The purpose of this paper is to identify and analyze the contributions of Edward Bellamy to planning history and theory and utopian thought through a comparison of his two novels Looking Backward (1888)and Equality (1897). It endeavors to answer the question of whether or not his perspectives are as relevant today as they were at the beginning of this century. The paper begins with a brief synopsis of Bellamy's background, continues with a review and analysis of his two utopian novels, shifts to perspectives offered by historians and political theorists and ends with this author's thoughts. It is my position that, despite the fact that the two books were published only nine years apart, they reveal a dramatic shift in Bellamy's ideological perspective. In Looking Backward, he is clearly a proponent of Micah's "City on the Hill" ideal while in Equality, he argues for the dissolution of our great cities. This shift centered on the role of the city in society, the influence of technology upon the formation of community, the place of nature in society and the ideal form of community. It is explained below.