This article reports the material evidence of roads in the northwestern Maya Lowlands that were in use from the Middle Preclassic (800–300 BC) through the Late Classic (AD 700–900) period in Chiapas and Tabasco, Mexico. The study includes archaeological evidence recovered from field research in an area covering approximately 670 km2 and 618 recorded archaeological sites. It presents the physical characteristics of a series of piedmont paths that connected the region from the Usumacinta River to the Tulijá River, including large population centers such as Palenque and Chinikihá. The study uses a geographic information system (GIS) least cost path (LCP) analysis to identify the location of roads and how they relate to regional settlement patterns. It also tests the use of modern computational models to advance regional studies in the Maya area. Study results show how the Classic Maya adapted and appropriated the region's topography to facilitate movement, long-term settlement, and the building of landesque capital.