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What Lurks on Cuba Road? A Firsthand Look at One of Illinois’s Haunted Highways

Image courtesy of the author.

“Have you been to Cuba Road?”

That question is how I first heard about the haunted stretch in Barrington, Illinois. Cruising Chicagoland suburbs in a sedan full of friends, the conversation died, threatening to rot the night with boredom. Then someone turned down the stereo and asked about Cuba Road. I seemed to be the only one unfamiliar with the place as everyone shared a story. Tales of the ghost gangster, vanishing lady, and spectral cars spiced up the night. Despite admitting I’d never been, after hearing about it, of course I wanted to go—straight away into the supernatural. Unfortunately, teenage economics dictated not wasting gas money on a forty-minute trek to Barrington. Still, what I heard always stuck with me.

Too many years later, I finally got a chance to see the fabled ghost road in the flesh, as it were. In the company of a good friend, we trekked out to Cuba Road not sure what to expect. Though we knew the legends, we didn’t know the reality.

Street sign for Cuba Road on a rain swept street
Rainswept Cuba Road. Image courtesy of the author.

Cuba Road is a sweeping twist of narrow lanes. Its green and irregularity hold a charm brick-and-mortar blandness can’t touch. Stimulating the imagination far more than suburban sprawl could ever hope to, that same appeal possesses an undercurrent. It’s easy to feel something lurking ahead as the avenue curves around a shrouded bend. The tree-lined roadside becomes a shadowy veil hiding potential horrors. The sway of branches in a breeze seems like signs of the paranormal. Whereas suburban streets are a clear line lit by lamps showing clear miles ahead, Cuba Road is a dark rural route ripe for an urban legend.

Those tales tell of various encounters which range from passive to outright dangerous. All of them, though, contain some unsettling element. Spectral cars, ghostly hitchhikers, a haunted cemetery, and a vanishing building—it’s the variety that makes Cuba Road alluring.

For instance, two ghost cars reportedly haunt the highway. Both instances vary the type of vehicle, but their behavior is markedly different. One is simply a black car that some witnesses claim is a limo cruising Cuba Road. There doesn’t seem to be anything special about it until the vehicle suddenly disappears. The other ghost car is often reported as a pickup truck. High beams blazing, it comes up frighteningly fast. Witnesses insist this phantom motorist gets right on their bumper, determined to run folks off the road. Then the vehicle vanishes, leaving bewildered drivers alone on an empty lane.

Tree lined and shrouded stretch of the rural route Cuba Road
Trees regularly shroud Cuba Road. Image courtesy of the author.

Spectral hitchhikers can be found as well, though one doesn’t wait for an invitation to ride. Witnesses say that they’ve glanced in the rearview and been shocked to see someone in the backseat. Smoking a cigar, the ghost resembles a classic gangster. That description almost comes as no surprise. Barrington, like much of Illinois, claims a history linked to the defiance of Prohibition. Bootleggers smuggled booze along the backroads, and far from the city of Chicago, the secluded town offered mobsters a quiet spot to vacation. The consensus, as such, is that the ghost who appears in the backseat is that of a Prohibition-era gangster.

The other hitcher seldom gets in the car. Drivers have reported seeing a woman wandering the roadside. Carrying a lantern, she signals for them to pull over. Those who do so claim she disappears before getting in the vehicle, while some say they’ve driven her awhile before she vanishes.

However, apparitions are just one of Cuba Road’s disappearing acts. There’s a building seen at night. Those who look away glance back to discover the house isn’t there anymore. Yet, that’s not the only strange structure here.

A crooked street sign reading Rainbow Road
Rainbow Road has its own haunts. Image courtesy of the author.

Connected to Cuba is a similar winding trail of rolling hills called Rainbow Road. A gravel stretch branches off of one of Rainbow’s curves. At the end are either the ruins of an old mansion or a dilapidated farmhouse, depending on who tells the tale. Some believe it to be the remains of an abandoned asylum. Whatever the case, many claim to have heard cries coming from inside. Disembodied voices calling out from within.

Finally, there’s White Cemetery. One could almost call it the heart of Cuba Road campfire stories. Not simply due to a pair of romantic phantoms passing the graveyard hand in hand but to the way some tales treat it as a focal point. The disappearing building is often seen within a block or two of White Cemetery. The ghost car occasionally evaporates at or emerges from the graveyard. The vanishing lady sometimes hitches a ride not far from there. Last but not least, strange lights and floating orbs are reported glowing among the tombstones.

Tombstones in White Cemetery out in Barrington, Illinois
White Cemetery tombstones. Image courtesy of the author.

The haunted road is nothing new, especially not in the United States. Illinois alone boasts at least ten stretches of paranormal pavement. From the Phantom Lady seen along Kennedy Hill Road in Byron to Boone County’s all too perfectly named Bloods Point Rd., there’s no shortage of horror story highways. Though that said, in many ways, the tales tend to blend a bit. Spectral ladies wander roadside and there’s usually a strange cemetery from a bygone era where unusual things get glimpsed. It gives the impression Illinois has a problem with wandering ghost women who can’t find their graves.

Still, for believers, similarity offers corroboration, as repetition denotes a certain credibility, although skeptics may take it as a sign one story influenced the lot. The point being the lack of variation is either a kind of confirmation or simply proof of paranormal plagiarism. Whatever the case, it certainly doesn’t hurt knowing the details in advance of any visit.

Part of the fun in exploring places like Cuba Road is the expectation. Driving down even the skeptical have to admit to a degree of hope defeating experience. Regardless of potential explanations, perhaps this time there will be some genuinely odd experience to report back.

A section of Rainbow Road
Shadowy rural routes slicing through Barrington. Image courtesy of the author.

It doesn’t hurt to have a rainy day as we did. In fact, it hits so hard in the realm of cliché I’m hesitant to admit, but a lead grey sky hung overhead during our visit. By the time we reached the cemetery, the rain came down steady. As far as atmosphere, the day literally dripped ghost story vibes. When a car parked behind us, obfuscated by cascading sheets, reason took a backseat and I found myself wondering, however minimally, if this might be a ghost car.

Oddly enough, when the storm stopped and the occupant got out to visit a grave, I didn’t exactly feel relief. It turned White Cemetery into someplace dreadfully real. The tombstones are less macabre set dressing and more what they are: markers remembering real people no longer alive.

I recalled folks in high school plotting trips to Cuba Road. Often in garages over the weekend, idle chatter shifted to local legends. Bored teenagers desperate for any kind of authentic extraordinary sought to break the suburban monotony sharing stories supposedly true. Tales heard from a friend whose trustworthy cousin certainly saw a specter wandering the Barrington roadside. And whether skeptical, curious, or just desperate for something different, someone always insisted we hit the road. When the ghosts are local there’s no reason not to risk encountering them. Yet, it rarely went beyond idle chatter.

Gravestones spread across White Cemetery
It’s easy to imagine ghosts in White Cemetery. Image courtesy of the author.

It leaves an individual wondering about the people who sought specters along Cuba Road. There’s a possibility expectation inspired some sightings that have more rational explanations. The winding nature of certain sections could easily explain seeing a house one minute then losing sight of it. The same is true of any car. Headlights gleaming off cemetery fences explain away any strange lights, and a roadway with a speed limit averaging 40 mph (64 km) isn’t the best stretch to catch details in passing, especially at night.

Still, even with such skepticism, there’s a genuine feel to the place. At least, after the stories have infected a visitor. As such, my friend put forward a quality idea.

In her opinion, the whole thing starts with White Cemetery. The earliest grave is from around 1847. Over time the graveyard fell into disrepair. Motorists and pedestrians could easily stray across dilapidated tombstones without warning. Then around 1983, Cuba Township took over the rundown cemetery. My friend believes that’s when the stories really take off. Prior to that, there may have been a smattering of ghost sightings. However, refurbishing White Cemetery drew more attention to it, and like a snowball rolling downhill, urban legends grew.

A single decrepit gravestone sinking into the ground in White Cemetery.
Every stone a spark inspiring spooks. Image courtesy of the author.

Following her logic, I looked at some of the burgeoning stories about Cuba Road. A relatively recent addition revolves around a supposed suicide near Cuba Road Bridge. The story goes that those who stop on the bridge and turn off their engine can hear a ghostly whistling as well as footsteps from an unseen source. While there are stories implying something paranormal prior to reconstruction, it seems that stories have been gaining traction since the renewal project began in 2014. Consequently, with the renamed Veteran’s Crossing Bridge open again, in my opinion, it’s only a matter of time until the ghost there joins the ranks of Illinois’s other haunted crossings like Airtight Bridge in Charleston, Monmouth’s Crybaby Bridge, and the Witch’s Bridge in Clarksdale.

Whatever the truth is, Cuba Road is an attraction for supernatural thrill-seekers. Not because it guarantees solid proof of the paranormal but because the area’s atmosphere is perfect for ghost stories. The road is right out of a horror movie in places and knowing the legends certainly primes a visitor.

It’s hard not to cruise along Cuba without constantly glancing in the rearview. Coming around a curve one wouldn’t be surprised to find an ethereal woman in white evaporating in the middle of the road. The rolling hills can make a person wonder if the car ahead simply disappeared down a dip or vanished entirely. And a ghost road is creepier than a haunted house given that it’s easier to enter by accident, especially in remote areas like Barrington, where some routes are unavoidable.

An empty stretch of Cuba Road with a dilapidated house roadside
A road ripe for ghost stories. Image courtesy of the author.

Still, what a person finds along Cuba Road almost says more about them than the reality of ghosts. Everyone goes there with their own expectations. There are the thrill-seekers who turn the graves of real people into an amusement park ride. Ghost hunters hungry for some sign spooks are real and that the rotting dead beneath White Cemetery isn’t the only future awaiting them. Then there are the skeptics, who come because they need to shatter a harmless fantasy. Although, it’s hard to say who is who at a glance. Everyone goes to Cuba Road for their own reasons.

The litter of empty beer cans and discarded vape pens in and around White Cemetery only seems to speak of bored teens. After all, a lust for the extraordinary isn’t just for the young, and what any visitors went looking for, let alone find, is their own secret to share or seclude as they choose. Cruising Cuba Road some may spot ghosts, while others might see themselves, or the future that awaits us all underground, and it’s hard to say which is the most unsettling. However, it’s all there for those daring enough to risk a look.

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Written by Jay Rohr

J. Rohr is a Chicago native with a taste for history and wandering the city at odd hours. In order to deal with the more corrosive aspects of everyday life he writes the blog www.honestyisnotcontagious.com and makes music in the band Beerfinger. His Twitter babble can be found @JackBlankHSH.

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