Walking 28 Miles Around the Island of Manhattan—in a Day

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I myself harbor no illusions of sanity, so of course I wanted to do the Great Saunter as soon as I heard about it.

The walk, the 30th edition of which was held on May 2nd this year, is organized annually by a New York-based nonprofit group called Shorewalkers. Starting at a tavern near the tip of southern Manhattan, the walk takes you up the West Side, past the George Washington Bridge, around the tippy-top of the island known as Inwood, through Harlem, and down the East Side back to where you started, 32 miles in all.

Walking is my preferred mode of transportation. Since equipping myself with a pedometer a few years ago, I have sought daily validation in my step count, sometimes only finding the motivation to leave my apartment by imagining the sad onscreen zero that would stare back at me otherwise. But my enthusiasm for walking results in actions like getting off the subway a few stops early or walking a mile to the movies. On a good day, I top out around seven miles. I was in no way prepared to walk 32. And I meant to prepare, really I did, but things came up. Jury duty, a vacation, a weekend out of town for a wedding, and before I knew it, it was the week of The Saunter.

A friend who completed the walk last year Gchatted to ask me if I was ready, and more specifically, what kind of footwear I'd be sporting. Surely I knew to wear good, lightweight wool hiking socks and to change into a new pair halfway through? I confessed that I didn't. I Googled furiously. I started several times to read up on training but usually closed the tabs soon after I read words like "four to six weeks of prep time."

I made emergency visits to Patagonia and REI and spent a combined total of $72 on high-performance socks. I Gchatted a friend who had signed up to walk with me. "How are you?" she asked. "Good good ... getting worried we're all going to die on this walk!?!" I answered back. Another friend who completed the walk told me she couldn't walk for days afterward, that she got black and blue marks under her toenails. I didn't even know that was possible. In the back of my mind, I started to acknowledge the very real possibility that I might not finish. And there was nothing, a few days out, that I could do to change that.

The morning of the walk, I had that day-of-the-big-test feeling I remembered well from high school. I wanted to interrogate everyone around me: How much did you prepare? We started at 7:30 a.m. (Saunter materials advised us to expect to finish around 7 p.m., gulp), and I couldn't help feeling guilty for dragging my friends out of bed so early for an activity that would surely only lead to pain.

Nevertheless, the weather was perfect, and my group was in good spirits. The beginning was the easiest, but it also felt long; it took forever to get to the numbered streets from the Financial District, then it took forever to get to what felt like a significant street number, like 50th, at which point we'd only have, oh, 150 more blocks until the halfway point. Because 32 miles is truly an insane amount of miles. More than a marathon, more than you've ever walked by two or even three times. More. Demi Moore? Just more.

Since nearly the beginning of the walk, the George Washington Bridge, toward the top of the island, loomed in the distance. Envisioning ever reaching it was like being 8 and imagining yourself as an adult: It seems like you'll never get there. That would be far away even if we drove, and we were on foot.

We walked through lovely park after lovely park; we took riverside pictures. When you visit all the places you'd always meant to have visited in your multiple years of occupying a city all in one go, it dawns on you that just maybe you are not using your time as productively as you could be.

We stopped a bunch of times to stretch, to sit down. My friends got tired, and I couldn't blame them. How I motivated myself, how I always motivate myself, was by picturing my next meal. We'd been told to pack food, and I'd dutifully brought some snacks, but my thoughts were, "I'll be damned if I'm going to walk that many miles and eat anything less than a feast." I was sure there'd be somewhere good to stop. In reality, lunch ended up being a hot dog from a hot dog cart and ice cream from an ice cream truck. Neither are known for their energy-boosting properties.

Around lunchtime is when my group started to break down. Two of our number peeled off at Dyckman Street. Knees and hips were starting to hurt. They'd walked 15 or so miles in about four hours, a respectable showing, more, really, than any normal person ever walks. The three of us who remained pushed on to Inwood Hill Park. We openly fantasized about splaying out with our shoes off at the halfway marker. Of course the park turned out to be endless, and the picnic tables set up with free chips that would herald our arrival to halfway-doneness were located at the very end of it. We sat down for a long time when we got there. By now, our feet hurt. There are only so many times you can pound your feet, protected by your humble and totally-not-built-to-walk-32-miles-in sneakers, before they start to fight back.

Nearby, we overheard a group, considerably peppier than we were at this point, refueling for the second half of the trip. They were pros, with special foot powders and arch-massaging devices. We got to talking with one of the women. The key, she said, was to do the walk backward, starting with the East Side and finishing with the West, so you'd be with the sun. "That way you don't get back to the starting point all cold and miserable," she said, knowing that's exactly what lay ahead for us. Another friend soon called it quits, and then there were two.

We pressed on through Highbridge Park, which was beautiful, with the trees in full bloom. I don't know when else I would have gotten the chance to walk through if not for the Saunter. Walking hurt, but so did standing still, so it seemed like we might as well keep going. By now we were pretty far behind where we were supposed to be, according to the timeline listed in the brochure.

Harlem took forever; in the absence of a shore-adjacent path, we walked through the city streets, and I marveled at yet another interesting, vital neighborhood that I was somehow only visiting for the first time. We were supposed to reach Carl Schurz Park, on the Upper East Side, around 4pm, but it was 6:30 by the time we strolled through. We'd stopped plenty, sure, but we'd been walking all day.

Before this, I can't remember the last time I blocked off an entire weekend day like this—no errands, no catching up on TV, just walking. For years I've struggled to take up any exercise routine that isn't walking. Other thing are more efficient, allowing you to burn more calories per hour, but I like being able to walk and talk and to enjoy my surroundings while I do it. The idea of walking all day also dovetails neatly with a secret dream of mine, which is to somehow frontload all my exercise into one action-packed unit of time, burning so many calories in, say, one day so as to allow myself to take off the rest of the month. Could circumnavigating Manhattan once in a while be my new workout plan? Obviously my logic here is flawless.

In Harlem, I thought that if we could just make it back to 100th Street, we'd be golden. 100th was practically 50th, which was practically the end of numbered streets and practically back where we'd started in FiDi. But my last remaining companion started flagging in the mid-70s. He suggested we stop for dinner, and we found a diner in the East ‘60s. I had hoped that by dinnertime we'd be celebrating having made it the whole 32 miles, but it was not to be. He determined he was too tired to go on; even the 10 blocks to the subway would be a struggle. Sitting for an hour had allowed my injuries to crystallize, and my feet were in serious trouble, my big toes getting squished and my pinky toes feeling like they were about to poke out of my sneakers. I also—how do I put this delicately?—had a bit of a butt-cheek chafing situation. But I wanted nothing more than to soldier on.

By now I was alone, it was after 8 p.m., and it was dark. Finishing—as in, making it back to the tavern where all the other finishers would be, celebrating—did not seem like a realistic possibility. Forever aiming for an A, I decided I'd be happy with 90 percent. Or I could at least live with it. I walked, or rather hobbled, another 30 blocks before unceremoniously boarding a bus that would take me to a subway that would take me home.

According to the Saunter's website, 1,235 people started the walk, and 618 finished it. I was not one of the 618. I did 28 miles, maybe 29. Maybe it's like that Tolstoy line: All Great Saunter finishers are alike; all Great Saunter quitters are quitters in their own way. I imagined the particular circumstances that led to all 617 of us who didn't finish throwing in the towel, each its own story that could be mapped onto a particular point on the island, each resulting in its own injuries and triumphs. Whether we'd quit or finished, we'd all have some pretty crazy blisters to compare the next day. Mine were bad, but to tell you the truth, I've mangled my feet way worse by wearing uncomfortable heels.