Weobley is situated several miles northwest of Hereford and a slightly greater distance southwest of Leominster. A brook runs, south to north, through its western half and skirts the west side of the church and the castle; at the latter point a water-powered mill was built. Roger de Lacy held the manor at the time of Domesday. The earthworks castle there, administrative base for the Marcher lordship of the Lacy family, could pre-date considerably its first mentions when it changed hands a couple of times (1138-40) in the context of the civil war. It could have been the work of Roger de Lacy, who is credited with erecting several castles in the region, notably at Ludlow, Ewyas Lacy, and Lyonshall, although it may also be slightly later. Roger having forfeited for rebellion, some of the Lacy estates later found their way into the hands of Pain Fitz-John, one of the relatively low-ranking 'new men' who had given loyal and able service to Henry I, before and after he became king, in military, administrative and judicial roles; Fitz-John's position as the Lacy successor was better secured when he was rewarded with marriage to a female of Lacy descent. Although it took some decades before the male heir of the Lacy family was able to regain his inheritance, it seems unlikely that the very busy Fitz-John was much engaged with Weobley prior to his death in 1137.

A church is heard of at Weobley in 1101 and the present church incorporates a Norman doorway and possibly some other twelfth century fabric, although is mostly a thirteenth and early fourteenth century rebuild. That a priest was mentioned in the Domesday entry points to the probability of a church having existed there in the Late Saxon period. The castle was rebuilt in stone by Walter II de Lacy soon after he, in 1213, regained possession from the king; the latter had confiscated it for its role in the rebellion of William de Braose, Walter's father-in-law, when it was used as a base for an attack on Leominster ca.1209. There is reference in the thirteenth century to the town having a defensive enclosure; although most of the line of this is unknown, such remains as have been identified suggest it was no more than a ditch and bank, perhaps topped by a wooden palisade, and may have encompassed mainly the western half of the town, including the church, the street connecting church and castle, and the brook.

No market licence is known, so it is possible a market town was established at some point in the twelfth century; we learn from an inquisition post mortem on a post-medieval owner that it was held on Thursdays. The fair may have been equally ancient, for we hear of it only when Walter II obtained royal approval in 1231 to shift the date from Easter to May – this may suggest a need for action to improve profitability, or fine-tuning of burgeoning commercial activity. It is, alternatively, possible that town foundation may have been the initiative of Walter II, perhaps connected to his rebuilding of the castle (see also Longtown), but we would have to assume either a gap in the record of market grants or a predilection on Walter's part to ignore the trend favouring royal licences, which does not conform to his 1231 initiative. After Walter's death in 1241, his estates were divided among grand-daughters and Weobley came into the hands of the Verdun family and later that of the Devereux. Neither change in lordship occasioned pursuit of a market licence; nor need it have, if Weobley's market was of some antiquity, although proving this in the era of quo warranto enquiries could be difficult unless a local jury was prepared to declare that a market had existed since beyond the bounds of living memory.

Weobley was treated as a borough for purposes of the eyre of 1255 and for representation in parliament from 1295 to 1307. Property transfers there are documented from the late thirteenth century and shops in 1294. None of these things preclude a twelfth century foundation date for the town. Although the authors of the Extensive Urban Survey report adopt [p.2] a mid-thirteenth century date for the foundation, this is mainly on the basis of the 1255 evidence, which tells us little about the town's origins. That the 1231 grant of an altered fair date proceeded without question suggests the fair had existed from the pre-licensing period, and it is probable enough the market and the town itself did too.

Despite the castle being ruinous and worthless by the time Edward III came to the throne, Weobley's growing prosperity is indicated by the presence there, in late thirteenth century, of a small Jewish community, and by the presence of some specialized trades in thirteenth and fourteenth centuries. The area produced a particularly high quality wool, and this was an important commodity in local commerce. An inquisition post mortem in 1332 on one of the co-parceners, – none of whom had evidently adopted Weobley as a residence – among whom the Lacy estates were divided over the course of time, following the extinction of the male line of the family in 1241, was informed that tolls from Weobley's markets and fairs were worth roughly £20 annually. Weobley survived as a market town into the post-medieval period, its proximity to Hereford and Leominster being more of an advantage than disadvantage, while its location outside of the Marches made it at least a little less of a target when hostilities arose – to which the survival of a large number of medieval timber-framed buildings is testimony. Not until the nineteenth century did Weobley decline from a borough to a village.

Weobley Castle stands at the south end of the site, on slightly raised ground, the church near the northern end, about a quarter mile from the castle; this separation hints at their establishment at different times. There was an axial street between church and castle, later known as Broad Street, but it was not a through-road, for that to Hereford lay slightly further east. The south end of Broad Street, after passing a cross-lane, widened out and was evidently the marketplace. That cross-lane ran westwards to meet the bottom of Church Street (which headed north to the corner of the church), and just beyond that junction lay a rectangular space known now as Bell Square, which might conceivably have served as village marketplace prior to the town being laid out along Broad Street. Where the Broad Street marketplace gave way, at its southern end, to an open area in front of the castle, streets from east and west converged on the market. The former, which later became the High Street, connected to the road to Hereford, while the latter ended at its junction with Back Lane, which ran roughly parallel to Broad Street as far north as Bell Square and doubtless serviced the rear ends of the burgage plots. No sign of a service lane has survived for burgage plots on the east side of Broad Street.

The centre of the marketplace and part of the open area in front of the castle, closest to the marketplace, underwent infilling in the Late Middle Ages, some of the buildings there having at one time, or still, fourteenth-century fabric. The west side of Back Lane and south side of the High Street (along the road to Hereford) may represent expansion after the foundation of the original town. Church Street and other areas around the church have plots that are less burgage-like and this is likely to represent the site of the pre-urban village. Fairly regular blocks of narrow tenement plots, characteristic of a planned town, were laid out on either side of the wider stretch of Broad Street and probably represent the initial planned town; most of these plots still have on them late medieval houses whose quality suggests they belonged to fairly prosperous residents. That such houses are also found dispersed across the rest of Weobley, along with infilling of parts of the marketplace, are reflections of population growth over the centuries following town foundation.