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Distinctly Milwaukee: My Experience at the Riverwest 24

Oct. 3, 2022 at 2:31PM

Curiosity got the better of me as my shift at work was coming to a close. It was around 7 p.m.—and a little over nine miles away, a 24-hour-long bike race was about to begin. I opened Instagram on my phone and clicked on the circular profile photo of a friend who was visiting from Colorado. A video of herself riding a borrowed road bike, drinking a beer while surrounded by dozens of other cyclists began to play. The text in the story playfully asked, “What are we doing?”

It’s a question that I’ve wondered at least once every time I participate in the Riverwest 24—usually around five or six in the morning.

What are we doing?

On paper, the Riverwest 24 sounds highly illegal. Regaling family members with tales of the event is often met with a response of either “Why would you do that” or “That sounds really dangerous.” Fair points. 

The Riverwest 24, often referred to as “The People’s Holiday,” is a 24-hour bike race throughout Milwaukee’s Riverwest neighborhood. The event started in 2007 as a way to get the community members involved in, well, the community. It’s a bike-positive event that sees riders racing down both main and side streets. Points are calculated by the number of laps that each team completes, but there are also bonus checkpoints—timed events throughout the 24-hour span that riders can stop at and gain extra points by completing tasks. In previous years, I earned points by writing and performing a haiku, scaling a rock-climbing wall, and hopping into a kayak for a quick paddle on the Milwaukee River. Riders can also sign up for a Riverwest 24 tattoo for even more points—I have two of them on my body that I wear like badges of honor.

This might sound kind of intimidating, but the event feels more like a huge, welcoming neighborhood party that never stops. Sure, there are always those bike jocks that take it very seriously, grumbling at you as they zoom past you on your left. But there’s never any pressure to ride continuously, and everyone is encouraged to compete at their own pace. 

I decided that, since most people just know surface-level details about the Riverwest 24, I would take notes during my team’s run in this 2022 race. And while many of the details are foggy thanks to a lack of sleep and a surplus of beer, I invite you, reader, to join me on a tandem bike ride through my memory of 24 hours of two-wheeled debauchery.

And they’re off!
And they’re off!

I show up shortly before 8 p.m.
We set up our home base in the backyard of a friend who lives on one of the race’s suggested routes—a convenient spot to start and stop at. The race began at 7 p.m., and because of work, I didn’t arrive until just before 8 p.m. The rest of the team wasted no time in starting the festivities, and I feel an urge to play catch up.

We shotgun a beer. A guy shotguns the fastest I’ve seen in a long time. 
A few of us decide to amp ourselves up by shotgunning beers. A guy who lives next door becomes really excited about this opportunity, and we would all soon learn why. In mere seconds after the seals on our beers are cracked and the shotgunning begins, I hear his empty can hit the lawn. Like a fraternity brother on game day, he has shown the rest of the group how to properly drink a beer fast. If only that were a skill that could earn us points.

9 p.m. Teammate crashes, bloody face. I tape his wrist band to my wrist, bloodstained. 
One of our teammates takes the liberty of doing the first few laps for our team. However, not too long after he leaves, we get a text that simply says: “Crashed.” He shows up back at the home base, face covered in blood. An issue with his bike’s chain caused the bike to seize up and launch him forward, sending him straight into the construction gravel. Since I missed the sign-up because of work and didn't have a wristband that qualifies racers to achieve points, I asked to take his. I used some Scotch tape to fasten the blood-covered band to my wrist. Where it once said “Don’t be a jerk,” now said the exact opposite, as the “n” and “t” had been scraped off from the impact. I was ready to ride.

9:30 p.m. We do our first lap, do belly dancing. 
I took my friends who were visiting from Colorado on our first complete lap. Afterward, we stopped at a bonus checkpoint at Company Brewing. The window of time that the checkpoint was available was coming to a close, so we begged the volunteer to let us participate. The checkpoint was belly dancing themed, so my friend and I approached the belly dancers to talk them into teaching us how to belly dance for points. They agreed and gave us the cliff notes version of the history of belly dancing. Next came the belly-dancing lesson, followed by a group participation session. I gyrated my hips, but it ended up being more butt than belly, and my buddy looked like he was just marching in place. After a few seconds of this, the belly dancers couldn’t take any more of our stiff movements, and we were let off the hook. We went to claim our points, but the volunteer wasn’t convinced.

“That was bullshit,” she said.

But I’m not one to put on a free show, and I walked out of there with my points.

12:41 a.m. Jordy is about to rap. 
After riding a lap or two with a teammate, we stop at a house for another bonus checkpoint. It’s my friend Jordy’s first Riverwest 24—he moved to Milwaukee shortly before the pandemic, and this is the first time that the Riverwest 24 has been back to its normal formatting since. For this bonus checkpoint, a teenager dressed up as a record producer asked each rider to “spit hot fire” over a hip-hop beat. The performances were recorded and presumably compiled for later viewing online. From what I can remember of the riders who rapped before Jordy, they could probably compile everyone’s verses into an album called The Whitest Shit You’ve Ever Heard Vol. 1. I don’t remember what Jordy’s rap was about, but like almost everyone else that stepped up to the plate to “spit hot fire,” I think it had something to do with riding bikes.

2:19 a.m. Shotgun contest: Jordy vs. the neighbor 
There’s something about trying to stay awake and motivated to do something that compels my friend group to shotgun beers. I don’t think it ever actually works. The neighbor from earlier wakes up and comes outside to smoke a cigarette. Some sort of unspoken camaraderie compels him and Jordy to shotgun a beer together. They realize they’re both pretty good at it, so they immediately try to race each other and shotgun a second beer. I don’t remember who won—it was way too close. I was blown away by how quickly they both finished two in a row. The neighbor then walked back inside, presumably to just go right back to bed. I make a mental note to suggest this method next time someone I know is having trouble falling asleep.

3:31 a.m. Annihilation 
As we sit around a fire in the backyard, our conversation somehow leads to the 2018 sci-fi film Annihilation. In that movie, a quarantined zone known as “The Shimmer” causes the main characters to be disoriented, at one point losing all memory of their journey. I think about how this point of the Riverwest 24 is like entering “The Shimmer,” where everything starts to get weird. Riverwest can already get a little weird at night, but throw in a 24-hour community celebration, and you’re bound to see some characters and experience interactions that stick with you. 

One time, our team stumbled upon two fully nude folks making love in the middle of a tennis court. In previous years, this was also about when a DJ would set up outside of Colectivo and start blasting death metal while handing out espresso shots. You just have to make it to the other side of “The Shimmer,” and you’re fine—in this case, that’s about 9 a.m.

4:16 a.m. Sunrise pact 
The group is struggling, but we make a pact to at least make it until sunrise. It feels really far away. 

4:34 a.m. Don Pastor still out here 
Those of us who are still awake and determined to fulfill our sunrise pact do some laps and then stop at a bonus challenge. There are two toilets set up, and we face off 1v1 to see who can throw a ball into their respective toilets three times first. Being the non-athlete I am, I start off slow but come back in the end for the upset win. I notice that a food truck called Don Pastor is still posted up serving tacos to fatigued riders. This is why food trucks are important.

4:55 a.m. Weird stick movie 
The next bonus checkpoint takes place in a garage with a projector set up. We grab a fake movie ticket and mingle with a group of other riders. Projected onto the screen is a video from 2001 called “Rejected.” It’s a video that I remember from the Dark Ages of YouTube—back when it was a lawless wasteland of goofy homemade animation. Oddly enough, being as tired as I am doesn’t make the video any funnier. The video ends, and everyone gets up from their seats—except for one rider, whose chin rested on his chest as he gently snoozed.

5:03 a.m. Don Pastor quits 
As we’re biking back to home base, we see Don Pastor, the food truck from earlier, begin driving off. The truck gives us one honk of encouragement as it rides off, presumably so its inhabitants can go to bed like normal humans. 

5:50 a.m. Grill on fire hot dog 
Back at camp, a friend awakens from a short slumber, throws the grate from a grill on top of our campfire, and cooks a vegan sausage. It looks dry, slightly burnt, and discolored, but it’s fuel.

6:43 a.m. More laps 
Before setting out on these laps, we participate in a challenge where roller derby girls ask you to come up with a derby name and then send you off on an obstacle course. After proudly stating my derby name—Michael Motorcycle—I weave my way through the obstacle course. I think to myself that this is like training for riding a bike on Milwaukee’s pot-hole-riddled streets.  

7:26 a.m. The bread is so dry. 
Checkpoint Two has a table set up with various breads and fruits for riders to stop and snack on. In my sleep-deprived state, the charcuterie of grapes and sliced sourdough feels like a mirage—like I’m stumbling upon an oasis in the desert. It’s incredibly dry, and for the first time all race, I decided that it might be time to drink some water. I probably should have been doing that hours ago.

7:55 a.m. Sleep 
Even though I know deep down that I’m using it as an excuse to take a breather, I go home to let my dog out and feed my cats. Afterward, I am drawn to my bed like a moth to a flame. I’m able to make a note in my phone before sleep totally takes over. 

11:49 a.m. Awake 
I rise from my bed like a mummy from its tomb, disoriented but ready to ride. Or maybe more akin to a zombie climbing from its grave, sluggishly hellbent on biiiiiiiikes and beeeeeeeer instead of braiiiiiiiiins. 

12:24 p.m. Legs are tired

1:26 p.m. Talked with Guy 
I stopped at the Daily Bird to grab a very necessary cold brew coffee. On my way back to home base, spilling a little bit of iced coffee as I very carefully ride over several speed bumps, I pass a gentleman riding his bike in the opposite direction as me. After he passes, I hear him call my name. I stop, and it takes me a few seconds to recognize an old chef named Guy, a relic from my days as a line cook. We often bonded over the Riverwest 24 when I worked for him, and even though he is either in his late 40s or early 50s, he rides in the race solo every year. It had been a long time since I had seen him—probably since before the pandemic. I had recently finished watching The Bear, a series that takes place in a Chicago restaurant. Watching it made me feel nostalgic for my days as a line cook, and running into Guy going opposite ways on a side street just felt like it was meant to happen. It reminded me of another reason why I love the Riverwest 24 so much—you see so many characters, often ones that you care for and haven’t seen in a while. We caught up, promised to see each other again soon, and went our separate ways.

Our team rider Pete, looking exhausted but staying hydrated with a Riverwest Stein.
Our team rider Pete, looking exhausted but staying hydrated with a Riverwest Stein.

2:11 p.m. Shotgun beer, back out 
As I mentioned earlier, our friend group seems to think that shotgunning beers is the motivation we need to keep this due-for-an-oil-change machine running.

2:36 p.m. Lego challenge 
This was probably my favorite challenge this year. The Milwaukee Robotics Academy set up a challenge where the team split into two groups—one group playing the role of engineer and the other group the role of assembly robots. The engineers had a Lego structure that was already put together but was out of the robots’ line of sight. Meanwhile, the robots had a small pile of Lego bricks. The engineers then had to verbally instruct the robots on how to build the Lego structure using the small pile of blocks within a time limit. Even though we were running on very little sleep, we passed.

3 p.m. Gatorade water beer 
This note made it difficult for me to remember what it was referencing while I was writing this article. Initially, I had assumed it meant I had acquired the holy trinity of drinks—sort of like when you go out to brunch hungover, and you have water, a coffee, and a Bloody Mary in front of you. But alas, I put the pieces back together and remembered this deception: While we were out riding laps, some kind folks on the side of the street were handing out refreshments, calling out “Gatorade! Water!” At the time, I could have really used either of those. I swoop in on my bike to ride by and grab one without stopping. Before I could realize that the “Gatorade” and “water” were actually cans of PBR, it was too late. I had acquired yet another beer.

3:21 p.m. Whiskey man on a stick 
There’s a mythical figure known to our friend group as Whiskey Man. He has a big, burly beard and hangs out at the second checkpoint with a seemingly never-ending bottle of whiskey from which he lets riders take shots. My friends and I were bummed that we hadn’t seen Whiskey Man at all this year. That is, until around 3:21 p.m. We pulled up to Checkpoint Two and noticed a small table with a bottle of whiskey on it. A big photo of Whiskey Man’s smiling face is attached to a stick behind the table. I don’t know what happened to Whiskey Man, but it was nice to see that even those who aren’t physically at the Riverwest 24 are there in spirit, thanks to some kind neighbors.

And gold guy
Was “gold guy,” as my notes call him, part of my imagination? Anytime I ran into “gold guy,” I first heard him coming—the Bluetooth speaker hanging from his person blasting up-tempo music forewarned his appearance—his pedaling synchronized to the beat. He’s wearing a golden onesie, and an infectious smile stretches across his face as he passes me. “Gold guy’s” sudden appearance felt more like a shining beacon to continue onward than just another enthusiastic racer. 

5:21 p.m. Back out, pick up trash 
We head out to ride laps again and stop at a bonus checkpoint. The checkpoint was simple and straightforward—you’re given a bag and take a Scout's honor oath to pick up any trash you come across. It’s a fine example of how the Riverwest 24 encourages neighbors to take care of each other and the neighborhood itself.

6:28 p.m. We realize how late it is 
We lose track of time, and before we know it, the end of the race is upon us. It’s always a bittersweet feeling—on one hand, we’re having so much fun that we don’t want it to end. On the other, it would be really nice to get some sleep.

6:40 p.m. We walk to the end ceremony.

The infamous cheese jump
The infamous cheese jump

6:58 p.m. Cheese jump 
There’s a small ramp set up with some canned nacho cheese spilled on the ground after it, daring riders to attempt to get enough speed to clear the disgusting-looking cheese puddle. We spend our final delirious minutes at the Riverwest 24 attempting to convince anyone who will listen to attempt the cheese jump. One rider just casually walks their bike through the goop, not even making the slightest effort to avoid the cheese. It was very much a post-Riverwest 24 vibe. 

Fast Forward a couple of hours, and I’m at a bar hanging out with some friends who weren’t participating in the race. I’m decompressing from it all to the beat of congratulatory “You did it!” remarks from the group. It’s a good feeling—I’m still standing after many beers, many laps, and very little sleep. I don’t reflect on the events of the past 24 hours—I honestly won’t do that until I begin writing this article. And even this writing barely scratches the surface of the weird conversations and hilarious shenanigans that ensue during a 24-hour bike race that’s essentially a neighborhood celebration. Those memories will surface as my friends and I reminisce months later, telling slightly-exaggerated tales of the 24-hour bike race that we put ourselves through every year.

Weeks later, I would run into our teammate who crashed on his first lap. He told my group the whole story—about how people rushed to his aid when he crashed, helped him clean up, and grabbed him a beer while he processed what had happened. He ended up running into two of the people who had helped him that night, and they asked if he was doing okay. I thought about how that probably wouldn’t have happened in many other neighborhoods or cities. It’s why the Riverwest 24 is often not described as a bike race but as a community event. It’s also a reminder to be human—to experience something weird, to hang out with your friends, and stay up way too late. To check in on your neighbors, explore your community, and support the local businesses. 

And if you get the chance, teach someone how to belly dance. Give someone a beer. Pick up litter. And as the Riverwest 24 constantly reminds us: Don’t be a jerk.

Photos courtesy of Scott Parker. Follow him on Instagram @sjparkerdesign

More Articles by Mike Holloway

About the author

Mike Holloway

Mike Holloway was the music editor for The Wisconsin Gazette until it ceased publication in Sept. He currently writes for 88Nine Radio Milwaukee, Milwaukee Record and Urban Milwaukee.