I did my years on the real 'Trail', mostly in Pennsylvania in our church's "Boy's Brigade". We'd hike all weekend and sleep in our hammocks.
Then when I was about 25, I broke my big toe, running up and down a 1-mile rocky trail up to the Appalachian, in the dark, trying to rescue my mom who stayed a minute too long to watch the sunset, and took the wrong trail, behind us. It was going to freeze that night, too, and she just had a light sweater. Don't ask me how we missed her - I think we thought she was ahead of us, and when we got to the car and she wasn't there, I high tailed it back up, didn't find her, then back down in the pitch black, and stubbed my toe repeatedly.
Turns out God sent a guy from dad's old church (20 miles away), who just happened to be out driving in that remote mountain area (he never explained that), stumbled across us, and my dad told him, and he said "I know where she'll come out if she kept walking straight". He drove around the mountain and found her coming out to the road, in the dark.
I haven't remembered that whole story in quite a few years. My toe still bothers me though, it's severely arthritic, according to the Doctor who gave me a shot of Cortisone in it this year. Thanks for that, mom.
So my hikes are short these days (although we did 9 miles uphill to a falls after the NC retreat, in the Smokies - that was after the Cortisone), I prefer my kayak, or bicycle.