The Goodnight-Loving Trail ran from Young County, Texas, southwest to Horsehead Crossing on the Pecos River, up the Pecos to Fort Sumner, New Mexico, and on north to Colorado. In the spring and early summer of 1866 Charles Goodnight and Oliver Loving drove their first herd of longhorn cattle over the Butterfield Overland Mail route from near Fort Belknap via the Middle Concho River and Castle Gap, to Horsehead (on some old maps marked Dead Horse) Crossing. Leaving the former mail route there, they worked up the Pecos, crossing it from time to time as the terrain and watering places required. They drove a second herd, bought from John S. Chisum, from his Concho River range to Fort Sumner later that same summer.
The northern extension of the Goodnight-Loving Trail was first blazed by Loving in the fall of 1866. Initially, it ran north from Fort Sumner up the Pecos to Las Vegas, then followed the Santa Fe Trail to Raton Pass and around the base of the Rockies via Trinidad and Pueblo to Denver, Colorado. Since that was a roundabout way, Goodnight in the fall of 1867 altered the route fifty or sixty miles to the east, crossing the Gallinas valley and the well-watered plains of northeastern New Mexico near Capulin Mountain before swinging back northwestward to Raton Pass. At Raton Pass "Uncle Dick" Wootton had established a toll station near the summit and charged Goodnight ten cents a head for passage. Goodnight complied, but not without protest. At the head of Apishapa Canyon, forty miles northeast of Trinidad, he set up a ranch and cattle-relay station.
In the spring of 1868 Goodnight entered into a contract with John Wesley Iliff in which he agreed to deliver his cattle to Iliff at the Union Pacific Railroad town of Cheyenne, Wyoming. From the Arkansas valley near Pueblo, Goodnight and his men struck out due north, passing east of Denver, to the South Platte River. They crossed that stream at the site of present Greeley and followed a tributary, Crow Creek, to Cheyenne, where the delivery was made. Afterward, Goodnight and his men went back to New Mexico to buy more cattle from Chisum at Bosque Grande. Returning north, Goodnight further "straightened out" the trail by leaving the Pecos north of Fort Sumner and traveling north to Alamogordo Creek and across the plains via Cuervo Creek and its tributaries to a spot on the Canadian River twenty miles west of Fort Bascom. From there he proceeded to the Cimarron Seco west of Capulin Mountain. In order to avoid Dick Wootton's toll road, Goodnight opened a new, easier passageway through Tinchera Pass into Colorado.
The Goodnight-Loving Trail was thus routed, and although Goodnight himself made only one more delivery at Cheyenne, many cattle concerns from Texas, New Mexico, and Colorado used all or portions of the trail extensively until the advent of railroads in the Southwest in the early 1880s. The trail was sometimes known simply as the Goodnight Trail.