The rural built environment, as a multiscale whole of human transformations aimed at accommodating agriculture-related activities, prompts various reflections on the bioclimatic approach in architectural design. This contribution, firstly, highlights the theme of the urban-rural continuum (an intermediate and contradictory place, which epitomizes on-going contemporary transformations) in order to demonstrate that the contrast between urban and rural—although it has been used, since ancient times, on both analytical and design level—has not only been superseded, but is also, theoretically, inadequate for identifying the rural built environment. The link between agricultural and construction activities confirms the overcoming of this contrast; a reading in technological terms is proposed, with reference to the spheres of the product and the process, whilst recollecting its remote and deeply rooted cultural origins. The possible dual and contradictory character (vernacular or scholarly) of the rural built environment is illustrated with reference to the specificity of the bioclimatic aspects recognized in traditional buildings (“ante litteram sustainability”), highlighting how the relationship with the site-factor (microclimatic characteristics and local construction culture) was almost annulled in the twentieth century, also creating the basis for a widespread emergency for the quality of the buildings employed in agricultural activities. Touching upon the question of whether the rural building can be a typology distinct from other production buildings, this paper highlights the importance of the relationships with the socio-economic aspects of the agricultural sector, underlining the fact that the main identity for rural buildings in every age, in addition to the role that they play in the landscape, should be a stronger bond with the environmental elements, showing the centrality of the bioclimatic approach in updating the primordial interactions between agriculture and construction. Furthermore, the distinction between vernacular or scholarly character of the rural buildings prompted a reflection on the contemporary epistemological bases of the bioclimatic approach to general architectural design, which risks being ineffective whether it remains on an empirical level or if it is confined to a hyper-specialized niche. Finally, the bioclimatic approach is indicated as a common analytical and design methodological basis, useful for addressing the contradictory nature of the urban-rural continuum, in the framework of contemporary challenges.