On February 17, 2006, at 1830 mountain standard time, a Cessna 177, N29377, impacted a sign during a forced landing on a road near Carefree, Arizona. A total loss of engine power preceded the forced landing. The airplane was substantially damaged and the commercial pilot/owner and his passenger were not injured. The pilot operated the airplane under the provisions of 14 CFR Part 91 as a personal cross-country flight. The flight originated from Payson, Arizona (PAN), about 45 minutes prior to the accident, and was destined for the Phoenix Deer Valley Airport (DVT). Night visual meteorological conditions prevailed and a flight plan was not filed. According to the pilot's written statement and an interview conducted by the National Transportation Safety Board investigator-in-charge, the pilot and his wife departed DVT and flew to PAN earlier in the evening. They ate dinner and were returning to DVT when the accident occurred. The pilot reported conducting a mental calculation of the fuel required to conduct both legs of the flight and believed he had adequate fuel on board. Therefore, he departed both DVT and PAN without refueling the airplane. Thirty minutes into the return flight, while in cruise, the engine lost power "due to fuel starvation." The pilot switched fuel tanks and the engine restarted for about 15 seconds, which afforded him some time to determine where he was going to land. He elected to divert to Sky Ranch at Carefree Airport (18AZ). The pilot attempted to restart the engine again, to no avail. The pilot then realized the airplane would not be able to glide all the way to 18AZ and opted to land on a road he spotted with the aid of an automobile's taillights. After the pilot landed the airplane on the road, the right wing impacted a road sign, which resulted in the airplane veering to the right into a ditch and brush. The pilot and passenger exited the airplane and called emergency personnel. The outboard 25 percent of the right wing was folded on top of itself and the fuselage, left wing, and horizontal stabilizer also sustained significant impact damage. When asked when the last time the pilot had refueled his airplane, he reported that the last time was earlier in the week. He further stated that after the last refueling he flew the airplane roundtrip from DVT to Sedona, Arizona, prior to the accident. The pilot purchased the airplane 3 weeks prior to the accident and accumulated 5 hours of flight time in the airplane. In addition to his commercial pilot certificate, the pilot held a flight instructor certificate for single engine, multiengine, and instrument airplanes. He was also a certificated aircraft mechanic. In the Pilot/Operator Aircraft Accident Report (NTSB Form 6120.1/2) under the section titled "Recommendations (How Could This Accident Have Been Prevented," the pilot responded by indicating he should have refilled the fuel tanks in either DVT or PAN before departing.