By Jason McDowell Creative Director Published Sep 14, 2022 at 10:01 AM Photography: Zachary Seib Photography

The bride is back in Hill Bill: Volume 2, presented by Educators Credit Union, this Sunday, Sept. 18. It's a cyclocross spectacle at The Rock Snow Park that includes a hundred-dollar hand-up, hard coffee samples, huge heart-pounding hills, a live drum set, novelty bottles and epic photos from Zachary Seib Photography to showcase the fun of cyclocross suffering. Plus there's the Hugh Jill fat bike race (just $10!) and a free Kiddo Cross race for those under 9 years old.

The day features racing for all ages and skill levels – cyclocross bike and lycra not required. 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 1.

The impressive climbs

A cyclocross racer ascends a hill overlooking the main staging area.
Last year racers went high; this year, the advanced racers are going even higher.
A cyclocross racer, back lit by beautiful clouds.
You won't make it above the clouds, but sometimes it might feel like you should be.

The crazy descents

A cyclocross racer begins their descent down a steep hill next to a sign that reads 'Heels down, butt back.'
Heels down, butt back - proper descending recommendations.
Three cyclocross racers descend a switchback on a snowless ski hill.
Switfly slalom down the switchbacks.

The Rebel Run-Up

Three cyclocross racers run up a steep run-up.
The steep grade of the Rebel Run-Up is sure to get hearts pounding again this year.
A cyclocross racer pushes her bike up a very steep, wall-like the run-up.
Hill Bill is a challenge between you and your closest rivals ... and your perhaps your own sanity.

The views overlooking the Root River Valley

Two cyclocross racers remount their bikes after a steep run-up overlooking the Root River Valley.
The view from the overlooks will make the trips uphill worth while. But don't stop too long to enjoy it.

The tricky off-camber switchbacks

Three cyclocross racers descend a tricky switchback.
Tricky switchbacks have racers riding on the edges of their tires along the sides of the hills.
Two cyclocross racers chase each other on an off camber switchback overlooking a beautiful valley.
Make the most of your skills to ride fast and stay grounded.

The feats of strength

A cyclocross racer rides a steep run-up between two others pushing their bikes.
As steep as it is, the Rebel Run-Up is rideable, if you have enough speed, strength and tenacity. It's a spectacle to see those confident enough to try.

The hundred-dollar hand-up from Educators Credit Union

A man dangles a burning dollar bill in front of an approaching cyclocross racer.
In Volume 2, $250 in hand-ups are out there for anyone to grab. The luckiest one may find themselves with a fistful of Benjamins.

The Hugh Jills

Three fat bike racers wend their way through the maze of race tape.
When Hill Bill meets Wheel & Sprocket's Hugh Jass, you get a fat bike race on a cyclocross course.

The suffering

A cyclocross racer dejectedly climbs a steep run-up.
You'll even see me, suffering under the machinations of my own creation.

Register now

Zachary Seib Photography returns for Hill Bill: Volume 2. Be sure to pre-register by midnight on Wednesday, Sept. 14 to save $10. Registration re-opens once again on race day.

More information can be found at

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.