Agricultural statistical data enable the detection and interpretation of the development of agriculture and the food supply situation over time, which is essential for food security evaluation in any country. Based on the historical agricultural statistics, this study produces a long spatial time-series with annual production values of three cereals relevant to global food security—wheat, maize, and rice, aiming to provide geographical and historical perspectives. Therefore, we reconstructed past and current production patterns and trends at the district level over 169 years, which supported a space–time cross-reading of the general characteristics of the regional agricultural production value distributions and relative densities in Portugal. Particularly, the production trends of wheat, maize, and rice showed three different situations: growth (maize), stability (rice), and decline (wheat). For decades, maize and wheat production alternated, depending on agricultural years and political aspects, such as the Wheat Campaign (1929–1938). The changes over time presented a pattern that, in the case of these three cereals, enabled a clear division of the country into major regions according to cereal production. Overall, maize and rice, both grown on irrigated croplands, presented a similar pattern in some regions of Portugal, mainly the central region. In this study, a preliminary analysis was presented and related to successive public policies; however, notably, there are more lessons to be learned from this long spatial time-series.