Africa contains some of the earliest evidence for humans living in high mountain systems, both near the equator but also at higher latitudes. The latter – temperate mountain systems with pronounced cold seasons – are important analytical settings because they pose severe resource stresses and logistical challenges that demand flexible, creative solutions. However, the processes by which humans came to first utilize and eventually master them are only beginning to be untangled. Pilot research at Likonong and Ha Soloja, two contrasting rockshelters in southern Africa’s highest mountain system, the Maloti-Drakensberg Mountains of highland Lesotho, suggests that early forager entanglements with these seasonal mountains were focused on the systematic and repeated exploitation of resource extraction sites. We suggest that over time, these visits led to landscape learning and the generation of cultural adaptive strategies eventually allowing for more sustained highland occupation and leading to the highly structured seasonal rounds characteristic of ethnohistoric hunter-gatherers. Importantly, the stresses placed on foragers by sub-freezing temperatures, snow, and extreme resource stress would have required more innovative and collaborative solutions that were unachievable to earlier hominins with lower levels of behavioral plasticity living at higher altitudes but in less seasonal locales.