Siege of Chester The Siege of Chester was a siege of the First English Civil War , between February 1645 and January 1646 , with an intermission during the summer of 1645 . From the beginning of the war , the city of Chester was held by forces loyal to the King . It was first besieged in late 1644 , but was relieved in March 1645 by Prince Maurice . With fighting continuing around Cheshire , the siege was not pursued again in earnest until September 1645 , continuing ferociously until the following January . At the Battle of Rowton Heath in September , King Charles himself failed to lift the siege , suffering a disastrous defeat . Throughout the siege , which varied considerably in intensity , the garrison was commanded by Lord Byron , who in the final months strongly defended the city against great odds . In January 1646 ( 1645 , Old Style ) , faced by the starvation of the inhabitants , Byron was persuaded to surrender , and the city was occupied by forces of the New Model Army under Sir William Brereton } . Background . The city of Chester , in Cheshire , was an important stronghold in the English border country , commanding an important crossing of the River Dee and thus the approach to North Wales . With strong city walls , dating originally from Roman times , Chester was a Royalist stronghold from the beginning of the Civil War . Early in the war , between 1642 and 1643 , its walls were strengthened and a new ring of earthwork defences was added outside them . After Lord Byron was defeated at the Battle of Nantwich in January 1644 , he marched his remaining forces to Chester , making it his base for resistance to the Parliamentarian forces in Cheshire under Sir William Brereton . During the first half of 1645 , Brereton was able to gain control of most of Cheshire , but the king ' s men in Chester commanded the river crossing into North Wales , still held by the king , protecting it from a Parliamentary invasion . February to March 1645 . In February 1645 ( 1644 , old style ) Brereton mounted a determined assault on Chester , in the course of which a force of his men tried unsuccessfully to scale the walls near the Northgate . Defeated , he began to besiege the city . In March , Prince Maurice of the Palatinate arrived to relieve the city . However , having done so , when he moved on in April he took with him a large part of the garrison , including some 1 , 200 hardened Irish fighting men . Chester was left with only some six hundred regular soldiers , together with its own civilians who were able to bear arms . The summer of 1645 . On 14 June 1645 , King Charles ' s main army was decisively beaten at the Battle of Naseby by the New Model Army under Sir Thomas Fairfax . The king then withdrew to Hereford , hoping for more reinforcements from Wales and Ireland . Early in July 1645 , he lodged at Raglan Castle in Wales . On 10 July his army in the west of England under Lord Goring was heavily defeated at the Battle of Langport , and news also reached Charles that an army of Covenanters was marching south . At the beginning of August 1645 , Charles left Raglan with some 2 , 500 men , marching northwards along the Welsh border in the hope of rallying more royalists to his cause in the north of England . He reached Doncaster on 18 August , where he had news that both the Parliamentary Northern Association Army and a force of Covenanter cavalry were moving towards him . He quickly withdrew to Newark and then to Oxford , by way of a punitive attack on Huntingdon , Oliver Cromwell ' s home town and parliamentary base . On 30 August the king marched to the assistance of his forces at Hereford , by now under siege by Lord Leven ' s Covenanters , but as the royal army approached news reached Leven of Montrose ' s victory on 15 August at the Battle of Kilsyth . He abandoned the siege of Hereford , marching north , so that Charles was able to occupy the town on 4 September . The king returned to Raglan , where some two weeks later he received news that Prince Rupert had surrendered Bristol . After Lord Digby persuaded Charles that Rupert had surrendered prematurely , the King dismissed Rupert and the two were estranged . September 1645 to January 1646 . With his remaining forces , Charles marched north from Raglan , hoping to join Montrose , not knowing that on 13 September Montrose had suffered a catastrophic defeat at the Battle of Philiphaugh . The Committee of Both Kingdoms instructed Sydnam Poyntz to pursue and contain the king , and Poyntz advanced for that purpose with a mounted force of some three thousand cavalry and dragoons . The King moved northwards , without meeting Poyntz , and on 22 September he reached Chirk Castle where he received news of a new attack on Chester . With the surrender of Bristol , Chester had become the only seaport in England under King Charles ' s control where it would be possible to land the reinforcements he was awaiting from Ireland , which he hoped could save him from ultimate defeat . Early on 20 September 1645 , just before daylight , a New Model Army force of more than seven hundred infantry and an equal number of cavalry , led by Colonel Michael Jones , began a fresh assault on Chester . The attack broke through the outer Royalist earthworks around the eastern suburbs . After Jones had ordered the burning down of the urban areas in front of the Eastgate , he moved artillery up to St John the Baptist ' s Church to bombard the city wall . By 22 September , the king arrived at Chirk , but Jones ' s guns had already created a breach in the walls . The king made for Chester with all possible speed . Word that he was coming was passed on to the garrison commander , Lord Byron . The king reached Chester on 23 September with an advance party consisting of his Lifeguards , Lord Gerard ' s brigade of some six hundred horse , and a small number of foot soldiers . This force was able to enter the city from the western bank of the River Dee because it was still under Royalist control . Meanwhile , in the hope of trapping the besieging forces between the king ' s main army and an enlarged garrison within the city , Sir Marmaduke Langdale took more than three thousand of the king ' s cavalry northwards towards Chester , crossing the Dee over Farndon Bridge , Holt , at dawn on 24 September . Moving north - east , Langdale received reports near the village of Rowton that Poyntz ' s Roundhead cavalry was approaching Chester from Whitchurch , Shropshire . Poyntz , who had ridden through the night to meet the royal army , met Langdale at Rowton Moor . All morning , both forces held their ground , but at about 2 pm , Colonel Jones sent part of his siege forces to join those of Poyntz . King Charles is said to have watched the ensuing defeat of his forces at the Battle of Rowton Heath from the Phoenix Tower on Chester ' s city walls , when Parliamentary forces routed the remaining Royalist cavalry . The dead included the king ' s cousin Lord Bernard Stewart . On 25 September , leaving Byron in charge of the garrison , the king retreated from Chester to Denbigh in North Wales with only five hundred mounted men . As Byron refused to surrender , the Roundheads extended their siege works around the city and continued their bombardment . For more than four months , the Royalist garrison resisted all Parliamentarian attempts to enter the city and even mounted counter - attacks . But as autumn became winter , many inhabitants died of starvation . In January 1646 ( 1645 , old style ) , William Ince , as Mayor of Chester , persuaded Byron to surrender the city . On 3 February , the forces of Sir William Brereton occupied Chester .