An indispensable part of understanding the present form of Canadian English is understanding the historical forces that gave rise to Canada's English-speaking population and promoted its expansion. Apart from being responsible for the very existence of Canadian English, these external, non-linguistic forces have played just as important a role as internal, linguistic forces in determining its modern characteristics. Given Canada's relative youth (at least from the European point of view), the current form of Canadian English is closely bound up with the history of immigration: who first established English in Canada and where they came from; how this initial settlement was built upon, with which people in which proportions; and, finally, where today's speakers of Canadian English come from. To address these questions, this chapter will examine the history of the establishment and further growth of Canada's English-speaking population. It begins with a chronological description of several phases in the settlement of Canada in order to establish the historical roots of Canadian English, then considers the possible origins of important features of modern Canadian English in light of that history. Readers less familiar with the geography of Canada may find it helpful to consult the maps at the front of the book for locations of places discussed in this chapter.