Born in Hopkins County, Kentucky, on December 4, 1812, Loving, the son of Joseph and Susannah Mary Bourland Loving, grew up to be a farmer in Muhlenburg County, Kentucky. He married Susan Doggett Morgan in 1833, and ten years later, he and his brother and sister, along with their families, moved to the Republic of Texas. There, he acquired over 600 acres of land in Collin, Dallas, and Parker Counties, where once again, he farmed and worked as a freight hauler.
In 1855, Loving moved his wife and seven children to Palo Pinto County, Texas, where they first ran a country store near Keechi Creek, and Loving started his ranching career. By 1857, he owned some 1,000 acres of land and a large cattle herd. He soon began to drive his cattle northward, often through dangerous territory, making good profits from the demand for beef. Successful in these early cattle drives, he soon earned the nickname of “The Dean of Texas Trail Drivers.”
During the Civil War, Loving was initially commissioned to provide beef to the Confederate forces, a profitable move. However, when the war was over, the Confederate Government reportedly owed him more than $100,000, and their money was worthless.
Sometime later, he met Charles Goodnight, a former Texas Ranger and Indian Scout. With Loving’s knowledge of cattle and Goodnight’s background as a Texas Ranger and an Indian Fighter, the two hatched a plan to run cattle from Fort Belknap, Texas, to Fort Sumner, New Mexico, northward into Colorado and Wyoming. Through dangerous Indian country, this new trail would become known as the Goodnight-Loving Trail.
In June 1866, they set out with some 2,000 head of cattle and 18 armed men to blaze the Goodnight-Loving Trail from Texas to Colorado. This went on to be a well-traveled route to both Colorado and Wyoming.
Upon reaching Fort Sumner, they sold beef to the army for $12,000 in gold. Loving continued to drive the rest of the herd to Denver, while Goodnight returned to Texas for a second herd. The profitable venture led to more drives, including a partnership with John Chisum.
However, in the summer of 1867, when Oliver Loving went ahead of the herd to negotiate contracts, taking only one trusted scout with him, he was attacked by Comanche and seriously wounded. Though he was able to reach Fort Sumner, New Mexico, he later died of his wounds on September 25, 1867. Goodnight continued the drive to Colorado but later returned for Loving’s body and returned it to Texas, where he was buried in the Greenwood Cemetery in Weatherford.