The story of the Winston Tunnel all started in the Spring of 1886, surveyors from The Minnesota and Northwestern Railroad hiked the exceedingly rugged countryside of Jo Daviess County to locate a 50 mile route from South Freeport, Illinois to the Mississippi River near Dubuque, Iowa. Because construction costs in the rugged countryside of Jo Daviess County would be extremely expensive, the railroad first constructed the Forest Home to South Freeport segment and acquired rights on the Illinois Central Railroad from South Freeport to Dubuque for one year. M&NW engineers knew that an expensive half-mile long tunnel near the Mississippi River would have to be built. The tunnel would be the longest bore in Illinois.