Notwithstanding this close watch and durance, Dudley and Major Elliotts contrived to break out of gaol, making their way over the tops of the houses, afterwards passing the guards at the city gates, and escaping into the open country. Being hotly pursued, they travelled during the night, and took to the trees during the daytime. They succeeded in reaching London, but only to drop again into the lion's mouth; for first Major Elliotts was captured, then Dudley, and both were taken before Sir John Warner, the Lord Mayor, who forthwith sent them before the "cursed committee of insurrection," as Dudley calls them. The prisoners were summarily sentenced to be shot to death, and were meanwhile closely imprisoned in the Gatehouse at Westminster, with other Royalists. The day before their intended execution, the prisoners formed a plan of escape. It was Sunday morning, the 20th August, 1648, when they seized their opportunity, "at ten of the cloeke in sermon time;" and, overpowering the gaolers, Dudley, with Sir Henry Bates, Major Elliotts, Captain South, Captain Paris, and six others, succeeded in getting away, and making again for the open country. Dudley had received a wound in the leg, and could only get along with great difficulty. He records that he proceeded on crutches, through Worcester, Tewkesbury, and Gloucester, to Bristol, having been "fed three weeks in private in an enemy's hay mow." Even the most lynx-eyed Parliamentarian must have failed to recognise the quondam royalist general of artillery in the helpless creature dragging himself along upon crutches; and he reached Bristol in safety. His military career now over, he found himself absolutely penniless. His estate of about 200L. per annum had been sequestrated and sold by the government;[11] his house in Worcester had been seized and his sickly wife turned out of doors; and his goods, stock, great shop, and ironworks, which he himself valued at 2000L., were destroyed. He had also lost the offices of Serjeant-at-arms, Lieutenant of Ordnance, and Surveyor of the Mews, which he had held under the king; in a word, he found himself reduced to a state of utter destitution.