The rise of the BE Ving progressive has been argued to reflect a broader shift in the typological profile of English from a bounded to an unbounded language, leading to changing preferences in aspectual construal and narrative organization. However, it remains unclear whether BE Ving directly replaced a dominant pattern of bounded event construal or superseded alternative strategies that were already available to express progressive(-like) meaning before. The idea of a typological shift suggests that many more strategies may have been involved. This article investigates diachronic change in the expression of progressive(-like) meaning. To this end, use is made of a historical parallel translation corpus consisting of eight successive English translations of Cervantes’ Don Quijote, giving insight into how the same meanings were expressed over time. The results suggest that the expression of progressive(-like) meaning in English went through a pragmatic stage, in which progressive meaning was mainly expressed through invited inference, followed by an experimentation stage, during which speakers of English resorted to a variety of lexical and (semi-)grammatical options to express these meanings semantically, and resulting in the current situation with the emergence of the grammaticalized marker BE Ving as an uncontested default coding option.