The 12th and 13th centuries proved to be turbulent times for the city, and aside from numerous accidental fires (in 1113, 1189, 1202 and 1299), significant havoc was wrought by the various rebellious and loyalist armies of the time trying to secure and hold the strategic river-crossing at Worcester.In 1139, during the Civil war between King Stephen and Matilda (Henry I’s only legitimate heir), the castle held out against Matilda’s supporters, while King Stephen captured and burnt the city in 1150 - but failed to capture the castle!

In 1151 King Stephen attacked the castle again, building two temporary forts overlooking the road to Leominster and Bewdley (between Henwick Road and the river, which cuts sharply into the west bank in this location) and the London/Oxford Road, at Red Hill. This attempt failed, although the next year the castle fell into the hands of Stephen’s supposed ally, the Earl of Hereford, who in fact did a deal with William Beauchamp (Urse’s descendant and the castle’s constable) to acquire the castle without a fight. In 1155 Worcester castle was re-fortified by Hugh Mortimer, against Henry II, while in 1216 (during the reign of King John) Worcester declared for the French Dauphin, Louis, under William Marshall, son of the Earl of Pembroke. The city was taken by way of the castle, which was ‘not faithfully watched everywhere’, and King John gave control of the castle to John Marshall to guard against the French threat - although Henry III later threatened to pull down the city walls unless the citizens paid £100 fine for their insurrection. On his death in 1216, King John was buried in Worcester Cathedral, and it was probably on his father’s wishes that Henry III ordered the northern part of the castle bailey - which had been annexed by Urse d’Abitot in 1069 - to be given back to the Priory.

Following the partition of the outer bailey, and the move of the Beauchamp family residence to Elmley Castle, the castle’s strategic military significance waned, and by 1221 it had become the King’s prison. By 1263, during the Baron’s War, the castle had become a weak spot in the city’s defences, providing the rebel Earl of Derby with an easy entry to take the town - although both were retaken by Prince Edward in 1265. By 1459 the gaol had fallen into serious disrepair, with stone being taken from it to repair the city walls, and by 1540 it was observed that ‘the castle...is now clene downe...The dungeon hill of the castle is a greate thinge overgrowne at this time with brush wood’. While the castle mound was re-fortified during the Civil war, the site returned to being a gaol until 1814 when the prisoners were transferred to the new County Prison on Castle Street. The Dean and Chapter finally acquired the site in 1823, and the gaol was demolished in 1826. Between 1826-46 the motte was quarried for sand and gravel, bringing to light many Roman and prehistoric artefacts which give a glimpse of what important remains may have survived there buried by the Saxon and Norman earthworks - the site today lying within the grounds of the Kings School.

While documentary evidence for Worcester’s medieval city defences is patchy, it is clear that the town wall and ditch were complete by the first quarter of the 13th century (during King John’s reign) enclosing, with the castle, an area of c.33 hectares (83 acres). The wall was constructed of red sandstone (with some green) from the quarries at Holt and Ombersley, with a chamfered plinth at the base of the wall lining a steep sided ditch, on the eastern flank, and would have had a wooden fighting platform on the inside. While work on the wall probably started during the 12th century, the nature of the references suggest either that the circuit was not complete at this time, or that it kept being destroyed. The wall, whose features can be seen quite clearly on Speed’s map of 1610 (see Old Maps & Plans), ran from the Bar Gate at the bridge - with St Clement’s Gate to the north providing access to the east bank of the Severn and Pitchcroft Meadow - along the south side of The Butts (where it is still visible) to the Foregate (North Gate) on Foregate Street (demolished in 1702). From the Foregate the wall ran along the south side of Sansome Street, curving round to the east and then south along Queen Street, where the postern Trinity Gate provided alternative access form the city into Lowesmoor. From here the wall ran across the Cornmarket to St Martin’s Gate (demolished in 1787), and thereon southwards to the bridge across Frog Brook which became the Sidbury Gate (demolished by the early 19th century). At this point, the natural course of Frog Brook was altered to run into the outer ditch of the castle defences, which ran along the line of present Severn Street (Frog Lane as was), with the Frog Gate providing access to the marshy land adjacent to the Severn on the north side of the Diglis basin, and to a mill which is recorded in this location. The Cathedral had its own Water Gate, or Priory Gate, leading to the river, and radar survey has shown that a slip led up from this into the Close, providing a private mooring facility for the Bishop and Prior. In 1226 the Greyfriars living on Friar Street were given permission to build a postern gate in the wall, known as Friar’s Gate, to allow them to collect firewood, although this had disappeared by 1820 when Union Street was built.

While there are references to five towers on the medieval city wall in 16th century documents, only part of one still survives (the bastion at St. Martin's Gate), and the location of the others is unknown. Although a Leominster Tower is recorded as being somewhere between St Clement’s gate and the Foregate, and Speed’s map provides us with several possible locations for this, the destruction caused in this area during the Civil War has probably removed all surviving evidence for the feature. Within the city walls the street network of the Saxon burh, which itself had incorporated old Roman alignments, was consolidated into a pattern which has recently been deconstructed from the detailed surveys carried out by the Ordinance Survey in the 1890’s. As the city became more prosperous, and demand for land within its walls increased, the relatively large and open plots which had characterised the earlier medieval town were sub-divided, providing greater rental incomes to the landowners and beginning a process which led to the network of properties evident for the later medieval city. It was within these later, narrower, plots that the densely packed timber framed buildings most commonly associated with the medieval city (and other medieval city's generally) developed, and evidence is gradually accruing to suggest that many of these in the town centre (primarily either side of the High Street) replaced large stone, or stone founded, buildings which had been built at the back of the larger 12th/13th century plots - away from the hustle and bustle of the street frontages.