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.