When i was going to college (years ago) I did some skateboarding, but not the way most people do. I went to some skate parks, but I limited myself to riding while sitting on the skateboard. I did get up on the walls, but never caught air. The people running my local skate park allowed me to also use a skate car (street luge type thing) that I bought from a friend of mine who built it. That was a lot of fun until I did something stupid. Instead of my usual path, I decided to go straight down the side of a bowl. At the bottom, when the skate car got to the bottom, I heard a loud crack. The wood that the skate car was made of shattered. I never rode it again.
My skate car was also used my my friends and me on a remote road on a mountain near where I live. We stayed safe by having a regular (gasoline powered) car drive behind us to honk the horn and warn us of anyone coming from behind who might run us over. Cars coming from the other direction were few and far between. When we saw one coming, we just put the brakes (our shoes) and pulled over until they passed. The ride down the mountain was several miles and took quite a while since we never went that fast.
When I was the age of a typical skateboarder, the only skateboards available had metal wheels (sometimes covered in a layer of cork.)
Later, my wife and I took up rollerblading, but we kept it slow and easy. We had fun exploring the local college campus that way. I have a high center of gravity, so I never got as adventurous as I did when I was younger.
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-Author prefers to be anonymous.