In 1833, he became a farmer in
Muhlenberg County, Kentucky. Ten years later, with his brother and his brother-in-law, he moved to the
Republic of Texas with their families. In Texas, Loving received 639.3 acres (2.59 km2) of land in three patents spread through three counties
Collin,
Dallas, and
Parker. He farmed and, to feed his growing family, hauled freight in his early years as a Texan. By 1855, he moved with his family to the future
Palo Pinto County, Texas, where he ran a country store and ranched on
Keechi Creek. By 1857, he owned a thousand acres (4 km2) of land. To market his large herd, Loving drove them out of Texas and in that same year he entrusted his nineteen-year-old son, Joseph, to drive his and his neighbors' cattle to
Illinois up the
Shawnee Trail. The drive made a profit of $36 head and encouraged Loving to repeat the trek successfully the next year with John Noble Durkee. On August 29, 1860, together with John Dawson, he started a herd of 1,500 toward
Denver, Colorado to feed miners in the area. They crossed the
Red River, traveled to the
Arkansas River, and followed it to
Pueblo, Colorado, where the cattle wintered. In the spring, Loving sold his cattle for gold and tried to leave for Texas. However, the
American Civil War had broken out and the Union authorities prevented him from returning to the South until
Kit Carson and others interceded for him. During the war, he was commissioned to provide beef to the
Confederate States Army and drive cattle along the
Mississippi River. When the war ended, the Confederate government reportedly owed him between $100,000 and $250,000. To make matters worse, the usual cattle markets were inadequate for the available supply. In 1866, having heard about the probable need for cattle at
Fort Sumner, New Mexico, where some eight thousand
Native American Indians had been settled on a reservation, he gathered a herd, combined it with that of
Charles Goodnight, and began a long drive to the fort. Their route later became known as the
Goodnight–Loving Trail. The two cattlemen sold beef to the army for $12,000 in gold, and then Loving drove the stock cattle on to Colorado and sold them near Denver, while Goodnight returned to
Weatherford, the seat of Parker County, Texas, with the gold and also for a second herd. The two men were reunited in southern New Mexico, where they went into partnership with
John Chisum at his ranch in the
Bosque Grande, about forty miles south of Fort Sumner. (Chisum's sister Nancy was married to Loving's cousin, B.F. Bourland and had known Chisum for many years.) They spent the winter of 1866-67 there and supplied cattle from the ranch to Fort Sumner and
Santa Fe. ==Personal life==