This case study is about the politics of incorporating active-living elements into a concept plan for a new community of about 68,000 people on the edge of the Portland, Oregon, metropolitan area. Development on the rural-urban fringe is ongoing in metropolitan areas around the United States. In this article, we evaluate the product of the concept-planning process from the standpoint of the extent to which environmental elements conducive to active living were included. We also analyze four issues in which challenges to the incorporation of active-living features surfaced: choices related to transportation facilities, the design and location of retail stores, the location of schools and parks, and the location of a new town center. Overall, the Damascus/Boring Concept Plan positions the area well to promote active living. Analyses of the challenges that emerged yielded lessons for advocates regarding ways to deal with conflicts between facilitating active living and local economic development and related tax-base concerns and between active-living elements and school-district planning autonomy as well as the need for advocates to have the capacity to present alternatives to the usual financial and design approaches taken by private- and public-sector investors.