White settlement began as early as the Texas Revolution in Cooke County. In 1865, the area of present-day Rosston was settled and promptly raided by Native Americans from Indian Territory in what would become the last raid of Native Americans on white settlers in Cooke County. Settlers from Grayson County established Rosstown, later Rosston, in 1870. The Ross family owned a general store, cotton gin, and mill to serve the farmers of the area. A post office opened in 1872 and it officially became Rosston.
The Butterfield Overland Mail route passed near Rosston, operating between Gainesville in Cooke County and Jacksboro in Jack County, Texas. Rosston, like many other small Texas towns, was bypassed by railway lines and slipped into obscurity in the 20th Century. One local claim to fame is that notorious outlaw Sam Bass used Rosston as a hideout, and the town celebrates Sam Bass Day every year on the 3rd Saturday in July. It maintains a store, a volunteer fire department, two churches, and several homes.