An illustration of a rotary phone, pigeon, coffee, t-shirt, and flag
Madison McVeigh/CityLab

By winding through the city on a mission, our kids learned to look closely—and to trust themselves and others.

How did my family start training our kids to talk to strangers on neighborhood scavenger hunts? The same way people find their way in cities—with one idea flowing into another, and with help from strangers.

The hunts began four years ago, on Christmas Eve, when our kids were seven and three and my wife and I decided we would all do well to get some walk-around time before heading up to Grand Central to visit my parents in the northern suburbs. While we normally case parks, carousels, museums, and what have you, it seemed clumsy to lug overnight bags anywhere crowded.  

My wife hit on the idea that it would be quiet in our neighborhood, which borders the Lower East Side and Chinatown, and we could task the kids with a scavenger hunt for things we sometimes forget to notice. I wrote a list of such things—a cat in a store window, a takeout coffee cup—and then realized that they would remember the whole episode more proudly if they also had to talk to people who keep the city running. So I added autographs they had to get, via questions that pose no tricks or teases. The scavenger hunt is a mission to look more deeply and talk more openly.

That year, we tasked them with securing the autograph of a person who works for the city, and a tourist from more than 1,000 miles away. Nodding to the 28-degree temps, we honored our daughter’s request to look for tourists inside a swanky hotel. We found a pool table—which impressed upon me that the bon vivants visiting our neighborhood might secretly prefer plain-folks amenities, like I do—but no tourists. So we braved the cold again, and it was a gentleman from Brazil, with shimmering white sneakers, who gave the tourist autograph outside a tie store on Ludlow Street.

So a tradition began, and each December 24 it’s extended farther from home. In 2014 it went as far as the East River; in 2015 it crossed into Brooklyn; in 2016 it included Grand Central itself. Each year we've added map challenges, arithmetic, and facts about history and geography. The hunts always challenge our kids to tell east from north, read store signs (for misspelling), do math (for example by adding Rite Aid item prices that all end in .99) and—most importantly—talk to strangers.

In 2014, our kids had to ride bikes around Manhattan’s southern cone and find various examples of infrastructure—downspouts, solar panels, left-turn traffic lights, shredded basketball nets. That list wound past the motorized cartoon characters that stand guard outside Chinatown groceries and by the Manhattan Bridge ledge where pigeons hang out after rush hour.  The 52-degree rain made it a little tedious and my clues didn’t require as much talking—our daughter found “someone voluntarily making the city cleaner or safer” by noticing a woman pick up a sandwich wrapper and lob it into a trash can.

Over the next year, we started thinking about teaching our daughter to navigate our neighborhood—how to tell uptown from downtown, nearby from far, and form a rubric for asking for help if she ever found herself lost or uncomfortable. In that spirit, the kids had to figure out that they could only find some clues by crossing a bridge, and get themselves across that bridge. (I’d told them to bring scooters.) They warmed up for this by finding the closest subway stop, then looking to the left for a place where they could stand over the water.

And we wanted them to think and talk about the city as a place of immigrants and travelers. They had to get credible directions to JFK airport and find someone who could finish the Emma Lazarus poem at the base of the Statue of Liberty. They had to find people born east, west, north, and south of various cities around the world.

While we’d once taken the lead, my wife and I started hanging behind. We wanted our kids to feel more confident about navigating directions and jotting things down. But we also wanted them to gain a sense of support—to know that people would help them.

People took pleasure in the process. You heard it in the casual crackle of conversation with a woman who seemed like a grandmother, or a youngish mother and a baby in one of those shock-absorbent strollers outside a Williamsburg gift shop, who overheard our guys strategizing and leaned in to offer guidance. The hunts seemed to create a genial, adventuresome mood among strangers.

In 2016, the kids had to find out information without screens, like the number of miles in a 10K or the president who took the U.S. off the gold standard. (The people who helped them sometimes used screens, but hey.) They also had to do math, and talk to more strangers (who would divulge their birthplaces, and then locate those birthplaces on a map). Some people don’t want to talk. Others really enjoy it, like the tourist who overheard us talking about finding someone who’d grown up in a house with a rotary phone. He started waving his arms and became an early signer of the sheet.

Most just help. The kids found a “person who works with his hands” running his tailor shop on Allen Street, and a person who voted for Reagan managing the Payless on Delancey. A woman in a self-storage shop told our gang she grew up in Omaha, Nebraska, and confirmed that this is west of St. Louis; a guy in the grilled-cheese specialist next door was from Queens. The guy who knew about Nixon taking the country off the gold standard wore jingle-bell suspenders; the guy who voted for Bernie ate at a table where the woman in business school waited on him.

The hunt isn’t about eliciting oohs and awws from the people my kids chat with. Instead, it’s about the kids realizing that the crowded city lures crowds because anyone in it holds knowledge or skill that someone else needs.

“Can I ask you something?” our kids generally say.

One woman’s reply sticks with me: “If I can answer, of course.” She was waiting for the question, thinking who knows what, but open.

If you want, you can treat this case as testimony for or against “helicopter” parenting or “free-range kids.” We obliged our kids to navigate and approach people on their own, and as they got older we stepped back from the interviews. At the same time, we remained easy to find—in part to reassure adults this was no two-child monte—and we stayed flexible when a particular item seemed remote. I had thought a horse would turn up early, vinyled onto the side of a Budweiser truck, but they saw none until they reached the pastoral print in my parents’ dining room. And props to my sister for singing the first verse to “America the Beautiful” when it seemed nobody else in Grand Central would.

Our scavenger hunts may never end: In the past couple years, our kids have written ones for us, and 2015’s remains open. (If you were born in Norway, please show up serendipitously on my commute, as I have a piece of paper for you to sign.) The adventures also needn’t be just for kids, or in hometowns. I’ve done the scavenger hunt in Baltimore, where a guy pulling espresso shots volunteered himself as an art student.

The prize is a handwritten sign that says something like “MASTER SCAVENGER,” but of course this just stands in for the larger reward. The guidelines for a fun hunt serve as a proxy for principles in urban citizenship, made up as we go along.

Here are some suggestions for starting your own:

Use a list that mixes conversation with observation and orientation. I like to include a few gimmes—things like a bank branch or a vacant lot—along with storefronts or parks with unusual spellings or striking scenery. Mix these with autographs from people you’ll likely actually meet (public servants, baristas, dog walkers, whatever) and the hunt picks up its rhythm.

Go where people aren’t driving. Walk around. Cross zones or borders. Go over a bridge, through a tunnel, from one side of an eight-lane to another.

Talk to people. And listen to them as well. If they ask why you want to know something, explain. Say please and thank you. Don’t treat them as props or ask them to fuss over you. Ban consulting screens, but accept help from people who themselves talk to Siri.

Gather facts from diverse people. Opinions and styles will come out anyway. You might find racism. I hope you wouldn’t, but you might. And you might find a way to zap it when you do.

It’s all a matter of looking in layers—the horse could be on a Budweiser truck or the awning of a bar, or a cop could be riding it. Keep looking for answers, and for input. You may end up helping someone feel appreciated, or at least helping someone engage with the day.

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