The Beauty And Boredom Of 500 Laps Around The Same .148-Mile Loop

Ladd’s Addition is one of the oldest residential developments in Portland, Ore. It is a big square anomaly in the middle of Southeast Portland’s standard grid formation, bordered by historic Hawthorne Boulevard on the north, SE 20th Street on the east, SE Division Street on the south, and SE 12th Street on the west, not far from the Willamette River. In the middle of the square sits Ladd’s Circle Park and its large rose garden. On a map, the roundabout and the four parallel streets leading into it form an X that makes the odd little sub-neighborhood easy to find; on the ground, the neighborhood stands out for the massive green canopy created by the over 250 elms lining its streets. There are some old Portland houses, a few small apartment buildings, several churches, and a single cafe called Floyd’s Coffee House and Wine Bar. 

For the last eight years, with a break during the height of the pandemic, the roundabout in the middle of Ladd’s Addition has played host to the Ladds 500, a relay that floods the roundabout with bicycles. Those bikes and their riders turn left for hours and hours at a time, racing toward 500 total laps around Ladd Circle Park.

A man on a bike during the Ladd's 500 relay in April 2024.
Photo: Corbin Smith

This year’s edition, held on Saturday, April 13, was by far the most heavily attended in the history of the event. My source for this claim was every single person I spoke to who had been at any previous iteration. We witnessed: thousands of cyclists, a grip of rollerbladers, skateboarders getting hauled around by cyclists, lookie-loos and reporters like myself, local politicians looking to swap a little palm grease, grillers, chillers, public drinkers, people handing out hot dogs and ice cream to passing riders, a man who appeared to be handing out psychedelic mushrooms to passing riders, more penny-farthings than one cares to remember, a bike that appeared to be more accurately two halves of a bike sawed and then rejoined by a gigantic spring, a boy dressed as an avocado, children on those little bikes with no pedals trying to keep up with the hurricane of motion around them, a gigantic party-bike, a blue flag with a picture of a shrimp on it, a dog wearing goggles, one person who was operating a small moving karaoke station for six straight hours, unicyclists, people doing wheelies for multiple laps at a time, children vibing in backseats, and two separate Mario Kart-themed teams. (“I appreciate it,” a member of one team said of the other’s presence. “Because there were some characters that we missed.”) There was also a bunch of other shit that I couldn’t manage to chronicle if you gave me 20,000 words and a book deal. Some spills, nothing catastrophic. The weather was nice. 

A dog wearing goggles at the Ladd's 500 relay in Portland, Oregon.
Photo: Corbin Smith

“Portland has a specific kind of bike community that lends itself to events like the Ladds 500,” said Taylor Griggs, a reporter at the Portland Mercury. Portland, you may have heard, is a lovely place to ride. Some of that is structural: Unlike Seattle, which is a nightmare labyrinth of cliffs looming over the Puget Sound, Portland is relatively flat. Some of it is policy-oriented. No American city is like Copenhagen, Amsterdam, or other European cities that have given away as much road as possible to pedestrians and cyclists, but Portland really has tried to create an alternate city-wide infrastructure that serves the needs of non-drivers in the limited space that American highway culture allows. There are designated bike greenways that cut through neighborhoods; the Tilikum Crossing is a bridge that spans the Willamette and is completely closed off to cars; beautiful bike paths line the river; and there are bike lanes on major thoroughfares.

A woman on a bike who is not so much dressed as Toad from Mario Kart as she is just wearing the same kind of hat, at the Ladd's 500 relay in Portland in April of 2024.
Photo: Corbin Smith

Griggs has become an ace reporter on the lively bike scene that has sprouted from that fertile infrastructural soil. That scene pivots around Pedalpalooza, an online group calendar that promotes group rides in which orgies of cyclists riding in tandem fill streets and make them inhospitable to cars. Sometimes those events have fun themes, sometimes not. To ride them all the time is to be inducted into a sprawling, informal community, with its own lore, beefs, and rituals. 

“If you ride every day, you’ll have the same kind of encounters with people on a smaller scale,” Griggs told me. “You’ll see people who you’ve seen at Pedalpalooza rides. I think there’s opportunities for connection and magical experiences, even on an everyday basis.” A few people I spoke with described the Pedalpalooza scene as the main way they make friends in Portland. One lady named Martín told me about how she likes to hand out homemade banh mi sandwiches at rides she attends. She gave out 40 at Ladd’s that day. 

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A man on a bike wearing a Freddy Krueger "Follow Your Dreams" t-shirt at the Ladd's 500 relay in Portland in April of 2024.
Photo: Corbin Smith

The Ladds 500, which functions as a de facto kickoff for group ride season, is simultaneously the season’s strangest and most accessible ride. It’s scalable to whatever bicycle experience you bring—you can get with some friends, do as many laps as you’re comfortable with, hang out in the park or on the sidewalk, cop some free food from all the people around. Anyone can have a good time, but there’s also no way around the strangeness of this thing. Thousands of people riding in the same .148-mile loop for six straight hours is weird.

I attended without a bike, and the sensory experience was wild. It begins loud and enthusiastic. Everyone is HERE and PARTYING and all kinds of WILD STUFF is happening. As the day goes on, though, the laps drag and the energy settles into something slightly more sedate. There’s the sense of everyone realizing, at their own paces, that they are doing exercise. Music is pumped into the space from all over: the aforementioned karaoke bike, a big setup from a local radio station, various people’s speakers blasting what they want. The aural experience shifts depending on where you are in the circle; wherever that is, you will hear 10 or so different playlists bleeding in and out of each other. 

To sit and watch the bikes go by is deeply hypnotic. Someone you’ve never met rides by you, you register them in your mind just a little and then forget them, and then, 90 seconds later, they’re back again for a few seconds before exiting once more. Everyone moves in a big unceasing blob; it doesn’t turn so much as it undulates, at medium speed. Crossing from the street into the park in the middle of the ride feels perilous but really isn’t; people are generally polite and will slow down for on-foot crossers. Later in the day, the ride started to form these inexplicable clumps: a long stretch with very few people, right until a guy with a fat boombox on his rack blasting The Field heralded about 300 riders coming around the corner.

Absurdity inevitably breaks through. That was the founding principle, the one that guides the project to this day: “Let’s do something stupid.” Transcendent moments on a bike are the ones that feel like adventure. You finish climbing a hill and luxuriate in the view. You ride through a field on a clear day, no one in sight, the open sky punctured only by the mountains in the distance. You ride around a corner and see the environment change in a heartbeat: valley into river, city into country. To ride 70 miles in one circle, over and over, seems like a mockery of the spirit of cycling itself. But still it moves.

A little kid in a bike helmet and an inflatable avocado costume with a big pit on his tummy at the Ladd's 500 relay in Portland, in April of 2024.
Photo: Corbin Smith

The first-ever Ladds 500 was in 2016. “It was that brief period where Facebook was still useful for organizing events,” said David Barstow Robinson, the relay’s founder and executive director—“both ridiculous and accurate,” he said of the title, which he gave himself this year. “It was basically a glorified shitpost where I made the event, wrote ‘It’s spring, let’s do something stupid, 500 laps,’ etc., etc. That was the original pitch, and it remains essentially unchanged. I invited the people I rode bikes with at the time, the groups of people I went out and explored the city and had fun with. Enough people came out that it became a lot of fun. It was a time when I was starting to ride bikes farther than just kind of boppin’ around the city. For a while there I was doing ultra-distance races, and this was as I was kind of working towards that. It was a way to trick my friends into coming on a long ride with me.”

Barstow Robinson’s original intent for the event was that teams would ride one at a time until they reached 500 laps, a true relay. But he is not the sort of person to embrace rules, so that was discarded almost immediately. “Counting is bullshit,” he told me, a mantra that is a secondary motto for the event. “Folks maybe bend the rule about having one team member on the course at any given time, that’s one way it can go a little quicker. That’s the original way of cheating, actually. The Beligerantes, back at the very first one, were just grilling all day, and they were at, like, 150 laps as things were starting to wrap down. I went to them and I said ‘Are you guys gonna finish?’ They’re like an old, old Schwinn club in Portland. Then, they went out with eight or 12 people, side-by-side, on Schwinns and just racked out all their laps counting by 12 every time they went over the line. So that was when the ‘Laps are to be run consecutively, not concurrently rule’ was introduced, but also when the ‘Cheating will be tolerated if it’s funny’ rule came in.”

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A bulletin board at the Ladd's 500 relay in Portland, in April of 2024.
Photo: Corbin Smith

The organizers have to insure the event and book the park, but there is actually nothing they have to do to acquire exclusive use of the roundabout. “I permit the park,” Barstow Robinson said. “And the rules state that I am allowed to be in the park, and you are allowed to be on the road.” All four of the roads that feed into the Ladd’s roundabout are lined by stop signs, giving whoever is in the roundabout the right of way. When there are, for instance, hundreds of people in the roundabout, making it physically impossible for a car to enter the circle, this constitutes a de facto closure of the roundabout to car traffic. From a certain perspective, it can appear that the road has been taken from cars by force. 

A rider in the Ladd's 500 wearing a really intense drop-crotch onesie type thing and a rainbow wig.
Photo: Corbin Smith

To be in the world, or just online, at this moment is to see culture war in everything, so pardon me if that feels like a stretch. This is an event in Portland, which is a pretty nice place that is relentlessly portrayed as a hellhole by right-wing maniacs and local politicians serving the desires of the downtown landlords still feeling the squeeze of the new work-from-home paradigm. 

So how Portland is the Ladds 500? There are liberal-to-left signifiers everywhere, a little bit of drinking in public, people smoking weed here and there, even though children are present. From the perspective of someone so inclined, it looks like urban excess manifest, right down to these freaks commandeering the road so they can ride bicycles in a space that’s supposed to be for cars. Someone less reactionary might see it the same way, but with the polarity and emphases reversed such that it becomes something much sweeter. 

“When I see events like this, it’s like a radical denial of accepting that we have to live in a world of violent structures,” said Mitch Green, an economist running for Portland’s newly reformed city council. “Every day when you drive a car, when you’re moving around the city, you’re at risk of being mowed down by somebody who’s in a hurry in a truck that’s too large. This is a joyous statement that we’re just gonna kinda … take this space. That’s ours right now, and we’re gonna define our own rules.”

A blurry action shot of riders in the Ladd's 500 relay in Portland.
Photo: Corbin Smith

We can’t keep driving everywhere. Everyone knows this, even when they act like they don’t. One of the alternatives is cycling, which is healthy, carbon neutral, good for local air quality, and fun. The main problem is that it’s not always safe, especially when cyclists interact with cars, and especially in communities that don’t prioritize cycling and pedestrian infrastructure—which, in America, is pretty much every city. Portland has been on the cutting edge of this stuff, but the politics of American urban planning still impose an upper limit on what is possible

“It should be like this every Saturday,” said Aaron Kuehn of Bikeloud, a local cycling advocacy organization. “Everybody here looks like they feel safe, so riding a bicycle is safe, riding a bicycle is fun. It’s only not safe and not fun when there’s a bunch of cars on the road. If we had more streets that were dedicated to bicyclists, something like this could happen more often. But we don’t have that.” 

A tattooed man in black jeans and an orange safety vest riding a bike with the old-timey cruiser handlebars in the Ladd's 500 relay in Portland.
Photo: Corbin Smith

“I think bicyclists are pretty vulnerable people when they’re on their bikes.” said Tom Ulrich, a six-year participant in the ride. “It feels great. Portland is a great bike city, everyone comes here, they come together, you start to recognize people year after year.” I asked Tom the most laps he’s ever done in the relay. He said 50 or 60, then told me something strange: “There’s a slight hill. And it’s probably only five or 10 feet but when you start getting up to 30 or 40 laps, you start to really notice that there’s a slight incline and decline. Because it feels flat, but eventually you start to notice that it’s not totally flat.” 

A guy in a baseball hat does a wheelie in the Ladd's 500 relay in Portland.
Photo: Corbin Smith

What is it like to ride such an extraordinarily long distance, over such a notably short distance? Some people have done all 500 by themselves in the past: this year, the event was very crowded, making that prohibitively difficult. The highest individual total of anyone I spoke to was about 300 laps, which was 47 miles, according to the rider’s smartwatch. How does it feel to fight one’s physical limits in this repetitive space, to be in motion but not in transit for six hours at a time?

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“I have yet to complete my own event under my own rules,” Barstow Robinson told me. I asked him if this fact haunted him a little. “No.” he said. “I have a half Tilikum …” he corrected himself, “er, a half Everest on the Tilikum Bridge. I’ve done plenty of dumb things on bikes.” What is that, exactly? “Everesting is a… call it a challenge, that originated from some guys in Australia. The goal is to do a single bike ride, repeating a single climb, over and over, until you have ridden the cumulative height of Mount Everest. Turns out to be a daily substantial endeavor.” This makes sense, given that it corresponds to the highest mountain on Earth. “On a bike, yeah, it’s a machine, but climbing, descending, climbing descending, it’s a pretty substantial physical feat.”

A woman rides her bike in the Ladd's 500 in Portland.
Photo: Corbin Smith

“As an idiot,” Barstow Robinson continued, “I decided I was going to do that on the Tilikum Bridge.” Portland’s newest river-spanning bridge connects Downtown and Southeast Portland across the Willamette; it’s about 780 feet across its longest span, and rises. To attempt an Everest on a space so small involved crossing the bridge hundreds of times. A quick look at Robinson’s Strava entry for the ride shows these hundreds of small peaks and descents, one after another over the course of 15 hours, 29 minutes, and nine seconds. “At the time, I didn’t succeed,” he said. “And at the time they didn’t count half-Everests.” Eventually, they did, and so Robinson’s attempt was enshrined. 

I asked Barstow Robinson how he felt 12 hours into that experience. “Oh, it’s glorious,” he said. “It’s miserable, it’s all of the things. The nice thing about a bicycle is that it’s one of the last places where hard work actually translates into tangible results. You get out of it the effort you put in. For a period in my life, I was working as a messenger and pursuing this amateur athletics thing, not all of it as dumb as the Tilikum. But yeah it gets really hard and… I did quit at 5 a.m. If I had made it to sunrise, who knows what would have happened. But I didn’t quite make it through the night. It’s fine.” 

Two people on a tandem bike and one person (obviously) on a unicycle during the Ladd's 500 in Portland.
Photo: Corbin Smith

I mentioned that the Ladds 500 experience seemed similarly counterintuitive. What can someone possibly get out of reducing such a long ride to such a microscopic space? “The idea of doing a 600-kilometer ride within a mile of my house was funny,” he said. But, I say, 10 hours in, your body must not be registering it as a joke anymore, right? “No, it’s still honest work. It becomes a mental exercise.

“The nice part of the Tilikum Bridge is, as scenery, you get to see the weather change,” Barstow Robinson said. “The way at night, how the lights on the bridge change depends on the height and the flow of the river. You get to see, in the morning, the commuters going one way, then at night you see them going back the other way. You see drunk people on dates coming out in the middle of the night. You see all of these different walks of life, just by being in a place while still working really hard.

“It’s not the same beauty as some of my longer rides. I did Route 66 from Chicago to Santa Monica, I did Australia from Perth to Melbourne. My long, long ride was the Trans-Am bike race from Astoria, Oregon to Yorktown, Virginia. It’s not, you know, riding through the Big Hole Valley. But there’s something simple in plugging into a bike and seeing what you can actually get done. Even if it is just: ride across this bridge, turn around, ride back, repeat. It remains beautiful.”

Riders in the Ladd's 500, with a child's bike, with training wheels attached, in the foreground.
Photo: Corbin Smith

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