This study explores processes and policies that facilitate the development of community trails. With funding from Active Living Research and the research framework of the Physical Activity Policy Research Network (PAPRN), we conducted a multiple-site case study. A total of six trails in Hawaii, Massachusetts, Missouri, North Carolina, South Carolina, and Washington were chosen for study. The goals of this case study were to identify the policy influences on trail development, explore the roles of key players in trail development, and compare and contrast findings from the different trails. Trail development can be a long process. Some of the trails took over a decade to complete because of funding, opposition, and roadblocks in the form of design standard policies. Work in trail development requires a team of many players, and it is necessary to balance their varied motives to accomplish a shared overall goal. Foresight through the master planning process is also a vital component of successful trail development. Finally, community involvement is key. Communities contemplating trail development should explore the effects of policy on the trail projects reported here to proactively identify potential influence.