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

Agenda 2026: Will Zohran Mamdani’s Left-Progressive Backers Mobilize for Faster Buses?

New York's new mayor must mobilize the coalition that got him elected if he wants to avoid his recent predecessors' failure to speed up buses.

December 2, 2025

Opinion: One Less Lane Ought To Fix It

Federal inaction means states must lead on reducing emissions — but their reluctance to reallocate road space for cars may doom climate goals.

December 2, 2025

Tuesday’s Headlines Fight Fire With Fire

Berkeley, Calif., is far from the only city where the fire department dictates transportation policy.

December 2, 2025

Investigation: How Trump’s U.S. DOT Is Loosening Safety Rules Meant to Protect the Public

In Trump’s second term, the agency opened 50-percent fewer investigations into vehicle safety defects, concluded 83-percent fewer enforcement cases against trucking and bus companies and started 58-percent fewer pipeline enforcement cases compared with the same period in the Biden administration.

December 1, 2025

Monday’s Headlines Go Cold Turkey

Life is a highway, and Congress is going to ride it all night long.

December 1, 2025

OPINION: Where Cities are Investing, Vision Zero is Working 

As the Vision Zero Network turns 10, it's time to look at what works and what is achievable (a lot!).

November 28, 2025
See all posts