All of these happened with my college teammates:
During the very first workout of my college career, I saw a guy getting arrested at the park that we ran through quite a bit.
Saw someone literally hugging a tree.
Was on a long run and encountered a deer. There was also a group of girls running the opposite direction as us. This was in area where you basically run across a lower land bridge that goes across a reservoir. When the deer realized it couldn't run anywhere, it panicked and dove into the water and started swimming. We looked back about 5 minutes later and it was still swimming across (probably swam at least 1/4 of a mile by that point).
Tried inventing a new route and wound up in someone's backyard. They had a sign that said, "Get caught, get shot"