The key to understanding a landscape is through its connections, which tie together people and environment within and beyond that landscape and across many different periods. This is particularly true of the northern face of the Ochil Hills in central Scotland, which is characterised by dense networks of connections between lowlands and uplands, local and regional. To trace those connections we integrate the results of walkover survey, aerial archaeology, excavations, documentary analysis and place name analysis, revealing significant continuities and differences in the networks and relationships that have connected this landscape across time and space. Iron Age hillforts used their prominence and monumentality to guide people along very specific routes across the Ochils. Regular seasonal movements of cattle and herders in the medieval and post-medieval periods were closely related to the agriculture and settlement they encountered on the way: this interaction can be clearly seen in the elaborate intertwining of paths, braided cattle tracks, farmsteads and enclosures, most strikingly in the 18th century. Such intricate connections across the landscape are equally keyed in to the specifics of particular locations and to much broader networks and historical change.