Sam Anderson

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.

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.

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.

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 Ossining, I went to Briarcliff Manor, where one of the old Leatherman'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 leatherman used to knock on the drainpipe so the owner would give him coffee and sandwiches. I knocked. No one was home.

From Ossining, I went to Briarcliff Manor, where one of the old Leatherman'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 leatherman 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 leatherman 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 leatherman 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.

I passed a house where the old leatherman 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 leatherman 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 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.

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.

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.

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.

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.

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.