The charismatic, day-flying buck moths of the Hemileuca maia species complex are among North America’s most enigmatic groups of Lepidoptera regarding their evolutionary history, ecological specialization, and taxonomy. While the group is geographically widespread, populations are highly localized and stenotopic, exhibit considerable ecological and morphological variability, and display widely variable specificity to host, habitat, and sex pheromone attraction. As such, they are an ideal model for investigating patterns and constraints of local adaptation and the effects of ecological specialization on speciation. Here, I report on recent efforts to combine genomics and chemical ecology to understand the evolutionary history of this group. This work includes generation of a chromosome-scale genome assembly, population genomic and phylogenomic analyses using both reduced-representation sequencing and whole-genome resequencing, transcriptomics, and gas chromatography of female sex pheromones. This genomic foundation provides a novel lens with which to assess host and habitat specificity, diversification of sex pheromone components, and taxonomy of the group, including several species of conservation concern.