A skateboard with positive camber steering includes a frame and a board pivotally coupled to the frame. A steering assembly coupled to the frame includes an upper truck arm, a lower track arm and one or more wheels. The upper truck arm and the lower truck arm are spaced apart relative to the frame and are each rotatable about an axis of travel parallel to the skateboard's line of travel. The upper truck arm is coupled to the wheel above the axis of rotation relative to the surface, with the lower truck arm coupled to the wheel below the axis of rotation relative to the surface. Thus the upper truck arm extends farther from the frame than the lower truck arm creating a positive camber in the direction of steering.