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

Friday Video: The London Neighborhood Where Bikes Outnumber Cars

...and how they got to that impressive milestone.

July 11, 2025

Friday’s Headlines Battle Galactus

Like the Marvel supervillain, U.S. interstate highway system seems to eat up everything in his path. A new book explores how to stop it.

July 11, 2025

New Report Shows Pedestrian Fatalities Drop — But Experts Say Not Enough

The Governors Highway Safety Association report showed a 4 percent drop in the number of pedestrian deaths last year, putting a slow on a dangerous trend — but advocates say the drop isn't nearly big enough.

July 11, 2025

Talking Headways Podcast: Localities Subsidize the State DOT

Adie Tomer of Brookings on how to improve regional coordination around infrastructure.

July 10, 2025

Five of the Ugliest Transportation Policies In the ‘Big, Beautiful’ Bill

Here's a rundown of some of the transportation provisions in the Republicans' reconciliation package, and what they might mean for your community.

July 10, 2025

Viva La Thursday’s Headlines

Why is French transit ridership up 10 percent since before the pandemic, while American transit ridership is down 23 percent?

July 10, 2025
See all posts