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, Illinois, just off Blackjack Road, near the tiny community of Rice. It has sat empty since 1971, and nothing but a few intrepid explorers and the rattlesnakes that make their nests in the damp and murky interior have ventured inside. Carefully navigating the slippery and steep slope off to the side of the entrance, it is easy to wonder what it must have been like for the engineers roaring through the dark tunnel in their steam locomotives.
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, visitors must park in a gravel parking lot off Blackjack Road (County Road 8), a mile or so north of Rocky Hill Road. There is a trail that leads from the parking lot to a grassy clearing next to a creek. Do not follow this trail too far. The abandoned ruins of the watchman’s house will be on your right. Just south of there, along the creek, there will be a large amount of concrete blocks and debris leading up the side of a steep hill. Believe it or not, these used to support a bridge that spanned the creek and the small valley. Head up the path located on the right side of these concrete blocks.
Once you climb to the top of the remnants of the bridge, you will face a long, straight trail. With each step, visitors can feel the old wooden railroad ties mostly hidden under the grass, demonstrating how quickly nature reclaims whatever mankind builds. In a few years, visitors will hardly notice that used to be a railroad bed. Still, the tunnel is hidden from view. Then, slowly but surely, a white sign appears in the distance. It seems to hover in a small area of darkness, but pretty soon you will realize that this is the entrance to Winston Tunnel.
The old pump house is gone now. It was torn down in 2007, but the bricks used to build its walls still remain. The spring thaw leaves a swampy mess near the tunnel entrance, so come in the fall or summer if you want to avoid climbing along the steep ridge. The path is full of pitfalls, rusted steel supports, and rotting timber. It is very dangerous – if you go, make sure to wear jeans and good hiking boots. The opposite side of the embankment is much easier to navigate. Although it is located in a public forest preserve, entrance to Winston Tunnel is strictly forbidden. The site is currently maintained by the Illinois Department of Natural Resources, and is subject to their rules and regulations.