I grew up in a congregation with almost exclusively rural territory, so there was really no such thing as walking from the KH or from the arrangement to the territory. When I was in my last few years of high school, my best friend and I would go out on Friday afternoons after school to do return visits...which just happened to be a good 45-minute drive to the very far corner of my cong's territory. We would take the loooooooong way of course, and stop and get a snack on the way. Other times, we would go with my best friend's mother and younger siblings, and very often some other young people would come along, then after service we would go back to my best friend's parents' house; all of us teenagers would make dinner and we had a blast.
And the last year I was in the JWs, the summer I was 17 I auxiliary pioneered in August. We had a great time; aside from the fact that we had to do door-to-door (which I generally despised), I got to spend time with a lot of other young people and we had a lot of fun.
Definitely the worst thing was running into someone I went to high school with. I HATED calling on those homes, and as I knew where people lived, I would volunteer to go to the house right before those ones, so that my turn wouldn't be up when their homes came up.
I still have nightmares about going in service.