Since for much of its history humankind's natural habitat was the road, it is possible that the reverence for the road is born of a kind of nostalgia, bearing with it a sense of the sacredness of paths to known places of rest and safety. In such a mobile ancient world, those who knew the roads, and crucially the crossroads, would be unusually culturally empowered. As Cresswell says, culture is more ‘about routes than roots’. The status of crossroads in the popular imagination is therefore intrinsically bound with culturally specific ideas of the road, its possibilities and dangers. The roads which intersect are themselves often invested with meaning that their crossing serves to amplify and therefore the reason crossroads are enchanted begins with the reason any road might be enchanted. In looking at this delimited geography we must therefore refer ‘not only to the site as a hermetically sealed space but also to those roads which lead in and out of that space’, as Sanders recommends. This chapter explores roads as sacred or cursed, and their liminality in relation to boundaries and borders.

The early modern was a time of new social and geographical mobility whose emerging cartographic instincts culminate perhaps in John Ogilby's Britannia (1675). The title page of this significant work shows a surveyor directing two men as they measure a crossroads. Since this is a direct route map, all crossroads are displayed as open options with place-named directions attached. Ogilby's project functions to demystify the road networks of the country for the practical purposes of his own day. Roads in themselves, however, are often very ancient, often following the most natural routes, with each succeeding culture overlaying its own surfaces on the ones of those before them. Given their nature also as natural land borders, roads are also often literally liminal to the areas they traverse or separate.

In her detailed study of Lincolnshire, Dorothy M. Owen gives a sense of how parish boundaries often followed such ancient byways as she maps thirty-five parishes divided by the line of the prehistoric High Dyke, which forms a section of the ancient Roman road known as Ermine Street running from Woolsthorpe-by-Colsterworth towards Bracebridge Heath.