Apparatus, systems and methods for creating a dynamic riding terrain for wheeled sports, having a translating cylinder assembly and a flexible riding surface. The assembly includes a cylinder supporting frame, a cylinder having an axis, which is rotationally supported by the cylinder supporting frame, and opposing transition frames extending from the cylinder supporting frame, generally in a direction orthogonal to the cylinder axis. The transition frames have a proximal end adjacent to the cylinder, a distal end adjacent to a support surface when the assembly is placed thereon, and a gliding surface affixed to an upper portion thereof. A dynamic riding terrain is created when the assembly is used in conjunction with a flexible riding surface placed over the assembly and moved, either by a self-contained motor or external forces. The transition frame can be modified to alter the gliding surface profile or the location of the proximal end.