He served in the Boston garrison until the city was evacuated in March 1776, then on through the lightening campaign that secured New York City and New Jersey at the end of that year. The new year, however, brought a change in fortune for Workman and his regiment.
The 17th Regiment was at the center of the battle of Princeton on 3 January 1777. The regiment fought valiantly in that clash and suffered greatly. Serjeant Workman was one of over 50 men taken prisoner, a better fate than the 20 or so who were killed. We haven't determined whether he was sent to Connecticut or into Pennsylvania for captivity, but he had the good fortune to be exchanged within about a year. By early 1778 he was again with his regiment in Philadelphia.
Serjeant Workman made it through the famous battle of Monmouth as the British army worked its way back to New York. The summer of 1779 found the regiment posted up the North River (as the Hudson River was then called) at an outpost called Stony Point. This fortification was still a work in progress when it was assaulted on the night of 16-17 July by an American force under General Anthony Wayne. The attack was a complete surprise and Wayne's soldiers, relying only on their bayonets, swept through the British works. They took almost the entire garrison prisoner, including John Workman, who for the second time was marched off into captivity.
This time Workman took advantage of his pre-military skills and went to work at the Continental Shoe Factory, a facility in Philadelphia that was part of the nascent infrastructure of the American army. This contribution by British prisoners to the American war effort is little known and deserves more study. It was certainly a way for prisoners not only to occupy their time but also to provide for themselves and for their families, for many wives and children accompanied their soldier-husbands even into captivity. An October 1779 return lists 214 British, Loyalist and German prisoners of war being "At Work" in Philadelphia including 22 from the 17th Regiment.
John Workman, an experienced soldier, may have had a different motive. In late November he absconded from the shoe factory; he may have gone to work there in the first place as a way to effect his escape. He was advertised in a local newspaper:
Forty Dollars Reward.
N. B. It is supposed he inclines to go to sea; therefore all masters of vessels and others are desired not to harbour or carry him off at their peril.
He did not go to sea. Along with other escaped prisoners, he made his way through the countryside with the assistance of quietly loyal residents who had created a network to help British soldiers make their way into New York. They provided food, civilian clothing, directions and sometimes even served as guides from one safe haven to the next. This is another aspect of the war about which there is little literature. Roger Lamb wrote at length of his escape experience and the help he received along the way. That Workman also received assistance is known because one of the Loyalists petitioned the government for aid at the end of the war; Serjeant Workman is among the men mentioned on the claim, and was one signer of an affidavit stating that they had been "furnished... with Provisions and Necessarys provided guides for us and did every thing in his power to facilitate our Escape at a Verry Considerable Expence and Risque."
Workman made it back to New York, but he did not join his regiment. Although the Stony Point prisoners had been exchanged early in 1781, the regiment then sailed to join the British army in the south. It is not known whether Workman literally missed the boat, or if was left behind in New York to recover from his arduous experience. Due either to his illness or his absence his rank had been reduced to private soldier, a common practice to allow a fit and present man to take the serjeant's post; this sort of shuffling was necessary because each regiment had an established number of non-commissioned officers.
Because he stayed in New York, John Workman was spared from becoming a prisoner for a third time. He remained in New York through the end of the war, once again joining his comrades when they were repatriated at the close of hostilities. As the regiment was being reorganized at the end of the war, discharging men who were no longer fit for service or who had completed their wartime enlistment contract and entertaining new men who enlisted after being discharged from other corps, John Workman was appointed drummer. This seems like an unusual post for a man now 44 years old (his age was misstated in the newspaper advertisement), it was a fairly common path for former non-commissioned officers who'd been reduced to the ranks. Apparently it was a way to get these men into a position of higher pay and responsibility; we don't know if he ever actually played the drum.
John Workman was discharged from the 17th Regiment as a serjeant in 1791 at the age of 52. Like many dedicated and long-serving soldiers, he received a pension so that he did not need to return to his former profession of making shoes.