Next, Swilling was briefly part owner of a flour mill in Tucson, apparently in partnership with his neighbor Charles T. Hayden. Quickly tiring of Tucson, he returned to Yavapai County where he prospected, owned gold mines and gold milling operations, and farmed. In addition he also was the mail contractor between Prescott and the Pima villages below the Salt River Valley on the Gila River. In the midst of all this activity, Jack Swilling married a young Mexican woman of Spanish heritage named Trinidad Mejia Escalante (1847-1925). They were married on April 11, 1864, at Tucson's San Agustin Cathedral when Trinidad was about seventeen. Over the next fourteen years they had seven biological children, five girls and two boys, and adopted two Apache orphans, a boy and a girl.