Preservation is a constantly evolving dialogue between past and future, new and old. Yet as the formal and aesthetic precedents of traditional urbanism are adopted by New Urbanist practitioners to cloak new construction with the guise of historic continuity, the draw of Main Street communities is quickly fading. Where once downtown had the advantage of distinctive architecture and walkability as a competitive edge over sprawling suburban retail centers, large cities and small towns alike now face the challenge of competing with savvy Main Street imitators sprouting up on the urban fringe. This trend towards New Urbanist style retail is hurting businesses on Main Street, but the increasing marketability of these formats provides an opportunity for historic commercial corridors to take advantage of evolving consumer preferences. Several communities are already adapting to this new set of challenges by utilizing New Urbanist planning and design approaches to reposition their historic commercial corridors through infill development and urban restructuring. These interventions do not always make the headlines, yet they continue to gain strength. Some preservationists argue that there is little need for “new” urbanism when a wealth of old urbanism already exists. Yet what is desperately needed is a new way of thinking about urban places. Reasserting the historic role of Main Street communities as bastions of progress and innovation will enable a future in which strong communities, sustainable growth patterns and quality of life are rooted in the legacy of previous generations while providing for the demands of the next.