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

Wednesday’s Headlines Have Consequences

The Trump administration's actions on climate change have consequences for future generations. Industries might not like what they get in return.

February 18, 2026

Trump’s Canada Bridge Tantrum Could Be Bad News For An International Bike Trail

A multi-use trail along the Gordie Howe Bridge would be a key component of an epic cross-continental trail route — if Trump doesn't prevent the entire structure from opening.

February 17, 2026

Disturbing Utah ‘Bikelash’ Bill Takes Aim at Salt Lake City Traffic Calming

Utah state legislators aren't traffic engineers — so why are they writing laws that would force the review of specific bike lanes already on the roads in their capitol, and preemptively stop Salt Lake from building more?

February 17, 2026

The Explainer: How Big Tech Push For Cheap Car Insurance Hurts Victims

In New York State, Gov. Kathy Hochul is distorting the notion of "affordability" to do Big Tech's bidding.

February 17, 2026

Tuesday’s Headlines Let Kids Be Kids

Cops should not be arresting parents for letting their kids walk or bike around the neighborhood.

February 17, 2026

Monday’s Headlines Slow Down

Cities have proven measures they can put into place to slow down speeding drivers and save lives.

February 16, 2026
See all posts