I have read and heard different stories about how skateboarding started, some say 1940's, 50's, 60's and even 70's, but the book that I trust the most says that skateboarding started out in the early 1900's. But they were nothing like the skateboards you will see today. The skateboarders would take the bottoms of roller-skates and connect them to the bottom of a 2x4. They would then attach milk crates to the top of the 2x4 for the purpose of a kind of handle. The wheels back then were steel so you can imagine the vibrations of going down hills.
(The Concrete Wave: The History Of Skateboarding)
This style of skateboards stayed around for a while until the late 50's when trucks were invented. And by the late 50's clay wheel were introduced increasing the popularity of the skateboard in the surfer community. The surfers called it sidewalk surfing. It was something for them to do when they were not on the ocean.
When the 60's came around, surf magazines started to endorse the skateboard launching the popularity. The First skateboarding contest was held at a middle school in 1963. I find this a bit interesting because they held the competition at a middle school. Because where skateboarding is today, it is a crime to set foot on any school's property, in my case the janitors yell at me, and then they get the principal out to call the police. I also find it interesting how back in the 60's and what not they could skateboard anywhere, yet there were not that many skateboarders. But now when there are so much more people skateboarding they confine us to skateparks which are few and far between, plus some cost money, and you can still get arrested at parks for not wearing...