Gorontalo is currently known as the City of Serambi Medina due to its distinctive features. Distinctive features in each era of Gorontalo demonstrate the unique progression of the city across time. Its defining feature is the mosque serving as the focal point of activities, encircled by the residences of the olongia or the tribe chiefs. Here, one's place in the mosque is determined by one's proximity to the center: the closer one is, the higher one's position is; conversely, the farther one is, the lower one's position. This study examines the progression of its urban development patterns at different points in time. The study was carried out at Gorontalo City, Indonesia.It employs a qualitative method utilizing phenomenological techniques. Data was collected through participant observations, structured interviews and a literature survey. Data analysis involves examining the attributes of Gorontalo City through qualitative descriptive methods.The paper reveals that the city has arisen from the original Islamic Kingdom, which was produce two patterns due to the relocation of the kingdom. Specifically, in Tuladenggi, the city's development has been characterized by an axial design, with structures placed along lines and experiencing linear and continuous growth. In Biawao and Limba, the locations differ from the prior places due to their grid-shaped development pattern characterized by a continuous linear growth along the major road. Throughout the colonial era, the development pattern has consistently followed a grid layout in the imperial metropolis, whereas the settlement growth pattern has shifted to a discontinuous radial one. Urban development trends currently reflect colonial grid-shaped layouts with unsustainable radial growth. This ongoing radiation is the precursor to the urban sprawl in the city of Gorontalo. This city development pattern offers valuable lessons on how to achieve harmony with Nature.