Roads and waterways have long fascinated historians of the East Indies. Their interest, however, skews to modern infrastructure strengthening colonial power, epitomized by the Great Post Road built by governor-general Herman Daendels in 1808. In contrast, ever since the sociologist Bertram Schrieke defined pre-modern routes as unchanging, little attention has been paid to their equally dynamic nature. When it comes to warfare, the prevalent view on roads and routes distorts the constant crossings of troops characterizing early modern armies. Small numbers of troops moving from one coast to the other, from sacred mountain tops to rice fields and from towns to villages did not only influence battles but constituted the bulk of armies. Kings, Sultans and Governor-Generals continually negotiated with warlords coming from all over the archipelago to gather forces and advance further. These warlords could always choose to walk to the other side if conditions were more favourable there. Luckily most of their itineraries were recorded during the conflicts tearing Java apart in the 1670s and 1680s. After entering this data into a historical GIS, it turns out routes were constantly adapted to opportunistic needs. Moreover, they were created to gain power on a much more regional level than, for instance, the Great Post Road. The regional scale of pre-modern routes led to their ongoing adjustment to incoming troops. My talk will select several roads and waterways from the Historical GIS and elaborate on their temporality in light of the crossing of military forces during the late seventeenth century.