According to the 145-hour pilot of the Cessna 152, she departed on a cross-country flight with the intent of stopping at several airports along the way. The pilot performed a touch-and-go landing at one airport and subsequently made a full stop landing at the next airport. The airplane was serviced with 6 gallons of fuel, and the pilot then restarted the airplane and departed for her original airport. About 10 minutes after taking off, the engine lost power. The pilot followed the published emergency procedures and attempted two unsuccessful restarts of the engine while searching for a forced landing area. The pilot landed the airplane on a road, but it nosed over and came to rest in the inverted position resulting in the substantial damage of the airplane. Examination of the airplane by a Federal Aviation Administration inspector revealed no obvious mechanical deficiencies with the engine. The inspector also observed that the gascolator contained a significant amount of water. In an interview with the inspector, the pilot stated that she drained the fuel tank sumps before her first flight but did no do so before the accident flight. The pilot also stated she did not drain the gascolator prior to the accident flight.