After flying for about 1.5 hours on a training flight, the pilot of the helicopter returned to the operator’s hangar and aborted two approaches after encountering vortex ring state. He decided to land at a nearby facility to have the occupant disembark to reduce the gross weight of the helicopter, and to improve the power available margin. He departed and attempted a third approach to the hangar. At about 300 ft agl, the helicopter again encountered vortex ring state; however, there was not enough altitude to successfully complete the same recovery maneuver. The helicopter began losing altitude rapidly and while descending it impacted the tops of several trees. A main rotor blade then contacted the tail rotor drive shaft, which immediately resulted in a surge of the engine, followed by a yaw of the helicopter to the right. The pilot then conducted an autorotative landing into the middle of a nearby road. The helicopter’s tailboom, main rotor, and fuselage were substantially damaged during the accident sequence. The pilot reported that there were no preimpact mechanical malfunctions or failures of the helicopter that would have precluded normal operation.