One of historic preservation planning’s greatest tools is the preservation plan itself, which coordinates the various interests and activities of planning into one comprehensive document. While a growing number of localities are publishing preservation plans, comparatively little analysis exists that focuses on preservation plan implementation and effectiveness. The intention of this thesis is to further contribute to the critical reflection of this discipline, through a case study-oriented analysis that focuses on preservation planning history and plan implementation in several cities, in order to determine the usefulness of such plans and methods of improving successful implementation. The case study cities analyzed in this thesis are: Providence, Rhode Island, Lancaster, Pennsylvania and Staunton, Virginia. The selected preservation plans vary in form, content and implementation, and also represent a diversity of localities. These case study plans were analyzed not only through study of the plans themselves, but by examining implementation and success of preservation activities in each locality after its publication. As a result, the analysis presented here includes both a “quantitative” study of outcomes, directly linking plan recommendations with future results, as well as a qualitative assessment of success in each city, primarily based on insights expressed by local preservation professionals through interviews. Themes that are explored here include the planning process, citizen involvement, educational outreach and preservation incentives.