In this chapter we will learn about the earliest and most deeply rooted processes of colonization which have shaped the English language, in what used to be known as the “Old World” and the “New World.” English itself is shown to be a product of colonization, namely of the settlement of the British Isles by Germanic tribes more than 1,500 years ago, similar to the effect on language of colonial expansion in the modern age. British English was influenced and shaped by contact with an indigenous language (Celtic) and with later “adstrates” (Scandinavian and French, mostly). We then look at the initial stages of the colonial diffusion of English in the seventeenth century, to North America (ultimately producing American English as we know it today) and to the Caribbean (with the forms of English found there being largely products of a major restructuring process, creolization). In each of these cases I will survey the general sociohistorical context and will then zoom in to a closer, exemplary discussion (including a text sample) of one characteristic regional variety of English found there.