The Stephen Cross journal consists of 60 pages of entries, spanning March 1, 1756-January 22, 1757. The journal begins with Cross' agreement to travel to Fort Oswego with eighteen others from his town, in order to "build some vessels for the King's service" (March 1, 1756). In mid-March and April, he provided a detailed account of his travel from Newbury, Massachusetts, to Oswego, New York, via Boston, Providence, Newport, Block Island, New York City, and Albany. During this period, Cross frequently described the difficulty of navigating the terrain of upstate New York, his encounters with Native Americans, and the details of his work, which included cutting and hauling timber to construct ships and to rebuild Fort Bull after its destruction by the French (April 27, 1756). On May 12, 1756, Cross mentioned an incident in which friendly Native Americans saluted his party with their muskets, resulting in confusion and a supposition that their greeting was "an ambush laid for us." Luckily, the misunderstanding was quickly discovered.
Cross and his party arrived at Fort Oswego on May 14, 1756, and he subsequently recounted the process of preparing for a siege. On May 23, 1756, he reported a bizarre incident in which a soldier survived a scalping while in a drunken stupor. He also described several desertions (May 30, 1756), the frequent discovery of enemy spies, and occasional skirmishes. On August 14, 1756, he gave a detailed description of the Battle of Fort Oswego and its aftermath, including his capture and the drunken antics of his fellow prisoners.
After his capture, Cross described his experiences as a prisoner of war, including imprisonment in Quebec City, crossing the Atlantic en route to France (August 22, 1756: “[W]e are confined to our dark and wretched hole below both decks, only allowed to come on deck twice a day”), several near shipwrecks, and various plots to escape. On November 20, 1756, he gave an account of the escape of several prisoners from Brest and their eventual return to prison because of starvation. He also noted his dislike of General Shirley's regiment (the 50th Regiment of Foot), consisting of fellow captives on their way to France and, Cross supposed, "convicts" (November 15, 1756). The last entries concern imprisonment in a castle and the kindness of a wealthy widow to the prisoners (December 27, 1756). In January, he expressed his fear of going to the hospital, where an increasing number of men were dying. The journal ends with Cross' admission to the hospital on January 22, 1757.