Category 1: Visiting Without A Car
a) How can you get to the city?
Milwaukee has increasingly frequent train service to Chicago in one direction and Minneapolis/St. Paul and points west in the other. It also does have an airport, but hardly ideal transit service from the airport (though some of those same trains do serve it).
New York has Acela, which in the US at least is a gamechanger, and high frequency bus service from the Port Authority. It also has two major airports in town (JFK and La Guardia) and one close by (Newark) all of which are accessible by transit, though famously not easily or smoothly integrated into the city's transit network.
VERDICT: Milwaukee 0, New York 1
b) How do you get around?
Downtown Milwaukee is quite walkable in the times when temperatures and weather allow it to be (to be fair to the city, I visit a lot in deep winter) and features a skyway of interconnections that allow travelers to roam major parts of downtown with minimal time outside. There is also a burgeoning streetcar network, the Hop, which is free to ride, and a BRT system, Connect, with level boarding and off-bus payment, and integration into a larger bus system with a digital fare card. If it works right.
New York has probably the best subway in the US if not North America, a much more extensive bus network, a railway to Long Island, and that's not even touching the New Jersey transit in the greater metro region. There can be quibbles with its transit, but that isn't something Milwaukee is prepared to take advantage of.
VERDICT: Milwaukee 0, New York 2
c) What are the limits on a visitor without a car?
Well, in Milwaukee your access without a car is limited to basically downtown. In New York there are places it is hard to get to, but nowhere it's really impossible.
Even, sometimes, by boat.
VERDICT: Milwaukee 0, New York 3
Category 2: Living Without A Car
a) Can you expect to get to work?
For Milwaukee this will
depend heavily on where you live and work, but the answer is probably no, especially not year-round.
In New York the answer is yes.
VERDICT: Milwaukee 0, New York 4
b) Can you live the rest of your life?
Again, Milwaukee certainly has neighborhoods and places you can do this. New York just has a lot more of them, and they are distributed throughout the metro area. Jersey City and Hoboken, just across the river, might be the easiest places to do this in the US.
VERDICT: Milwaukee 0, New York 5
c) How are the basic amenities?
Here I'm going to speak on behalf of Milwaukee as I did for the Quad Cities in the Seattle matchup: it really does have the basics here, with good libraries and parks, and both the art museum and children's museum (easily accessed by transit) are excellent. New York is amazing, but until we raise the standards in round 2, we'll call this a push.
VERDICT: Milwaukee 1, New York 6
Category 3: Miscellaneous
a) Are there people on the street?
Milwaukee doesn't, not to the same extent as New York at least. Maybe it's climate, maybe it's culture, maybe it's city design, but for all Jane Jacobs may have thought the old eyes on the street design was going away in New York, it's still pretty darn good at it.
VERDICT: Milwaukee 1, New York 7
b) Where is the city's urbanism going?
Milwaukee is really improving. It has built the tram and BRT, the trains are running more often to Chicago, and they plan to keep it up.
New York just implemented congestion pricing and is finally starting construction on the Second Avenue Subway after years and years and years.
Until the government retracts congestion pricing, or rather until a court permits them to do so, it's going to have to be New York.
VERDICT: Milwaukee 1, New York 8
c) Is it functionally diverse?
I mean, as always, there are lots of bad things to note here. Milwaukee has been called the most segregated city in America in my lifetime. NYC has major issues with school segregation, still. Milwaukee is actually plurality Black, but that's just the city limits, and it has a reputation as an awful place for African-Americans to live. NYC has its own significant issues, particularly with the aforementioned schools and policing, but not to that extent.
VERDICT: Milwaukee 1, New York 9
d) How do people there react to knowing you're not using a car?
This is as simple as some of the living without a car ones: NYC has less than 2/3 of a car per household; Milwaukee is pretty average in the US for car ownership in larger communities. While I visit Milwaukee and leave my car, that's only because of my very specific touristy attitude (and a hotel connected to a food hall). No one at all would be confused by someone without a car in NYC, whereas it would definitely be worth comment in Milwaukee.
VERDICT: Milwaukee 1, New York 10
e) How do people react to people living close together?
Again, the densities involved make it simple. NYC and its environs are basically the densest part of America. Milwaukee is a bit more than 20% as dense, which is high for the US but not comparable. NYC is very, very used to living close to others, and Milwaukee isn't bad at it but not on the same level.
FINAL VERDICT: Milwaukee 1, New York 11
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