This essay explores the historical evolution of Yankeedom, one of the eleven regions of the United States, as identified by Colin Woodward. It discusses the origin, evolution, and constant development of the states focusing on Yankeedom, over the years through the American Civil war to the present day. The literary piece by Colin Woodard on the cultural history of North America is extended over a series of twenty-eight chapters or episodes which extensively describe the eleven rival nations and their fight between each other resulting in the famous Civil War.