Ballast flight significantly affects the safe operation of high-speed railway. A wind tunnel experiment and computational fluid dynamics simulation were performed to investigate the occurrence and development mechanism of ballast flight from the perspective of individual particles, which was based on the capture, reconstruction, and analysis approach of ballast features. The dynamic characteristics of ballast particles under wind load, the flow field characteristics such as the distribution of air pressure and streamline, and the influence of the ballast mass and shape, windward direction, and wind speed on the ballast flight were investigated. The results show that the critical velocity of the ballast weighing from 5 g to 200 g is between 14.22 m/s and 29.89 m/s. The massive ballast with the shape of an oblate is unlikely to fly. The air pressure difference is proportional to the square of the wind speed, and it increases 14.9 times when the wind speed increases from 10 m/s to 40 m/s. In order to avoid ballast flight, recommended suggestions include limiting the proportions of the small and the ellipsoid ballast praticles, laying the ballast with high density and a large size on the top of the ballast bed, and reducing the degradation and fouling of the ballast bed.