In recent decades, there has been a considerable growth of scientific interest in the question of travel and mobility in the ancient Mediterranean and Near East. As far as the southern Levant is concerned, this interest has yielded much research about travel and mobility in Late Antique Palestine (including the Roman imperial road network), leaving the question of pre-Roman travel and mobility a much-understudied field of study. However, recent archaeological discoveries have revolutionized our state of knowledge about material remains of pre-Roman roads, which were once believed to not have been preserved. Namely, remains of several pre-Roman roads have been discovered on the ground in modern Jordan and Israel: the Aroer Ascent, “Glueck’s Road,” Naqeb Dahal, the Wadi Zarqa-Main road, the Callirrhoe–Machaerus road, and the Masada–Hebron road. In this context, the aim of this paper was, first, to study the spatial and archaeological features of the archaeologically attested ancient pre-Roman roads, and second, to evaluate all of the available types of remote data as tools serving in the detection of artifacts (especially archival cartographic, aerial, and satellite data; archaeological data; and least-cost simulations of Geographic Information Systems [GIS]). As a result, several conclusions are suggested. First, old topographic maps are a very promising source of data for potential new discoveries since they contain both explicit and implicit hints at the existence of ancient roads. Second, information about archaeological data and the Roman imperial road network may also offer important reference points if the quality of databases is improved in the future. Third, the use of GIS simulations based on 30 m digital elevation models has very substantial limitations. In particular, the use of least cost paths and corridors for simulating short-distance travel has turned out to be fruitless. At the same time, the use of least cost corridors for predicting long-distance travel offers some promising results.