During the civil war, Monmouth was justly considered as a position of vast importance. After the defeat of the King’s army at Marston Moor, Prince Rupert directed his attention to the marches of Wales. He resolved to fortify Beachley, and with troops of horse to secure the isthmus between the rivers Severn and Wye; but in this attempt he was out-manœuvred by Colonel Massey. Lieut.-Colonel Kyrle afterwards negotiated with Massey to deliver up the town of Monmouth, then held for the King. Having revolted from the Parliamentary army on the loss of Bristol, he was willing to purchase reconciliation at the price of Monmouth. He proposed to Colonel Massey to feign a sudden return with his forces from Beachley to Gloucester, when he agreed to make a sortie from Monmouth, as if to fall on his rear, which might then drive him back, and in the pursuit enter the town with him. Massey, accordingly, gave out the necessity of a retreat; and having marched three miles, lodged his troops in the Forest of Dean. This was no sooner reported at Monmouth, than Kyrle drew out his men to follow in the rear of Massey. Accordingly, about a mile from Colford, he was surprised by Massey, and all his horsemen were led towards Monmouth. But the town having been alarmed by an officer who had escaped, the garrison were on the alert; yet, as Kyrle himself advanced to the drawbridge with a hundred horse, and pretended to be returning with many prisoners, the officers and soldiers were thrown off their guard; and with the consent of the governor, Colonel Holtby, the drawbridge was lowered, and the town was entered. “The governor and most of the garrison escaped, some prisoners were made, and the rest were put to the sword.” The loss of Monmouth, so justly considered the key of South Wales, alarmed the garrison of Raglan Castle. The old <g>Marquess</g> called in the assistance of Prince Rupert’s cavalry, which obtained some advantages over the flying parties of Massey, but could not disturb his possession of Monmouth, in which he was strongly fortified.