Founded in 1882 as a section house for the Galveston, Harrisburg and San Antonio Railway, which was building its tracks through Terrell County. The community soon became a hub for local ranches and ranching businesses. The Dryden Hotel was built in 1912 and population numbers stayed relatively steady.
Two units of U.S. Army troops were stationed in Dryden from 1913-1917, to serve as extra protection for the American citizens from raiders during the Mexican Revolution.
Population remained steady until the railroad moved its crew and closed the depot during the Great Depression. Although the US Postal Service still maintains a post office for the community, recently the population has dwindled to fewer than 20 people.