The day he was commissioned he stood sponsor and his wife a witness to the baptism of Anna, daughter of Thomas, his brother, born on that morning. On July 21st following, Captain Barry's wife, Sarah Austin Barry, became a Catholic and was baptised, conditionally, Anna Barry, wife of Thomas, being the only sponsor. At this time Captain Barry was cruising in the West Indies. Judith, "the slave of Captain John Barry," an adult, was also baptised on August 19, 1779.
In the "Delaware" Captain Barry made two cruises to Port-au-Prince. Of his first voyage no record has been discovered, but of his second there is sufficient in the account given by his Mate, John Kessler. The "Delaware" sailed on its second cruise in the fall of 1779 in company with three other Letter-of-Marque brigs and one schooner. Of this fleet Captain Barry was made Commodore. He was always so appointed whenever two or more vessels were assigned to one cruise or expedition in which he engaged. When abreast of Cape Henlopen the British sloop-of-war the "Harlem," with eighty-five men and fourteen four-pounders, was taken without resistance, though the officers escaped in boats after heaving overboard all the guns.
The "Harlem" was sent to Philadelphia. The crew was delivered to the militia at Chincopague. Captain Barry reported to the owners that "the commanders in our little fleet are very complaisant and obliging to each other." That the "Harlem" had fourteen four-pounders and eighty-five men. The guns and other things were thrown overboard without firing a shot. The Captain, with ten men, went off in a whale-boat, "but," reported Captain Barry, "we have reason to think, is since overset." The prisoners were taken out, a prize crew put on board, the "Harlem" sent to Philadelphia and the men landed at Sinipaxan, Virginia, as they were too many to keep with safety on board the little fleet. "We have every reason in the world to think we shall catch more before long," reported Barry. The "Harlem" was "a fine vessel and had been a cruiser since the enemy took New York, but at present she is much out of tune," he added.
Of the rest of the voyage out and home nothing specially noteworthy occurred except that a merchant ship from Liverpool was captured and later retaken by the noted Goodrich and carried into Bermuda.
During the war there was often contention between the commanders of the Continental and those of the States' service. The Continentals, when in need of men, often impressed the seamen of the States' fleet and also those of merchant vessels. On Captain Barry's return to the Delaware River the Continental frigate "Confederacy" lay at Chester. She had been impressing the crews of merchant vessels coming up the river. The pilot gave this information to the crew of the "Delaware." It alarmed them very much and many desired to be put on shore. Captain Barry addressed them saying, "My lads, if you have the spirit of freemen you will not desire to go ashore nor tamely submit against your wills to be taken away, although all the force of all the frigate's boats' crew were to attempt to exercise such a species of tyranny." This address, records Kessler, satisfied them, as it implied his consent to their defending themselves. They resolved to do it at all hazards, and for that purpose put themselves under the command and direction of the boatswain and armed themselves with muskets, pistols and boarding pikes, and thus arrived within hailing distance of the "Confederacy." Her commander ordered the brig's maintopsail to be hove to the mast. Captain Barry answered that he could not without getting his vessel ashore. The commander of the frigate then ordered that the brig should come to anchor.
Captain Barry gave no answer but continued on his way, beating up with tide and flood and wind, when a gun was fired from the frigate and a boat, manned, left her and came towards the "Delaware." Captain Barry directed that the officers of the boat should be admitted on board, but as to the men with them, the "Delaware's" crew could do as they pleased. The boat soon arrived and two officers, armed, jumped on board and on the quarterdeck, ordering the maintopsail halyards to be cast off, which, however, was not done. Captain Barry asked whether they were sent to take command of his vessel. The boat's crew were about coming on board when the "Delaware's" men threatened instant death to all who came on board.
The officers after trying to intimidate our boatswain by presenting their pistols at him, and finding it of no avail, hastily sprang into their boats and left.
Another gun was fired from the "Confederacy." Captain Barry ordered the guns cleared and declared that if a rope-yard was injured he would give the "Confederacy" a whole broadside. A third gun was fired. Captain Barry hailed and asked the name of the commander of the frigate.
The answer was "Lieutenant Gregory."
Captain Barry addressed him: "Lieutenant Gregory, I advise you to desist from firing. This is the brig 'Delaware,' belonging to Philadelphia and my name is John Barry."