The Zamość fortress has been an object of careful study for a long time. However, the problem of interconnection/ interrelation between the town and, generally, waterscape have not received its full attention. The context of water have impacted different aspects of city life. Zamość is not excluded with that general tendency. Jan Zamoyski, together with his architect, Bernardo Morando, two ambitious men with vision took the challenge and started building the town which, has become a symbol of Renessaince ideals of universality, harmonious proportion and ,,sincere bow’’ to natural landscape. The consecutive architects of the town, over the centuries, together with the next Zamoyski family members, continued to shape the town. Over the years, the town has evolved and altered its form, confronting challenges of militarization period of XIX c., then, after demilitarization of 1866, demolish of substantial amount of its architectural substance and gradual restoration of its compositional value. Local Revitalization Programme 2017 – 2023 and recently introduced Municipal Revitalization Programme 2023 – 2030 ,,has been carrying on this torch of spatial and social progress. The paper aims to present historical value of the spaces surrounding the Zamość fortress from the south and their key importance in forging a town brand that would be recognised worldwide. Two fragments of the Łabuńka River Boulevards were compared, under physical, urban/ compositional, social criteria in order to diagnose specific needs of the terrain and its users.