Our cities are too often disconnected. They are disconnected in the sense of a failure to relate neighborhoods and districts to each other. This is especially true for cities which lack effective public transportation. Isolation is almost always the result of these disconnects. In turn, physical, cultural and economic barriers are created between different neighborhoods and districts of a city. These barriers negatively affect both the advantaged and the disadvantaged alike. This thesis will examine the economic and social consequences of city planning and urban design with an emphasis on change over time. The city of St. Paul, Minnesota is to be used as a study. More specifically, the relationship between the highly residential Frogtown neighborhood and the city’s highly commercial Downtown area is to be explored. Solutions to this specific disconnect will be discovered and designed in order to benefit both areas. Sustainable strategies will be emphasized for cultural, economic, and environmental reasons.