In 1871 a new railroad station was built by the Southwestern Branch of the Chicago Rock Island & Pacific Railroad on a high point in Daviess County, halfway between Gallatin and Cameron. At this point a community began to take shape around the depot. At first the town was named Crofton, in honor of one of the donors of the land for the town. But in 1872 with the arrival of a post office, the town changed its name to Winston.
Winston was incorporated in 1878. The town grew rapidly, having three and sometimes four doctors, three attorneys, drug stores, general merchandise stores, grain and lumber dealers, livery stables, a newspaper, a millinery shop and a hotel. The population at one time grew to exceed 600, but by 1937 the population dwindled to 400 and by 1978 those living at Winston numbered less than 200.
The Winston depot lives on in James Gang legend and lore as the site where the 1881 train robbery commenced. Ten years earlier, when the depot was new, the first station agent was T.F. Jefferies, a native of Somersetshire, England. Two sets of tracks were to the front of the depot and were used for switching cars. Another set of siding tracks ran on the north side of the depot building.
The depot stands at the south edge of Winston, at the junction of Highway 69 and Route Y. The legal location is as follows: NW 1/4, Sec. 3 Twp 58, Rng 29.
The building sat vacant when a historic inventory was conducted at various sites located throughout Northwest Missouri. Its interior and exterior condition was listed as “poor.” The building was used to shed road maintenance equipment.
Eventually, the Winston Historical Society organized and converted the depot into a community museum. The organization organizes and hosts an annual festival, Jesse James Days, at the adjascent city park and at the depot.
— sources: Omar Baxter and Harl A. Garner of Winston; Daviess County Centennial edition; and a historic inventory report prepared by Mary Virginia Croy for the Daviess County Historical Society (1978)