Bob Siegel, 86, developed San Francisco’s 17-mile Crosstown Trail, a walking route from Candlestick Point to Lands End. It opened in 2019 and has no signs or paid staff.

Siegel, a former City College of San Francisco instructor, began working on local trails after retiring in 2003. He recalled recruiting friends to help establish the Crosstown Trail in less than a year and a half for $600.

Other walking routes have since appeared across the city. The 15-mile Double Cross, from Fort Funston to Pier 23, launched in 2024; the 38-mile Roundabout traces the city’s perimeter. Organizers are promoting Walktober this month, with walks that include hill climbs, art outings and history tours.