The aim of this project report is to investigate and identify the needs of the historic area (focus area) in the City of Milpitas, to positively contribute to the City’s planning process, and to make recommendations for the focus area’s future development. In the first chapters, City and focus area research results are presented. Currently, there is a lack of exclusive regulatory standards for attractive development in the City’s historic core. The project report then discusses the results of a short empirical everyday user survey, a parcel-by-parcel land use survey, and a walkability analysis. Research results indicate that the focus area could benefit from historic identity preservation, additional public open space and recreation, and economic development. The project report then identifies three case studies and analyzes each under an urban design framework regarding walkability and gateway development. Here, the project report draws on a number of sources regarding positive place making and urban design to highlight the focus area’s opportunities and constraints. In conclusion, the project report argues that the City’s location in the Bay Area and proximity to Silicon Valley requires accommodation and competition for development while coordinating current focus area development to contribute to an overall well-designed site plan with a focus on walkability and an attractive gateway image. Recommendations are provided in the form of design guidelines.