In prevailing societal perceptions, mountains are often considered socio-spatial realms distinct from urban areas, frequently characterized as rural or wild landscapes. However, in the context of contemporary “planetary urbanization,” does this perspective remain analytically valid for examining mountainous regions? Do the categories of “wild,” “rural,” and “urban” continue to serve as useful structural and functional constructs for investigating current socio-spatial processes in these areas? What unique urban characteristics delineate such regions? Employing a theoretical framework that synthesizes the concepts of planetary urbanization and verticality and drawing upon case studies from both the Global North and South, this paper aims to investigate, through the lens of urban montology—the sustainability-focused, transdisciplinary study of urbanizing mountain environments—the interconnections between rural and urban spheres across varying altitudinal gradients. Given the distinctive features of elevation and terrain configuration, the infrastructural, demographic, economic, and sociocultural linkages in mountainous areas exhibit numerous particularities. Flows of mountain ecosystem services, cable cars connecting valleys and peaks, vertical spatial mobility of populations, and the intentional promotion of alpine environments and identities to brand mountain cities for investors and tourists are just a few examples highlighting the growing interconnectedness between traditionally “urban” cities and “rural” or “wild” mountain areas. Recognizing these connections is paramount when examining and facilitating the transformation of urbanizing mountain spaces into desirable habitats for both humans and nonhumans.