During the operational phase of the expressway, a significant challenge arises concerning substantial differential settlement in the transition zone connecting the culvert and the general subgrade, affecting its smoothness. In order to address the issue of abrupt stiffness variations within the transition section and to mitigate the occurrence of differential settlement, a gradient pile–reinforced-concrete slab composite foundation was implemented for the first time within an expressway culvert–subgrade transition section. At the same time, an in situ vibration test was conducted through the SBZ30 vibration exciter to comprehensively understand the vertical dynamic responses in the culvert–subgrade transition section under various axle loads and speed conditions. Furthermore, continuous monitoring was conducted to track the long-term settlement of the roadbed. The findings indicate that the utilization of gradient pile–reinforced-concrete slab composite foundations can significantly mitigate the amplitude of the dynamic response parameters. Moreover, dynamic parameters and attenuation coefficients exhibit a gradual reduction as the depth increases. Dynamic stresses, acceleration, and displacements on the roadbed surface exhibited positive correlations with both the axle weight and vehicle speed. However, at deeper depths, the load weight exerted a more pronounced influence. As the speed rose, acceleration decayed faster, affecting a shallower depth. Conversely, the increased load slowed the acceleration decay. The cumulative deformation of the roadbed and the number of excitations followed exponential function characteristics. Settlement values progressively increased while the settlement rate gradually diminished, eventually reaching a stable state, ultimately stabilizing within 4.7 mm. These research outcomes offer valuable guidance and serve as a reference for the implementation of gradient pile–reinforced-concrete slab composite foundations within the culvert–subgrade transition section.