The expansion of agricultural, forest plantation, and urban areas is among the main drivers of worldwide land use/cover change. However, little is known about the changes in the extent of highly profitable crops in the temperate zones of South America and their association with other land use/cover changes, especially in south-central Chile, which has experienced massive changes in recent decades. In this context, we aimed to assess land use/cover and fruit crop area changes at the regional and county levels in the Araucanía region, Chile. Hence, the quantity and location of past and future changes were identified using cross-tabulation, Markov chains and cellular automata. The results showed that agricultural land and meadows have decreased by 18% and 26%, respectively, between 1997 and 2013, mainly due to the expansion of forest plantations and urban areas. However, the fruit crop area increased by 645% between the years 2000 and 2019 and will continue increasing to 2033. These changes modified the relative weights of economic activities within the region, changing from cattle raising and marginal agriculture to more profitable activities such as fruit crops and forest plantations. Finally, this work shows a need to move toward the spatial monitoring of agriculture and fruit crops within the country.