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Medieval Lincolnshire is an interesting area in linguistic terms, not only because the boundary between the Northern and East Midland dialects in ME possibly ran horizontally across the shire, but also because historical dialectologists have proposed that some linguistic features could have diffused into it from the south, the west and the north. In this paper, we intend to reconstruct some socio-historical aspects of late Anglo-Saxon and early Norman Lincolnshire (c.900–c.1250) which could have contributed to this linguistic panorama in ME. Not disregarding the proposal that patterns of Danish settlement and contact between OE and ON could have affected the diffusion of innovations throughout this shire, attention will be given to other aspects of the process: (a) the characteristics of the medieval landscape which, by hindering or favouring communication, may have conditioned the distribution of language variants; (b) aspects of early political history and their possible linguistic sequels; and, mainly, (c) the specific socio-economic and demographic characteristics of the area which could have favoured the spread of linguistic features by promoting the concentration of people in urban settlements as well as the mobility of speakers and, in general, the loosening of some close-knit networks of interpersonal relations and the establishment of weaker ties between individuals.