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.

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.

The Morrison House at Winston, MO, in 1910. (courtesy Ellis Antiques, Jamesport)

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]

This photo shows 2nd Street in Winston, MO (date unknown)

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]


The following was presented by Lynn Martindale, president of the Winston Historical Society, to the Gallatin Rotary Club in May, 1990. His speech was entitled, “Expansion, Contraction, and the Winston Depot”:

The first workable railway locomotive was invented in England in 1829. By 1831, the United States had its first organized railroad — the Baltimore & Ohio.

When the American Civil War broke out in 1860, the nation had a reasonably fine network of railroad tracks east of the Mississippi River. One of President Lincoln’s problems during the Civil War was that of keeping California from seceding or from joining the Confederacy. For that he needed a railroad. The Union Pacific and Central Pacific railroads were chartered in 1862 but were not joined until 1869, just two years before the Winston depot was built in 1871,

Following the American Civil War, there was a major thrust to push railroad trackage west of the Mississippi In this period the Chicago & Southwestern Railroad laid tracks between Gallatin and Cameron, among other places. Historically, local traffic was important to sustain the profits of railroads so that railroad companies were anxious to develop towns alongside their tracks. The Chicago & Southwestern wanted to develop a town site approximately halfway between Gallatin and Cameron. Several persons donated a tract of land to the railroad and this tract became known as Crofton Junction. Among its advantages was that it had the highest elevation of any tract of land in Daviess County.

The name of the town was soon changed to Winsonville, named after Frederick Winson, president of the Chicago & Southwestern. But by 1885 it was being called Winston and was incorporated under that name.

The Chicago & Southwestern Railroad Company was organized for the purpose of building a railroad, not of operating it, so when the construction job was completed the responsibilities of ownership and operation passed to the Chicago & Rock Island Railroad Company.

The expanding railroads of the 1870s faced a major problem. They all wanted to carry traffic to California but between Missouri and California there was a vast area which was then called the Great American Desert. Tracks had to be laid, rolling stock had to be run over those tracks and people had to be hired to operate the railroads in areas in which the traffic would not generate enough revenue to pay the total cost of railroad operation. Additionally, most railroads were built with borrowed money. Clearly, railroads were vulnerable to periods of economic downturn. Many railroads failed in the panics of the 1870s, the 1880s, and 1890s.

Railroad property was also subject to natural disaster, storms, Indian uprisings and fires. The Winston depot burned during the 1890s and had to be replaced.

During the first World War (1914-18), railroad traffic reached its all time maximum. After 1918 the flow of railroad traffic fluctuated from year to year but generally downward as newer forms of transportation took hold. Faced with falling revenue, railroads began to economize. They discontinued service to less profitable locations. The Rock Island halted service to Winston in 1938. Eventually the railroads sought to get out of the passenger-carrying business entirely because of all the things that can be carried by train, people are the most expensive to transport. In order to generate some one-time sources of revenue, many railroads took up their tracks and sold their rights-of-way. Many small railroad stations were taken over by local units of government for non-payment of taxes.

The former Rock Island train depot was being used as a township road maintenance barn in 1985. Then the Winston Historical Society converted the building into a community museum, focusing on its history in connection with the 1881 James Boys train robbery.

For many years the Winston depot was used as public property. At various times, the City of Winston or Colfax Township used the building for equipment storage or for other public purposes.

In 1987 some people organized the Winston Historical Society because they had a vision of what might be done with the Winston depot, which was looking rather dilapidated by that time. The vision was to restore the building to something akin to its earlier condition and to use it as a museum to attract visitors to Winston. The new historical society acquired title to the building, and its members devoted a tremendous amount of effort and expertise to the project… The Winston Historical Society has three sources of revenue: membership dues ($10 per person), donations, and fundraising activities. At this time there are approximately 75 members… Until recently, donations have not been significant but now the organization is legally recognized as a non-profit entity, thus making donations tax deductible for donors. The bulk of revenue comes from fund raising projects — chili suppers, ice cream social, Jesse James Days events, softball and basketball tournaments, and from sales of caps, jackets and T-shirts…

At the present time the outside of the building is in good shape, and there is electricity in the building. The east half of the interior is sub-floored and the beadboard on the walls is almost wholly installed. The walls are insulated. We’re expecting to use that area for a display of some exhibits at the annual Jesse James Days celebration on July 14-15. Unfortunately, the west half of the interior is still largely untouched, even to the dirt floor. It will require a lot of work and a lot of money to bring the condition of that half of the building up to the point where it can be used…

When the Winston depot was built in 1871, a wave of optimism was sweeping the country. A lot of people risked a lot of money in the railroad industry because they believed that railroad transportation was the wave of the future. They believed that this country would be knit together by a network of steel rails that would make the world available to every hamlet in the country. We, too, are optimistic. We believe that tourism in Northwest Missouri is a growth industry. We believe that our depot will help attract tourist dollars to this part of the state, and that we, in turn, will benefit from things that are going on in Gallatin and Jamesport.

Volunteers performed various tasks renovating the Rock Island train depot in Winston, scheduling work days spanning years. The work was coordinated by Gary Caldwell through the Winston Historical Society which organized to save the depot from decay.

The Chicago, Rock Isand & Pacific Railroad and depot promoted growth and prosperity for Winston and Daviess County. Winston was originally named Crofton in honor of one of the donors of the land for the town. In 1872 a post office located; Winston incorporated in 1878. Soon three and sometimes four doctors, livery stables, a newspaper, millinery shops and a hotel comprised the town. The population peaked between 600 and 700 people; by 1937 Winston’s population was 400 which halved by 1980.