Skip to Content
Streetsblog USA home
Streetsblog USA home
Log In
Dallas

Final Four Parking Madness Matchup: Milwaukee vs. Dallas

We're down to just four cities: Milwaukee, Dallas, Houston, and Tulsa. But only one can be the champion of Parking Madness, our hunt for the worst parking crater in an American downtown.

Today is a very exciting day, because we're kicking off the Final Four with two venerable parking competitors: Milwaukee and Dallas.

Milwaukee has been holding strong through two contests -- thanks, presumably, to the sheer expanse of its parking crater.

Reader "Aaron from Milwaukee" submitted this area, saying "the desert covers about a half mile south of I-794 to the Milwaukee River, and east of Milwaukee Street."

This wasteland is part of Milwaukee's Third Ward, not far from the lakefront. "It’s acres of parking over the former bustling wholesale food warehouse district, mostly serving eight or nine weekends and 10 full days each year associated with Summerfest and Milwaukee’s various ethnic '-fests,'” Aaron says.

Here's a panned out view that shows this parking travesty's position between the Third Ward and the lakefront.

It's definitely ugly, but is it championship worthy? Let's take a look at the competition.

Here is Dallas. James Howard Kunstler featured this spot in his ongoing "eyesore of the month" series:

Kunstler described this area as “a wilderness of surface parking, freeway ramps, and pointless ambiguous ‘green spaces.’” It's certainly an impressive expanse.

Let us know which one you think is the worst.

[poll id="42"]

Our final Final Four matchup Monday will be Tulsa versus Houston.

Stay in touch

Sign up for our free newsletter

More from Streetsblog USA

Why Anti-Trans Laws Are Terrible For Transportation, Too

A disturbing new Kansas law revokes trans people's driver's licenses. Here's how it will make our communities more dangerous.

March 2, 2026

Sunbelt Cities Rank Last in National Street Safety Index

Cars and drivers continue to dominate the newest and sunniest cities in the United States.

March 2, 2026

Americans Demand Congress Fund Active Transportation In Next Infrastructure Bill — And Not Just The Bike/Walk Advocates

A "back to basics" surface transportation bill — as Republicans are seeking — would be devastating for road safety and small businesses.

February 27, 2026

Friday’s Headlines Take a Lot to Laugh, Take a Train to Cry

I ride on a mail train, baby. Can't buy a thrill.

February 27, 2026

Talking Headways Podcast: The Future of Transit

Yonah Freemark talks with Jeff Wood about the state of the trains across the world.

February 26, 2026

Are Roundabouts Just For Rich People?

And if not, how do we get more of them in the low-income neighborhoods that need life-saving infrastructure the most?

February 26, 2026
See all posts