What's the best way to explore a city?

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I learned to walk early, at the age of around 9 months—and I never stopped. As a kid, I traipsed to and from school, through the center of our small Massachusetts town, upstream through creeks, down the long, manure-smelling farm roads to the mall. In college I crossed Paris for the first time on foot, near midnight, perhaps on or after Christmas Eve, with my friend Dan. In nearly three decades in New York, I’ve walked almost every Manhattan block below 57th Street and run across every bridge from the Queensboro south to the Verrazzano. When I traveled, for the New York Times and others, to Tirana and Tokyo and Venice and Jakarta and Tunis and Singapore and everywhere else, I walked and walked and walked, to the often sweat-soaked, rain-drenched point of absurdity. Yes, I took buses and subways and taxis, but I did so usually so I could remain on my feet, moving at my own pace, free to stop and look and talk and backtrack and be wherever I was more fully.

Once, I walked from Vienna to Budapest. That was crazy.

It was also, I’m coming to think, wrong-headed, as was my conviction that to be a pedestrian was the highest, purest form of travel—the one true way to understand a place.

In fact, I’ve discovered, there’s another way. It’s called driving a car.

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Last week, we took a family road trip to visit colleges in the Midwest. From Brooklyn, the four of us—me, Jean, Sandy, and Sasha, the 16-year-old for whose benefit the adventure was planned—drove to Oberlin, Ohio, then Ann Arbor, Michigan, then Chicago, where we spent four nights before heading home, stopping in Pittsburgh along the way.

Much of the driving was unexceptional, especially once we crossed into Ohio, where the flat expanses had us discussing “prairie madness,” the 19th-century phenomenon of immigrant farmers developing mental illnesses in response to the bleak winters, howling winds, and geographic isolation of the Great Plains. But when we hit Chicago, things got interesting. And by interesting, I mean insane.

At first, Chicago seems so orderly. To the east, you have a big lake. Opposite the lake, the city itself, more or less a grid whose rectilinearity is enhanced by the gorgeous forest of skyscrapers at its center. There are occasional disruptions and perturbations of the grid—the Chicago River, Navy Pier, the stacked seashell towers of Marina City—but these only serve to heighten the feeling of order everywhere else. You are otherwise in the forthright Midwest. To go north, you go north. To go south, you go south. Lakeshore Drive may be America’s pokiest thoroughfare, but at least it’s a straightforward answer to a straightforward problem. It’s not the motherfucking BQE.

But right in the heart of the city, in the Loop and the riverbanks, that forthrightness evaporated when I attempted to park our car—at one of the underground garages of Illinois Center. Down and down and down we went, and around and around and around, and… up? and back down? GPS failed. We were on Upper North Columbus, then Lower Beaubien Court, passing subterranean vans that had been parked so long they’d accumulated layers of sediment. Few homeless people had even camped here, although at one point, at a stop sign, I was waved down by a pair of confused pedestrians, who asked me where they could find the impound lot.

“I can’t help you,” I said. “I’m from New York!”

“So are we!”

Quickly, we learned the app Spot Hero was essential, not just for booking parking spaces in advance but for its first-person-POV video directions on how to find the garages themselves. For us neophyte Dantes wandering the hell below the Windy City, Spot Hero was our Virgil.

The more I moved in and out of that underground zone, the more it perplexed me: An incomprehensibly large swath of downtown Chicago sits atop two or three (or more) stories of steel and concrete substructure—substructure that happens, technically, to be aboveground. All those skyscrapers—some dating back a century or more, others of recent vintage and stretching 1,000 feet up—sit not directly in bedrock but on a chaotic manmade labyrinth whose construction, as we learned on an excellent boat tour run by the Chicago Architecture Center, began in the 1860s. Apparently, this was so that the early city could develop a sewer system, and they needed it to flow downhill—into the river, of course. The fact that it’s still around, that it continues to support millions of tons of buildings and that it appears to be unmapped by our sophisticated software systems, is a testament to the utter lunacy of generations of Chicagoans.

That is, what seems simple and honest is nuts. We need a sewer system, so let’s lift our entire downtown 40 feet up, buildings and all. The river is polluted, and it’s polluting our drinking water from the lake, so let’s just reverse the course of the river! Let’s build a (slow) mass-transit system way out into the urban prairie, where you’ll still spend 30 minutes on foot trying to get anywhere, so you might as well just drive anyway, even if half of Lakeshore is always blocked off by orange cones.

This is not a complaint—I loved it! When we walked in Chicago, I could clock each building, each block, each neighborhood. But to drive in and around and under and through Chicago, I started to gain a sense of how the city as a whole was put together. On foot, I felt like I was in another version of New York; at the wheel, I was elsewhere—a Bizarro World mash-up of… Baltimore and Los Angeles? Sure, why not.

Chicago may have hidden its craziness beneath its buttoned-up grid, but Pittsburgh let it all hang out. What psychopath decided to build a city here? Sure, you’ve got the confluence of three navigable rivers, which I admit makes for a fine 19th-century trading post, but the rest of the city is a random profusion of hills and gorges, swerving roads and perilous climbs. There are no straight lines, no obvious sightline routes from one place to another. It’s as if M.C. Escher and Jackson Pollock had gone into urban planning.

We didn’t stay in Pittsburgh long enough for me to feel like I really knew my way around, but I got enough of a taste of it that I could imagine how delicious such mastery would be. This seemed like a city where such esoteric knowledge could define you, confer on you an aura of divine wisdom—or maybe occult sorcery. While we swooped from a brief stint on an interstate to a slow roll through quiet neighborhoods, I imagined being able to hold the entirety of Pittsburgh’s trippy topography in my head like some kind of higher-dimensional object. I’m not sure the human mind is up to the task.

As we drove around, I was impressed, too, that mankind had built and maintained¹ a city like this, where caution and logic bowed to necessity and improvisation—except when they didn’t. And it reminded me of other places I’d felt the same: speeding in a Suzuki through switchbacks in the Blue Mountains of Jamaica, hitting curves with enough Gs to frighten my local passengers; cruising in sixth gear in a rented Fiat under and through and up the Apennines, climbing high enough to where snows forced turnarounds; and roaming the back roads of Nagano, where precarious villages, some now abandoned, testified to the tenacity of humans to settle anywhere they damn well chose.

It’s this that I especially love—how we as a species can settle into an environment, both mastering it and remaining within it, living by its rules even as we push their limits. To be sure, we overdo it a lot of the time, perhaps all of the time, and we are clearly now paying the price for our errors and greed. But when we do it right, when the tracks we lay and the homes we build pull off that Schrödingerian trick of overlapping dominance and submission, the results are sublime. And to witness that sublime from your own little high-speed steel box, your high-tech turtle shell, is a joy you should not easily dismiss.

And the best thing about driving is this: When you’ve located that magical place, when you’ve found that transcendent moment and need to make it last, you can always pull over, get out of the car, and stretch your legs. 🪨🪨🪨

Read a Previous Attempt: Hate Cars, Love Driving

A slightly different take on the ethics of owning a car.

1  Debatable, I know!