Introducing CityBracket 2025

For the summer (at least here in the Northern Hemisphere) I thought I'd try something new on this blog. Instead of a weekly blog about topics that occur to me, I'm going to try to do a twice-weekly blog, but with a continuous theme: what I'm calling CityBracket. And in my hubris I've decided to call it CityBracket 2025 in case I last doing this long enough that I do another someday.

The basic idea is this: an 16 city bracket (hence the name) divided into four groups, ending with a championship. Each matchup will be evaluated on urbanist characteristics as I have personally observed and experienced them, as well as through more generally available information, with the winner advancing to the next round, and ultimately crowning a winner.

As I said, I'm going to base this on my own knowledge: that means the cities in CityBracket 2025 will be cities I know well, divided into four regions for the bracket. The Homes region consists of the 4 cities I've lived in longest. The Stays region is represented by 4 cities I've lived in for a shorter period but at least three months. The Family region is 4 cities I've visited a lot for, well, family reasons. And the Travel region is the 4 cities that I have visited most frequently just for fun.

That means the contenders are:

The Homes region:

The Quad Cities 

Seattle 

Boston

Chicago

These are the cities I've spent the longest in, and thus have the best knowledge of, but that doesn't mean they're necessarily going to score highly for urbanism.

The Stays region:

Rochester, NY 

Baltimore

London, UK 

Oxford, UK

This region is notably unfair to Rochester, where I lived for four years, but that's still less time than I lived in any of the Homes region places.

The Family region:

Louisville 

Lincoln 

Detroit

Washington, DC

A notable omission here is Portland, OR: undoubtedly a better transit city than, say, Lincoln, but one I don't visit my family in nearly as often.

The Travel region:

Vancouver, BC

Toronto

Milwaukee

New York

This region has some heavy hitters, especially as I often do tourism explicitly for travel reasons. But that doesn't guarantee anyone anything, of course!

Midweek this week I'll introduce a brief rundown of my criteria for matchups, and next Sunday we'll kick things off with the first matchup in round 1! Feel free to let me know in the comments if you disagree with how I've grouped the cities or the results of the matchups: after all, I'm hardly perfect, just like the transit and urbanism in these cities!

Transiting Toronto

Since I visited there and have a bunch of pictures, I thought I might discuss this week what taking transit in Toronto feels like as a visitor. To be clear, I have visited a lot over the years but never lived there, so I'm speaking to not just this trip but overall experience, but not to what it's like to take transit as a resident.

Also, they're building quite a bit there but it's not done yet, so I'm not speaking to that either.

1. It'll Get Ya There

I discussed as part of a larger post last week the issues with traffic and delays that can come with Toronto transit, but the biggest point for me about Toronto transit has always been that within the urban core there is good solid coverage along the major streets. It may be slow sometimes, it may be less cheap than it used to be, but between the ¥ shaped subway and frequent buses/streetcars on major streets, you can basically treat Toronto as a grid and go up one major street, over another, and make it anywhere.

King Street streetcars: an east-west link.

The 1 line, a north-south link.

To me, this was the biggest thing about Toronto when I first visited over two decades ago: I could get basically everywhere and I could figure out how to do it, because the transit really did cover it all.

2. Strange Accessories

The GO regional transit system overlaid on the TTC is a bit eccentric. Now, they're planning to significantly upgrade it. But they have not finished that yet. They did finally connect the Union-Pearson Express to the airport, so there has been progress! But right now you have this:

So much rail! Right downtown! And yet: do you see any actual trains?

How about here?

It's got wonderful potential, and I'm so glad they're planning to do more with it, but right now, it's a regional transit system that has maximal promise but isn't there quite yet.

3. Multimodal and Proud

Toronto has a great number of transit modes that work together.

Ferry!

The aforementioned Union-Pearson Express!

GO Trains (this is the yard; still didn't manage to photograph one in motion).

Subway!

Streetcar (or bus, as here)!

Regular bus!

Bikeshare!

(Some) separated bike lanes!

And all of these work together to bring you across the city. 

Is Toronto transit perfect? No. Certainly not. But it's a pleasure to visit, and it compares positively with basically every American or Canadian city I've visited.