The pilot departed on a 615-nautical mile cross-country flight, that reportedly would take him about four hours and fifteen minutes to complete. The pilot reported he had about five and a-half hours of fuel on-board, and that he received a weather briefing before departing. Additionally, marginal visual flight conditions en route to his destination was anticipated. During the flight, stronger than expected winds were adding about 10 minutes to his flight, and about 50 miles from his destination, he started his descent from 9,500 feet with a solid cloud layer below him. So, the pilot contacted air traffic control and received an instrument rules (IFR) flight plan for an approach to his destination airport. The pilot stated as he broke out from the clouds, it was too late to make a landing on the airport. At this time, the engine quit; he switched fuel tanks and the engine re-started. Air traffic control asked the pilot if he had enough fuel to a make an alternate airport, located about 44 miles away, to which the pilot responded that the right fuel tank showed one-third full. About 3 miles from the alternate airport the engine quit again, this time the pilot could not get it restarted. The pilot then elected to conduct a forced landing on a road. During the forced landing the airplane’s horizontal stabilizer impacted a signpost, causing substantial damage to the airplane.