SF Resident Built Citywide Walking Trails on a Budget
The 17-mile Crosstown Trail launched in 2019 and grew to include the 38-mile Roundabout loop by 2025.
Updated on Oct. 4, 2026 in Hiking
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San Franciscans now have a network of walking trails designed to help them rediscover the city, created by 86-year-old retired City College instructor Bob Siegel. Siegel launched the project in 2019 with the original 17-mile Crosstown Trail, which was built for less than $600.
Why it matters
These trails encourage residents to explore diverse neighborhoods beyond typical tourist hubs by using accessible, volunteer-led navigation tools. The project relies on community engagement rather than physical signage to keep costs low and build local connections.
The original Crosstown Trail cost under $600 to build and covers 17 miles, while the recently added Roundabout loop extends 38 miles. Organizers continue to scale operations with future events expected in 2027.
The players
Bob Siegel
An 86-year-old retired City College instructor who founded the Crosstown Trail network.
The details
Rather than installing permanent infrastructure like signs, the organizers use digital maps and apps to guide walkers from endpoints like Lands End to Candlestick Point. Leadership recruits new volunteers informally, often meeting potential contributors for coffee to discuss the trail network. The routes pass through significant areas including the Presidio and Glen Park, where hikers can navigate the Burnside Steps.
Timeline
2003: Bob Siegel retired from City College.
June 1, 2019: The Crosstown Trail officially launched.
2024: The 15-mile Double Cross trail launched.
2025: The 38-mile Roundabout loop arrived.
October 2026: Walktober events occur.
Across the Bay
While the 550-mile Bay Area Ridge Trail connects broad regional ridgelines, this urban trail system focuses on walking city streets and neighborhoods. It represents a shift toward low-cost, community-managed infrastructure that relies on digital maps instead of physical trail markers.
If you plan to walk the trails this October, you can join group events or use the provided digital maps to navigate routes like the Double Cross, which stretches from Fort Funston to Pier 23. You can find detailed maps online to plan your weekend route through local neighborhoods.
The takeaway
The Crosstown Trail proves that meaningful civic improvements can be built with minimal funding through community coordination. Keep an eye on local volunteer announcements to see how you can help maintain these routes or participate in upcoming 2027 expansion events.
What happens next
Residents interested in organized group walks can look for events throughout October 2026 during the scheduled Walktober program.
Further reading
For more ways to explore the city on foot, browse our guide to San Francisco hiking.
Source note: This article includes information reported by San Francisco Chronicle.
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