The Siege of Chester and Battle of Rowton Heath

Although the King's army was scarcely adequate for the task, he marched from Oxford on 30 August to relieve Hereford, which was besieged by Lord Leven's Covenanters. As the Royalists approached Hereford early in September 1645, the Covenanters withdrew and marched away to the north. It appeared that Leven was unwilling to fight but coincidentally, as the King approached, Leven received news of Montrose's victory over the Marquis of Argyle at Kilsyth and hurried north to the aid of the Covenanters in Scotland. The King's army occupied Hereford on 4 September and further attempts were made to raise recruits in south Wales. King Charles himself returned to Raglan Castle where, around the middle of September, he received news of Prince Rupert's surrender of Bristol to the New Model Army. Lord Digby convinced Charles that Rupert had betrayed him; the King angrily dismissed Rupert from his service.

Gathering what forces he could, King Charles set out on a march to the north in the desperate hope of joining forces with the Marquis of Montrose in Scotland. He was unaware of the decisive Covenanter victory over Montrose at Philiphaugh on 13 September. Meanwhile, the Committee for Both Kingdoms ordered Colonel-General Sydenham Poyntz of the Northern Association to cover the King's army and prevent it from breaking out into the midlands. Poyntz advanced towards the Welsh border with 3,000 cavalry and dragoons. The King hurried north through the Welsh hills, evading Poyntz until he arrived at Chirk Castle on 22 September. Here he learned that the stronghold of Chester was in imminent danger of falling to the Cheshire Parliamentarians. With the loss of Bristol, Chester was the last landing place held by the Royalists for the troops from Ireland which Charles still believed would save his cause. Sending messengers urging the defenders to stand firm, the King diverted his forces to relieve the beleaguered city.