© 2020 The Author(s). Grassridge rock shelter is located in the high elevation grassland foothills of the Stormberg Mountains in the Eastern Cape of South Africa. This places Grassridge at an important biogeoclimatic intersec-tion between the Drakensberg Mountains, the South African coastal zone, and the interior arid lands of southern Africa. First excavated in 1979, the approximately 1.5 m stratigraphic sequence was divided into two major occupational components: a 50–70 cm thick Later Stone Age component dating between 7–6 ka and an underlying 50–80 cm thick Middle Stone Age component dated to 36 ka at the base. Here we present a reanalysis of the Grassridge stratigraphic sequence that combines new optically stimulated luminescence and radiocarbon age estimates with sedimentological and microbotanical analyses to evalu-ate site formation processes and the palaeoenvironmental context of human occupations. Results indicate a complex history of geogenic, anthropogenic, and biogenic inputs to the depositional sequence that are interspersed with pulsed human occupation from 43–28 ka, 13.5–11.6 ka, and 7.3–6.8 ka. Microbotanical remains indicate a cooler, drier grassland environment in MIS 3 that transitions to a warmer, moister grassland environment dominated by summer rainfall in the middle of MIS 1. The pulsed occupational sequence identified at Grassridge is characteristic of the Pleistocene and Holocene record across the greater high elevation grassland region of South Africa, which, based on comparison with other currently available evidence, seems linked to a complex system of forager mobility entwined with rapidly fluctuating palaeoenvironments across the last glacial to interglacial transition.