The northwestern corner of South America, represented by the current territory of Colombia, is a key region to assess some relevant issues linked with the initial human peopling of the area, including population dispersals, cultural diversity, and early adaptations to the changing environmental conditions experienced by lowland and highland north-Andean Neotropical ecosystems at the Pleistocene/Holocene transition. The aim of this paper is to present a synthesis of the archaeological research about early peopling carried out in Northwest South America during the last four decades. Specifically, it will focus on the adaptive strategies and the cultural diversity patterns exhibited by the early hunter-gatherer groups that entered the region since late Pleistocene times. The classic ideas about the time of arrival of the first settlers, the dispersal routes, the incidence of the climate change in on the rate of dispersal and colonization of different habitats, and the role of the megafauna in the subsistence will be reviewed, prior to the formulation of new hypotheses about the meaning of the apparent intraregional diversity of the archaeological record and the evolution of economic strategies over time.