Prishtina, the capital of Kosovo, has a unique and diverse cultural heritageCultural heritage shaped by centuries of history and the influence of various empires and civilizations. The city’s architectureArchitecture reflects its complex past, with Ottoman, Austro-Hungarian, and Yugoslavian influences visible in its urban fabric. Despite its turbulent past, Prishtina is now a rapidly developing urban center home to a growing population and a thriving arts and culture scene. Its streets are a testament to the city’s social and spatial stratification, with different layers of history and contemporary influences intersecting to create a dynamic and vibrant urban environment. In this chapter, the authors use the art of urban sketching to explore the many layers of Prishtina’s evolution, taking readers on a visual journey through the city’s streets and landmarks. Through sketches, they document the changing urban landscapeUrban landscapes of Prishtina, along a time domain from the Ottoman influences to the modernist architectureArchitecture of the post-war era. Ultimately, this chapter serves as a fascinating case study on using urban sketching as a tool for observing and documenting the evolution of a city. By capturing the distinctive character of Prishtina’s urban environment through sketches, the authors offer a new way of seeing and understanding the complex interplay of history, culture, and architectureArchitecture that shapes the built environmentBuilt environment, capturing the essence of a place in a few lines and strokes of the pen, offering a glimpse into the world as it is and, as it could be, a testament to the beauty and complexity of urban life.