I walked 48km (30 miles) to win a bet with a friend.
The wager was a case of beer.
The counter-bet was that he could ride 240km (150 miles) in a day on an old single-speed bicycle.
I won that bet too, cause his chain broke 20km before the finish line.

Probably not the farthest but when I was about 14 I walked 4 miles through a forest, train yard and across a highway, in a snow storm, to make it to dinner at steak n shake with my first girlfriend. A friend was supposed to give me a ride but he ended up in after school detention. It was a dumb, freezing cold, no sidewalk trek that took nearly 3 hours.

About 25 miles. About 30 years ago, I had a stint with meth, short-lived, thankfully. I walked from the north end of my city to a suburb south of the city to my sisters house to detox after a bender and running out of money. Funny thing, in retrospect, I had just enough money left for bus fare but when I got on the bus, I was still so sketched out (paranoid) that I couldn’t bear to be around other (sober) people. So, I got off the bus immediately and walked. Not my finest hour.

I walked just short of 50km to see if I could. I was hungover and stopped for a smoke every hour or so, but I made it. I also had a big water bottle and music headphones to keep me pushing forward

7.9 miles to get home from high school. Missed the bus.

I guess that might not be the farthest but it’s the farthest I remember.

Some girl yelled “loser!” at me from a car halfway. No idea who she was.

4 days in a row about 40 kilometer (about 25 miles) during ‘De Nijmeegse 4-daagse’ a big walking event in the Netherlands. It was fun! Lots of spectators along the way making a it one big party.

I walked about 500 miles. Then I walked about 500 more.

Walked around like more than 14 kms in 2 hours. Went to a competition on a different districts women’s college. No mode of transport was there, only buses were available but men aren’t allowed in. Got to walk around the border of the district to got the bus.

16 miles. I was hungover, stepped out of my flat for a can of coke, and then just didn’t stop walking until my headphones died. Took the train back home.

21 kilometers, up to Torres del Paine and back down.

I don’t know if it was the furthest but it was some of the hardest. In college I took my GF backpacking with me. We were both pretty out of shape, but one day we did 12 miles of trail in the heat. On a couple of occasions I discovered that she wasn’t behind me, and I went and backtracked and she was just standing there. She said that she had just lost track of what she was doing and just sort of blacked out.

We were both pushing really hard, for no good reason other than we were young.

It was a fun trip. We saw a lot of the rural midwest on that trip. She was from Chicago and grew up upper middle class, and she said she understood me better after she saw the sort of area I grew up in.

One funny thing. We were talking about lottery tickets, and the irrationality of it, and she kept noticing how every place had so many lottery tickets for sale and how every gas station we’d stopped at had people buying lottery tickets. She said “is that a big thing here?” and I said yes. And we ended up discussing it for a long time, and the end of the discussion was we decided to buy a lottery ticket just for the experience of it, being conscious that we would lose. I can’t remember why we decided to do that. So we bought a ticket, specifically for the experience of losing the lottery, and won $50. It was so funny.

21 miles, was deep in the backcountry and our food had spoiled, we were then short a day’s worth of food and had to make it to the next camp. It was pouring down rain and a long summit day, but an unforgettable trip.

15-25 kms Monday to Friday, every week for the past 8 years. I’m a meter reader, I get paid to walk. The most I did in 1 day was 33 kms. I’m in Australia so 40 degrees centigrade (over 100 F) are not uncommon. I walk whatever the weather.

5mi starting from my place to my then-gf’s neighborhood.

She wasn’t home at the time. I knew she wasn’t going to be home. Stupid me just wanted to see if I could make the journey on foot. After I made it, I ate McDonald’s at a nearby mall and Uber’d straight home…

About 10miles this past year , just curious how hard it would be. Boring more than anything else. Next time is 20.