This study applied a supervised machine learning classification and intensity analysis of Landsat imageries to examine the spatio-temporal dynamics of woody vegetation cover in Barbados for two-time intervals: 2001-2015 and 2015-2019. The results show a larger persistence and concentration of woody vegetation in the East Coast (the Scotland District) of Barbados. Woody vegetation cover declined by approximately 11 km2 from 2001 to 2015, and 1.5 km2 from 2015 to 2019. Intensity analysis showed that total observed change in the landscape was slow in the first time interval but fast in the second. Categorical gain-loss showed a systematic targeting between woody vegetation and other vegetation. Built-up and woody vegetation, however, systematically avoided each other. Woody vegetation remained active in both time intervals but the intensity of change was larger in the second interval. In conclusion, the systematic targeting between woody vegetation and other vegetation (mainly agriculture) provides a focus for management, conservation and spatial expansion of the latter.