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- Prehistoric people lived in Gobbler Shelter, located on a small tributary canyon of Live Oak Creek. Earliest known Native American tribes are Tonkawa, Lipan Apache, and Comanche.
- 1590 Spanish explorer Gaspar Castaño de Sosa leads a mining expedition of 170 who pass through the western section of Crockett County to reach the Pecos River.
- 1684, May 22 - Juan Domínguez de Mendoza and his expedition cross the Pecos River and camp at San Pantaleón.
- 1849 John Coffee Hays expedition charting waterholes for transporting people and freight.
- 1852 U. S. Army Colonel Joseph K. Mansfield recommends establishing a new post on Live Oak Creek to protect travelers.
- 1855, August 20, Fort Lancaster is established in response to Mansfield's recommendation.
- 1866 The Texas legislature provides three battalions of Texas Rangers to protect settlers in the area.
- 1868 Camp Melvin established.
- 1875, January 12 - Crockett County, named for Davy Crockett, is formed from Bexar County.
- 1880s Sheep and cattle ranchers establish themselves in the county. Kirkpatrick Hotel built to serve stagecoach passengers and cowboys.
- 1885 W. P. Hoover becomes one of the first settlers, on the Pecos River. Crockett County becomes a subsidiary of Val Verde County.[5]
- 1887 Crockett County is further reduced as Sutton and Schleicher counties are formed from it.
- 1889 Emerald becomes first town in Crockett County.
- 1891 Crockett County is organized. Ozona becomes the county seat. The first water well is drilled at the First Baptist Church in Ozona.
- 1900 Stagecoach service begins in Crockett County. County reports seven manufacturing firms.
- 1902 Crockett County Courthouse built, Empire style, architect Oscar Ruffini. The building does multiple duty for courtroom and county offices, as well as a community center and dance hall.
- 1925 First producing oil well within the World oil field, on L. P. Powell's ranch in north central Crockett County, by Chester R. Bunker's World Oil Company.
- 1938 Ozona erects a statue of Davy Crockett in the town square.
- 1939 Ozona opens the Crockett County Museum. In 1958, it was moved to its current location on the town square.