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

Parking Madness Kicks Off With Milwaukee vs. Jersey City – Cast Your Vote!

Earlier this month we asked you: What is the worst parking crater in America? What is the ugliest parking scar draining the life from a downtown?

And Streetsblog readers answered. In all we received 23 submissions from nearly as many states, from the blazing blacktop of San Bernardino, California, to the asphalt expanses of Philadelphia -- and a lot of pockmarked places in between. We received so many, we had to break it down into a March Madness-style tournament, matching up 16 finalists in a single-elimination bracket.

Who will take home the championship? That's up to you. Over the next two weeks, we'll be matching up city versus asphalt-maimed city and asking for your vote to determine who will advance. Ladies and gentlemen, the bracket:

We're kicking off the competition today with a matchup between two proud metros. One gave us the Champagne of Beers, the other gave us Frank Sinatra. It's Milwaukee versus Jersey City.

Remember to vote at the bottom.

Milwaukee

This submission comes courtesy of reader Aaron from Milwaukee:

Aaron writes:

I nominate Milwaukee's Third Ward, which is fantastically redeveloped until you get east of Milwaukee Street. Then 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." The desert covers about a half mile south of I-794 to the Milwaukee River, and east of Milwaukee Street.

Certainly impressive. One wonders, is this parking field visible from space, like the Great Wall of China?

Jersey City

Thanks to reader Will Wittenberg for sending in this bird's-eye-view:

Will writes of his submission:

Once an industrial area, it has been redeveloped over the last 10 years with high end residential and only one stop outside downtown/financial district NYC. Jersey City as a whole very much resembles Brooklyn with parks and brownstones. This area, however, is very sterile, lacks pedestrian activity and street life.

Choose who will move on to the round of eight:

Winner: Milwaukee!

UPDATE: We forgot to mention, the person who submitted the "winning" city will receive a free Streetsblog t-shirt.

Tomorrow, we'll continue our tournament, matching up Philadelphia vs. Tulsa. Stay tuned!

Stay in touch

Sign up for our free newsletter

More from Streetsblog USA

Talking Headways Podcast: Live from MARS To Change the ‘Crash First, Fix Later’ Mentality

Welcome to MARS: Modern Analytics for Roadway Safety. Let's talk about it in a special edition of the podcast.

September 18, 2025

Thursday’s Headlines Freak Out, Give In

Doesn't matter what you believe in, at least regarding the current debate over how safe it is to ride transit.

September 18, 2025

How Many Americans Live in Walkable Neighborhoods?

...and how does your community measure up?

September 18, 2025

It’s a Bird, It’s a Plane, It’s Wednesday’s Headlines

Is our Jetsons future is finally upon us? Plus, a new and better way to measure streets' level of service.

September 17, 2025

Op-Ed: Congress Has A Big Opportunity to Connect America By Intercity Bus

The next federal transportation bill could be a chance to connect rural America with buses like never before — and it will have spillover benefits nationwide, the CEO of one top bus company argues.

September 17, 2025

Breaking: US DOT Pulls Grants For Projects That Aren’t Focused on Cars

The Trump administration bias for "vehicular travel" — and the burning of fossil fuels that it requires — rears its ugly head again.

September 16, 2025
See all posts