Winston Tunnel

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Winston Tunnel – Elizabeth, IL
By Michael Kleen

The entrance to the Winston Tunnel, covered with iron bars like a gatehouse in a medieval dungeon, sits deep in the woods several miles southwest of Galena near the tiny community of Elizabeth. It has been abandoned since 1971, and nothing but the rattlesnakes that make their nests in the damp and murky interior have ventured inside.

At 2,493 feet, the Winston Tunnel was the longest railroad tunnel in Illinois. It was built in 1888 for the Minnesota and Northwestern Railroad, a line that ran from Chicago to Minneapolis, Omaha, and Kansas City. It took 350 workmen (and $600,000) more than nine months to complete the tunnel. Shortly after, the Minnesota and Northwestern became known as the “Chicago Great Western Railway.” At least one worker is known to have been killed during construction of the tunnel, which was so long a pump house had to be built to ventilate it. In fact, it is said that the ghost of this Finnish laborer still haunts the site to this day. Two engineers, one stationed at the east entrance and one at the west entrance, stood watch.

Today, the Winston Tunnel is not easy to find. The east entrance has been covered over with dirt and debris, and the west entrance is quite a walk. To get there, you must park in a gravel parking lot off Blackjack Road (County Road 8), a mile or so north of Rocky Hill Road…

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