Top 10 Creepiest Roads in Illinois

Creepiest roads, Illinois
Photo by Bara Cross on Unsplash

Mysterious Heartland is proud to bring you our list of the “Top 10 Creepiest Roads in Illinois.” Any of these roads makes an excellent spooky night-time trip, but remember, always be conscious of other motorists – especially if they might be ghosts!

10. Kennedy Hill Road

Between mid-December and early January 1980/81, dozens of people reported seeing a young woman in various stages of dress walking down Kennedy Hill Road outside of Byron. By January 20, 1981, the sightings had reached a fevered pitch. Motorists parked their cars in the frigid temperatures along the narrow rural road to catch a glimpse of what became known as “The Phantom Lady of Kennedy Hill Road.” Newspaper reports reached as far away as Chicago, and the Rockford Register Star ran five consecutive articles on the sightings.

Explanations for the phantom varied from the ghost of a woman who had been buried in a nearby cemetery, to a mentally disabled girl who ran away from home, to even a transvestite who wore his girlfriend’s clothes after she died in an accident. The phantom disappeared after the snow thawed that spring and was never seen again.

9. Shoe Factory Road

An old, derelict Spanish Colonial revival style house and an abandoned farm formerly stood along Shoe Factory Road in Hoffman Estates. Both were rumored to be haunted. The unique, stone house was at one time the Charles A. Lindbergh School, named after the famed aviator. According to local historian John Russell Ghrist, it was built in 1929. The school closed in 1948 and spent the next 30 years as a residence, until it became abandoned sometime during the late 1980s.

Local teens believed that the stone house became abandoned after a child living in the home killed his parents. They claim the ghost of this child, who plays with a knife, could be seen sitting on the steps. The haunted farm, and its nefarious barn, had several stories associated with it. One story involved the farmer going insane and murdering his family, then burying them in the middle of a circle of trees. The other had the family being murdered and hung in the barn by a mental patient. Both of these buildings were torn down in 2007.

8. Cherry Road

Similar to Spring Valley’s “Help Me” Road, Cherry Road outside of Oswego is said to have been the scene of a tragic accident. While predominantly straight, there is a sharp, 90 degree angle toward the end of the road. A young couple allegedly wrecked their car after prom while taking that curve too fast. The boy crawled from the wreckage and wrote “help” in his own blood on the pavement. His girlfriend’s ghost can be seen at the bend. Over the years, local teens have painted “Help” on the road with red spray paint.

7. Dug Hill Road

The first story concerning Dug Hill is a classic haunting rooted in the past. In 1863, Union army deserters ambushed and killed a provost marshal named Welch along Dug Hill Road. There are two versions of the story, one involving three deserters, the other involving a dozen or so. In the second version, Welch’s own friend betrayed him and led him into the ambush. Since then, his ghost has been seen along the road. Another legend concerns a man named Bill Smith, who reportedly witnessed a spectral wagon pass over his head.

A third story pertaining to the Dug Hill area concerns a creature known as “the boger.” The boger, or the boger-man, was something cooked up by parents who want to scare their children. Two men have reportedly seen this boger along Dug Hill Road in the past. The creature appears as a nine-to-eleven foot tall man who wears black pants, a white shirt, and a long scarf. No one has yet come forward to explain where this creature found someone to tailor his gigantic clothes.

6. Seventh Avenue Dead End

Just east of downtown Sterling, 7th Avenue ends in front of a railroad track that runs parallel to the Rock River, which divides Sterling and Rock Falls. Several people have drowned or have been hit by a train in the area. Although 7th Avenue is nearly identical to the other nearby side streets, eyewitnesses have reported seeing or hearing the ghost of a woman there. She is said to be searching for her missing child along the riverbank just over the railroad tracks. While no one really knows who this young woman was in life, many locals have heard the story.

5. “Help Me” Road

A local legend maintains that in the 1980s a couple was returning home along this road from a night of drinking at a nearby biker bar when their motorcycle crashed. Both riders were terribly injured, but the man managed to write “help me” on the road in his own blood before he died. Attempts to remove the words from the pavement failed. Even when the county repaved the road, the words mysteriously returned. Some have suggested that “help me” was written onto the road in tar by a mischievous construction worker. The road has recently been repaved and the words are no longer visible—for now.

4. Cole Hollow Road

Stories of bigfoot and other mythic creatures are not often associated with Illinois, however, in the 1970s the Illinois River Valley was abuzz with sightings of the Cole Hollow Road Monster, or Cohomo, for short. It was first sighted along Cole Hollow Road, just outside of Creve Coeur, south of Peoria. It was described as a three-toed beast, eight to ten feet tall, with a coat of thick white fur. There were so many sightings in the summer of 1972 that the Tazewell County Sheriff’s Department organized a search party to hunt for the creature. Encounters with Cohomo tapered off after that, but one man believed he caught a glimpse of it in the headlights of his car one night in July 2000, further north up the Illinois River near Essex, Illinois.

3. Blood’s Point Road

A cornucopia of urban legends have attached themselves to this aptly-named rural avenue and its neighboring cemetery. Visitors have reported seeing phantom vehicles and a dog with glowing red eyes. According to legend, the railroad bridge was the scene of a deadly school bus accident, as well as more than one hanging. These hangings have also been attributed to a bridge along nearby Sweeny Road. The cemetery itself is said to be visited by a wide variety of phenomenon—from orbs, to a phantom dog, to a vanishing barn, to the disembodied laughter of children and electrical malfunctions. Blood’s Point was named after Arthur Blood, the first white settler of Flora Township. Some locals maintain that he brought a curse with him that remains to this day.

2. Lebanon Road

On or around Lebanon Road are seven railroad bridges, some no longer in use. All of them are heavily coated in graffiti—a testament to their popularity for nighttime excursions. Local visitors have crafted a hellish tale around these seven bridges, which they dubbed the “Seven Gates to Hell.” The legend is that if someone were to drive through all seven bridges and enter the last one exactly at midnight, he or she would be transported to Hell. In some versions, the person entering the final tunnel must be a skeptic. In other versions, no tunnel can be driven through twice in order for the magic to work. Like Cuba Road in Barrington, an abandoned property near Lebanon Road has given rise to rumors of a “death house.”

1. Cuba Road

Cuba Road sits nestled between the towns of Lake Zurich and Barrington, both upper and upper-middle class retreats. It is the setting of a plethora of paranormal phenomenon, including a phantom car (or cars), a pair of spectral lovers, and a vanishing house. A side street called Rainbow Road formerly had the distinction of being home to an abandoned mansion that some believed was an old asylum. Along Cuba Road sits White Cemetery, which author Scott Markus has referred to as the Bachelor’s Grove of the north-Chicago suburbs. This small, rectangular graveyard dates from the 1820s and its ghostlore concerns mysterious, hovering balls of light.

Check out these places and more in Michael Kleen’s Haunting Illinois: A Tourist’s Guide to the Weird and Wild Places of the Prairie State! Three years in the making, the 3rd edition of Hunting Illinois is your ticket to adventure in your own backyard. This edition contains 60 new listings and 35 new pictures, for a total of 260 haunted or mysterious locations and more than 120 photos and illustrations. Divided into eight distinct regions and listed by county and town or neighborhood, each location features a description, directions, and sources from a wide variety of books, articles, and websites. Haunting Illinois challenges you to get off the couch and start exploring our wonderful State of Illinois.


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