The Daily
The Sunday Read: ‘What I Found on the 365-Mile Trail of a Lost Folk Hero’
Sun, 23 Mar 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.
Chapter 1: Who was the Old Leatherman and why is he a mystery?
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 Leatherman.
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 Leatherman, origin stories that people just made up about him. I think he was kind of 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 Leatherman 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 asks me, what are you thinking about? And 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.
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Chapter 2: What was the Old Leatherman’s route and significance?
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 Leather Man. I suppose that many of the readers of your valuable paper have heard of the Old Leather Man, 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 Leather Man 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 mealtimes, 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 Leatherman 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 Leatherman 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 Leatherman 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 Leatherman was walking in a giant loop, roughly 365 miles around.
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Chapter 3: How did the Old Leatherman become a media phenomenon?
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 Leatherman 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, Jules made a big investment right before the market crashed. The company was ruined. The marriage was forbidden.
And Jules, 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 leatherman's gravestone.
In the meantime, year after year, namelessly trailing this ever-expanding cloud of stories, the old leatherman continued to walk. Today, the old leatherman 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, 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 leather man 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?
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Chapter 4: What theories and stories emerged about the Old Leatherman?
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 Leatherman 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 Leatherman. 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 step-parents.
I've 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 Leatherman. 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 Leatherman 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 Leatherman'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, Allison 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.
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Chapter 5: Why is the Old Leatherman relevant today?
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 Ossining 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 Leatherman 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 6th, 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, 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 Ossining. 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.
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Chapter 6: How did retracing the Old Leatherman’s path impact Sam Anderson?
In Woodbury, I walked to the site of Alexander Gordon Sr. 's tannery, where the old leatherman 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 Austin-ing, 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, Gage Road, Spring Lake Road, Judds Bridge 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 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 woodpecker 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.
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