Sugarcane cultivation has played a key role in the development of the Caribbean since the seventeenth century A.D. The Eastern Caribbean island of Antigua in the West Indies was almost exclusively dedicated to sugarcane monoculture from the mid-1600s until its independence from Britain in 1981. This research seeks to better understand the landscape legacies left by long-term sugarcane monoculture at the site of Betty's Hope Plantation in Antigua. This study creates a 400-year simulation of crop yields using the USDA's Erosion Productivity Impact Calculator (EPIC), and evaluates the simulated trajectory of landscape change using historical information about the plantation's agricultural yield and a geoarchaeological analysis of the regional landscape. Findings suggest that some parts of Betty's Hope have experienced degradation due to long-term sugarcane monoculture, but degradation in other parts of the region may be the result of the cessation of commercial agriculture in 1972, when human investment in the highly engineered landscape ended. If these results are representative of other parts of the island, then they suggest that current erosion and degradation experienced today cannot be attributed to intensive plantation agriculture alone, but rather are part of a complex mosaic of human- environmental interactions that includes abandonment of engineered landscapes.