Coffeehouses emerge as vital keystones in the intricate urban mosaic of Damascus. Their significance extends far beyond their physical structures, embodying a rich cultural and social heritage that has shaped the city's recreational culture and urban identity over centuries. This research delves into the historical and architectural essence of Damascene coffeehouses, particularly “Al-Nawfara,” within the city walls, and “Bāb al-Salām,” a converted tannery outside the city, during the transformative 17th and 18th centuries. These establishments are pivotal in understanding Damascus’s urban landscape and socio-cultural dynamics. The study seeks to answer how these coffeehouses epitomize the cultural, social, and architectural narrative of Damascus, exploring their role in shaping the city's recreational culture and urban identity and as symbols of socio-political shifts. The thesis posits that these coffeehouses are reflecting the city’s historical evolution, socio-political shifts, and cultural heritage, marking them as integral components of the city’s identity. Employing a multidisciplinary approach, the research intertwines historical analysis with architectural examination, scrutinizing historical texts, architectural records, and contemporary accounts to trace the evolution of these coffeehouses and their socio-cultural significance. The findings uncover rich historical narratives and architectural details, revealing their transformation and the socio-political narratives they encapsulate, illustrating how their design choices mirror socio-cultural norms and the dynamic urban fabric of Damascus. The study concludes that Damascene coffeehouses are emblematic of the city's rich cultural and architectural heritage, offering unique insights into its historical and socio-cultural dynamics and advocating for the preservation of such cultural keystones, emphasizing their role in maintaining the socio-cultural fabric of urban centers.