It was on the stormy evening of 25th August 1642, that King Charles I unfurled his standard at Nottingham, and the great Civil War began. Already a week previously the people of Reading were busy setting up posts and chains to guard the roads leading into their town. Danger indeed was near. The King marched across England to Shrewsbury, and from Shrewsbury he bent his course upon London. On October 23rd, he fought the Battle of Edge Hill, which was neither a victory nor a defeat, and six days later he rode into Oxford in pomp. On November 3rd, he sent a stern order to the Mayor and Aldermen of Reading that they should make Caversham Bridge strong enough for the passage of his army by eight o'clock on the next morning. On November 4th, he crossed the bridge and led his troops into Reading. Three days earlier the officer who had held Reading with a small garrison for the Parliament had fled. The King halted at Reading a good part of the month of November, forcing all the tailors there to work hard in order to make, for his army, a thousand suits of clothes. He was checked in his further advance upon London and, on November 28th, he retreated to Oxford, which henceforth became the Royalist headquarters.
The King had decided that Reading would be a useful outpost to him. He felt that while he held Reading his enemies could not safely advance upon him from London. When, therefore, he marched away in November 1642, he left behind him a garrison of 2,000 foot and a regiment of horse, under Sir Arthur Aston as Governor.
It was now that the hardships of Reading began. Both sides, especially the King's, were short of money. One after another the military Governors of Reading set to work to wring money from the town. Aston twice demanded a loan of £2,000, besides a heavy contribution every week. In order to pay these sums, the Corporation had to borrow money on the security of their wool hall, their market tolls and other properties. They appealed desperately to the King, but they obtained little satisfaction from his vague promises of repayment.
Meanwhile, the town was converted into a fortress. The Free School became a magazine of arms. Soldiers were quartered in John Kendrick's house of industry in Minster Street, at the Friary, at the Royal stables in the old Hospital of St. John and in Thomas Harrison's barn on Whitley Hill. All passage to and from the town was strictly guarded. Nearly 3,000 soldiers were quartered upon 5,000 inhabitants. Quiet townsmen went in fear of their lives. Houses were broken into; some were burned down; the very magistrates were beaten in the streets. By day and by night there were frequent alarms that the Roundheads were about to assault the ramparts. The cloth trade was ruined, for no waggon or packhorse dared venture on the roads. The one thing that kept the clothiers busy was the forced task of making clothes for the garrison, for which payment was seldom, if ever, to be had.
On 13th April 1643, the Earl of Essex, at the head of a Parliamentary army left Windsor, bent upon wresting Reading from the Cavaliers as the first step to an attack on Oxford. With the Earl, a staunch old soldier whom the soldiers called "Old Robin," were 16,000 foot soldiers, 3,000 horse and a train of siege guns. With him also were Philip Skippon, a veteran who had fought in the Low Countries, and the famous John Hampden at the head of his Buckinghamshire greencoats. Essex drew near the town on its western side, seized Caversham Bridge, and thus made it difficult for Reading to be relieved by the King at Oxford. He then sent a stern message to Aston, the Governor, bidding him surrender. Aston retorted that either he would hold the town for the King or he would starve and die in it. Essex, therefore, resolved to lay siege to Reading. His headquarters was the old moated manor house of Sir John Blagrave at Southcote. During the night of April 15th, his soldiers threw up their batteries and, early on the following Sunday, April 16th, the guns of the Parliamentary army opened fire upon the town. This was the first siege that had as yet taken place in the Civil War. No such Sabbath had ever dawned in Reading.
Aston seems to have had about 3,000 men. In cannon, he was not so strong as Essex. He had plenty of food and he had well fortified the town. The "main bulwarks" were in the shape of a four-sided figure. From the Friary (Grey Friars Church), the line of ramparts ran to the north-east corner of the Abbey enclosure. Thence they turned southward and, following roughly the line of the modern Sidmouth Street, they crossed the London Road and turned westward about half-way up the ascent of the present Kendrick Road. Thence they passed westward over Katesgrove Hill and down the steep slope to the Kennet. The meadows between Katesgrove Hill and Castle Hill were flooded, so that none could cross them or break in that way. At the top of Castle Hill, the earthworks began again and, from there, they passed in a straight line to the Friary. In addition to this long line of encircling ramparts there were a number of separate forts. There was a fort on Caversham Hill, one on Whitley Hill and one on Castle Hill, and at points along the ramparts, especially where roads entered the town, there were smaller redoubts and forts. It is said that the earthworks were in some places strengthened by wooden palisades and by the woolpacks of the clothiers.
Day after day the guns of Essex thundered upon the town. He beat down the steeple of Caversham Church, upon which Aston had mounted a cannon. He raised the drawbridge at Caversham Bridge and, little by little, he pushed forward his men within musket-shot of the garrison on the west and south-west. On April 18th, a force of Royalists was descried on the Oxfordshire hills. The Royalist officer who led them saw that he could not enter the town by Caversham Bridge. He therefore pressed on to Sonning, and from Sonning he managed to send 600 musketeers and a supply of ammunition to Reading in boats. By the 19th, Reading was beset on all sides. On the same day, Sir Arthur Aston was wounded in the head by a splinter of brick thrown up by a cannon-ball. Colonel Richard Fielding took his place as commander. It is also said that the besiegers' cannon battered to pieces the steeple of St. Giles's Church.
On April 22nd, a messenger from Oxford slipped through the besiegers' lines, swam across the Thames and announced the joyful news that relief was at hand. But this plucky messenger was caught by the soldiers of Essex on his return; and therefore, the surprise attack on the Roundheads could not be made. The King now became much alarmed for the safety of his garrison at Reading. He summoned Prince Rupert from Lichfield; and on April 24th, Rupert, the gallant leader of cavalry, joined the King, already on his way to Reading to relieve the garrison.
But on the very day that the King drew near, and just before lie began his assault on the forces of Essex, Fielding hung out a white flag and agreed to surrender. Almost at the same moment, the Royalist musketeers, a thousand strong, burst upon the Parliamentary guard at Caversham Bridge. Charles and Rupert led the charge as they dashed upon the bridge. From the hill above, their guns supported their attack. At first they seemed likely to prevail, but as they crowded upon the narrow bridge they offered an easy target to the Parliamentary sharpshooters who lined the opposite bank of the river. Now was the time for Fielding to sally forth from Reading and join forces with the King. The King knew nothing of the flag of truce and he was bitterly disappointed that Fielding did not come. The Royalists failed to force their way across the bridge. A sudden storm of hail and rain, breaking the April skies, beat in their faces and completed their discomfiture. They withdrew up the hill, hotly pressed by the victorious Roundheads, leaving many dead and wounded behind them. The King himself went to Caversham House. Later in the day, he heard of the surrender. Reluctantly, he agreed to it. Next day, he crossed the hills to Nettlebed.
On April 26th, the articles of surrender were signed. Early on the 27th, the trumpets blew and the King's garrison at Reading mustered to march out with the honours of war. At ten o'clock, a long procession began to move towards the old Oxford Road, which then left the town at the Friary. First, in a litter borne by horses and covered with red hangings, came the wounded Governor, Sir Arthur Aston. Then came waggons with the sick and wounded. After them, came four ccannon, dragged by teams of horses. Lastly, marched the main body of the soldiers. With colours aloft and lighted match, with. drums beating and trumpets sounding, horse and foot passed through the ramparts and took the road by Caversham Bridge to Oxford.
Disgraceful scenes were now to take place. At Friars' Corner, the soldiers of Essex stood ranked ready to enter the captured town. From Jeers and insults towards their beaten foes, they proceeded to violence. Waggons were plundered, weapons were snatched away and riotous scenes followed the entrance of the victors to the town. Houses were sacked, taverns were broken open and, soon, drunkenness was added to the tumult. Not until after two days did discipline return. On Sunday, April 30th, the Puritan earnestness regained its sway. Morning, noon and night, the churches were crowded. But the Cavaliers never forgave the breach of faith shown by the soldiers of Essex.
Reading remained in the hands of the Parliamentarians until the end of September 1643. It changed hands more than once, but in the end it passed permanently into the keeping, of the victorious Parliament.