Understanding trends of vegetation evolution and its spatial characteristics is critical for sustainable social development in the Greater Mekong Subregion (GMS), which is densely populated and still has uneven economic development. Through Theil–Sen/Mann–Kendall tests, polynomial regression and bivariate local autocorrelation analyses, we investigated vegetation greening trends and their spatial correlation with bioclimatic and environmental variables. The study yielded the following results: (1) Land cover in the GMS has changed significantly over the last 20 years. Conversion between forest and grassland was the main type of change. (2) The upward trend in the forest enhanced vegetation index (EVI) significantly exceeded the downward trend in countries over 20 years. In GMS, the spatial variation in forest trend slope values ranged from −0.0297 a−1 to 0.0152 a−1. (3) Anthropogenic activities have played an important role in forest greening; planted, plantation and oil palm forests exhibit the largest contributions to greening. (4) Changes in forest EVI were most spatially correlated with radiation (12.19% for surface net solar radiation and 12.14% for surface solar radiation downwards) and least spatially correlated with seasonality precipitation (8.33%) and mean annual temperature (8.19%). The results of the analysis of EVI trends in vegetation and their spatial correlation with bioclimatic and environmental variables can provide a reference for strategies aimed for protecting the vegetation ecology.