By Jason McDowell Creative Director Published Sep 12, 2023 at 6:01 PM Photography: Zachary Seib Photography

We did what Quentin Tarantino couldn't. Hill Bill is back for Volume 3 - The Bigger They Are, the Harder We Climb, this Sunday, Sept. 17 at The Rock Snowpark.

OnMilwaukee's Hill Bill is an extreme cyclocross spectacle that features several laps of racing across 5 big climbs and variable terrain. Whether you're in it for the competition or just a personal challenge, Hill Bill features racing for all ages and skill levels (including the return of the Hugh Jill fat bike race and a free Kiddo Cross course for those under 9 years old). Otherwise, spectating is free.

Winners will receieve a custom stem cap inscribed with the race motto.

A stem cap inscribed with the Hill Bill logo and motto.
Whenever you need inspiration while going up, just look down.

Whenever you need inspiration while going up, just look down.

To add a little fun to the CX challenge, we're bringing back the $100 hand-up, free samples of ZOA Energy Drink, a live drum set at the top of the run-up. Zachary Seib Photography will be there to capture the magic and madness of the day.

Afterwards, Chiros in Motion will be on-site offering soft tissue work and prizes.

Other prizes include swag from Orthopaedic Associates of Wisconsin, Chiros in Motion, ZOA Energy Drink, The Rock Snowpark.

Pre-register before midnight on Wednesday to save $10; otherwise registration then re-opens at 8 a.m. on race day.

Here's a look back at the hill-arious madness of Volume 2.

Cyclocross racers pushing bikes up a hill.
Cyclocross racing involves both riding and running with your bike.
Youth cyclocross racers navigating an off-camber descent.
Cyclocross is an all-terrain obstacle course.
Cyclocross racers zig-zagging down an off-camber descent.
Coasting is easy, but it's still hard.
A cyclocross racer reaching out to grab money off of a fishing line.
There will be hand-ups, but keep an eye out for the $100 hand-up.
A group of cyclocross racers navigating a downhill descent.
Going down means you just gotta go back up again.
A cyclocross racer with limbs akimbo going over the bars on a descent.
Sometimes going slow is the best way to win a race.
A cyclocross racer zipping around a pole.
Amber Markey was last year's Elite Women winner.
A cyclocross racer pushing a bike up a steep hill.
If you can't ride the run-up, you gotta be fast on your feet. Erin Feldhausen was last year's 35+ Women winner.
Behind a cyclocross racer about to drop down a descent overlooking a beautiful wooded area.
While the racing may be brutal, the overlook is beautiful.
Looking down on two cyclocross racers pushing bikes up a steep hill.
Mountain bike or CX bike? The eternal debate.
A profile of ski hill terrain that cyclocross racers are racing on.
A profile of The Rock Snowpark.
A cyclocross racer aggressively corners in front of fans.
Michael Lambert was last year's Elite Open winner.
A man squirting a water bottle onto a hot cyclocross racer as they remount their bike.
Cool and hydrated is key to fast, functioning legs.


A line of cyclocross racers riding up a steep hill.
And yes, I'll be back to suffer under the machinations of my own creation.

Register now

Zachary Seib Photography returns for Hill Bill: Volume 3. Be sure to pre-register by midnight on Wednesday, Sept. 13 to save $10. Registration re-opens once again on race day.

Jason McDowell Creative Director

Jason McDowell grew up in central Iowa and moved to Milwaukee in 2000 to attend the Milwaukee Institute of Art and Design.

In 2006 he began working with OnMilwaukee as an advertising designer, but has since taken on a variety of rolls as the Creative Director, tackling all kinds of design problems, from digital to print, advertising to branding, icons to programming.

In 2016 he picked up the 414 Digital Star of the Year award.

Most other times he can be found racing bicycles, playing board games, or petting dogs.