On a rainy December day in 2022, I did what most New Yorkers loathe to do: I took the train to Times Square. I made my way into a testing center used by the New York City Department of Consumer and Worker Protection, somewhere between Margaritaville and Madame Tussauds. No, I had not been subpoenaed; rather, I was one multiple-choice test away from becoming a licensed sightseeing guide. All I had to do was answer 150 questions about history, architecture and transit in the five boroughs.
In the testing room, I clicked through questions ranging from the tedious (Identify the crosstown buses in Manhattan) to the arcane (Q: Where did Katharine Hepburn live? A: Turtle Bay Gardens). It took over two hours, but I passed, and a few weeks later, after I certified that I owed no one child support and paid my $89.76 in fees to the city government, I received my plastic city-issued sightseeing ID by mail. I was one of several thousand licensed guides in the city. But the truth is that almost anybody can experience the joys of researching, writing and leading their own neighborhood tours. It’s a rare and rewarding opportunity to invite people to walk around inside your mind.
A friend introduced the idea to me back in 2016. I had just moved to New York for graduate school, and I hated the city: It was too loud, I was always lost and everything reeked. But I was an active Wikipedia user, and began accumulating mostly useless facts in the hope that they’d make the city make sense. Walking down Wooster Street, I would stop and tell my companions to look up. “On the second floor of this building, there’s a room with nothing but 280,000 pounds of dirt in it,” I’d tell them. “It’s called ‘The New York Earth Room,’ by the artist Walter De Maria.” Passing by the famous Flatiron Building on 23rd Street, I’d allow out-of-town visitors a moment of silent appreciation before pulling them across Fifth Avenue. “This is not just any Starbucks,” I’d say. “This is the house where the novelist Edith Wharton grew up.” In isolation, each detail amounted to little more than a point in bar trivia. Individually, those facts felt meaningless; together, though, they made me feel at home in the city. I imagined that leading a real tour would give form and function to all the information rattling around inside my head.
Even after I earned my license, I struggled to make the leap from fact hoarder to talking-while-walking-backward guide. Did other people even care about this stuff? And if they did, who would want to listen to me opine? In the spring of 2023, a friend finally persuaded me to put our licenses to use and start leading free walking tours across the city. We purchased clipboards, horse-training flags to wave as we walked and — after a few complaints that traffic drowned us out — cheap speakers to hang around our necks and project our voices. Through the nonprofit Municipal Art Society of New York, we’ve organized some walks that emphasize how we see the city’s history and politics expressed in its built environment. Others are for friends, family and whoever else might find us on Instagram, presumably via their own niche interests.
When preparing a 90-minute tour, my friend and I amass something like 25 pages of raw notes that we refine into a comprehensible storyline and plot out on a map. Together we’ve unspooled everyday mysteries, like why Staten Island Ferry rides are free (nixing the once-50-cent fare that helped Rudy Giuliani shore up his mayoral re-election) and how pigeons came to dominate our streets (our architecture supposedly resembles rock ledges, their natural habitat). With each tour we’ve pressed ourselves into this city, like a flower into a many-authored book.
Initially, I saw the esoteric test and overserious licensing process as a personal challenge: Passing would be proof that I really understood this dense and mutable city. But as my test prep stretched on, I began to envision myself excavating hidden histories like so many layers of dirt. In hindsight, it was a mistake to think a guide must claim expertise, or even pursue it. Each tour is collaborative cartography, a map we draw together. As guides, we share what fascinates us about the city. In return, our attendees (and a surprising number of passers-by) give us even more to love — whether it’s a firsthand account of the 1977 blackout, insights into life inside a Jewish eruv in Crown Heights or a recommendation for Caribbean food nearby. Tours are also a means of envisioning possible futures. What would a city with fewer vermin look like, and how would we get there? Will this railroad track in Queens become the next Hudson Yards? And could Staten Island ever really secede from the city? I can contemplate these questions alone, but tours remind us that they can only be answered as a collective.
One possible etymology suggests the word “guide” is related to weisen — a German word meaning “to point.” But a truly skillful guide brings people together to witness. As with any live performance, what exactly people see, and how they make sense of it, morphs with each rendition. The spirit of a guide, licensed or not, is more enduring. You’ll know us by our rapt attention to the name inscribed on the park bench, and the furtive looks at the ConEdison crews exposing an entire world beneath the asphalt. Every pointed finger is, in fact, an invitation: Look with me.
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