A system and method for a skateboard (300;350) and for propelling the skateboard, The skateboard system includes a board including a first end and a second end, the first end offset from the second end, and the second end defining a board plane. The skateboard system also includes a truck assembly (304;352) attached near the first end of the board, and a caster assembly (302;354;500;602;700) attached near the second end of the board. The caster assembly has a caster pin at an angle with respect to the board plane. Other embodiments are also disclosed.