open Space Preserve
- Skyline Ridge Open Space Preserve
- Monte Bello Open Space Preserve
- Coal Creek Open Space Preserve
- Russian Ridge Open Space Preserve
- Windy Hill Open Space Preserve
- La Honda Creek Open Space Preserve
- Wunderlich County Park
- El Corte de Madera Creek Open Space Preserve
- Huddart County Park
- Purisima Creek Redwoods Open Space Preserve
- Miramontes Ridge Open Space Preserve (as of November 2025, this is closed)
I’d love to hear from anyone else who has done this (or aspired to do it), and whether I’m missing any trailheads or important details.
demTICKSdoe
I don’t know why jiglet.net randomly popped into my head tonight. Glad to see you’re doing well after all these years!
John
I’m glad it did. Still alive and kicking. Good to hear from ya my man. Thanks for checking in!