A hill station is a town or city situated in mountain regions in the tropics founded during the western colonization in the nineteenth and early twentieth centuries. Hill stations have moderate temperatures, and are known for their relatively good natural environments, which generate valuable ecosystem services that benefit the local population. However, rapid urbanization threatens the sustainability of these areas. This study evaluates the sustainability of the urbanization process of Baguio City, a hill station city in Southeast Asia and the summer capital of the Philippines, by determining the relationship between its velocity of urbanization and velocity of urban sustainability based upon various perspectives. From an equal weight perspective (of the triple bottom line of sustainability components, namely environmental, social, and economic) and a pro-economic perspective, the results revealed that the urbanization of Baguio City has been moving toward a “sustainable urbanization.” However, from the environmental and eco-sustainable human development perspectives, the results indicated that it has been moving toward an “unsustainable urbanization.” The paper discusses the implications of the findings for the planning of sustainable development for Baguio City, including some critical challenges in sustainability assessment and the applicability of the framework used for future sustainability assessments of the other hill stations in Southeast Asia.