The eastern Adriatic and western Balkans are key areas for assessing the environmental and population history of Europe during the Late Pleistocene and early Holocene. It has been argued that the Balkan region served as a Late Glacial refugium for humans, animals, and plants, much like Iberia and the Italian Peninsula and in contrast to the harsh conditions of Eastern and Central Europe. As post-glacial amelioration occurred and sea level rose, these regions to the north and west of the Balkan Mountains became forested and were populated by Mesolithic forager-fishers. Meanwhile, to the south, the domestication of plants and animals in the Near East began to cause large-scale environmental as well as lifestyle changes. Even as the Balkan Peninsula was a likely crossroads on the route for the spread of agriculture and herding from Southwest Asia into Europe, issues such as pre-Neolithic settlement, the discussion of human-environment interactions, and the role of climate events such as the 11.4, 9.3, and 8.2 ka cal BP in this critical landscape are often overlooked. Efforts to counter this challenge have been hampered by an apparent lack of data, so that the region hardly occurs in distribution maps. In part this is due to patchy research and a complicated political history, which have contributed to a fragmented archaeological and paleoecological record. Yet, as we show here, there is in fact plenty of evidence available for review. We present a survey of different proxies for environment and settlement throughout the Late Pleistocene and into the Early Holocene, combining radiocarbon data with zooarchaeological, lithic, and palynological records. By mapping this evidence, we are able to discuss the impact of climate change during the Pleistocene/Holocene transition and consider the role of environment and landscape on human population distribution at this crossroads in place and time.