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Paleo-Indians were the first inhabitants. Archeological artifacts indicate hunter-gatherers hunted the mammoth, mastodon, saber-toothed cat, and giant ground sloth. Later Native American inhabitants included the Comanche. In 1871, Ranald S. Mackenzie fought Quanah Parker and other Comanches at the Battle of Blanco Canyon. The campaign established the Mackenzie Trail used by the first settlers in Crosby County in the late 1870s.
The Texas Legislature formed Crosby County from Young and Bexar districts in 1876. Bavarian Heinrich Schmidtt (Henry “Hank” Clay Smith) and his wife Elizabeth Boyle and their six children became the first permanent settlers in the area in 1878; Hank was active in the county's organization.
Confederate veteran Paris Cox first visited the Caprock Escarpment of the Llano Estacado with a group of buffalo hunters in 1879. Estacado was named the county seat in 1886. By 1900, the beef industry was thriving, supporting 30,618 head.
The country and western song (Ghost) Riders in the Sky was inspired by a legend of a stampede that took place in Crosby County in 1889.
In 1908, the Bar-N-Bar Ranch began selling acreage to farmers.
Crosbyton became the new county seat in 1910. 45,400 acres in the county were planted in cotton, and 15,000 apple and peach trees were growing in the county in 1920. By 1929, farmers owned 83,000 chickens and sold 395,000 dozen eggs that year.
The first soil conservation district in the county was formed in 1941. In 1955, oil was discovered in the county.