SHOE LEATHER
WALK ON

Last summer, Caleb Smith, a thirty-four-year-old librarian at Columbia, came across an old Times story with the headline “navy officer near the end of 4-year project of walking in every street on manhattan.” The article, from December, 1954, was about an eccentric sixty-five-year-old named Thomas J. Keane, who, in the course of taking carefully planned weekend strolls, had managed to traverse some three thousand blocks and five hundred miles of Manhattan terrain. Smith, himself an inveterate walker, was then a little more than two years into his own all-encompassing Manhattan project—and, he estimated, about three-quarters of the way done. Why not pick up the pace and aim at finishing on the fiftieth anniversary of his predecessor’s achievement?

That was two Sundays ago, and Smith, to commemorate the occasion, invited a handful of friends to watch him walk his last untravelled block—Thirty-third Street between Fifth Avenue and Broadway, at the foot of the Empire State Building. His final stats: thirty-one months, four pairs of shoes, one ex-girlfriend, and one aborted mugging, all culminating in a last, leisurely stride and a pervasive (if unspoken) feeling of “What next?”

You might ask: had Smith, in all his wandering, really never walked past the Empire State Building before? Taskoriented walking, it turns out, is distinct from destination-oriented walking or dog walking—all walking, in fact, that has an alternative purpose. In Smith’s grand design, a block remained technically unwalked until he colored it black on his laminated map (Hagstrom, pre-digital edition). Being officially “on the walk” required him to be alone, in possession of a notebook, a camera, and a Sharpie. He instituted the solo rule early, after a frustrating experience spent crossing the West Village with a friend. “I kept saying, ‘No, we have to go down this other street,’” he recalled the other day. “And she got impatient.”

A few days before he crossed the finish line, Smith made an exception to this rule and allowed a reporter to tag along as he sought out some last, elusive stretches of road up near Inwood: a cul-de-sac off 186th Street called Washington Terrace; the perimeter of Bennett Park, where Fort Washington once lay; Colonel Robert Magaw Place, between 181st and 183rd.

“Obviously, there’s some sort of psychological thing going on that I don’t quite understand,” he said, emerging from a Dunkin’ Donuts on 181st Street with a cup of hot coffee—essential, in cold weather, for maintaining the manual dexterity necessary to record his route. Before beginning this project, he explained, he had walked the length of Broadway—the full length of Broadway, from Yonkers to the Battery—and snapped a photograph at every block along the way. (“The pictures were kind of boring.”) He had also once done Staten Island, top to bottom. (“It’s a lot bigger than you think.”)

As he walked west toward the George Washington Bridge, Smith began recapping his excursions. Harlem had the best architecture, while Washington Heights, where he had been forced to dodge errant baseballs and spurting fire hydrants, had the best street life. Downtown had been less satisfying. “Greenwich Village and the Financial District were almost a total loss, because you’re looking at the map the whole time,” he said. “I’m clearly going to have to go back and do them again.”

Smith, who is from Albuquerque and moved to New York in 2000, loves what he calls the “rock-star sites,” such as the Statue of Liberty and Times Square, but he is most passionate about the less heralded landmarks and oddities of the city: coal chutes and watchtowers and rock formations. Approaching Bennett Park from Pinehurst Avenue, he stopped and pointed at an outcropping of Manhattan schist. “This is the highest spot in Manhattan,” he said, beaming. Then he retrieved his map from a beat-up manila folder and made a minuscule mark with his Sharpie: another one down.

The two questions Smith is most frequently asked, he said, are “Why?” and “So are you going to do Brooklyn next?” He doesn’t answer the first (“If you’re an urban explorer, it’s pretty obvious”), and no, he isn’t doing Brooklyn. If you must know, he is contemplating Central Park—those countless paths and walkways. In the meantime, he is recording his adventures and discoveries on his Web site, NewYorkCityWalk.com. He might, for instance, post his observation that the island’s cuisine falls into two categories: Chinese Mexican, or Asian-owned restaurants that serve tacos, which can be found below Ninety-sixth Street; and Mexican Chinese, or Hispanic-owned restaurants serving fried rice, which are more prevalent above Ninety-sixth. He prefers the former.

Before completing the project, Smith made a final, ceremonial exception to the rules, and, as though passing the torch, arranged to walk the streets of upper Inwood with an apprentice, Mike Epstein. Epstein, who runs the photo blog Satan’s Laundromat, has so far logged just two dozen miles, but he has plans for one-upmanship. He intends to do Roosevelt Island.
— Ben McGrath