When calling a place “picturesque”, do we mean “pretty”, or perhaps “predictable” or “superficial”? Over a century ago, when symbolist artists sought melancholic views to express the hidden soul of things, were such “picturesque” places suitable?  One way to find out is to scrutinize painted, printed and drawn portrayals of a city labelled both picturesque and symbolist: the Belgian city of Bruges. Each of Bruges’ identities around 1900 - “Bruges the Beautiful” and “Bruges the Dead” - resulted in an artistic corpus that scholars so far have treated separately. Cityscapes by the “Bruges School” are mostly labelled “picturesque”, with a connotation of “superficial”. This school also actively constructed the town's picturesque image in tourism posters. On de contrary, symbolists’ melancholic works are said to “penetrate to the soul of things”, showing a “higher” reality. This research scrutinizes how and to what extent this binary division was made in art practice and criticism between 1886 and 1914. It thus fills an interdisciplinary research gap between art history, literature and architectural theory, by combining different methods: analysis of form, iconography and critical reception. It contributes to recent scholarly attention for postcards, lesser-known artists, and the nuanced divide between romanticism and symbolism. Finally, for the first time, it compares artistic portrayals of Bruges and Venice, two quintessential symbolist and picturesque cities.