Bojonegoro is a regency in East Java province with a population of 1,322,474 (BPS, 2022) and high population density. Population growth is strong, and demand for land is increasing. Increased human activity leads to land conversion, which could impact regional development. The objectives of this study are to: 1) Analyze the dynamics of land cover change, 2) Compare the SDI (Sub-district Development Index) scores of 2008 and 2020 in Bojonegoro Regency, and 3) Analyze the factors affecting the level of Regional development in Bojonegoro Regency. The methods used are overlay (GIS analysis), scale plot analysis, and geographically weighted regression (GWR) analysis. The most significant land cover change occurred in forest cover, with the area decreasing from 99,815 hectares (2000) to 84,845 hectares (2020), while the built-up area increased from 12,665 hectares (2000) to 22,901 hectares ( 2020). Bojonegoro sub-district has the highest SDI of 44,043 (2008) and 44,917 (2020) because it has the largest population and become a capital district and central business district (CBD). Based on the results of the GWR analysis, the highest local R2 is located in the eastern part of the Regency. In contrast, the lowest local R2 is located in the western administrative district of Bojonegoro Regency. The results show that the driving forces influencing regional development in Bojonegoro Regency vary spatially.