This paper introduces the results from our excavations of the open-air late Upper Paleolithic site of Kalavan 6, Armenia. The site is embedded in a sedimentological sequence spanning from the Last Glacial Maximum (LGM; 26.5–19/20 ka) to the Holocene (i.e., from MIS 2 to 1). Our findings are presented together with chronological, environmental, and climatic data. Luminescence dating provides a temporal framework for reoccupation of the Armenian Highlands after the LGM, while two vegetation proxies (pollen assemblages and leaf waxes) characterize the environment. Based on these pollen data, a quantitative climate reconstruction (temperatures and precipitation) is offered. Techno-typological characterization of the lithic assemblages is presented together with the sourcing of the entire obsidian assemblage by portable X-ray fluorescence, providing insights into the occupants’ exploited territories. Such a framework, which incorporates both environmental reconstruction and hunter-gatherer behaviors, enables us to contextualize possible links between population dynamics during the height of the LGM and post-LGM environmental oscillations. We suggest that, during the LGM between ca. 24 and 19 ka, the combination of declining temperatures and the extension of the winter season limited the occupation feasibility of the region. The regional occupation resumed when environmental circumstances ameliorated. These results support our interpretation that temperatures and the duration of the seasons conditioned the past hunter-gatherer's occupation of the region.