Globally, native semiarid grasslands and savannas have experienced a densification of woody plant speciesleading to a multitude of environmental, economic, and cultural changes. These encroached areas are unique in that the diversity of tree species is small, but at the same time the individual species possess diverse phenological responses. The overall goal of this study was to evaluate the ability of very high resolution drone imagery to accurately map species of woody plants encroaching on semiarid grasslands. For a site in the Edwards Plateau ecoregion of central Texas, we used affordable, very high resolution drone imagery to which we applied maximum likelihood (ML), support vector machine (SVM), random forest (RF), and VGG-19 convolutional neural network (CNN) algorithms in combination with pixel-based (with and without post-processing) and object-based (small and large) classification methods. Based on test sample data (n = 1000) the VGG-19 CNN model achieved the highest overall accuracy (96.9%). SVM came in second with an average classification accuracy of 91.2% across all methods, followed by RF (89.7%) and ML (86.8%). Overall, our findings show that RGB drone sensors are indeed capable of providing highly accurate classifications of woody plant species in semiarid landscapescomparable to and even greater in some regards to those achieved by aerial and drone imagery using hyperspectral sensors in more diverse landscapes.