The Riverwest 24 spins up for its 18th year in the neighborhood for which it is named, bringing a communion of cycling and neighborhood pride, for a solid 24 hours. And while this pedal-powered event has evolved over the years it still bears the beating heart that made it what it was in its early years.

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When the race started in 2008, the concept was simple: Ride your bike around a roughly five-mile loop around Milwaukee's Riverwest neighborhood, to each of the four checkpoints, and stop to get your manifest stamped. They also provided opportunities to ramble off course and participate in optional local community checkpoints to earn two extra laps.

The first year brought in something like 160 or 180 participants, many of whom were interested in the thrill of underground, alleycat-style racing, so the prospect of doing activities that were something other than riding a bike real fast was less interesting and these bonus checkpoints were skipped altogether.

Bonus checkpoints: The key to the 24

This "laps laps laps" mentality caused the first major change in scoring. To encourage participation in every checkpoint, riders were granted an additional five laps on top of their existing bonuses, but only if they completed every optional checkpoint.

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Here's some basic math: if a reasonably swift rider could complete a lap in 15 minutes, the additional bonuses would make it hard to say no to what amounted to roughly 75 minutes worth of riding, to say nothing of the 30 minutes granted by the bonus checkpoint itself. The math gets a little fuzzier if you consider a small number of checkpoints could take over 40 minutes, but most bonuses took less than 10 minutes, so no matter how you calculate it, those five free laps could easily make up the difference.

It would be hard for even the fastest riders to overcome that challenge. Optional was essentially now required.

Year two: Year of the tattoo

The second year also brought about the second significant change: Tattoos.

At the end of the first year, event organizers emblazoned themselves with the iconic RW24 logo; but this wasn't a public endeavor. 2009 marked the official entry of the tattoo into the bonus points pool, offering an additional five free laps during that year's race. This crazy idea was a hit, and the official slots to get the tattoo filled up quick. Thereafter, a new design was created each year. If you want to see the designs throughout the year, there is a blog at littletinyfish.com that has kept track of each one.

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Secure your spot: volunteer

After the second year, the event became a bonafide hit, growing year after year while still selling out faster and faster. But the priority was always focused on the neighborhood. With the influx of out-of-towners, internet registration was cancelled, requiring in-person registration. Then people began throwing up tents and camping out in the park days before registration opened. Garden Park (often referred to as Wu-Tang Park (affectionate) due to the shape of its prominent sculpture) filled up with a line snaking back-and-forth, managed only by a donated Sharpie to mark your number in line.

In 2011, its fourth year, the registration model was changed up again. The standard May Day registration landed on a Sunday and, likely due to fears of folks setting up camp as early as Thursday (or even earlier) the new policy was: if you volunteered during the Riverwest 24 the year before, you were guaranteed entry for the subsequent year. Those who didn't volunteer had to hope for entry with a raffle ticket, with fewer and fewer places up for grabs.

Volunteers are the true lifeblood of the event, a significant key to its longevity all these years. This year the raffle lasted barely 20 minutes before the event was sold out.

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New team classes, new manifest checkpoint

The first decade held the same four categories of racing and the same four standard checkpoints. As far as categories were concerned you could pick your poison between:

• Team A (Up to 6 people using only 1 bike)
• Team B (Up to 6 people using 6 bikes)
• Solo
• Tandem

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But in 2018 new categories arrived: Elder (55+ riders) and Convoy (Up to 6 people all riding at the same time). 2019 saw the addition of Perfect Strangers, in which two unknown riders were paired together. 2024 saw the retirement of the Team A category, which was frequently talked about, but never enjoyed much participation.

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2018 also saw Checkpoint One shift from Keefe and Booth to Fratney and Townsend.

This year will usher in additional changes: Checkpoint One will move again, this time to the northwest Beerline at Holton and Townsend. And while Checkpoint Three will remain at the south end of the Marsupial Bridge the dance party will be moved to Checkpoint One as well.

Lessons from COVID: Embrace the slowness, enjoy the bonus

As the years progressed organizers strove to slow down the competition and bring more of a sense of presence to the neighborhood, making the event less and less about crushing laps and more and more about being in the community. The COVID-19 pandemic forced the cancellation of the event in 2020 (though a few party laps with tight friend groups still persisted).

Even though the Riverwest 24 is an outdoor endeavor, it's still a dirty, sweaty, and frequently saliva-covered endeavor. As participants try to work their way through crowded checkpoints as quickly as possible, manifests are often stored and held via various parts of the body. In 2021 the pandemic's lingering effects continued to bring worry of transferring germs, which caused organizers to take the next big swing: no laps, just bonus checkpoints. 

That year the event did not require handing off stamped manifests at the four primary checkpoints. Instead, they removed the laps and doubled the bonus checkpoints from 24 to 48.

This significantly dialed down the need for speed and instead dialed up the need for patience and communication. Riders would be spending significantly more time standing next to their neighbors, rather than blowing past them in the streets.

This year the bonuses have been re-tuned slightly and capped at 36.

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More info

The Riverwest 24 starts on Friday, July 25 at 7pm, but assorted community activities—such as the community dinner at the Riverwest Co-op—begin in the late afternoon and early evening. The event ends on Saturday, July 26, 24 hours later. You can find more information, or follow the leaderboard at riverwest24.com.