“I said, ‘Well, the city’s not going to do this,'” Siegel remembers. “I called all the people I knew \u2026 and said, ‘Who wants to join me in making this happen? ‘ In less than a year and a half, and with $600, we had a 17-mile trail.”<\/p>\n
After the Crosstown Trail became a bucket list item, the 15-mile Double Cross <\/a>launched in 2024 from Fort Funston to Pier 23 (which, along with the original, forms a giant X across the city). Last year marked the arrival of the 38-mile Roundabout<\/a> loop along the perimeter of San Francisco. This month organizers are promoting the most inclusive project yet: Walktober, a full calendar<\/a> of hill climbs, art walks, pub crawls and history tours with something for every walker in the city.<\/p>\n At the center of it all is Siegel, an 86-year-old former City College instructor whose retirement in 2003 was the beginning of a new journey. He had unflagging energy, a lot of free time and an ambitious yet straightforward goal: Build “instant urban trails,” get San Franciscans walking, and watch them fall in love with the city again.<\/p>\n All it takes is a lot of friends. And a few simple rules.<\/p>\n The Hunters Point gantry crane, as seen from Sunrise Point near Candlestick Point, is among the views on the Crosstown Trail, launched in 2019. (Jessica Christian\/S.F. Chronicle)<\/p>\n Don’t call it a hike.<\/p>\n For such a genial, enthusiastic, golden retriever of a man, Bob Siegel has a lot of instructions. His voice is in my head as I write this, reminding me to get the terminology right.<\/p>\n That’s Bob the teacher, raised in New Jersey and a former Peace Corps volunteer who was fluent in four languages and once spoke Swahili and spent 23 years teaching English to immigrants at City College’s Chinatown campus. Words have meaning. And a walk is not a hike.\u00a0<\/p>\n “Because if you’re a walker, all you need is your feet and shoes,” Siegel says. “You don’t need hiking boots. You don’t have to have a wide brim hat. Put on a baseball cap and go.”<\/p>\n Siegel had a lot of gas left in the tank when he retired at age 63. He could have traveled the world, visited every ballpark in America, or settled in a good easy chair to sample the region’s IPAs. Instead he started volunteering to build and maintain the city’s trails, eventually joining the Bay Area Ridge Trail board to help shepherd that 550-mile loop<\/a>, removing some asphalt and adding some dirt.<\/p>\n That’s where he embraced the maxim about forgiveness and permission, negotiating with seven different land managers who had seven different sets of rules. After the Crosstown Trail concept started with environmental nonprofit Nature in the City founder Pete Brastow and Sutro Stewards cofounder Craig Dawson, Siegel urged the growing team gathering in his Mission District living room to forego physical signage and rely on apps and easy-to-print maps for navigation.\u00a0<\/p>\n When he started meeting with parks officials and board members who oversaw the land, their response to his don’t ask, just tell policy was a surprise: They seemed relieved to speed past the red tape. A Candlestick Point State Recreation Area steward gave him a three-hour tour, helping choose the best path. He worried how Presidio officials would respond. They seemed thrilled.\u00a0<\/p>\n “I said, ‘We’re coming through the Presidio Trust, and I just wanted to let you know,'” Siegel says. “I remember there was one woman who said, ‘Who are you guys?’ And then she said, ‘This is wonderful!'”\u00a0<\/p>\n The Crosstown Trail cuts through Strawberry Hill in Golden Gate Park. (Salgu Wissmath\/S.F. Chronicle)<\/p>\n Meet people over coffee.<\/p>\n Karen Rhodes remembers her first sit-down at a cafe with Siegel, who often shows up to meetings in his powder blue Crosstown Trail T-shirt and a worn Crosstown hat. Rhodes had recently retired from a communications job at UC\u00a0Berkeley, and when she hit the sidewalk after that Bob talk, she had a new job working on advocacy for the Crosstown Trail. She wasn’t quite sure what hit her.\u00a0<\/p>\n “This is what he does,” Rhodes says, smiling at the memory. “Once he figures out that you’re a candidate for getting roped into one of his crazy ideas, he invites you out for coffee and listens. Then he picks up on what you’re passionate about, and just lets you run with it. And he kind of puts you on the spot, as if you’ve already decided to do the thing.”<\/p>\n Confronted with this, Siegel gives an impish laugh, denying nothing.<\/p>\n “I say, ‘Let’s get together in person for coffee,'” Siegel says. “You’ve got to look them straight in the eye and see who they are. And let them see who you are.”<\/p>\n The results are undeniable. The Crosstown Trail leadership is an eclectic “Oceans 11” group with well-honed skills, including expert mapmaker Ben Pease<\/a>, the SF Urban Riders mountain biking group and Marcus Brandford, who leads the group that fine-tunes the site and its essential point-by-point navigation. Siegel’s late wife, artist Pat Koren<\/a>, designed the logo. The trail launched on June 1, 2019, National Trails Day, with a media blitz including a rave by Chronicle columnist Carl Nolte<\/a> and a glowing New York Times feature<\/a>.<\/p>\n Then a worldwide pandemic hit, and the worst thing for the city became the best thing for the route across it. The Bay Area was full of people with time on their hands, looking for COVID-safe outdoor experiences. Seventeen miles of San Francisco beckoned – from lush and surprising Visitacion Valley Greenway<\/a>, to the striking vistas of Grandview Park<\/a>, to the magic-trick reveal of the Golden Gate Bridge as walkers descend toward Baker Beach.<\/p>\n Grandview Park in the Inner Sunset, part of the Crosstown Trail, offers stunning views of San Francisco and the Pacific Ocean. (Salgu Wissmath\/S.F. Chronicle)<\/p>\n Strike up conversations with everyone.<\/p>\n Can a trail go viral? That’s the best description for what happened to the Crosstown Trail in 2020. Organizers have never measured traffic with a hand-clicker, but walking, working on the trails and monitoring web visits, they noticed the sharp uptick.\u00a0<\/p>\n “You never know with these things,” says Matthew Blain, chair of the SF Urban Riders and an early Siegel ally working on the Laguna Honda Community Trail Project,<\/a> which became the last missing link and one of the best surprises of the trail.\u00a0<\/p>\n “Is it just a short trend? And then two years later everyone is eating cupcakes or something instead of walking across the city. That was the surprise. Every year, we’re realizing, ‘Holy s-, it’s even bigger now.'”<\/p>\n Siegel celebrated the success. But mostly he saw focus groups.\u00a0<\/p>\n During an hourlong interview near the Burnside Steps in Glen Park<\/a> along the route, Siegel engaged nearly everyone who passed in conversation. An elementary school teacher collecting flowers for bookmarks, who has walked both the original trail and the Double Cross, gets a business card and an invite to Walktober. A group of walkers on a trek to Glen Canyon Park hadn’t heard of the Crosstown Trail, but they know it now.\u00a0\u00a0\u00a0<\/p>\n By the time pandemic restrictions lifted in 2021, the trail was a bona fide sensation. Siegel engaged in a new round of media interviews<\/a>. Now in his 80s, he’d offer to walk the entire trail with journalists, no advance notice required.\u00a0<\/p>\n Rhodes said she and Siegel would walk northwest to southeast, in reverse, so he could meet more passersby.<\/p>\n “And our palms are getting tired, high-fiving all these folks,” Rhodes says. “It has become a bucket list thing. Gotta do the Crosstown Trail. Gotta do the Double Cross. People are doing the 38-mile Roundabout in one frickin’ day.”\u00a0<\/p>\n A BART train passes over tennis and basketball courts at Cayuga Park Playground, part of a hiking perimeter adjacent to the Crosstown Trail. (Jessica Christian\/S.F. Chronicle)<\/p>\n Keep moving forward.<\/p>\n Two years ago I led a group of Chronicle readers on the Double Cross<\/a>, an eight-hour trek across San Francisco. I was wiped out by the end, but\u00a0Siegel seemed unfazed, likely adding another couple miles traversing our pack to meet new friends and make sure all 45 people (and two dogs) stayed together.<\/p>\n Every time I’ve run into Siegel since, I check for some sign of him slowing down. I haven’t seen it yet, but he acknowledges he hasn’t done the full Crosstown walk in more than a year. A recent bike accident led to a fractured collarbone. Today, I’m seeing a side of Siegel that’s new: caution.\u00a0<\/p>\n And yet his fire hasn’t dimmed. He calls his Crosstown Trail years “a second birth of some kind.”\u00a0<\/p>\n “If you have interests and you’re in good health, and good health is the important thing, then retirement is an opportunity,” Siegel says.<\/p>\n Asked why he focused on San Francisco, when the whole world was out there, Siegel rejects the premise. Why go to Mount Tamalpais or Yosemite, he says, when you can “get your jollies here?” After all, San Francisco is so full of sights old and new, not even Bob Siegel could possibly see it all.<\/p>\n Bob Siegel, 86, launched the Crosstown Trail, which bisects San Francisco diagonally from Candlestick Point to Lands End, as a retirement project. (Jessica Christian\/S.F. Chronicle)<\/p>\n This month, hundreds of people will join Walktober groups discovering neighborhoods, parks and peaks throughout the city. There’s more than a walk a day on the event calendar<\/a>, and Siegel knows there will be even more in 2027. Most walkers won’t know they have Siegel to thank for the Crosstown Trail and the movement it created. But he’ll be on the trail for as many walks as he can take. Making new friends. Getting new ideas. Putting one foot in front of the other.<\/p>\n “We didn’t know this was going to take off like it did,” Siegel says, walking the last few blocks of the trail before we part ways. “Who would have thought it?”<\/p>\n Subscribe<\/p>\n There’s more to San Francisco with the Chronicle. Subscribe today for just 25\u00a2.<\/a><\/p>\n![\"The](\"https:\/\/www.newsbeep.com\/us-ca\/wp-content\/uploads\/2026\/10\/https:\/\/media.zenfs.com\/en\/san_francisco_chronicle_hearst_178\/bde4defc94d493984fd8f942b432a262.jpg\"\/)
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