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

The Talk of D.C.: Rumors Flying that Trump Admin Wants to Undo Bike Lanes in Capital

The feds appear to be mounting an argument that bike lanes cause congestion in the nation's capitol — and advocates are bracing for a fight.

January 26, 2026

Monday’s Headlines Fund Transit (Mostly)

A federal transportation bill keeps most of the funding for transit from the Biden administration's infrastructure act, except for steep cuts to intercity rail.

January 26, 2026

New York State’s Car Insurance ‘Affordability’ Pitch Will Shortchange Crash Victims

Gov. Kathy Hochul's Uber-backed bid to make car insurance affordable hides harmful policies for victims of car drivers.

January 25, 2026

Big Tech is Secretly Behind NY State’s Auto Insurance Rate Cut Push

Is Uber really interested in a more affordable, safer New York?

January 25, 2026

Friday Video: Why The Latest Wave of E-Bike Restrictions Are So Stupid

New Jersey just set a new standard for over-reaction on e-bikes by passing a victim-blaming law. Here's why no state should follow suit.

January 23, 2026

Friday Video: The Fight to Expand A South Carolina Freeway … For Bikes

Greenville is looking for the good kind of induced demand — by expanding a popular rail-trail.

January 23, 2026
See all posts