The long-term monitoring of transportation infrastructure assets at a lower cost and with short mobilization time is of significant interest to both state and federal transportation agencies in the U.S. Because of the significant improvement in spatial and temporal resolution of synthetic aperture radar (SAR) remote sensing systems and a notable reduction in the cost of data acquisition, SAR has now become a viable method to provide economic and rapid condition assessment of transportation assets. A research study was developed and performed to comprehensively perform the inspection and characterization of a pavement surface based on the amplitude of backscattering of an X-band radar. In situ characterization of the test site was first performed using traditional inertial profilers and aerial photogrammetry with unmanned aerial vehicle (UAV) surveys. The results from these in situ methods were compared with the corrected amplitude of the SAR data, which indicated that the distribution of surface roughness values computed from the inertial profiler, UAV, and SAR exhibited similar probability densities at various segmental lengths considered in this study. This suggested that the problematic areas that are evident during in situ characterization can be delineated and quantified based on the normalized radar cross section of the pavement surface. Overall, the outcome of this research exhibits the potential of SAR for future transportation asset management undertakings, and the systematic framework developed as a part of this research could be of significant interest to engineers and transportation practitioners.