By Jason McDowell Creative Director Published Jun 20, 2025 at 10:10 AM Photography: Jason McDowell

This is the third year I've been honored to design the poster for the Tour of America's Dairyland (which has already started!), but each year presents its challenges.

This year the main ask was creating a poster that was less concerned with the racing aspect and more about what the community brings. As I cooked up some ideas, I remembered back to a photo by Hamilton Reinbold I saw last year of Skylar Schneider sprinting for the win in Bay View.

A bike racer sprints to the finish line in front of a crowd of spectators
Photo: Hamilton Reinbold
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And while her epic performance was something to behold, my eyes were drawn to the animated spectators behind her.

So eventually we settled on an idea: What if we focus on the fans?

So I put away my engineer specs, technical rulers and protractors needed to render a racing bicycle and instead set to work laying out heads, arms and cowbells. 16 crazy fans (to celebrate 16 crazy years) imbued with the enthusiasm that overflows from the folks who hang out (and over) the back side of the barriers.

Here's a gallery of that illustration process from start to finish.

1. Rough sketch

This is the first sketch that was sent to the ToAD organizers. These sketches don't have to be good, they just have to convey the idea succinctly.

Rough sketch of a group of bike racing fansX

2. Blow it up

I knew there had to be a lot of detail in the crowd, and everyone had to be doing something fun, so I decided to work at a larger size.

A sketch blown up and printed out on two sheets of paper.X

The refined sketch

For the refined sketch I separated out the fans and the racers onto separate sheets of paper, because I knew this illustration was going to appear in several different mediums (poster, t-shirt, digital ads) and I knew I was going to have to reposition both elements according to the needs of those mediums.

Several sketchs of fans at a bike race.X

All inked up

Inking the design helps lock down the detail and clean up the artwork.

Inked artworkX

Digital correction

As I played around with different poster layouts in different orientations, I ultimately came to the conclusion that the crowd needed to be closer together. It's a very horizontal image, but the poster is vertical. I didn't want to lose any one of my 16 fans, but I still wanted the illustration to fill the space as much as possible, so I had to digitally cut out and move everyone a little closer together, person-by-person.

Sometimes this meant flipping them to the opposite direction.

Original design versus digital correctionX

We also decided to remove the beer from the reveler in the middle and give him a more thematically-correct jug of milk, instead.

Color blocking

Next was getting the colors layed out.

Initial digital coloring of artwork.X

Lights and shadows

Then on to adding dimension with lights and shadows.

Adding lights and shadows to the colors.X

Painted textures

I always like to collage in paint and textures from real mediums whenever I can, to add a little extra warmth and humanity to my illustrations. In this case I was looking for something that would indicate the blood, sweat and speed that goes into racing.

Painted textureX

The final illustration

The illustration is done, but the work isn't quite over yet.

Completed illustration for ToAD 2025 by Jason McDowellX

The final poster design

And here is the illustration set within the poster itself. All of the excitement of bike racing without any of the bikes.

Tour of America's Dairyland 2025 posterX

Where to find it

Like it? You can get your very own poster or t-shirt by visiting the merch tent at any of the stops on the Tour of America's Dairyland.

Two people with Tour of America's Dairyland teesX
Poster seen in the wild.X
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.