Radiocarbon dates of Mesolithic sites in the forest-steppe zone of the Volga basin are collected and analyzed. The calibrated dates are 8600–8200 BC (Starotokskaya), 8000–7500 BC (Chekalino II), 7800–7500 (Chernovka I), 7100–6600 (Luzhki II), 8400–6200 (Kochkari I), 7200–6500 (Syezzheye), and 9900–8800 plus 7300–6500 BC (Gora Mayak aka Sidelkino II). The comparison of these estimates with the typology of tools suggests the direction and chronology of ties between the cultures of the Volga forest-steppe and those of adjacent territories. The most apparent ties throughout the Mesolithic are those with the southern and eastern Urals (Romanovka-Ilmurzino and Yangelka cultures) and possibly with the Middle Volga forest zone (Russko-Lugovskaya culture). The first direction is attested by sites with typologically impoverished toolkits and singular asymmetric trapezoids, and the second one, by the few flint points and cutting tools. The Bayesian MCMC interval modeling suggests the existence of Mesolithic sites in the region between major climatic events of the Holocene—Preboreal oscillation and the global cooling of 8.2 ka BP. The Bayesian KDL chronological modeling reveals a chronologically irregular exploitation of the territory represented by the respective sites, with decreasing intensity coinciding with minor climatic events of the Holocene (10.9, 10.3, and 9.3 ka BP). The established agreement between the chronological boundaries of Mesolithic sites and major climatic events might account both for the Paleolithic-to-Mesolithic and the Mesolithic-to-Neolithic transitions in the region.