Since the mid-19th century, rare prehistoric wooden carvings and human skeletal remains have been dredged from Pitch Lake, Trinidad, during commercial asphalt mining. Establishing a chronology for these objects is challenging, due to both a lack of stratigraphic and contextual information and the necessity to completely remove any pitch to ensure accurate radiocarbon (14C) dates. A range of solvent extraction protocols was tested to identify the most suitable one for pretreating the Pitch Lake artifacts, and then applied to ten wooden objects and a human cranium recovered from the lake. Several of these objects yielded earlier dates than expected, raising concerns that pitch had remained after pretreatment and had affected the dates. Pyrolysis-GC/MS and optical microscopy techniques were applied to material from the human cranium, a weaving tool, and a small bowl. These techniques, as well as routinely applied laboratory quality assurance procedures, indicated that there was no residual pitch within the cranium or the weaving tool after pretreatment, giving confidence to the dates. However, the small bowl was observed to still be contaminated with pitch after extensive pretreatment, indicating that the date is too old and can only be considered as a terminus post quem.