The flight school reported that the private pilot submitted a night visual flight rules flight plan for authorization by the school, and then intentionally flew a route for which he had not received proper mountain flying endorsements from the flight school. During the night cross country flight, the pilot reported that he did not refuel at any of his stopover airports and became lost over mountainous terrain. The pilot further reported he attempted unsuccessfully to contact air traffic control, but after 4.3 hours of flight the fuel was exhausted and the engine lost power. After the loss of power, he reported that he glided towards a winery and impacted power lines, which resulted in substantial damage to the fuselage and right aileron. The pilot reported that there were no preimpact mechanical failures or malfunctions with the airframe or engine that would have precluded normal operation.