We inquire into Definite Article Reduction (DAR), a phenomenon known to characterize northern British English Dialects. For this research we collected data from speakers at the North Yorkshire/Lancashire border. While previous studies have largely addressed DAR from a phonological perspective, we examine whether and to what extent DAR is grammatically conditioned. The pattern we identify is that DAR is most frequent when speakers refer to something (i) that is in their immediate environment (situational reference) or (ii) that was just mentioned in the conversation (anaphoric reference). Noting that these contexts seem reminiscent of demonstrative usage, we speculate on the emergence of DAR, drawing on evidence from the historical record.