Five teen boys and two grown men, squished into a huge SUV, hemmed in by skateboards, video gear, sweat-skanked clothes. Doritos bags, soda cans, and water bottles at their feet. A record-breaking heat wave simmering outside, the air conditioner groaning. Seven of us, lost in Cleveland, and I’m wondering why I thought this was a good idea.

Sean, fourteen, the older of my two sons, sitting beside me in his cutoff jeans and Thrasher T-shirt, pokes our iPad screen, zooms in and out on a digital map, trying to find a skate spot he’d seen on YouTube. Using Google Maps in between chugs of Gatorade, he searches for a little plaza surrounded by housing projects. “We’re close, we’re close!” he yells, unsure. Pinch and zoom, treasure-hunting for a patch of Cleveland concrete.

We’ve been on the road for five days, and our adventure is imploding. We should be sprawled out in a converted 1972 school bus, but the bus died in South Carolina before rolling a foot. “The last thing we need right now is getting lost in a Cleveland slum,” I say, eager to keep pushing toward Detroit. I want to support Sean, but I have that nagging feeling I’d had in New Orleans five years earlier, driving through the Lower Ninth researching a post-Katrina book—I feel like a ghetto tourist.

“We’ll be back on the road in thirty minutes,” Sean says, then scolds: “And it’s hardly a slum, Dad.”

I appreciate my sons’ curiosity about the off-piste corners of the world, which YouTube and their online skate community have helped shrink. They’ve come of age at a time when a Seattle kid in the back of a Ford Explorer can find an inner-Cleveland skate spot with an iPad. I’m cool with that. But we’re behind schedule. And our stinky SUV is due back to Budget Rental at the St. Louis airport in three days. Unless we find replacement wheels we’ll be stuck halfway into our cross-country skatepark tour.

Still, one reason we’re on this fathers-and-sons trek is to experience a nontouristy, mostly urban version of America, including the concrete jungles that have become my kids’ playgrounds. So I grudgingly pull off I-77 and follow my kid’s spotty instructions. “Don’t worry,” says Sean. “We’re really close. I think.”

After a few laps around a neighborhood that could be a stand-in for Baltimore’s The Wire, Sean yells, “Turn here!” A few hundred yards later we’re in an alley, and Sean checks his on-screen satellite view and yells, “Stop!” He jumps out, turns down a side alley, and with a glance back at the SUV is gone. My first thought: my wife is going to be so pissed.

Sean finally emerges from the alley and skips back, wide-eyed and giddy. “We’re here!” The other boys grab their boards, and my pal Lou and I swap nervous looks as all five boys—his son, my two, and their two friends—skate past the “No Guns!” signs toward a plaza of concrete ledges, banks, and a trapezoid-shaped platform topped by a Japanese-looking sculpture. I’m thinking: We risked our lives for this? Sean, as if hearing my thoughts, says: “I’m not scared . . . Maybe I’m a little scared.”

The boys roll across the plaza and begin ripping ollies and kickflips, rock-to-fakies and board slides. Another skater arrives, then another, and the plaza is transformed into an impromptu skate park. A young girl walks by, tugging twin toddler boys in matching cargo shorts and Gap T-shirts, and Leo, my thirteen-year-old, rolls up and offers his board: “Wanna try?”

The twins’ eyes light up and they look to the girl, who shrugs. Our crew starts giving skate lessons, holding the twins’ hands, towing or pushing them. One kid juts out his arms and strikes a surfer’s pose, “Check me out!” It’s cute, but I’m thinking: What if he falls and cracks his skull?

Later, as we head toward Detroit, Leo’s buddy Nathan writes our daily blog post, summing up the Cleveland detour: “Most parents wouldn’t have done that.”

I’m not sure if I should feel proud or ashamed.

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