The 64th Regiment came to America in 1769, landing first in Boston but then spending a few years in Halifax before returning to Boston in 1772. Hutchinson joined the regiment in America as a recruit in 1777, and although he was “a good Soldier & was very clean,” he seems to have had other ambitions than remaining a career soldier.
As the 64th was preparing to sail south in late 1779 under General Sir Henry Clinton to besiege Charleston, South Carolina, Richard Hutchinson deserted. It was not unusual for men to desert shortly before their regiments were preparing to remove to a new location; apparently it was seen as an opportune way to avoid recapture. Staying in New York, however, was not a safe option because the 64th, like most regiments on campaign, left a small contingent behind to mind regimental goods left in storage; usually a few sick men remained behind as well. Hutchinson signed on to the British privateer General Pattison and went to sea, either due to a genuine inclination towards seafaring, aspirations of wealth from prize money, or simply as a way to escape from the garrison city.
Several months later the General Pattison returned to the New York area from a cruise. While the ship was still outside New York harbor the officer of a British guard ship came on board and took Hutchinson in order to press him into service on the guard ship. Apparently unwilling to do this duty, Hutchinson admitted to being a deserter which resulted in his being sent to the main guard in New York. He remained in confinement until the commandant ordered him released to his regiment for reasons that are not recorded.
The 64th was still far away in the south, but Hutchinson joined the contingent caring for the regiment's storehouse at a place called Coenties Market in what is now Lower Manhattan; today there is a historic walkway in the area called Coenties Slip. Hutchinson did not remain long. About three weeks after joining the detachment he deserted again. This time the regiment advertised for him:
Deserted from the 64th Regimental Store at Coenties Market; Richard Hutchinson, private Soldier in the 64th regiment, born in Ireland, about 5 feet 7 inches high, short curly hair, much freckled in the face; had when he went off, a crimson coloured jacket, a pair of new duck trowsers, (was lately on board the General Pattison privateer.) Whoever will give information of the said Hutchinson, to Serjeant M’Donald at the said store, so that he may be apprehended, shall receive One Guinea Reward. All Masters of ships are hereby warned not to harbour the above-mentioned Hutchinson, at their peril. M. Wood, Ensign 64th Regt.
In addition to the non-regimental clothing described in the advertisement, Hutchinson took his necessaries (that is, his shirts, stockings and shoes) with him, a sure sign that he had absconded intentionally rather than just wandering off.
It was not long before Hutchinson was discovered. He had managed to go to sea again, but was soon brought back to New York by another privateer, the General Rodney. It is not clear whether the General Rodney was a privateer in the British service or was a captured American privateer. Regardless, Hutchinson, now wounded, was put on board the infamous Jersey prison ship in New York harbor. Here he once again declared himself a deserter. Serjeant John McDonald and private John Williams of the 64th went to the Jersey to collect him and put him into confinement once again.
At his general court martial in September 1780, Hutchinson offered no testimony except to beg for the mercy of the court. It is unfortunate that he did not relate the details of his activities at sea. The two soldiers of the 64th who brought him off the Jersey provided the testimony upon which the above narrative is based. Surprisingly, the court did in fact show mercy to this repeat deserter. Rather than sentencing him to death, he was ordered to receive 700 lashes (somewhat lighter than the usual sentence of 1000 lashes for desertion, and that more typical for ‘accidental’ desertion rather than deliberate moves like Hutchinson’s) and then to be drummed out of the service, a particularly rare sentence. Gaps in the 64th Regiment's muster rolls leave us with no specifics about when or how Hutchinson left the regiment; he was listed as 'sick in New York in the second half of 1781, but is not on the next available roll covering the beginning of 1783.