The Wine of Saint-Martin’s Day, one of Pieter Bruegel’s master pieces currently exhibited in the Prado Museum in Madrid, has yet to reveal its latest secrets. In this regard, the team comprising an archaeologist of the Royal Museums of Art and History (Belgium) and a historian of the Archaeology Department of Brussels Urbanism and Heritage, recently analysed the painting and came up with some surprising insights. The analysis is composed of a critical study of the architectural elements depicted by Bruegel such as a fragment of the Brussels city wall with one of its gates and two sanctuaries, a chapel and a church at either end of the composition. These elements, combined with the theme of the painting as ‘wine feast’ has led to insightful conclusions relating to the painter’s visual inspiration in depicting this scene. What follows is an investigation of architectural and topographical viewpoints used by Bruegel in his work and a reflection on Bruegel living in Brussels in the mid-16th century, during his most productive period. In the painting he displays his many talents, most expressly his resourcefulness, his sense of humour, and a command of colour and composition, bearing in mind the rate of consumption and use of wine as a contemporary commodity.