The community was founded in 1882 and named for Eugene E. Dryden. He was the chief engineer of the Galveston, Harrisburg and San Antonio Railway, which established a section house at Dryden when building its tracks through Terrell County. Over the next several decades Dryden became a small center for ranching-based businesses. The headquarters for the Pecos Land and Cattle Company were established in Dryden in 1884. The company drilled a well that supplied the area with water.
By 1912 the Dryden Hotel had been established, along with a combined schoolhouse, community center, and church. Dryden had a population of nearly 100 by 1929.
Two units of U.S. Army troops were stationed in Dryden during the 1913–17 Mexican border unrest. During the Great Depression of the 1930s, the railway closed the Dryden depot and relocated its crews, and the area’s ranches were eventually broken up. The population had dwindled to approximately fifty by 1970. The population continued to decline, to thirteen by 1988, although a general store was still operating in 1995.[2][3]
The post office dated from 1888; however, the United States Postal Service no longer maintains a post office in Dryden.
Wayne Sutton, a local sheep farmer and director of Dryden Water Supply Company,[4] has been[when?] appointed mayor by the other residents.
Amtrak's Sunset Limited passes through the town on Union Pacific tracks, but makes no stop. A stop is located 20 miles to the west in the nearby town of Sanderson.