Reinforced soil walls, which are civil engineering structures, are subjected to catastrophic collapse when concrete panels fall off in cold and snowy environments. One of the methods to predict such collapse is soil temperature monitoring of the reinforced soil wall. However, in cold and snowy environments, health monitoring requires a lot of effort because the snow load breaks the wires connecting the data logger to the sensors, whereby the collected data fail to reach the logger. In this study, we developed a prototype wireless and battery-free soil temperature measurement system using wireless power transfer (WPT), and conducted field observation experiments for about nine months on a full-scale test reinforced soil wall and an in-service highway. The seasonal variation of the temperature data obtained from the WPT method was consistent with that of the temperature data obtained continuously by the traditional method.