Winston and its Rock Island Train Depot

In 1871 a new railroad station was built by the Rock Island 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.

In 1871 a new railroad station was built by the Rock Island 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.

This blank check was circulated prior to the time the community of Emporia, MO, later became Winston, MO. [courtesy Dorothy Olson]
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.

Mr. and Mrs. Ebberdeen [courtesy Greg Lawson of Edwardsburg, Mich. The couple were friends of his great-great-grandmother who is buried in the Winston Cemetery in 1922, Ephrium Kuhns]
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)

This is the Rock Island train depot in Winston, MO, where James Gang members embarked in order to pull off their 1881 robbery. The depot was built in 1871 on a high point in Daviess County, halfway between Gallatin and Cameron. The first station agent was T.F. Jefferies, a native of Somersetshire, England. Two sets of tracks fronted the depot and were used for switching cars while a set of siding tracks ran behind the depot. (date unknown)
This is the interior of the Winston Rock Island train depot when restoration by the Winston Historical Society commenced in 1989. The township previously used the depot as an equipment storage shed.
This railroad stone culvert located east of Winston, MO, is commonly associated with the James Gang robbery of a Rock Island train in 1881. Before this, a wooden trestle was used instead of this huge stone arch.
A rare view of the “dump” taken from inside the railroad stone culvert east of Winston, MO, circa 1930. [Barb Caldwell, Winston Historical Society]