A multi-proxy study of a sediment sequence from Braamhoek wetland, covering the last c. 16,000 years, reveals a record of regional climate and vegetation dynamics in the Drakensberg region, South Africa, including signals from both the organic sediment fraction (fossil pollen, charcoal, n-alkane abundance, n-alkane δ13C, TOC) and the inorganic fraction (mineral magnetic properties). The reconstruction, supported by a robust chronology, indicates two major periods of increased regional wetness during the late Pleistocene to early Holocene phase (c. 13,800-12,600calyrBP; c. 10,200-8500calyrBP) and one during the late Holocene (c. 2000calyrBP to present). Drier conditions are recorded during the Younger Dryas (c. 12,600-11,300calyrBP) and mid-Holocene (c. 7000-2000calyrBP). A major decline in fynbos vegetation during the early Holocene suggests a shift towards warmer temperatures and possibly towards less pronounced winter rains in eastern South Africa from c. 8500calyrBP. Comparison with records from interior of South Africa show relatively high inter-site variability, however, the Braamhoek moisture proxies do co-vary with the speleothem isotope records from Makapansgat, suggesting a similar hydro-climate evolution in eastern and interior parts of the summer rainfall region during the studied period. On multi-millennial time scales, an inverse hydro-climatological pattern is evident between these two South African records and reconstructions from tropical locations in southeast Africa. Such a rainfall dipole between eastern tropical and southern Africa, has previously been identified on shorter time scales, i.e. on inter-annual to millennial scales. The Braamhoek study suggests that a similar dipole pattern is acting also on a multi-millennial perspective. These long-term precipitation anomalies are tentatively coupled to teleconnections from multi-millennial changes in the dynamics of the Indian Ocean Dipole (IOD) and El Niño-Southern Oscillation (ENSO).