This study explores the use of Computer Vision models in predicting the age of male whitetail deer from trail camera imagery. More than fifty classification algorithms were evaluated, spanning traditional machine learning approaches to Convolutional Neural Network (CNN)-based deep learning methods. While traditional classifiers reached a maximum accuracy of 57%, transfer learning with CNN ensembles achieved across-validation accuracies of 70.8%, representing substantial improvements over both morphometric methods and human performance while \"aging on the hoof\" (60.6%). Specifically, the ResNet-50 ensemble achieved the highest cross-validation accuracy (76.7% +/- 5.9%), exceeding the 70% threshold that wildlife professionals consider useful for management decisions. Analysis of the ResNet-50 ensemble\'s attention maps reveals that the CNN identifies and focuses on the same morphological features (neck, chest, stomach) that human experts use in age assessment, suggesting the model learns biologically relevant age indicators rather than spurious correlations. This represents the first application of computer vision to whitetail buck age estimation and offers a practical tool to assist wildlife professionals in reducing the manual workload of age assessment while maintaining quality standards.