Stephen Cross was born in October 1731, in Newbury, Massachusetts, the son of Ralph Cross and Sarah Johnson. The elder Cross worked as a shipbuilder, and Stephen and his brother joined him in the family business. In March 1756 Cross was recruited, along with 18 others from his town, to build vessels at Fort Oswego, New York, for a planned attack on the French-held Fort Niagara. British soldiers accompanied the shipbuilders as they traveled through the Mohawk Valley, reaching Fort Oswego on May 14, 1756. Cross and his fellow carpenters were present at Oswego when the French fleet attacked and destroyed the fort in August 1756, although it is unclear whether they actively participated in its defense. The French captured the men in the garrison, including Cross and several other shipbuilders.
On August 19, 1756, the French Army sent the prisoners to Quebec; the captives camped at Montreal before reaching Quebec City, where they were confined to stone barracks. After a month of imprisonment, all the Newbury shipbuilders were sent to France in October 1756. The journey was difficult, with 144 men crowded into a small vessel. Cross and his fellow prisoners landed in Brest and were marched to Dijon, France. While imprisoned there, Cross became ill; the journal ends with his admission to the hospital in January 1757.
Cross eventually recovered and returned to Massachusetts. He and his brother Ralph became successful shipbuilders in Newburyport, and built several frigates used during the Revolutionary War. In 1759, he married Hannah Beck and they had eight children. Cross died in 1809.