In 1954, B K Thapar excavated the multicomponent site of Maski (Raichur District, Karnataka) to establish an archaeological sequence for the southern Deccan region of India. Thapar identified four major periods of occupation, now known as the Neolithic (3000–1200 BC), Iron Age (1200–300 BC), Early Historic (300 BC to AD 500), and the Medieval periods (AD 500–1600). Renewed research at the site by the Maski Archaeological Research Project (F.1/8/2009-EE) has investigated the development of social differences and inequalities in south Indian prehistory. This article reports the first ever radiocarbon assays from habitation and megalithic burial contexts in the vicinity of Maski. Accelerator mass spectrometry (AMS) dates of charcoal sampled from exposed occupational strata on Maski's Durgada Gudda hill and subsequent Bayesian analyses indicate that the site was extensively occupied during the 14th century AD, corroborating interpretations of numismatic and inscriptional materials. Associated artifacts with these 14C samples have significant implications for recognizing late Medieval period ceramics and occupation in the region. AMS assays of four charcoal samples from exposed megalithic burials just south of the Durgada Gudda hill, similar to those recognized by Thapar, indicate that burial practices commonly attributed to the Iron Age predate the period, and thus are not precise chronological markers. However, the results also suggest that megalithic burial practices became more labor intensive during the Iron Age, creating a cultural context for the generation of new forms of social affiliations and distinctions through differential participation in the production of commemorative places.