In this paper, we bridge work in rock climbing route generation and grading into the computational creativity community. We provide the necessary background to situate that literature and demonstrate the domain's intellectual merit in the computational creativity community. We provide a guiding set of desiderata for future work in this area. We propose an approach to computational route grading. Finally, we identify important gaps in the literature and consider how they may be filled. This paper thus also serves as a pilot study, planting a flag for our ongoing research in this domain.