This study aims to examine the effect of rainfall on integrity assessment on unpaved roads using electromagnetic waves and cone penetration. An unpaved road testbed is prepared with sandy soil in densely- and loosely-packed conditions. Site investigations using a time domain reflectometry (TDR), ground penetrating radar (GPR), and dynamic cone penetrometer (DCP) are performed on the testbed under before and after rainfall scenarios, and an additional laboratory compaction test using the soil samples is conducted. The results show that the spatially scaled GPR signal converted by the TDR signal can accurately estimate the interface depth. In addition, rainfall may reduce the accuracy of GPR signal polarity-based analyses for anomaly detection on unpaved roads. This study reveals that TDR, GPR, and DCP with simple laboratory compaction tests and physics-inspired effective stress-depth models can be a powerful tool for underground mapping when subjected to rainfall season.