Constructed in 1888, The Winston Tunnel played a pivotal role in the railroad history of Illinois. At 2,493 feet long, it was the longest railroad tunnel in the state at the time, becoming part of the Minnesota and Northwestern Railroad line that connected Chicago to other the major midwest cities of Minneapolis, Kansas City, and Omaha. Today, the tunnel is closed but you can take a hiking trail that leads to it at the Winston Tunnel State Natural Area, a 230-acre preserve in Galena.

In 1886, The Sheppard, Winston, and Company was contracted to build the tunnel. Construction of the Winston Tunnel, named after the construction company, took nine months to complete with approximately 350 laborers.

Abby Smith/AllTrails

Working conditions were dangerous as the landscape is quite rugged in this area and building the tunnel had to be done by hand. At least one worker was killed during that time.

Megan Bunyer/AllTrails

The cost to build the tunnel was $600,000. Once construction was completed, the railway line became known as the “Chicago Great Western Railway.”

Lloyd Bare/AllTrails

In 1968, the merger of Chicago and North Western lines was the beginning of the end for the Winston Tunnel which became a financial burden due to the cost of maintenance and rugged landscape surrounding it. The line was soon abandoned and the last train traveled through in 1971.

Roland Williby/AllTrails Soon after trains ceased travel through the Winston Tunnel, it was sealed off to prevent trespassers and squatters.

Today, you can take a two-mile hike to view the historic tunnel. It will take about two hours and you will encounter some steep and possibly muddy areas, so be prepared with proper gear for the trek. This hike can be quite strenuous and dangerous.

Pat Quellmalz/AllTrails

Part of the trail will take you over the old wooden railway ties leading to the tunnel, but entering is strictly forbidden, with steel bars sealing the entrance.

Roger Pavey/AllTrails

Although Winston Tunnel was the longest tunnel in Illinois for many decades, two longer tunnels were later built along the Illinois Central (now Canadian National) Edgewood Cutoff Line. The longest tunnel is referred to as Tunnel #2 and it is still in use. But Winston Tunnel has played a key role in the history of train travel in the state of Illinois.

Abby Smith/AllTrails

Megan Bunyer/AllTrails

Lloyd Bare/AllTrails

Roland Williby/AllTrails

Soon after trains ceased travel through the Winston Tunnel, it was sealed off to prevent trespassers and squatters.

Pat Quellmalz/AllTrails

Roger Pavey/AllTrails

Have you hiked to Winston Tunnel?

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