The tunnel was located on the CGW main line 152 miles (245 kilometers) west of Chicago in the isolated and hilly Driftless Area of extreme north-western Illinois.
The tunnel was originally braced by wooden beams when it opened to rail traffic in January 1888, but these eventually proved inadequate, and were replaced in 1902 by brick and reinforced concrete.
Piecemeal solutions failed to work, and by 1912 the railroad was forced to install a huge fan, powered by a 310 horsepower (230 kW) diesel motor and staffed by operators day and night, to ventilate the tunnel.
The steep grades of the line and the obvious financial burden of the Winston Tunnel also played a role in the decision to completely abandon the Great Western's trackage in the area.
[8] A 1973 attempt to turn the right-of-way through Jo Daviess County, including the Winston Tunnel, into a rail trail, failed when ownership of the land reverted to nearby property owners.
Nature has reclaimed the right-of-way; the fan house, unused since the 1940s and damaged by the elements, was demolished in early 2007, and the eastern bore, located on private property, has been almost completely sealed with earth.
[citation needed] The western half was purchased by the Illinois Department of Natural Resources as a "satellite area" of Apple River Canyon State Park.