Greendale, Wisconsin, was intentionally created with many of the design and planning principles that active-living advocates promote today. This case study examines the processes behind sustaining these particular planning and design principles over time in light of economic and regional challenges that have faced not just Greendale but most town centers over the last fifty years. Despite these challenges, the walkable nature of Greendale's center remains strong today, in terms of both activity and community identity. While many circumstances are specific to this particular town, useful lessons can be drawn for those new urbanist (NU) communities being developed in greenfields and suburbs today, many of which are strikingly similar to Greendale - relatively small, low density, and located within metropolitan areas. Greendale's success resulted from (1) attending to the retail/commercial product mix; (2) attracting nonresidents to use the community's retail and public space; and (3) capitalizing on community investment not simply from residents' organizing efforts but, more important in this case, from corporate community involvement by a Greendale business firm whose interests and values coincided with those of the community.