Situated on one slope of a valley of a stream leading to the River Rea, the manor of Cleobury was, from the time of Domesday, in the hands of the Mortimer family, kin to William Fitz-Osbern the Conqueror's first Earl of Hereford; Ralph de Mortimer had obtained it in 1075 after Fitz-Osbern's son had forfeited. The Wigmore barony branch of the family made Cleobury its principal Shropshire residence and administrative centre, building a castle there before 1154. The local church is of thirteenth century fabric, but its location immediately east of the castle suggests an earlier existence and we have a documentary reference to it in 1179; Domesday mentions no church but does refer to the presence of a priest at Cleobury.
It was a Hugh de Mortimer (not the same Hugh who was lord of Richard's Castle and Burford) who, having remained loyal to John during his baronial troubles and continuing as a strong supporter of Henry III during his minority, obtained from the royal government in 1226 grant of a three-day fair in September, though this was soon adjusted to August. No market licence is extant, which may mean a market had long been in existence on the manor. This Hugh, who married a daughter of William de Braose, lord of Bramber, had no known association with any market foundations, despite holding estates in several counties, though his parents, Roger de Mortimer and his wife Isabelle, daughter of the lord of Lechlade (Gloucs.), had obtained for that place a licensed market and fair in 1210, with Isabelle credited, after the death of her husband (1214), with founding at Lechlade a town comprising about 40 burgages, though this act may in fact have coincided with the market grant, three years prior to which Isabelle had obtained custody for life of the Rutland market town of Oakham.
It may, on the other hand, rather have been a grant to Roger de Mortimer (Hugh's nephew, son of Hugh's immediate successor Ralph) of enhanced jurisdictional privileges for the manor of Cleobury, in 1266 – part of Roger's post-Evesham reward for key support against the Montfortian party – that led to development as a borough. This grant consolidated a number of manors into a single large seigneurial unit and gave it, effectively, the status of a hundred, while granting it privileges comparable to those of a Marcher lordship, administered through Mortimer's court at Cleobury; among the jurisdictions it administered was the assize of bread and ale.
Roger had by 1247 married the eldest daughter and co-heir of a different William de Braose (lord of Abergavenny, d. 1230), whose family had long held one of the earliest Norman castles built in Wales, probably by William Fitz-Osbern, at New Radnor (then within Herefordshire); Roger thereby came into possession of the lordship of Radnor and it may have been he who shortly thereafter established a planned town by the castle, for which the inquisition post mortem on his son Edmund (1304) mentions 262 burgages, a market and a fair. The Braose inheritance of his uncle Hugh had already brought Roger another castle-town in the same region, at Knighton, for which his father Ralph had obtained a fair grant in 1230, and there we hear in 1304 of 162 burgages held at 12d. rent each. It must have been the same Roger who, around 1274, rebuilt a family castle at Cefnllys (Radnorshire), where his son Edmund founded a market town prior to 1297, when Edward I confirmed Edmund's charter referring to the determination of its market pleas. In addition to the market town of Wigmore (Herefords.) and the border-town of Presteigne, Edmund's extensive estates also included further castle-towns in Wales, and (through his marriage) a share of the Somerset planned town of Bridgwater, and a share of the market tolls of the planned town of Newbury (Berks.).
In 1274 we hear of men from Cleobury taking oxen to sell at Ludlow's fair. In Edmund de Mortimer's inquisition post mortem in 1304 there is reference to 103 burgages at Cleobury, and a deed of 1382 mentions two burgages in the 'new street' of Cleobury, which appears to be on the edge of town. Its taxation assessment in 1334 suggests a modest level of prosperity, as does the 'new street'. It certainly had borough status in the Tudor period, even though Leland could not perceive it as more than a village and was unaware of any market there; decline of Mortimer fortunes in the late fourteenth century may have adversely impacted Cleobury.
The church was on the north side of a through-road, with the castle immediately behind the churchyard; the through-road follows a roughly east-west direction, but curving to swing around the church/castle complex. The portion of the through-road in front of the church (now Church Street) widens into a High Street as it proceeds west, and this seems the likely location of the market. Tenement plots along the High Street, opposite the church, and further east along the through-road suggest a simple planned layout along an axial street with back lanes and, on the southern side, the stream. The 'new street' heard of in 1382 is thought to have been a planned extension of the original town at the eastern end of the axial street.
