Running Every Single Street in San Francisco with Rickey Gates

30 Sep 2025 · 31 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Podcast Episode Summary: Running Every Single Street in San Francisco with Rickey Gates

Podcast Information

  • Title: Wild Ideas Worth Living
  • Host: Shelby Stanger
  • Guest: Rickey Gates
  • Episode Title: Running Every Single Street in San Francisco
  • Description: In this episode, professional athlete Rickey Gates shares his unique approach to exploration through running, discussing his adventures ranging from running across America to tackling every street in San Francisco and his current project involving 50 classic trails across North America.

Key Concepts and Discussions

Rickey Gates

An Overview

  • Background: Professional athlete and endurance runner with a passion for exploring on foot.
  • Past Achievements:
  • Ran 3,700 miles across America in 2017.
  • Completed every street in San Francisco in 2018.
  • Currently working on identifying and running 50 classic trails across North America.

Exploration Through Running

  • Philosophy: Gates sees running not just as a sport but as a means to explore, connect with nature, and understand communities.
  • Personal Connection: Discusses how running quieted his mind and allowed deeper self-discovery and connection with the environment.

Early Inspirations

  • Childhood: Growing up in Aspen, Colorado, Gates was introduced to trails and nature, which shaped his love for running.
  • Wild Ideas: His adventurous spirit was ignited during a gap year where he traveled extensively in South America and Italy.

Running Across America (2017)

  • Purpose: Aimed to explore the country and seek a deeper understanding of people and landscapes.
  • Journey Details:
  • Started in South Carolina and ended in San Francisco after 153 days.
  • Focused on meeting people and taking photographs rather than speed.
  • Encountered acts of kindness from strangers, reinforcing a belief in the goodness of humanity.

Running Every Street in San Francisco

  • Motivation: Wanted a project close to home after completing his run across America.
  • Execution:
  • Ran 1,173 miles of streets, which increased to about 1,350 miles due to backtracking.
  • Used maps to methodically cover neighborhoods, discovering hidden aspects of the city.
  • Documented experiences through photography and interviews, leading to a short film titled "Every Single Street."

Current Project

50 Classic Trails

  • Collaboration: Partnered with Jonji to run and document iconic trails across America.
  • Trail Selection: Each trail can be completed in a day by a strong runner, ranging from 17 to 94 miles.
  • Goals: To provide recommendations for must-see trails while exploring the history and ecology of each area.

Reflections on Adventure

  • Post-Adventure Blues: Discusses feelings of emptiness after completing major adventures and the search for new goals.
  • Desire for Connection: Emphasizes the importance of engaging with people directly, noting the overload of information in modern society.

Keys Takeaways

  • Mindfulness in Exploration: Encourages listeners to savor experiences through running and exploration.
  • Community Engagement: Highlights the power of human connection and kindness during adventures.
  • Wild Ideas: Advocates for pursuing personal wild ideas, emphasizing that adventure can lead to personal growth and fulfillment.

Conclusion Rickey Gates demonstrates through his experiences that exploration and adventure are not solely about distance but about the connections made and the insights gained along the way. His journey encourages others to embrace their wild ideas and explore the world around them.

Additional Resources

  • Rickey Gates Website: [rickeygates.com](https://www.rickeygates.com/)
  • Instagram: [@rickeygates](https://www.instagram.com/rickeygates)
  • Fifty Classic Trails: [Website](https://www.fiftyclassictrails.com/) and [Instagram](https://www.instagram.com/fiftyclassictrails/)

Call to Action Listeners are encouraged to follow the podcast for more inspiring stories and to reflect on their wild ideas worth living out.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:07Rickey Gates:Professional athlete Rickey Gates isn't your typical runner. While he started his career racing at an elite level, he's always dreamed of crossing huge landscapes at his own pace. Rickey is now making those dreams a reality. In 2017, he ran 3 ,700 miles across America. The following year, he spent a month and a half running every single street in San Francisco.

0:32Wild Ideas Worth Living Host:How many miles of streets are there in San Francisco? And I just Googled it right then and there, and it just came up immediately. 1 ,173 miles of street in San Francisco. I'm like, oh, that's like going from Denver to San Francisco on foot. That took me six weeks or seven weeks. I think I can do that here.

0:56Rickey Gates:Ricky completed that project almost seven years ago, and now he's taking on a new challenge, identifying and running 50 classic trails in North America. As with all of Ricky's endeavors, this wild idea is about more than the miles. It's a way for him to explore, connect, and see the world in a whole new light. I'm Shelby Stanger, and this is Wild Ideas Worth Living, an REI Co-op Studios production presented by Capital One and the REI Co-op MasterCard.

1:31Rickey Gates:Ricky Gates, welcome to Wild Ideas Worth Living. You are a man of many, many wild ideas. What about running Lord Yuan? You could have been a soccer player, you could have been a motorcycle rider, you could have done anything, but it seems like you're naturally good at running. Did your brothers and sisters run or was there just something about it that, I don't know, for me when I found running, it quieted my mind in a way that nothing else did. I think I was born with more energy than the average person and I had to burn it or it was a little destructive, but also I just loved what my mind did when I ran.

2:10Wild Ideas Worth Living Host:Yeah, I, so I think that like kind of going back to the early years for it is that it just like, I appreciated team sports, but like the solo aspect of running, the loneliness of the long distance runner, even though, you know, cross country is definitely a team sport. It really comes down to me, the individual and like pushing yourself and kind of going inside yourself in a way that I hadn't found with any other sport. And then part of, you know, the cross country program that I grew up in, in Aspen, Colorado, the coach that I had moved to Aspen from, I think, Pennsylvania, in order to be on the trails in Aspen.

3:01Wild Ideas Worth Living Host:He made sure that we were on the trails at least two runs a week. It was important to him to expose all these high schoolers that might not see those trails otherwise to their incredibly beautiful backyard. So that was really, to me, that was magical. It was getting out into the mountains, onto the trails, being one with nature, quieting my breath. And to this day, it's like the most important thing to me and, and, uh, looking back on 22 year old version of myself that, you know, would do a two hour run on a trail and not stop. Um, and the 44 year old version of myself does that same run and like takes a nap on the trail or like is seeing which birds are out there or like identifying flowers, you know, that, that same two hour run now takes me four hours, not cause I'm running that much slower, but because, you know, the curiosity just keeps getting deeper and deeper about the environment that I'm going into.

4:08Rickey Gates:I'm curious where your first big wild idea started. Like, what was it? Was it in college or was there something even before then?

4:17Wild Ideas Worth Living Host:Let's see. I guess it would be kind of in between high school and college, kind of the normal path for so many people is to immediately go on to college. I did exactly that before realizing that I was going to go completely into debt for many decades, paying for that education out of my own pocket. So I took two years off from school, and I traveled down to South America for five months, went to Italy for six weeks, came back to Aspen, worked what I still consider to be one of my favorite jobs that I've had in my life as a backcountry hut maintenance person during the wintertime and then went back to school.

5:06Wild Ideas Worth Living Host:But by that point, the travel bug had very much set in. And so I looked for a study abroad program that I could ride a motorcycle to. And I found one in Valparaiso, Chile, and rode my motorcycle from Aspen, Colorado to get to my first class on time. Wow. Yeah, I guess it's been going on a while.

5:30Rickey Gates:What is it about pursuing kind of these wild ideas that really lured you in and attracted? Was it knowing that you would grow or was it just like, oh, this sounds fun?

5:41Wild Ideas Worth Living Host:I think the very first one, it sounded fun going to South America for five months. And it was new and scary. and I wasn't too concerned about safety. I remember buying either three or four Lonely Planet guidebooks because the internet was... I was able to send emails back home, but it wasn't a source for where I was going to stay or anything like that while I was traveling around. This is Bolivia, Ecuador, Northern Chile, and Peru. and so I just kind of like put my trust in those books and just kind of went for it. The second trip, which was a few years later on the motorcycle going from Colorado to Chile, that one, there were a lot more unknowns.

6:36Wild Ideas Worth Living Host:So yeah, I would say that trip more than any other trip just put a lot of faith in myself and into adventure and to embracing the unknown. Like it's always going to work out some way or another and kind of getting rid of the fear factor there. Maybe not getting rid of it, but like acknowledging it and not succumbing to it became super important and really fueled a lot of adventure and crazy ideas that I had going forward from there.

7:14Rickey Gates:Riding his motorcycle from Colorado to Chile gave Ricky a taste for long-distance travel. He learned that he loves taking it slow, meandering through small towns, quiet back roads, and meeting new people along the way. Once he came back to the U.S., his life started to shift. He had taken a break from cross-country running during college, but once he graduated, he decided to return to the sport.

7:44Wild Ideas Worth Living Host:I entered my first mountain race, and I met a few people at the finish line that said, like, oh, you should maybe try mountain running. Like, there's the U.S. mountain running team, which I had never heard of before. They're like, go out to Mount Washington next year and try out for the team and see how you do. And that's kind of where the current path of running started for me.

8:09Rickey Gates:Ricky made the team and he spent the next few years competing around the world. Still, his fondness for open-ended adventures never went away. Eventually, it led him to a new wild idea, to run across America.

8:28Rickey Gates:Why did you decide to run across America in 2017?

8:32Wild Ideas Worth Living Host:So it had been in my mind for quite some time. I had also recognized that the desire to compete was waning. Of course, it's not a win or lose sport. We all compete for ourselves. But in reality, if you're pursuing an athletic career, and especially in a sport like mountain running or trail running, it is a win or lose sport. Like people aren't talking about who came in second place. At least they weren't a few years ago. They just talk about the winner. And I just wasn't really quite there anymore and didn't have the desire to chase that top spot on the podium. Um, and so my then girlfriend, now wife, Liz, uh, she was in grad school in Madison, Wisconsin, which left very little room for the relationship for our relationship.

9:32Wild Ideas Worth Living Host:Um, which is, which isn't to say that there was much negative about that other than that. Like I felt like I wanted to do my own sort of project. I had intended to do my run across the country regardless of how the election went that year in 2016. When the election went a direction that I didn't anticipate and a lot of my peers didn't anticipate, it just occurred to me that it was going to be a much more interesting run than I had originally thought. And I take an immense amount of joy in planning these trips. Like I don't lay out an entire route, but I do know kind of approximately where I want to go.

10:24Wild Ideas Worth Living Host:I wanted to start in the South because I'd spent very little time in the South. I think that it can be a rather misunderstood part of our country. I wanted to pursue as many trails, hiking trails as possible. And so I looked for as many trails that were kind of in an east-west trajectory. So I found a lot of trails that I was able to connect up. I know that through hiking trails, the Appalachian Trail, the Pacific Crest Trail, are becoming super popular. They have become popular. I think they're amazing. I think that going across the country is a similar sort of feat for those that are curious about people, curious about the diversity of ecosystems.

11:14Wild Ideas Worth Living Host:You know, I went across one, two, three, four, four mountain ranges and then several sub mountain ranges. The Great American Desert, you know, just so much out there that I was able to really dive into just based on the way I went about it.

11:34Rickey Gates:Ricky started his journey in South Carolina and ended in San Francisco five months later, running about a marathon a day for 153 days. All expenses for the trip came out of his own pocket, so he kept things minimal with just a sleeping bag, a thin sleeping pad, water, food, and a camera. As he ran, Ricky took photographs of the people he encountered. He also met up with a videographer at the beginning, middle, and end of his run. Together, they made a beautiful film called Transamericana. Aside from occasionally linking up with that cameraman, Ricky traveled completely alone. He wasn't focused on speed.

12:16Rickey Gates:His priority was to meet people and see the landscape.

12:24Rickey Gates:What did you learn about people?

12:27Wild Ideas Worth Living Host:Almost immediately, it occurred to me, like if you're feeling down on people or down on yourself, like a long walk will cure pretty much anything. So much kindness. People stopping by the side of the road, just checking up on me, like making sure that I had food, water, complete strangers inviting me into their house, giving me a shower, washing my clothes. I had one gentleman in Arkansas that stopped by the side of the road and he, he got out of the car. He had like a bandage around his arm. It, it, it appeared as though he'd just got out of the hospital. Um, and he comes over to me and says, uh, I don't, I don't know, uh, what your cause is, but I, I want to, I want to contribute.

13:26Wild Ideas Worth Living Host:and I'm like I don't I don't really have a cause uh he's like well I'm contributing and he pulled out his wallet and he literally like I saw his wallet he pulled out every bit of cash that was in his wallet and handed it to me it was 160 and I I was like trying to give it back to him and he pointed to his uh the bandage on his arm and he's like you can see I've I've been somewhere but I just I just need to do this and I'm like all right like and then so I took the money from him. Yeah, just even seven years later, I just think about that guy.

14:04Rickey Gates:You're gonna make me cry, Ricky, that is so sweet. Like people really are good. And it sounds like what you learned from crossing the country is that, you know, we have different views, but I think most of us are kind and want the same thing.

14:20Wild Ideas Worth Living Host:Yeah. And it's, it feels important to me again, And I do think that we need to stay informed about what's happening around the world. But I also recognize that we have never had as much access to information in the entirety of human history as we do right now. And that it's okay to kind of turn that dial down a little bit and receive a little bit less information and go talk to people one-on-one. And I was exposed to that before, but I never felt it as intensely as I did during my run across the country.

15:14Rickey Gates:On August 1st, 2017, Ricky finished his journey across the country in San Francisco. Though it was the end of this wild idea, in many ways, Ricky's grand running projects were just getting started.

15:43Rickey Gates:runner ricky gates takes on projects that are less about speed or miles and more about places he goes and people he meets after a stint as a competitive trail runner ricky turned to a different kind of adventure, running 3 ,700 miles across the U.S. in 2017. That journey turned out to be the beginning of Ricky's unique project-based runs, epic adventures that often last more than a month and require extensive planning.

16:17Rickey Gates:So how soon after you ran across America did you have this other wild idea, which was to run every single street in San Francisco.

16:27Wild Ideas Worth Living Host:So finished in 2017. Yeah, the finishing a journey like that, like without question, opens up a massive void in what my purpose was. Oh, yeah.

16:45Rickey Gates:We talk a lot about this on the podcast. I mean, not enough people talk about these post-adventure blues, but they're real.

16:52Wild Ideas Worth Living Host:They're very real. And like the very next day after finishing my run across the country, just kind of like, you know, psyched to be done. But I was wearing normal clothes again at that point. And I just walked into a store and like, no one's looking at me here. Like, you know, something's been kind of taken away from me or something's missing. and so it was you know I came to terms with that but also just recognized like I had more in me I knew what my body was capable of I knew what my mind was capable of and I knew that I wanted to do an adventure that was sort of similar to what I had just done but I didn't want to leave my girlfriend for, you know, another month or two months, you know, I wanted to find an adventure close to home.

17:46Wild Ideas Worth Living Host:And being that we were living in San Francisco at the time, I just like, I don't like, yeah, wild ideas. Where did this one come from? I have no idea. But I had this question, how many miles of streets are there in San Francisco? But I just googled it right then in there and it just came up immediately 1173 miles of street in San Francisco I'm like oh that's like going from Denver to San Francisco on foot like that took me six weeks or seven weeks like I think I can do that here and so then the planning it just went off from there like had anyone ever done this before I'd learned about a guy that had done all the streets in San Francisco over a seven-year period.

18:31Wild Ideas Worth Living Host:And I tried reaching out to him, couldn't get a hold of him, but he had left some articles around, and it just looked really cool. And I started looking at all the neighborhoods in the city. I'd lived there for six years at that point, all the neighborhoods in the city that I'd never even set foot in. And it just occurred to me that there was so much about this city that I had the opportunity to get to know in a similar way that I had just gone across the country, uh, that I am like, all right, I'm going to run every single street in San Francisco. Um, I don't know how this is going to go, but I, uh, I had a four of the very small Ford transit van and, uh, I'm like, all right, I'm just going to plant myself out of the van and treat this like a proper mission and set off, I think it was the day after Halloween from the Golden Gate Bridge and moved very methodically throughout the entire city, neighborhood by neighborhood, covering about 30 to 35 miles a day and printout maps.

19:44Wild Ideas Worth Living Host:It was easier for me at the time to just kind of use printout maps and covered every street in San Francisco. It was, yeah, it was amazing.

19:55Rickey Gates:So when you cover every street in San Francisco, you have to backtrack. Like you can't just do every street once. Like you have, it's a maze. So you have to go backwards and then forward and then backward and forward. So you end up running a couple of streets twice. It seems like it was a bit of a math problem.

20:10Wild Ideas Worth Living Host:Yeah. Let's see. The math problem is called the postman problem. And it's, It is an actual math problem. So if you can imagine a postman going from door to door, you know, they are going to cover every single street and there's inherent redundancy. So that 1100 miles ended up being more like 1350 miles, an additional 200 miles of streets of just backtracking in order to cover all the streets.

20:46Rickey Gates:It took Ricky 46 days to run every street in San Francisco. Along the way, he saw new parts of the city that had been the backdrop of his life for the past six years. Each day, he ran for about 11 hours. And several times a week, he spent the night in his van in the city, which made it easy for him to pick up where he left off the previous day.

21:10Rickey Gates:What did you notice as you ran through the city that most people miss?

Read the full transcript

21:14Wild Ideas Worth Living Host:oh so much uh wonderful graffiti and very small graffiti like in particular like I started paying attention to they're called water plate covers um they're the size of a coaster that you would set your beer down on and they're on these sidewalks they're on every single sidewalk and I had never I'd never seen them before never really paid attention and then I started paying attention and recognize that nearly every single one of them has a very small tag on them written in white out. And so like I imagined like someone probably shoplifting a white out pen from from your the the office office max or wherever, and like literally getting on your knees to write your little tag in tiny little letters on this little water plate that 99.9 % of people are not even going to see.

22:18Wild Ideas Worth Living Host:But it's just kind of like this fulfilling this desire to be seen in the city, even if it's being seen by your own eyes, you know, going by that water plate the next day and like, yep, there's me. Like I was here. So I just started like, for me, it became a scavenger hunt through the entire city. Oh, gosh, what other little things there? I from for that project, it was much more challenging for me to approach people and get portraits of them. I found that not having, you know, I call it a costume, not having the costume that I was wearing while running across the country, and the nature of just being in a city.

23:09Wild Ideas Worth Living Host:People were more standoffish, less easy to, you know, strike up a conversation with. But I did get quite a few portraits of people out there, you know, just kind of explaining to people what I was doing. A lot of people just not really believing it and shrugging it off. But yeah, you can get a lot out of just being in a neighborhood for an entire day. And some of those neighborhoods being as big as they are several days, just absorbing the vibe, the feeling of that place.

23:52Rickey Gates:along with the portraits ricky also recorded interviews with folks he met as he ran both are featured in a short film about his project titled every single street ricky's storytelling has attracted partnerships with different outdoor brands solomon sponsored his early films and now he's on janji's field team in fact ricky's current project running the 50 classic trails of america came about through his connection to the brand.

24:23Wild Ideas Worth Living Host:John G. actually learned about this project that I have been thinking about and talking about for over a decade, the 50 Classic Trails of America, that I had never really gotten off the ground. And they approached me and said, like, this is a really cool idea. let's let's work together on this and we'll support you on on these 50 trails um three months into working on the project uh the co-founder of of the company sent me a text message and he's like hey do you know these guys uh Andy Cochran or Ian McClellan and I'm like no he's like oh well um they're also working on a project called the 50 classic trails of America and I'm like oh no and And he's like, do you want to meet them?

25:13Wild Ideas Worth Living Host:And I'm like, I guess I was hesitant about it. All of these things like I've just done on my own and like I was determined to do this one on my own. And so we got a Zoom call together, me and these two other guys, and compared notes and just recognized that our projects were nearly identical. And we just agreed to work together on this project.

25:39Rickey Gates:When are you going to start and which are the 50 classic trails?

25:44Wild Ideas Worth Living Host:So the list is our list, and it's based on the parameters that we agreed on. And to differentiate, these trails can all be done in a single day by a strong person. So our shortest trail is 17 or so miles. our longest trail is the Wonderland Trail 94 miles in Washington that goes around the base of Mount Rainier but the happy zone in there is like in the 25 to 40 mile range where you're not completing half of the trail at night time that you are enjoying it in its daylight hours I believe our tally right now is that we've run 37 or 38 of them. So it's a project that's very much happening right now as we speak.

26:41Rickey Gates:Wow, I didn't know that. That's awesome.

26:43Wild Ideas Worth Living Host:Yeah, and it's been super fun. Like, you know, whereas I was in years past training to make sure that I could, you know, finish on the podium in a race in a place where I knew nothing about or maybe didn't speak the language. Now I'm training a little bit more casually in order to be sure that I can cover 42 miles in the Southern Sierras in daylight hours. You know, the parameters for me are a lot more approachable and friendly on a trail that I'll spend literally hours and hours and hours finding as much material on that trail and on that region. who came before us, you know, settlers, native people, who built the trail, you know, what the geology of the trail is like.

27:36Wild Ideas Worth Living Host:So all of these things, it's just like this, this self-appointed goal of like being able to give a little TED talk about every single one of these trails that I'm doing. And in order to be able to say confidently, like, to a friend or to a stranger, like, oh, you've got a three-day weekend, like this is a bucket list trail. You can go across the country, do this trail, and you will not forget about it for the rest of your life.

28:06Rickey Gates:I love that. So you're just flying to these places, running them, going for it, or driving to some.

28:10Wild Ideas Worth Living Host:Yeah, flying, running to them, or yeah, driving to some of them. Yeah, there's, you know, it's the funnest part about our discussion is, you know, deciding which trails are on the list and which are off the list.

28:33Rickey Gates:All of your wild ideas seem to have this like methodical mathematical ring to them. Why do you think that is?

28:41Wild Ideas Worth Living Host:That's a good question. I, yeah, I suppose that's maybe how my brain works. I, like, I love numbers. There was a time I couldn't do it now, but there was a time that I could tell you the exact elevation of every peak that I'd ever climbed. I just loved it. I loved, you know, collecting baseball cards growing up. I knew the stats of the baseball players and some of their birthdays. Like, they would just go into my brain and just stick there. And, yeah, so, and if that's, for me, if that's what drew me into it was just numbers, then that's fine. You know, if that gets me out onto the trail, listening to birds and, you know, taking a nap in some aspen leaves in the fall, then whatever it takes.

29:37Rickey Gates:You can find both of the films about Ricky's big runs on YouTube and we'll link them up in our show notes. Ricky and his colleagues are also working on a book about the 50 classic trails in America, and Ricky's photography skills will be on full display. I can't wait to get my hands on it. To follow Ricky's adventures, you can follow him on Instagram at Ricky Gates or on his website, rickygates.com. That's R-I-C-K-E-Y-G-A-T-E-S. Wild Ideas Worth Living is part of the REI Podcast Network. It's hosted by me, Shelby Stanger, produced by Annie Fassler, Sylvia Thomas, and Sam Pierce Knitsberg of Puddle Creative.

30:22Rickey Gates:Our senior producers are Jenny Barber and Hannah Boyd. Our executive producers are Paolo Motula and Joe Crosby. As always, we love it when you follow the show, take time to rate it, and write a review wherever you listen. And remember, some of the best adventures happen when you follow your wildest ideas.

From the publisher

Rickey Gates is a professional athlete and endurance runner known for redefining what it means to explore on foot. After racing at an elite level, he ran 3,700 miles across America and later completed every street in San Francisco. Nearly seven years later, Rickey is tackling his latest challenge: identifying and running 50 Classic Trails across North America. His adventures go beyond distance—they are a way for him to explore, connect, and see the world in a whole new light.

Connect with Rickey: 

Take the 5-minute Listener Survey!

Thank you to our sponsors: 


Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

More from Wild Ideas Worth Living

All 68 episodes
Running Every Single Street in San Francisco with Rickey GatesWild Ideas Worth Living · 31 min
Listen in VO