The first type of skateboards were actually more like scooters. These contraptions, which date back to the early 1900's featured roller skate wheels attached to a two by four. Often the wood had a milk crate nailed to it with handles sticking out for control. Over the next five decades kids changed the look of the scooter and took off the crate and started cruising on two by fours with steel wheels. Tens of thousands of rollerskates were dismantled and joyfully hammered on to planks of wood.

In the 1950's modifications were made to the trucks (the device that hold the wheels) and kids started to maneuver more easily. Towards the late 1950's, surfing became increasingly popular and people began to tie surfing together with cruising on a board. By 1959, the first Roller Derby Skateboard was for sale. Clay wheels entered the picture and sidewalk surfing began to take root.