This paper discusses the urban development history of Samara and the nuances of how its urban pattern was formed. The paper highlights the key milestones in the history of the city’s development, addresses how the unplanned and planned cities were structured, and considers the city’s main historic squares. It also analyzes the part the city squares play in modern Samara. The definition of the term architectural landmark provides the basis for several primary classifications of architectural landmarks, identifying the historic landmarks of Samara. Also considered is the part that the primary architectural landmarks played in forming the historical and modern urban environment as well as how that part changed as the city grew and developed. The paper also addresses the effect that later development has had on the historic landmarks. Keywords: city, urban development, architectural landmarks, city structure, planned city.