This story aired in the March 11, 2025 episode of Crosscurrents.
If I were to describe San Francisco to you, you might imagine a picturesque scene of cable cars and iconic landmarks against steep hills and a sparkling Bay backdrop.
But even if you know this town like the back of your hand, it still has plenty of surprises to offer us. The Crosstown Trail offers up a lot of those opportunities for charm and whimsy. It’s a 17 mile walk from Candlestick Point to Land’s End.
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Story Transcript:
Sound of zipper
REPORTER: I thought I’d be hiking the Crosstown Trail before dawn, but I slept through my alarm and didn’t set out from Candlestick Point until 10:30.
Sound of footsteps
REPORTER: Before long, things get complicated.
REPORTER IN FIELD: I have just reached mile one. The zipper of my very cool secondhand cargo pants broke off. So my fly is going to be down for the next 16 or so miles, which is really classy.
REPORTER: I’m new to San Francisco, I’ve only been here a few months.
REPORTER IN FIELD: I’ve reached John Mclaren Park. I’ve never been here.
REPORTER: Even though I grew up in the Bay, trying to restart here as an adult after living on the East Coast for seven years has been isolating. I heard this trail was 17 miles long and thought, “This could be a good way to get out of my room, but also just get out of my head.”
REPORTER IN FIELD: There's an engraved plaque with this quote from Barry Lopez’s, Arctic Dreams, 1986. It says, “The perceptions of any people wash over the land like a flood, leaving ideas hung up in the brush like pieces of damp paper to be collected and deciphered. No one can tell the whole story.”
Sound of footsteps
REPORTER: The day before my walk, I get coffee with Bob Siegel. He’s the force behind the Crosstown Trail.
BOB SIEGEL: A little bit of cream, no sugar. I’ve never been enamored with cars, you know, if you go by car then you don't see anything but nonsense in a way…
REPORTER: Bob grew up in New Jersey, before spending some time in the Peace Corps in Africa and moving to San Francisco in the 1970’s. He taught at City College in Chinatown and retired 20 years ago. Bob is always moving: walking, biking, and designing trails.
SIEGEL: If you bicycle you see more but when walking you can stop and you can communicate with people, or if you see something interesting, just keep, keep looking at it. I just find walking in the city fascinating. I think some of my better thoughts are when I'm walking.
REPORTER: The Crosstown Trail was dreamt up by a small group of outdoor enthusiasts. (Bob credits three people in particular: Peter Brastow, previous head of Nature In The City, Craig Dawson, founding member of Sutro Stewards, and cartographer Ben Pease, who designed the trail’s map.) They wanted to make a diagonal path across the city.
Since it went public in 2018, The New York Times did a piece on the trail. So did National Geographic. Other cities have followed San Francisco’s example: there’s now a 27-mile urban trail through Boston. Bob’s vision was to get locals off the beaten path, to shake up their perspective on a town they thought they knew.
REPORTER IN FIELD: I'm almost two and a half miles in. I just stopped at Mission Blue Cafe.
Sound of door
REPORTER: This cafe in Visitacion Valley is a well-known stop on the trail. They even sell merch, like hats and patches with the trail logo. (The logo is designed by Bob’s wife, artist Pat Koren.) Next to it all is Bob’s Venmo username. He says profits either go right back to the trail, for things like signposts, or giving back to youth groups and green spaces. I buy a hat and leave Bob a note in my Venmo payment, just saying “Hi” and “thank you” before I continue walking.
REPORTER IN FIELD: I'm on, oh, 4.44 miles. That's gotta count for something. I just passed the Oxbridge Market* in Excelsior, and I think I'm gonna walk back because I want a sandwich. Not right now, but I'll order it and keep it in my bag and Just know that I have it and that'll power me to keep going, you know?
Sound of ordering sandwich
REPORTER: When I was planning my move back to California, I had such a romantic vision of it. I was imagining camping all the time, and surfing, and going fishing. Essentially just becoming a different person. Right when I moved here, I tried to have a bonfire on the beach. I went to the store, and there was no wood left, and then there was no parking on the beach. Reality was different, it was disappointing. I was depressed. I was having a hard time leaving the house. I felt totally disconnected from my surroundings. I think I was, in a way, surprised that my full range of moods came 3,000 miles along with me. I thought the scenery and the fresh start were supposed to transform me. When they didn’t, I thought, “What the hell?”
REPORTER IN FIELD: Oh, speaking of, I just took a completely wrong turn a ways back, so now I'm turning around.
REPORTER: The trail does me this sort of magical favor, by handing me a structured mission, like “Here. Do this. I dare you.” Accomplishment in the most primal sense. It demands that you stay present. It demands one foot in front of the other. It’s intensely grounding.
Sound of footsteps
REPORTER IN FIELD: What makes the trail interesting is how uninteresting certain parts are. The sightseeing buses aren’t passing through many of these neighborhoods. And because of that, they’re so fresh to me. Reality is more interesting than fantasy. Maybe the grocery store being out of wood is a better story than the perfect beach bonfire.
Sound of traffic
REPORTER: Somewhere around mile five, I cross the Bernal Cut – It’s now known as San Jose Avenue, and it started as a railroad. Just afterwards, I dip into Glen Park’s Bird and Beckett -
Sound of bookstore
REPORTER: This bookstore is another well-known stop on the trail. It’s owned by Eric Whittington.
ERIC WHITTINGTON: Oh, 25 years ago there was a little store in this neighborhood that went up for sale because they couldn't quite figure out how to make money running a bookstore. So I've spent 25 years not making money running a bookstore. Yeah, if I got out of bed earlier, I would see a lot more hikers because I don't open the store until noon. But they come through all times of day.
REPORTER: I hike through the dense and brambly Glen Canyon at dusk, and then down through the woods that surround Laguna Honda Hospital, the Gold Rush almshouse and former asylum. The green area around the hospital used to be a dumping ground for bedpans, glass medicine bottles, and other medical garbage. It was known as “Bedpan Alley.” A biking group in the city called SF Urban Riders helped clean this area up and define the trail.
REPORTER IN FIELD: I’m getting philosophical, I just hit mile 10. The trail is, it's a line of communication in a way. This trail could last a really, really long time. And when you're doing it, you're kind of communing with the person who invented it or the people who've walked it before you. You arrive at these spots that other people have been to. And you're almost meeting them there. Even if they're not there at the same time. Am I starting to sound a little bit crazy?
REPORTER: I remember Bob telling me about a woman he met on the trail who walked it every day for a month. Seventeen miles a day. Every day. For a month. She was a doctor in the Bronx during COVID, where most of her patients died on her. She told Bob that walking the trail over and over again helped her work through her PTSD.
Sound of footsteps
REPORTER: By now, I’m walking in the dark.
REPORTER IN FIELD: My legs hurt. My feet hurt. My shoulders hurt from my backpack. It's all catching up to me.
REPORTER: That’s when I get a notification on my phone. Bob had commented on my Venmo payment from that morning.
REPORTER IN FIELD: He says “Hi Eliza. Thanks for your support of the SFCT. The fact that you bought the merch so late in the morning, I fear you are not going to reach Land's End today. But who cares, as long as you're digging the CT. Bob.” I was like, “I'm gonna have to stop. I have to stop early. I can't walk out to Land's End tonight in the dark.” And then I got that comment from Bob. And now I have to. What's a couple more steps?
REPORTER: And I keep on walking, right through Golden Gate Park and into the Richmond District.
Sound of bar
REPORTER: I stop at a bar to rest and meet Gerard, sitting on the stool next to me. He’s giggling with the bartender and sipping a pint, and tells me he moved to San Francisco from Ireland in the 1980s.
REPORTER IN FIELD: Would you walk 17 miles through San Francisco?
GERARD TYNAN: Ah, no. What, to walk around just looking at the scenery, or? Would it be something better to look at, like? You want to walk down the road in front of me?
REPORTER: Bartender Signey Swanson hasn’t heard of the trail either, but she seems to embody the point of it.
SIGNEY SWANSON: The news says all these bad things about San Francisco, right, or only shows like one part, but I've met some really great, genuine people here, and if you don't find them, you just keep meeting more people until you find them.
Sound of footsteps
REPORTER: When I reach the entrance to Land’s End, around 8:30 PM, I have to use my flashlight to read the sign, and I can hear waves crashing.
Sound of crashing surf, footsteps
REPORTER IN FIELD: It got really spooky and I thought I heard something, and I couldn't stop thinking about someone jumping out at me. It's really dark. So let's see. I am 16.54 miles into the 16.9 mile San Francisco Crosstown Trail, and I'm turning around. Does this make me a fraud? I'll go back in another time. I promise I will.
REPORTER: There’s no ceremony at the end of it all. Standing in the dark, brainstorming the quickest way home, I couldn’t process how far I’d come.
But in the coming days, pieces of it come back to me in flashes, whole neighborhoods I’d walked through and forgotten about, as if the day was still downloading in my brain. I was building a new mental image of my town, a new map. Everything felt within reach. Everything felt interesting. A switch flipped, and it’s still on.
*Correction: An earlier version of this story referred to the Hillcrest Market in Portola. It is now called the Oxbridge Market.
