Weeks before Riverwest 24, Instagram inspiration came from one of my favorite coaches, Ted Gustus. He posted, “We don’t stop playing because we grow old, we grow old because we stop playing.”

Coach borrowed the quote from George Bernard Shaw, a fascist bastard with no claim to anything reminiscent of Riverwest 24, aka “The People’s Holiday.” And the quote rings true for all who rode with our team, “Ye Olde Geezers.”

Ye Olde Geezers at the starting line (from left, myself, Brenda, Carol, Pauline, Colleen, and Molly) sport team T’s created by Molly’s niece, Laura

Nice of Laura to remind us who was riding behind us all the way

A year older since my first round-the-clock ride around the Riverwest neighborhood of Milwaukee, in 2025 I would rely more on experience and less on the sheer athleticism that carried me through the 2024 event. The 4.6-mile route changed slightly from the previous year due to road repairs, but the rules and spirit remained the same.

The rules, in short: Despite a “suggested route,” riders can roll any way they want, accruing completed laps by passing through each of the four checkpoints, in order, and having their team manifest stamped. Manifest punches gained by visiting fun and quirky “bonus checkpoints” add to a team’s total. The spirit, in short:

We six teammates who officially registered for the ride, lasting from 7 p.m. Friday July 25 to 7 p.m. July 26 spent our Friday afternoon together, along with my daughter, Eleni, an unofficial special guest rider. We first walked from Molly’s apartment, aka “Ye Olde Geezers” HQ, to check in at RW24 HQ and pick up our wristbands and bonus checkpoint passports.

Back at Molly’s, we set up a caprese sandwich assembly line and drank beer in the heat while watching the Dead Man’s Carnival circus troupe set up their stage on the street below Molly’s balcony. We charged headlights and taillights, tested brakes, and called each other Geezers whenever anyone lost or forgot any equipment. Eleni tuned up the second-hand Bianchi touring bike she lent me and did such a good job that she almost got the rear tire to stop rubbing the frame.

Around 6, we left for the pre-ride vegetarian dinner served at communal tables on the street outside the Riverwest Co-Op. There, the merriment escalated. Tall bikes rolled through the crowd, passing costumed riders, such as a circa-Mad Men flight crew complete with pillbox hats, and un-costumed riders who risked sunburn on their most sensitive appendages.

After dinner, the throng packed as closely as possible to the starting line. Bike bells chiming in anticipation were drowned by a confetti cannon boom that signaled the start. The going was so slow that we snuck in just a couple laps before returning to Molly’s balcony to watch Dead Man’s Carnival.

As the carnival wound down and thousands of fans dispersed, Eleni planned to ride with Carol’s daughter, Julia, and her friends. They named their crew, of course, “Young Geezers.” Then, Molly explained what else was about to take place while she and Colleen went downstairs to Art Bar for the underwear party.

Carol took off before I did. Holding our team manifest, only her lap count and bonus checkpoints mattered. I would catch up with her whenever I could, relying on text messages to locate each other. Meanwhile, I rode the course randomly, entranced by sights like this:

Carol’s text came in: “Meet at start?” So we did. Carol, Pauline, and I took a lap, bombing downhill on Humboldt Ave. through the soft, humid night to Water St., then over the Marsupial Bridge and winding up the switchback at Kadish Park with the downtown skyline in the distance.

Atop the switchback, a sign spoke truth to us.

With burning passion and burning thighs, Ye Olde Geezers hit the dance floor at this bonus checkpoint named Marvelous Michelle’s Mostly Midnight Mayhem and Menashery. Here is the Marvelous part:

And here is the mayhem:

It may not seem like it, but I was having a great time. I was just too tired to smile.

We decided to skip the Mud Wrestling bonus checkpoint, because at 1 a.m., the line was too long. We lost Pauline somewhere. Or maybe she called it a night. Our next bonus checkpoint stop was First Practice. Those of us in line were led five at a time down a set of stairs into someone’s basement to play musical instruments as loudly as possible for two minutes. Carol gave her keyboards a Jerry Lee Lewis treatment, and Mark Knopfler might have said I was “banging on the bongos like a chimpanzee.”

Last stop before I headed in at about 2:30 was the bonus checkpoint called Leave Your Tennis in Shorewood, which turned out to be a glow-in-the-dark pickleball game at the Pumping Station Park. After 23 miles of cycling and about three points of pickleball, my Geezer knees were not having it.

I rode back to team HQ for a nightcap of caprese sandwiches and beer that helped me wind down enough to sleep from 3 to 5. One challenge of Riverwest 24 is that you suffer FOMO even in your sleep. Two bonus checkpoints opened and closed in those two hours!

Rain that didn’t let up until 9 kept all of us off the course except Carol, who never sleeps during the 24 hours and rarely stops riding. Once Ye Olde Geezers hit the streets in full effect, our first bonus checkpoint was Peddle Pedal Petal Power at the Riverwest Grown plant shop, where I “planted” a gladiolus for Val in the community garden.

Next was Take Off You Hoser!!! at Milwaukee Fire Station 21. Eleni and I took turns spraying targets, which was way more fun than I ever imagined, and got me thinking maybe I should have stuck with my first career aspiration instead of this one.

To re-assemble Ye Olde Geezers, we met at the Kids 24 ride where Molly and Colleen were volunteering.

A raucous rock band, a thousand or so kids all more mature than Molly but somehow under her supervision, and shaving cream pies…what could go wrong?

Soon, but never soon enough, it was time to hit Black Husky Brewing for a traditional Milwaukee brunch of Bloody Mary and beer and a Ye Olde Geezers strategy planning meeting. Having taken leave of our senses, we agreed with Carol that we should set a team record of 21 laps by the end of the ride.

We started slowly by stopping across the street for the bonus checkpoint at Wu Tang Park, so named for its signature sculpture.

Then we put the hammer down, fueled by funk played at Black Husky’s live remote of WMSE’s Barry Johnson Saturday Afternoon Boogie Bang, plus other cuts covered by live bands along the route. It sounded like this:

Of course, the rest of the ride was not without its detours, mishaps, and other challenges. A little kid clipped Colleen’s back wheel on a downhill and both riders miraculously stayed upright. Not so one inebriated non-Geezer, who fell hard off her bike, and then, as her friends helped her re-mount, fell even harder.

Carol’s chain fell off on an uphill. We had to stop for free tacos. Because they were free. And they were tacos. We got caught behind the dozens of slow riders chanting for a free Palestine.

Sometimes the sun scorched. Other times the sky drizzled. My arms went numb. The last three or four laps were excruciating.

But on the last big downhill on Humboldt — where on earlier laps I pumped the brakes for stop-and-go lights or just plain fear — I hit every green. I sped like never before on a bike and felt wild and free, sure of a strong sprint across the Marsupial Bridge and laughing through the agony of the last Kadish Park switchback climb with Molly while We Olde Geezers tried to remember the name of the band that played Never Been Any Reason, which for some reason now blared from a nearby speaker for the first time since high school.

From there, all that remained was the last mile or so until the finish line of our 21st lap.

Oh, yeah, and taking our seats on the curb in front of the High Dive bar on Center St. to watch Julia’s attempt at the famous post-ride Cheese Jump.

The Young Geezer did us proud. Not surprisingly, any dares for any of Ye Olde Geezers to try that trick fell on deaf ears. However, we will again heed the call for Riverwest 24 in 2026.