Hurricanes Irma and Maria have recently demonstrated once again the susceptibility of contemporary populations across the Caribbean to climate-driven events. For islands such as Antigua in the eastern Caribbean, this vulnerability is partly a legacy of prior land use. As such, the actions of pre-Contact and historic period inhabitants are intertwined with contemporary socio-ecological challenges faced by Antiguans today. This research sought to understand the relationship between land use and land degradation from ca. AD 100 to the present in eastern Antigua utilizing two markers of anthropic activity: soil stability and soil quality. Specifically, this research sought to examine how past anthropogenic actions have shaped landscape dynamics across two regions (Ayer’s Creek Basin and Indian Creek Basin), where archaeological research has revealed a long-term, continuous sequence of occupation dating back 2,000 years. Prior research suggests that contemporary environmental challenges in both regions may be linked to prior land management practices. However, it is unknown to what extent historical land use and its interactions with local geomorphology account for these challenges. The main research question was: In what ways and to what extent has past land use (as recorded archaeologically) impacted the landscape (as recorded by soil stability and soil quality) in the Ayer’s Creek and Indian Creek Basins in eastern Antigua? This research determined that contemporary soil erosion and soil quality loss may be attributed to historic land management practices, but mitigating these challenges is impeded by local perceptions of soil health.