After the Civil War, cattle were nearly worthless in Texas due to an overabundance, but were in high demand in the North and the East. Determined to find a way to sell these cattle, many cattlemen sought ways of supplying the demand for beef and recovering from the depression that the war had left behind in the Lone Star State. One enterprising man by the name of Joseph G. McCoy, a cattle buyer from Illinois, persuaded the Kansas Pacific Railroad officials to lay track to Abilene, Kansas in 1867. He then began building pens and loading facilities and sent word to Texas cowmen that a “new” cattle market was available. That year, some 35,000 head of cattle were moved northward along the Chisholm Trail to Abilene and McCoy’s stockyard became the largest west of Kansas City. The number doubled each year until 1871, when 600,000 head glutted the market. Over the years an estimated five million head of Texas cattle reached Kansas over the Chisholm Trail.

The first herd to follow Jesse Chisholm's wagon trail to Abilene was O. W. Wheeler and his partners, who in 1867 bought 2,400 steers in San Antonio. At the North Canadian River in Indian Territory they saw wagon tracks and followed them. Others continued on the path that was referred to simply as the “Trail.” Later it was also called the Kansas Trail, the Abilene Trail, or McCoy's Trail. Though Chisholm's path was actually only north of the Red River, the Texas cowboy soon gave Jesse’s name to the entire trail from the Rio Grande to central Kansas.

The long trips up the trail from Texas were hazardous for both the cattle and the cowboys. The trip took anywhere from two to three months as the drives crossed major rivers including the Arkansas and Red Rivers, as well as traveling through canyons and low mountain ranges. In addition, the drovers also had to be concerned about Indian attacks, outlaw cattle rustlers, and cattle stampedes.

As the railroad expanded in Kansas, the trail changed a number of times and by the early 1870’s, the cattle business in Abilene had diminished. In its place, new cattle markets at Ellsworth and Newton were established. The Chisholm Trail moved south to Newton in 1871 and the city became one of the most notorious and violent cattle towns that ever existed. Just a year later, Wichita acquired the railroad and, along with it, the cattle business, which it retained until 1876. By 1880, the cattle only had to be driven to Caldwell, which competed with another popular cow town – Dodge City.