This study illustrates the impact of the Tamiami Trail on the people and environment of South Florida through an examination of the road’s origins, construction and implementation. By exploring the motives behind building the highway, the subsequent assimilation of indigenous societies, the drastic population growth that occurred as a result of a propagated “Florida Dream”, and the environmental decline of the surrounding Everglades, this analysis reveals that the Tamiami Trail is viewed today through a much different context than that of the road’s builders and promoters in the early twentieth century. While construction projects that aim to prevent, or limit the once celebrated environmental destruction caused by the Tamiami Trail, the unrelenting and economically stimulating growth of South Florida continues to uncover a “paradox of progress.”