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This article studies the Nakhon Ratchasima old town through the lenses of settlement, town planning, architectural style, and old house conservation. The authors investigated the city’s origins using survey research, historical research, and in-depth interviews coupled with primary and secondary documentary research. Our findings show that Nakhon Ratchasima has had an international relationship with neighboring countries relevant to the development of each. Two illustrations of this international context are: the emerging city was the focus of Siam’s first rail routes, acting as a fortress between Laos and Cambodia, and the city’s involvement in the kingdom’s political problems. There are 7 architectural styles present in the city: the clay house, wooden shophouse, Western influenced wooden shophouse, and bungalow, vernacular, sino-colonial, and modern. The popularity of each type depended on the way of life, ethnicity, and social life of the people building and using these buildings. These many layers of architecture show these changes over time. Early important vernacular buildings became covered by shophouses as new owners built new layers of history for their businesses. Unfortunately, some of the architectural history has been erased by demolition when people lacked a knowledge of local history. Meanwhile, we discovered the chronological importance of many historical layers: from Khmer civilization to Ayutthaya to Rattanakosin. The findings of this research can act as a model to improve the conservation of important places, to create community awareness about the significance of places, and to make residents proud of their home towns. This living heritage is evident in each layer of settlement, providing pieces of the giant jigsaw puzzle to gradually fill in the city’s history.