Transportation planning has long focused on large scale projects using a civil engineering approach of maximizing throughput and minimizing interactions with the surrounding environment. Such efforts greatly increased the overall mobility and accessibility of individuals within and across metropolitan regions, but it is clear that in the future such enormous initiatives are unrealistic due to political, financial, spatial and social concerns. The field of transportation planning is shifting away from this old model of planning towards one where transportation systems are considered part of the overall quality of life of communities. This dissertation explores how local transportation planning is adapting to these changing dynamics of transportation planning through three essays. The first considers how cities are already planning for transportation through their general plans without strong mandates from regional governments. The second essay estimates the spatial variation in commute mode choice in order to show the complexity of travel due to geographic factors of infrastructure provision and land uses. The final essay discusses what flexible localized transportation policies look like, using cruising for parking as an example. Ultimately this research highlights a way forward for transportation planning as a quality-of-life issue, traditionally the purview of local governments.