The Caribbean Archaic Age (about 3000–500 BC) is thought to represent the earliest migration of humans from South America into the Lesser Antilles. However, there is a conspicuous absence of these early sites on islands south of the Guadeloupe Passage. To date, only a single radiocarbon date derived from a Queen conch (Strombus [Eustrombus] gigas) shell at the Heywoods site on Barbados was indicative of an Archaic occupation in the southern Antilles apart from a scattering of poorly reported (and mostly undated) sites. Given a number of issues associated with reliance on a single date to establish a cultural horizon, along with other problems derived from possible carbonate cement contamination and dating marine shells of a longer-lived species such as Queen conch, 2 additional samples were taken from the same unit and context at Heywoods to confirm whether the site is truly representative of an occupation during the Archaic Age. Results from a Queen conch shell adze in Context 7 dated to 2530–2200 BC (2 σ) and overlaps with the only other Archaic date from the site dating to 2320–1750 cal BC, while a juvenile specimen of the same species from Context 8 at 3280–2940 BC (2 σ) indicates that Barbados may have been settled even earlier. This suggests that Heywoods may be the oldest site between Trinidad and Puerto Rico. While further confirmation is required, these new dates have implications for understanding the nature of migratory ventures in the Caribbean, such as whether the “Southward Route” hypothesis—which postulates that earlier migration events from South America during the Ceramic Age (beginning ∼500 BC) initially bypassed the southern Lesser Antilles—also applies to the Archaic, and if other phenomena such as active volcanism may have played a role in structuring settlement patterns. Questions also remain as to why Heywoods does not exhibit the typical lithic Archaic tool kit.