The pilot in the tailwheel-equipped airplane reported that, during the sixth flight of a glider tow operation, the control stick felt as though it had “some play” with regard to the ailerons. The control stick moved about four inches laterally before a corresponding movement of the ailerons could be observed. He landed the airplane, performed a flight control check and noticed a “little slack” between the control stick inputs and subsequent aileron movement. He determined that the control stick felt secure and took off on his seventh tow flight. During the climb out, the response to his control stick inputs diminished. The airplane encountered turbulence and the control stick separated from the torque tube assembly. He maintained control of the airplane by using trim, rudder control and throttle variations. The airplane subsequently landed on the grass surface to the right of the runway. During a firm landing, the airplane veered right, and the right wing collided with a berm. The airplane sustained substantial damage to the leading-edge of the right wing. A subsequent examination of the airplane’s flight controls, revealed that the bolt which secured the control stick to the torque tube assembly had backed out. The castellated nut and cotter pin which secured the bolt were not located.