Stringtown, in southern Hays County, was one of the earliest Anglo-American settlements in the county. The community got its name from the approximately four-mile-long string of houses that were built facing the old San Marcos to New Braunfels post road between Purgatory Creek, southwest of San Marcos, and York Creek on the Hays-Comal county line (now Farm Road 2439). This road lies at the foot of the Balcones Escarpment. The first traveler of record on this route had been Fray Isidro Félix de Espinosa in 1709 and again in 1716. Travel on this road accelerated after 1840 when Company H of the First Texas Infantry Regiment under Capt. Joseph Wiehl blazed a shortcut from Austin to San Marcos, causing travelers to prefer the new upper route to San Marcos and beyond. Gen. Edward Burleson was the first substantial landowner in the Stringtown area, having been awarded a grant for service in the Texas Revolution. In 1850 he sold acreage to his friend John D. Pitts, a fellow San Marcos resident who had been serving as adjutant general in Austin while Burleson was in the state senate. The first permanent settlers in Stringtown were the families of General Pitts and his brother, William C., and their slaves. Between 1850 and 1856 eighteen families, mostly their friends and relatives from Georgia, arrived to build log houses, a store, and a one-room schoolhouse that was also used for church services. In 1851 the James Purdy Matthews's home became a stop on the Austin to San Antonio stage route. On May 2, 1872, a post office was opened in the Dailey brothers' general store. At one time or another at least two cotton gins operated in the area, as well as a blacksmith shop. However, there was never a core business district as such. Frederic Law Olmsted in 1857, Jacob De Cordova a year later, and the journalistic team of Edward King and J. Wells Champney in 1874 commented on the prosperous appearance of the self-sufficient cotton and stock farming community through which they had passed. After the Civil War many of the original settlers used that prosperity to move their families into San Marcos, where their children might have better educational opportunity at Coronal Institute. The Anglo character of the community changed as Mexican American tenant farmers arrived to work the land.
The pace of change accelerated when the International and Great Northern Railway arrived in 1881 and the Missouri, Kansas and Texas followed twenty years later. The post office closed in 1883 and moved to nearby Hunter in Comal County. Since the mid-1930s Stringtown has been serviced through the San Marcos post office. When the Austin to San Antonio post road was slated for improvement by the federal government during President Woodrow Wilson's first administration, the San Marcos to New Braunfels segment became the first in Texas to be tarveated. Soon thereafter residents were treated to an impressive sight as Gen. Frederick Funston led a column of United States Army troops on a pre-World War I training mission from San Antonio to Austin, with the head of the column arriving in Austin before the tail left San Antonio. In 1990 the only surviving evidences of old Stringtown were a log cabin once used as a slave quarters, the former home of Gideon Thomas Johnson built in 1879, and the Pitts Cemetery. The San Marcos city limits have steadily encroached upon its former confines. There are a dozen residential subdivisions and a commercial feedlot along the northwest side of Farm Road 2439 and a slowly expanding commercial, industrial, and warehousing component on the southeast side. An estimated 6,480 people now reside in the area.