Freeways have had a strong influence not only on the urban transportation but also on downtown areas both physically and socially. Certainly, they have extended the commuting limits of the city and made lower land costs more accessible. However, many of the mid-century freeways, once championed by planners as tools for urban renewal, have created swaths of blight through city neighborhoods. Their negative impacts on the larger urban framework requires new ideas for healthier alternatives to aid in preserving and building sustainable cities. Removal of any downtown highway requires careful thought— even more consideration than when it was built. Quick solutions are what resulted in the problems that downtown highways of the Interstate-Era have today. If it is the simple interactions between people and place are that make up the positive aspects an urban environment, then what are the possibilities and strategies for removing urban highway, which are one of the primary impediments separating people in place in contemporary cities? This question is the focus of this thesis. At its core, the removal of freeways represents a trade-off between mobility objectives and economic development objectives. Evidence from other cities’ decisions to redesign or remove their downtown highways suggests multiple benefits. Making design changes, such as to replace a downtown highway with a well-designed surface boulevard, can stimulate economic activities without necessarily causing traffic chaos. Solutions come in different shapes and sizes. The selected case studies in this thesis reflect a diversity of approaches – suggesting no single strategy exists for addressing downtown highway issues. This reflects the fact that multiple alternatives must be considered in every situation because each approach varies in costs and opportunities. A typology of highway alternations derived from the case studies includes seven different techniques: burying, demolishing, taming, capping or bridging, elevating, retaining, and relocating. The final chapter applies the conclusions from the case studies to the Downtown Connector– Interstate 75/85– in Downtown Atlanta, Georgia. Urban design and transportation planning has an emerging new set of values. Transportation planning is seeking to promote alternate modes of transportation to the private vehicle, like transit, by foot, or by bicycle. We now understand that connectivity is not served only by highways but also by urban street networks that invite modes other than just automobiles. An important role for urban design will be to shape the way these interactions are made to benefit the citizens, its urban spaces, and the economy.