The Daily - The Sunday Read: ‘What I Found on the 365-Mile Trail of a Lost Folk Hero’

Episode Date: March 23, 2025

Sometime in the 1850s or ’60s, at a terrible moment in U.S. history, a strange man seemed to sprout, out of nowhere, into the rocky landscape between New York City and Hartford, Conn. The word “strange” hardly captures his strangeness. He was rough and hairy, and he wandered around on back roads, sleeping in caves. Above all, he refused to explain himself. As one newspaper put it: “He is a mystery, and a very greasy and ill-odored one.” Other papers referred to him as “the animal” or (just throwing up their hands) “this uncouth and unkempt ‘What is it?’”But the strangest thing about the stranger was his suit. Unlock full access to New York Times podcasts and explore everything from politics to pop culture. Subscribe today at nytimes.com/podcasts or on Apple Podcasts and Spotify.

My name is Sam Anderson. I am a staff writer for the New York Times Magazine. I kind of write about everything. I think my beat is subjects that I get totally obsessed with and then force my editors to let me write about. And a subject I've been obsessed with for so many years now is the old leather man. He's a sort of legendary folk hero from the 19th century who used to walk in this giant circle,

365 miles around through New York and Connecticut over and over and over again for decades. At such regular intervals that people said you could set your clocks by it. He wore this big funky leather suit that he stitched together himself, and no one knew where he came from or why he was doing this. He was a total mystery to the people who lived along his route. Newspapers published basically like fan fiction about the old leather man,

origin stories that people just made up about him. I think he was a perfect vehicle for people to express their own anxieties and fantasies. Just all kinds of trauma, tragedy people projected onto this mysterious guy. I stumbled across the old leather man while I was researching something else, and for whatever reason, it hit me like a bolt of lightning. I think what got to me was, number one, it's a great mystery, but number two, there was something really moving about this man and his relationship

to the towns that he walked through. There was such a generosity from people and genuine curiosity and empathy for him that I found really touching. And I think I really related to this guy as strange as it sounds. Like a lot of people, I think I feel sometimes alienated and strange or like I want to drop out of society. And here was someone who had done it in a totally fascinating way. So I would always fantasize about following in his footsteps.

Sometimes my wife asked me, what are you thinking about? I hesitate to answer because it's just the old leather man. Years passed and at one point an editor asked me, do you have any weird stories that you've never been allowed to write for the magazine? So for this week's Sunday read, I was able to fulfill my destiny and finally go

walking in the footsteps of the old leather man on his loop. I loaded up my backpack and I just for many, many, many days just walked and I wrote all about it. So here's my story. Our audio producer today is Adrian Hurst. The original music you'll hear was written and performed by Aaron Esposito. Sometime in the 1850s or 60s, at a terrible moment in U.S. history, a strange man seemed to sprout out of nowhere into the rocky landscape between New York City and Hartford. The word strange hardly captures his strangeness.

He was rough and hairy, and he wandered around on back roads, sleeping in caves. Above all, he refused to explain himself. As one newspaper put it, he is a mystery and a very greasy and ill-odored one. Other papers referred to him as the animal or just throwing up their hands, this uncouth and unkempt what is it. But the strangest thing about the stranger was his suit.

In summer and in winter, in every possible kind of weather, the man wore from head to toe an outrageous outfit he seems to have made himself. Rough leather patches stitched together with long leather strips like a quilt. It was stiff, awkward, stinky, and brutally heavy. It looked like Knight's armor made out of baseball gloves. To anyone encountering him on a quiet country lane, he must have seemed almost unreal. A huge slab of brown, twice as wide as a normal man, his suit creaking and squeaking with every step.

In the years following the Civil War, the wandering stranger became an object of curiosity, then a frequent subject of the newspapers. People gave him a name, the Old Leatherman. I suppose that many of the readers of your valuable paper have heard of the Old Leatherman, wrote someone from Rye, New York in 1870. Hearing the reports about this singular recluse, I, in company with others, paid his haunts a visit. The Old Leatherman was a sort of real-life northeastern Sasquatch. Curious citizens went plunging into the woods to investigate.

What they found surprised them. The old leatherman's caves were orderly, complete with primitive fireplaces, sleeping areas and stores of food, meat and hickory nuts. Under one slab of rock, he had dug out an apple cellar. In some forests he kept well-tended gardens. Month after month people watched the old leatherman clomp past their farms and through their woods and right up the main streets of their tiny towns. At meal times he would stop at sympathetic households, the same ones over and over, to ask with a grunt for food.

He rarely spoke, and when he did, his words were clipped, strange. In the silence, rumors grew. People speculated that the old leather man was French, or French-Canadian, or Portuguese. They said that he couldn't speak at all, or that he just couldn't speak English, or that he spoke English perfectly, but pretended not to. They said he came from a family in Hartford named Brown. They said he was immune to rattlesnake bites. The more he walked, the more fascinated people became. Year after year, the old leather man was like a song stuck in the whole region's head.

As residents compared notes, as newspaper coverage snowballed, some actual facts became clear. For one thing, it turned out that the old leather man was traveling great distances. His network of caves spanned at least 100 miles. Also, his wanderings weren't random. They were regular and repetitive. In an effort to map his route, people set up sting operations in the woods. They tailed him from town to town. Finally, in the mid-1880s, people realized something astonishing.

The old leather man was walking in a giant loop, roughly 365 miles around. It stretched from the Hudson River in the west to the Connecticut River in the east, from mountains in the north to beaches in the south. Along the way, it passed through something like 50 towns. One full circuit usually took him 34 days. His coming can be calculated with almost as much certainty as that of an eclipse,

one newspaper wrote. Another said, so regular are his habits that it is often said that he is the only sure thing that farmers can depend upon in this age of uncertainty. Soon the old leather man became a full-blown media phenomenon. The Hartford Globe published a front-page article complete with a timetable of his travels. In small towns, people lined the streets to watch him pass. School teachers let their students out of class to give him treats. A shop offered promotional Old Leatherman postcards. Artists produced woodcuts and paintings.

Photographers hid cameras in doorways or behind hanging laundry to capture his image. The Old Leatherman never sought the attention. If anything, he avoided it. He went out of his way to skirt the region's big cities, Hartford, Bridgeport, New Haven, and if a homeowner got too inquisitive, he would walk away and never come back. Once in Woodbury, Connecticut, someone presented the old leatherman with some recent articles about him. He grunted over them, the newspaper account read, but showed no enthusiasm at finding himself famous. Who was he?

Why was he doing this? People were obsessed. But try as they might, no one could figure it out. One of the most noted philologists in the state spoke to him in a half dozen different languages, the New York Times reported in 1884. He could get no reply but a guttural sound which meant nothing and which was more animal than human in its character. In the absence of real information, people were happy to invent things.

Theories emerged. The old leather man, one man claimed, was disguising himself to evade police. He was, quote, a fugitive from justice and a negro. Or he was a wealthy businessman brought low by a fire, mourning the death of his fiancé. In the end, one origin story conquered all the rest. It appeared in 1884 in the Waterbury Daily American under the headline, The Mystery Solved. Although it was fiction, it spread so far so fast

that it came to be accepted as truth. In this version, the old leather man was a Frenchman named Jules Bourglet. As a young man, he fell in love with the daughter of a wealthy leather merchant. But the merchant disapproved of the match, and so he issued a test. Jules could marry his daughter only if he joined the company, and over the course of one year, proved himself. Things went great until near the end, Jule made a big investment right before the market crashed. The company was ruined. The marriage was forbidden.

And Jule, driven mad by grief, moved to America, where he stitched himself this suit of leather scraps and walked alone in circles for the rest of his life. It was a real potboiler, a simmering stew of classic 19th century anxieties, class, economic bubbles, madness, immigration. And yet people believed it. Eventually the name Jules Bourglet would appear on the old leather man's gravestone. In the meantime, year after year, namelessly trailing this ever expanding cloud of stories,

the old leather man continued to walk. Today, the old leather man is one of those stories that you either really deeply know or have never heard of at all. I discovered it by accident 14 years ago. I was having a perfectly normal day, minding my own business, reading a book about local caves when suddenly this absolute molten chunk of American lore leaped out of the pages and installed himself in my brain. The old leather man hit me with an almost religious force.

He was a perfect little parable about something both universal and to me very personal. The tension between alienation and belonging, rejection and rejecting. Who gets to belong to a group? What are the smallest possible triggers for inclusion or exclusion? And what happens when someone flips that dynamic, when the individual is the one rejecting the group? And the individual is the one rejecting the group, rejecting in fact the whole society, but also refusing to go away.

To the people in my life, friends, family, editors, my infatuation with the old leatherman quickly became a running joke. More than once, my wife has banned me from discussing him in our house. I've had out-of-body experiences where I've watched myself droning on, unable to stop, making acquaintances late for trains. But what was I supposed to do? He struck me as a perfect existentialist hero, someone who spurned the false comforts of society, who stood by choice out in the cold harsh wind of

reality taking it full blast in the face. The old leather man was like Melville's Bartleby the Scrivener except that he refused to even say I would prefer not to. This guy I thought had it all figured out. He managed to remain a part of things while holding himself apart. In my private fantasy of myself, I was a spiritual descendant of the old leather man. I too felt alienated from society. The world annoyed me, enraged me in 10 million different ways. I spent my childhood pinging between Oregon and California, between apartments and houses, between stepparents.

I have always been odd, anxious, introverted. I sometimes burst into tears at strange moments. Lately, I've found myself thinking more and more of the old leather man. The 21st century, unfortunately, turns out to be the perfect moment to be obsessed with his story. America keeps spasming with increasing violence in many of the same ways it spasmed in the 1800s. The old leather man looped his loops during an era of assassination, insurrection, civil war, impeachment, economic collapse, and racial terror.

He walked during the rise of Reconstruction and the crimes of so-called redemption. All around him, the landscape was being transformed. Forests fell, church spires climbed, downtowns burned, and rose again. He watched farms die, and railroads boom, and aqueducts stretch between cities. We have no idea what the old leatherman thought of any of this, or if he thought of it at all. And that is exactly the point. All we know is that he kept walking. Every morning as I struggled to metabolize the daily news, I found myself dreaming of dropping out of society,

following in his footsteps, knocking on the doors he knocked on, sitting in the caves he sat in. In the same way other people fantasized about moving to Canada, I fantasized about walking the old leather man's loop. But how? As a practical itinerary, the loop turned out to be tricky. It was regular but also elusive. A network of highways, country lanes,

backwoods trails, and railroad tracks that could shift subtly on his tiniest whim. Once when one of his regular households got a pet dog, the old leatherman never stopped there again. As one of the great old leatherman researchers, Alison Albee, has put it, all effort to tie directions he is said to have followed into a single contiguous pattern seems utterly futile. Nevertheless, I tried.

I visited research archives, made long lists, studied hand-drawn maps. I tapped into the knowledge of other old leatherman obsessives, a scattered group of amateur enthusiasts who've been stockpiling data points for 150 years. I spoke with Steve Grant, a journalist who walked the old leatherman's loop for the Hartford Courant in 1993. Grant told me with a real sense of loss that most of his maps are gone. Years ago, some other old leathermanophile

borrowed them and never gave them back. I pored over an online cave guide compiled by Lee Stewart Evans, an outdoorsy Englishman transplanted to Connecticut. And I basically wore out my copy of Dan W. DeLuca's heroically thorough book, The Old Leatherman, Historical Accounts of a Connecticut and New York Legend. Eventually, I cobbled together what I thought was a reasonable

outline of the loop. It was a bizarre travel itinerary, as if someone closed their eyes and drew with a shaky hand the most random possible cross-section of small northeastern towns. There are once bustling river ports like Austin Ing and Old Saybrook, and former manufacturing centers, Bristol, Terryville, Plymouth, and destination antique shopping towns like Woodbury. You could live 1,000 very full lives and never think about any of these places. But that was also its appeal.

There's nothing obvious about this route. The old leather man was giving me an excuse to step outside my own life, to look at old American places firsthand, slowly, to think about how they had changed, to walk around like a weirdo, knocking randomly on doors, talking to people who I had no business talking to. I just needed the right inspiration to start. I started walking on November 6, 2024. For months I realized I'd been living inside of screens, vibrating on poisonous frequencies. And now the inside of my skull was itchy and all human language felt like packing peanuts in my mouth.

I had a very strong impulse to move. So I grabbed a backpack and drove down to the old leather man's grave. The cemetery is just off the Hudson River in Austin in New York on a street called Revolutionary Road. It is, by American standards, ancient. The headstones are thin with fancy font and odd spellings and little carved pictures full of feeling. The memorial to the old leather man is a big rock with a plaque. My plan was to start here at the end of his journey

and move clockwise, unspooling the story of his life. I stood there for a good, long, meditative while. And then, like the old leather man, I walked. I walked north toward downtown Austin. The day was strangely warm, 80 degrees. People's yards were full of leftover Halloween decorations, giant skeletons, the Grim Reaper, demon pumpkins. It was leaf season, so I tromped next to and sometimes on top of huge piles of crispy golden

brown leaves. All the green life of the year, dead, heaped up on the side of the road. I passed a historic tavern where George Washington might have slept. I found a $10 bill on the sidewalk. In people's yards, I saw a Gadsden flag, don't tread on me, and a United States flag so tattered, it looked like it had been through the Civil War. For the next several months, off and on, I walked. Day by day, I would load my backpack with hard-boiled eggs and gas station snacks, then

trudge up roads toward the points of interest on my map. From Austin, I went to Briarcliff Manor, where one of the old leather man's caves still sits tucked into the middle of a neighborhood near a dead-end sign. Then to Chappaqua, where the Clintons live. In Lewisboro, I walked past a house where the old leather man used to knock on the drainpipe so the owner would give him coffee and sandwiches. I knocked. No one was home. I passed a house where the old leather man felt so comfortable that he used to go inside

to eat when the weather was bad. Until one calamitous day, the family brought out a watermelon and set it on the table. And the old leather man stood up and walked out and never stopped at their house again. The old leather man stood up and walked out and never stopped at their house again. I walked 13 miles one day, 15 miles another day, 18 miles, 20 miles. In Woodbury, I walked to the site of Alexander Gordon Sr.'s tannery, where the old leather man used to stop to collect leather scraps and drink from the water trough, and where

he once allowed Gordon to oil up his suit. It's now a liquor store. Very slowly, clockwise, I crawled around the loop on my big giant map. I have to say, right away, walking made me feel better. Every morning when I stepped onto the road, I got a little less angry. It's easy to hate the world when it's just an abstraction that lives in your phone.

It's harder when you're out there in it, really looking, interacting. Tiny moments felt hugely healing. On the edge of awesomeness, a woman at a gas station called out asking if I would help her with something. And I was sure it was going to be some kind of scam. But it turned out she just couldn't figure out how to get her gas cap back on. And I helped her, and she said, thank you for your kindness.

I felt relieved to be living in reality again, following the small rhythm of my legs over the big rhythm of the landscape, noticing the world, the houses under the clouds. Block by block, mile by mile, I felt my soul begin to unclench, like one of those mattresses that get shipped super compressed in a tiny box. Stepping into the world opened the box. Step by step, as the days and weeks passed,

I felt my crushed soul stretching out to find its dimensions, expanding to fill the huge space of the whole expanding universe. I marveled again and again at the way the past and present sit on top of each other. I walked past 18th century mansions with electric gates and private basketball courts. I saw decrepit houses that looked held together more by

air than by wood. I ate a Ben and Jerry's ice cream cone while sitting on a rock where George Washington once allegedly ate his dinner. One day I stood staring fascinated at a decrepit brick house built in 1790, its windows broken in a way that made it look somehow like the embodiment of the fall of the American Empire. And as I stood there, a cyber truck drove by. On some days, the walking was heartbreakingly lovely. The names of certain roads still make me sigh. Wood Road, Gauge Road, Spring Lake Road, Juddsbridge Road.

Huge territories felt like outdoor museums, curated collections of old stone walls, curving gently and rising with the land. The wide, quiet beauty of old New England. I spent many hours alone with birds. I watched a giant woodpecker perched on a thin, rotten rotten tree pecking so hard that the whole tree shook and swayed, pumping its red head until giant chunks of bark flew off and it looked like the wood pecker was about to peck the whole thing apart and go plunging to the ground.

Hawks screamed at me for invading their space or they glided silently over my head staring down. I startled probably 10,000 squirrels, and as they shot off through the dry leaves, they were so disproportionately loud that sometimes I thought they were bears. I had plenty of bad times, too. There were days so cold my hands stung, even in gloves, inside my coat pockets, and the wind whipped up tornadoes of snow, and I could feel my mustache hairs freezing and crunching in the steam from my nose.

Other days, just as cold, I was sweating so hard I had to take off my coat and hat. I was reminded over and over that the modern world is not made for walking. I spent many miles trudging on high alert up traffic-y highways without shoulders. Cars came screaming around corners. I found myself tightrope walking along the tops of cliffs, clinging like a goat to the sides of hills, teetering on old stone walls.

I stepped over all kinds of roadkill, a freshly pressed groundhog, a pancaked hawk. A pickup truck speeding past so close that I felt a rush of wind, and at the last second a German Shepherd shot its head out the window, barking and snapping, actually trying to bite me. One car whipped around a blind turn so suddenly that I went leaping over a guardrail, bashing my shin. It left a swollen knot that's still there. That same day, fighting my way through roadside trees, clinging to a different guardrail for balance,

I sliced the heel of my hand open on a nasty piece of metal. It became clear to me very quickly that despite my fascination and my fantasies, I am not the old leather man. I never slept in a cave. In fact, it turns out that I'm afraid of caves. Every time I found one, I would stand outside it for a few minutes trying to peer in from a distance and then I'd throw in rocks and sticks to scare out any wild animals. And only then, cautiously holding my breath, would I creep inside. Instead, I slept in hotels. Or I just went home. I'd walk all day and then, exhausted, order an Uber back to wherever I'd started.

Usually a shopping center where I'd parked my car. The ride was always humiliating. In 10 or 15 minutes, it rewound the walk that had taken me all day. It turned out that I was much more a creature of society than I like to admit. I'd walk for a couple of days and then have to go home for a dentist appointment. Things wouldn't stop coming up. I took breaks from the loop because my daughter was visiting for Christmas. Because I got a nasty head cold.

Because my beloved wiener dog, Walnut, suddenly lost the use of his back legs and we thought he was about to die. He got better. One evening at the end of a particularly grueling 20-mile walk, my wife picked me up in front of a public library and we went out for Thai food. She liked to call me the old pleather man. Yet, over many weeks after maybe 100 miles of walking, my domestication started to wear off.

One night I came home after a few days on the road, after not changing my clothes, and everyone in the house stiffened. My smell was like I'd brought a whole other person home with me, someone none of us had met before. One Tuesday, in mid-January, I reached a man-made lake the old leatherman never would have seen. In his time, it was a river winding through a town, until they dammed it two years after his death to provide drinking water for New York City. Today it is the East Branch Reservoir. When its surface is low, you can still see the old foundations of flooded buildings.

I walked on its shore over honeycombs of dried mud. The water was frozen. Way out in the distance, on the surface, I noticed tiny shapes moving. Ice fisherman. I stepped out, cautiously, arms spread, and stood watching a man drill a fresh hole in the ice with a bright orange auger. When he was done, I asked him if he'd ever heard of the old leather man. Of course, he said, everyone knew about the old leather man. Used to walk around, sleep in caves. Back in those days, the man said,

that kind of lifestyle wasn't so unusual. People were more comfortable outside. In fact, he told me, even when he was young, growing up right near this reservoir, there were people who lived like that. One of them slept in the woods near his family's house. An alcoholic, friendly and harmless. He remembers going out as a kid to give the man bacon.

On my walks, this kind of conversation was surprisingly common. I would ask people about the old leather man, and they would end up telling me about some other figure who once lived on the fringes of society. One woman told me about a guy named Footsie, who used to walk around Watertown, Connecticut back in her father's time. Several people mentioned the tragic life of Sarah Bishop, a young American who was kidnapped during the Revolutionary War by British pirates only to escape and live the rest of her

life alone in a mountain cave. I heard about mythic figures, the Witch of Good Hill, the Green Lady of Burlington, some of whom still haunt the places where they died. Haunting I think is a nice metaphor for the social dynamics here. An in-group is haunted, more or less permanently, by the people it chooses to exclude. They hang around like obtrusive thoughts. And in the old Leatherman's time, New England was a deeply haunted place. After the Civil War, especially during the depression of the 1870s,

there was a widespread public panic about so-called tramps, unemployed men roaming by the thousands, begging, hopping trains, looking for work. The rhetoric in the newspapers about, quote, robbery, incendiarism, intimidation, rape, and murder will sound familiar to modern readers. In Bristol, a writer declared that the solution was vigilante violence, a trusty weapon in every house,

they wrote, and a disposition to use it on very slight provocation. Eventually, Connecticut passed a strict anti-tramp law mandating the appointment of special constables to hunt vagrants down, promising $5 bounties for warrantless arrests resulting in conviction. In this atmosphere, even the old leather man was suspect. Early in his wanderings, people locked their doors when he passed. Mothers used him as a kind of boogeyman to make their children behave. But although he looked terrifying, people quickly came to understand that he was harmless. He never stole, never created chaos, never accosted anyone. Even when he was actively harassed, when a group of children surrounded him in the street

shouting insults, or when two rowdy men bullied him, forcing him to drink alcohol, the old leather man didn't fight back. He just got away as quickly as he could. He was quiet and inoffensive, said a man who saw him regularly near Waterbury. And when a person came along driving a lively horse, he would get out of the way so that his odd appearance might not frighten the horse. Soon, all across old leatherman territory, a communal instinct kicked in. Residents didn't just tolerate him.

They protected him. They took pride in his visits. They made special food to prepare for his arrival. Mothers scolded children for staring at him in the street. One boy, out for a hike, found an old leatherman cave unoccupied and used the wood inside to make a fire. When he got home, his mother made him go back, in the dark, to replenish the wood. She didn't want the old leatherman to get cold. The townspeople regarded the old leatherman with a mix of closeness and distance, familiarity and alienation.

He was the insider's outsider. He didn't belong, but he was accepted. Wherever he went, he created a circle of civility. His loop tied together otherwise disparate communities, like beads on a string. The tramp laws, curiously, didn't seem to apply to him. By tramping so openly, he seemed to transcend the category. He was his own special category. He was the old leatherman.

Maybe my favorite incident in the old leatherman story happened in a small town called Shrub Oak. He had multiple admirers there. One family, the Irlands, kept a special bowl and spoon just to feed him. Down the street at Darrow's grocery store, the owner kept notes in his account book about the Old Leatherman's trips through town. In February 1885, when the old leatherman didn't show up on schedule,

the people of Shrub Oak were worried. The weather had been terrible, weeks of sub-freezing temperatures, brutal rain. A group went out to check his cave in the woods near the ruins of a sawmill. It was empty. So it was a relief when on Thursday, February 19th, Darrow, standing in his store, saw the old leather man clomping up the

street. He was several days late and seemed to be in a hurry trying to make up for lost time. Darrow called out. He motioned to the old leather man to come inside, and against all odds, for reasons no one could fathom, the old leather man did. He sat down next to the fire. Mr. Darrow gave him some cheese and crackers, and as he watched the old leather man eat, he decided to try something. He took out a pencil and a piece of paper. I am old, Darrow said, and he wrote down his age. Then he passed the paper and pencil to the old leather man.

How old are you? He asked. People had been trying and failing for many years to pry information out of the old leatherman. Sometimes he grunted or muttered a few words in what some people claimed was French. Mostly he just turned and walked away. But this time, according to the shopkeeper, he didn't. The old leatherman took the pencil and pressed it to the paper. In large, crooked strokes, he wrote a string of numbers. 1-5-3-4-2. A few days later, the Peekskill Blade printed a facsimile of this odd answer, just as the old leatherman wrote it. What did it mean? There were debates. Some thought the old leather man must have been writing his birthday in the European style,

15-3-42, or March 15th, 1842. This would have made him 42 years old. Some, drunk on the mythology of the old leather man, took it at face value as evidence that he was 15,342 years old. Decades later, the researcher Alison Albee offered this speculation. One guess being as good as another, perhaps the leather man, understanding neither the question nor the meaning of Mr. Darrow's figures, showed his own peculiar method of writing 12345. Or maybe it was some kind of inscrutable code.

This to me is the perfect old Leatherman story, an absurdly specific data point with no clear explanation. We know plenty of facts about him. His height, roughly 5'7", the weight of his suit, 60 pounds, the length of his homemade hatchet blade, 9 1⁄4". And yet, the man himself was, is, and probably always will be a mystery. This is what I love, what keeps me circling back to him, over and over. The Old Leather Man is an engine of infinite interpretations, a story about stories. He gave us so little, and in doing so, he gave us so much.

In the 19th century, he was a perfect blank screen onto which society could project its fears and fantasies. And he remains so today. This is the real old Leatherman's loop. The one that we all walk, every second, on every level, eternally. The loop between reality and meaning. What we know and what we imagine. The old leather man's last loop came in March 1889. For months, it had been clear that something was wrong.

The old leather man was sick. In the later photos, you can see it. His bottom lip is swollen, marred by what one writer described as a raw sore. This was almost definitely mouth cancer, almost definitely from the tobacco that he liked to either chew or to smoke in his homemade pipe. The old leather man would often stoop down in front of post offices and general stores to pick up cigarette butts that people had thrown in the dirt. When he ate, he covered the sore with a special patch of leather. One house he stopped at for breakfast belonged to a doctor, and the old leather man allowed him to examine his lip.

The doctor gave him some ointment. But things got worse. The sore deepened into a hole that eventually ate away half of the old leatherman's jaw. He could hardly eat. He had to soak his food in coffee, then drink it. And some of it would come pouring right through his face. His walking got slower and slower. He began to lose weight. Still he kept going. Finally, people along his loop decided to try something drastic. In Middletown, Connecticut, residents set up a sort of sting operation. When the old leather man stopped for a meal, as he always did at the house of Amy Guy,

she sent a messenger two miles up the road to his next stop, the Fisher House. When the old leather man showed up there, he encountered a group of strangers, the police chief, the town physician, some representatives of the Connecticut Humane Society. They basically arrested him, benevolently, and got him into a carriage. According to one of the fishers, he went with no reluctance and seemed to understand why, though the conversation was carried on by signs mostly. The old leather man was driven to the Hartford Hospital. Maybe the doctors there could save his life or at least ease his suffering.

But he refused to stay. Soon after he was dropped off, the old leather man walked out. He went right back to his loop. A week later, in very bad shape, he showed up for dinner at the Barnard House in North Haven, 30 miles from Hartford. He was muddy and wet. They managed to coax him inside, next to the fire. They offered him an apple, but he just pointed to his lip and shook his head.

Instead, he drank six large bowls of coffee-soaked food—bread, cake, pie. He was told to sit and warm himself as long as he liked, the Hartford Times reported later. He simply pointed up the road and, with an expressive gesture, indicated that he must go. That was in December. In mid-March, the old leatherman was seen heading in the direction of awsening. He was so weak by this point that he had to sit and rest every couple hundred feet. Eventually, he disappeared into the woods in the direction of one of his caves. Some days later, on March 24th, a carpenter took his wife to see something interesting,

a rock shelter on a local farm. Inside, face down, they found the old leatherman. His coat was off. He was only wearing one boot. They thought at first he was sleeping. He was dead. In Austin-ing, the old leatherman's body was put into a pine box and buried in an unmarked grave in a cemetery outside town.

His famous suit, meanwhile, went on to live a life of its own. It was made to sit upright in a chair and displayed in the window of a cigar shop downtown. Crowds came to stand in the street and stare. Eventually, it traveled to New York City, where it was displayed in at least two different museums. Around his loop, in the days after his death, people searched the old leatherman's caves and dug holes in the woods,

inspired by rumors of buried treasure. No one reported finding any. The old leatherman left behind a leather backpack, a leather pouch, one leather glove, some homemade pipes, a few simple tools, and according to the coroner, two books made of brown paper and full of figures and hieroglyphics, which could not be deciphered. No one knows what these were, journals or maps, and they don't seem to have survived. His suit, people think, was most likely destroyed in a fire on Coney

Island. When the old leather man died, the answers to his mystery died with him. The world moved on. Years later, someone stuck a metal pipe in the grass to mark what they thought was the spot of his grave. In the 1950s, that pipe was replaced with a formal headstone, identifying him falsely as Jules Bourglet. At the ceremony, a young American girl dressed in period costume stood next to a French flag. In 2011, the old leather man was finally given a proper memorial, the stone with the plaque where I started my loop. During this process, the grave site was moved deeper into the cemetery,

away from the road, which gave archaeologists one more crack at the mystery. The plan was to exhume the old leatherman's body and perform DNA analysis, a plan that went on despite community protests, including a website called Leave the Leatherman Alone. In the end, the protest wasn't necessary, because the archaeologists found the perfect thing. The old leather man was gone. It's possible that he and his coffin had already decomposed or that because the grave was originally unmarked,

the headstone had been put in the wrong place. Thematically, it's tempting to think that his body is still there somewhere, just eternally out of reach, that he's even maybe buried under the road. Someone once asked me what I would say to the old leather man if I can meet him. I thought about it for a minute. Nothing, I said.

That still feels like the right answer. I would just stand there with him, silently, in alienated communion. That's what I felt whenever I sat inside one of the old leatherman's caves. I was an intruder, but also at home. My body was filling the same pocket of rock that he once filled. And the very fact that I was there meant that the old leatherman was not. My presence guaranteed his absence. I was like a hermit crab moving into another crab's shell.

But it also seemed like he was still there, faintly, just vibrating on a different frequency. Like we were sitting in each other's laps across a distance of 150 years. We were alone, together. Sort of like two patches of leather woven into different parts of the same suit. This paradox is one of the things that fascinates me most about the old leather man. It is the black hole, you could say, at the center of his loop. He removed himself from society, obviously and dramatically. In doing so, he opted out of all the normal things. He never gossiped, never ate in a restaurant, never mailed a letter, never blew out birthday

candles. But he also never fully left. He didn't become a true hermit and disappear forever into the deep woods. Day after day, the old leather man put himself right in the middle of all the things he refused to engage in. He walked main roads, passed by schools and shops and town halls. And so he remained this bizarre in-between thing, an ever-present absence, a visible invisibility, a speck of isolation injected into the heart of society.

I felt this paradox most strongly in one of the earliest caves I visited, in the town of Bedford Hills, New York. The cave sits directly behind a combination gas station, Dunkin' Donuts, near the intersection of two major traffic arteries, Interstate 684 and the Sawmill River Parkway. If you know where to look, you can see its opening from the parking lot, a gash of black halfway up the hill.

To get to it, you have to look like a weirdo for about 10 seconds, walk past the parked cars, hop on top of a retaining wall, and squeeze between some decorative shrubs. But then you are all alone. You have entered the old leatherman's world. No one will see you fighting your way up the steep slope, which is covered in dead leaves and thorny vines and rotting logs, and which is so steep that I lost my footing multiple times

and once actually fell and skidded down so hard that my pants filled up with dirt and I lost my cell phone. I found it later perfectly wedged into the crook of a tree. The cave, after all that struggle, felt like a refuge. Its inside was cool and damp. Crickets lived on the ceiling. Although it was deep enough to disappear into with a slight right turn at the back, I found

myself drawn most powerfully to its opening. That switch point between worlds where the light stops and the darkness begins. I sat on a rock at the mouth of the cave and looked at the world outside. Commuters were streaming by at high speeds, north and south. Down below, the gas station looked like a theater set. I watched people coming and going, performing the mundane little dramas of everyday life. A man walked out double-fisting coffee cups. A woman in exercise gear walked her dog.

I saw a fender bender, and I watched the drivers argue. Eventually a policeman came. His arms were covered with tattoos. The driver of a beige station wagon methodically squeegeed his windshield. It started raining lightly and people hurried into the store looking for shelter. From the cave, I watched for well over an hour. And what struck me was no one had any idea I was there. No one ever looked up. Why would they? I might as well have been sitting in the middle of the 19th century. I was gone. Finally, as the sun slid down the sky, I slid back down the hill. And covered with dirt, with rocks in my pockets, I walked off.