This thesis is a first wave (Eckert, 2012) sociolinguistic study that presents perceptions of East Midland and South Yorkshire accents and dialects from the perspective of three generations of Chesterfield locals. Chesterfield is a town in North East Derbyshire, England, close to several administrative, perceptual, and linguistic borders: Derbyshire and Yorkshire, the Midlands and the North; GOAT and FACE monophthongal and/or diphthongal realisations. As such, Chesterfield is regarded as a border town, with the identity of Chesterfield locals hypothesised to be either ‘hybrid’ (Llamas, 2010: 235-6) or affected by a ‘heightened diversity’ (Britain, 2010: 200) due to its close geographical proximity with Sheffield, South Yorkshire. This study analyes the results of dialect recognition tasks that elicited how East Midland and Sheffield voices are indexed (Silverstein, 2003) to a largely Chesterfield audience. The same respondents were asked to position lines on a map task which asked for the placement of a North/South and potentially Midland dividing line in England to better understand regional identity from an East Midland location. These data are then compared against the same respondents’ word list data in order to comprehend more about the realisation of the GOAT and FACE vowels in Chesterfield across three generations, where the literature had previously understood both vowels to be more dipthongal in Chesterfield and more monophthongal in Sheffield (Finnegan, 2011). These data are interpreted using both qualitative and quantitative techniques, which suggest age could be a key variable both in dialect recognition and GOAT and FACE linguistic production in Chesterfield. A ‘scale of northern-ness’ is proposed to be instrumental in the placement of local voices, where the Midlands is understood to be a transition zone from northern to southern linguistic features by non-linguists. With historical rivalry and political differences between Chesterfield and South Derbyshire/Nottinghamshire still evident, Chesterfield appears to be northward facing despite the enduring wish to remain administratively separate from Sheffield.