Ploughfield is located in the Wye valley about half a mile south of the manorial village of Preston-on-Wye, mentioned in Domesday (just as Preston). The parish church within that village later served Ploughfield residents; the church nave dates to about 1190, although the village name points to an earlier presence of one or more priests, and so possibly an older ecclesiastical structure. The manor-house was south-east of the church, its role perhaps remembered when rebuilt in the early sixteenth century as a farm known as Preston Court; the fourteenth-century churchyard cross still survives on the Preston Court property. Settlement in Preston parish was scattered over a wide area, though the village itself likely lay around the church and manor-house – remains of house platforms having been observed in that vicinity – where a brook powered a mill and there were also several fish-ponds. The village lay near a road through the valley connecting Hereford and Hay-on-Wye and was of course connected to Hereford by the Wye itself, the means for transporting the stone for building the church.

The manor of Preston-on-Wye was one of several that formed the principal endowment of Hereford cathedral, prior to the Conquest, and was then known initially as Canons Preston, though the name Preston-on-Wye is encountered by 1221. It was the dean of the cathedral chapter who obtained licence in 1253 for a Friday market and an August fair. Before 1262 bishop and chapter reached an agreement with the citizens of Hereford that the market would stick to a Friday or, if changed, be held on a Wednesday. It would seem probable that this market, required by the licence only that it be held somewhere on the manor, was destined for Ploughfield, a town founded on less-used land, rather than the main fields closer to the village. These events fell within the tenure of Bishop Peter of Aigueblanche (1240-68), whose royal service as bureaucrat and diplomat won him a number of gifts from the king, including market and fair grants (e.g. Ross-on-Wye 1241, Ledbury 1249); however, he was often absent overseas, as in 1253, so it is uncertain whether he can be credited as founder of Ploughfield. In 1273 we find in the cathedral accounts 41s. 6d. in rents received from the burgus de Ploufeld, and fairs are also mentioned. That the parish church was rebuilt in the late thirteenth century, widened and extended, suggests growth in the size of the congregation, such as through settlement in a new town.

The new town was established on a north-south road that connected, near the church, to the east-west through-road. Groupings of tenement plots are along that road, although no planned layout or burgage-type plots can now be distinguished, as property boundaries have been much disturbed by later reoccupation. Location of the medieval market is unknown, though there were a couple of points, within the area of plots believed to represent the borough, where junctions of other roads or tracks with the north-south road formed wider, triangular spaces that might have been suitable for a marketplace.

We know little of the borough of Ploughfield after 1273, although the surviving manorial records have received little attention from historians, and no archaeology has been conducted there. The impression given, however, is that by the close of the Middle Ages it had ceased to function as a market town; it may have gradually lost to Weobley and Hereford any market share originally captured, and been unable to recover from the crises of the fourteenth century. The decline is illustrated in the presentments of Preston brewers infringing the assize, recorded in the manorial court rolls [reported by Judith Bennett, Ale, Beer, and Brewsters in England Oxford University Press, 1999, app.]: in the fourteenth century such presentments were being made on a monthly basis, but by the fifteenth century they took place only every few months, and the number of brewers presented dropped from about a dozen to three over that same period. Today Ploughfield is a neighbourhood within Preston-on-Wye – in fact the village centre, perhaps still reflecting a shift in the medieval focus at Preston.