This paper presents a unique case of the application of remote sensing methods in archaeological survey devoted to ancient pre-Roman Imperial roads in the Southern Levant. The results of our preparatory remote sensing research and subsequent fieldwork in Jordan and Israel between 22 February and 23 March 2023, within the framework of the research project entitled “Travel and Mobility in Hellenistic and Early Roman Palestine”, are reported and discussed. Part of this project is a large-scale, systematic research attempt to discover additional ancient pre-Roman roads and to suggest a working methodology for future research. The methodology is supposed to combine remote sensing research and archaeological survey. The project’s first fieldwork achieved several goals. First, the modern methods enabled us to provide a high-resolution capture of the detected features and artifacts, including the courses of ancient roads and the locations of road-related archaeological sites. Altogether, 105 road remains, 62 archaeological sites, and 14 pottery findings were identified; what is more, 11 GPS (Global Positioning System) tracks of ancient roads were registered. Second, we suggested necessary revisions to the previous state of research and reported new findings. For instance, newly discovered rock art evidence found along Glueck’s Road confirms the continuity of the use of this road long into late antiquity and early Islam. Third, some methodological conclusions were reached. For example, a multi-source approach to identifying ancient roads including the use of archival cartographic sources, archival and modern satellite and aerial imagery, and the databases of archaeological sites is still necessary. However, there can be no doubt that spatial analyses and remote sensing studies must be accompanied by archaeological fieldwork, which is absolutely necessary for determining the dating of the roads (by dating the settlement and pottery) and a detailed identification of the road courses (particularly through the discovery of road-related infrastructure).