Winston was platted by the Northern Pacific Railroad and soon settled by ranchers and farmers. It began with Fred Goudy’s Saloon, and was followed by the Duncan Hotel, a combined rooming house and restaurant. The Dodge brothers operated a rooming house in a rock building which, deserted and crumbling, stands today. Gold, silver, copper and lead mines were active in the area from 1908–1918 and 1926–1928. Winston was named for P. B. Winston, a contractor for the Northern Pacific Railroad.

One of Winston’s most notable characters was George Beatty, a young New York man who was “doomed to die” presumably from tuberculosis. He set out for Montana in the 1860s hoping the mountain air would add a couple of years to his life. He was so resolved to his fate that he brought his tombstone with him. Carved on it was:

Beatty stored the tombstone in a back shed. When he died at the ripe old age of ninety-two, it was placed on his grave in Helena where it can be seen today.