Ever wondered what Al Capone and Route 66 have in common? Buckle up for a spine-tingling road trip down America’s most infamous highway, where gangsters, ghosts and abandoned dreams lurk around every bend.
Route 66 is known for its neon signs, kitschy motels and quirky roadside attractions, but beneath its nostalgic charm lies a darker side. From notorious gangsters to haunted hotels and abandoned towns, these spooky spots add intrigue to your Mother Road adventure, sending shivers down your spine.
Congress Plaza Hotel in Chicago, Illinois
Al Capone, one of America’s most notorious gangsters, had a surprising connection to the Mother Road. Not only did Capone allegedly support the construction of the sleek new road, but the National Scenic Byway Foundation reports that ol’ Scarface used Illinois’ first fully paved highway to bootleg liquor during Prohibition, driving a bulletproof V-16 Cadillac painted green and black to blend in with the Chicago police cars back in the day.
For a spooky start to your Route 66 adventure, visit the Congress Plaza Hotel. Located near the route’s starting point, Choose Chicago says it’s one of the Windy City’s most haunted hotels, with the ghost of Scarface wandering the eighth floor near his old suite. If that’s not scary enough, consider this: America’s first serial killer, Dr. H.H. Holmes, the infamous subject of the book “Devil in the White City,” spent time loitering in the Congress Plaza lobby in search of new victims.
The Blackstone Hotel in Chicago, Illinois
For decades, The Blackstone reigned as Chicago’s premier luxury hotel. In addition to hosting royalty and Hollywood’s elite, the hotel welcomed 12 sitting U.S. presidents, from Teddy Roosevelt to Jimmy Carter, earning the nickname America’s Hotel of Presidents.
While the hotel’s guest list reads like a who’s who of American history, its basement barbershop was the favorite haunt of none other than Capone. Pierre-Louis Giacotto, the Area Managing Director of Sage Premier Collection that owns the hotel, shares, “Known for its windowless design, the barber shop was the perfect spot for Al Capone to hold secretive meetings while getting his hair cut. During our 2008 renovation, we found a hidden hatch behind the barbershop, which is said to have been used by Capone during Prohibition to store liquor, like Templeton Rye.”
Lincoln’s Ghost Walk in Springfield, Illinois
For a haunting historical experience, Lincoln’s Ghost Walk offers a 90-minute lantern-lit walking tour of significant Lincoln-related sites. But don’t expect a simple history lesson — this tour includes eerie tales about Lincoln’s life, death and the years that followed. Starting at the Old Capitol Plaza, the tour covers Lincoln’s final visit to his law office, his funeral train’s haunting history and macabre stories of grave robbing at Lincoln’s tomb. Although the tour is packed with strange and unsettling tales, this ghost walk in Springfield is a factual and family-friendly experience.
Lemp Mansion in St. Louis, Missouri
Built in the 1860s by a prosperous brewing family, the Lemp Mansion has become a famous stop along Route 66 in St. Louis due to its tragic history and haunted reputation. The Lemp brewing family’s saga includes mysterious deaths and suicides between 1901 and 1922, ending with the brewery’s auction after Prohibition.
Visitors and staff have reported numerous ghostly encounters. “Sightings of figures who simply vanish into thin air are common,” says Tim Trunnell, the mansion’s media director and historian. He notes other reported spirits, like The Guest at the Window and an entity called Oscar, often seen on the third floor.
While tucked into the corner of two thick brick walls to photograph a fresco ceiling, Trunnell recalls hearing a deep voice commanding, “Get out.” With a chill running down his spine, Trunnell says he looked around for anyone who might have been speaking. Finding no one, he took his camera off the tripod, packed up and left as instructed. The mansion’s apparitions, strange noises and unexplained phenomena make it a must-visit for those fascinated by the supernatural.
The Skirvin Hilton in Oklahoma City, Oklahoma
Built in 1911, this historic hotel is known for its elegant decor and a restless spirit. According to legend, Effie was a chambermaid who had an affair with the hotel’s widowed owner, resulting in a pregnancy. Effie was allegedly locked in a room on the top floor to avoid scandal. Driven mad by isolation and despair, she eventually jumped out of the window with her newborn baby.
As Rhys Martin, President of the Oklahoma Route 66 Association, says, “A road trip down Route 66 is often unpredictable.” He continues by warning, “Who am I to say that a night at The Skirvin won’t come with an unexpected guest?” Over the years, guests and staff have reported eerie occurrences, from strange noises to objects moving on their own.
According to Sportskeeda, Effie is particularly fond of male guests, especially NBA players. Despite a $46.4 million renovation, the Skirvin’s haunted reputation persists, promising visitors a memorable — and possibly spooky night.
Museum Club in Flagstaff, Arizona
The Museum Club in Flagstaff, known locally as The Zoo, offers a unique blend of spirits — both otherworldly and distilled. This quirky log cabin, built in 1931 as a roadside taxidermy attraction, later became a lively country-western dance hall, combining “Night at the Museum” with “Nashville” and a dash of “Poltergeist.”
In the 1960s, Don and Thorna Scott transformed it into a hotspot for country music legends. Tragedy struck in 1973 when Thorna died in a fall, followed by Don’s suicide years later. Both are said to haunt the club they loved.
Visitors report seeing Thorna’s ghost on the stairs or behind the bar, while Don lingers near the fireplace. Flickering lights, moving rocking chairs and unexplained fires add to the eerie atmosphere. The Museum Club offers live music, dancing and drinks — with a chance of supernatural encounters.
Amboy Ghost Town in Southern California
While Amboy may not have documented paranormal activity, it certainly puts the ghost in ghost town along Route 66. Once a bustling stop for travelers, this dusty desert town now stands as a stark reminder of what happens when the Interstate Highway System bypasses a place, leaving it to fade into history.
With its iconic Googie architecture and towering neon sign, Roy’s Motel and Café became a symbol of the American road trip. But when Interstate 40 opened in 1972, diverting traffic away, Amboy began its slow decline into a ghost town. Although deserted, Amboy has attracted photographers, filmmakers and Route 66 enthusiasts. In 2005, Albert Okura, founder of the Juan Pollo restaurant chain, purchased the town with a promise to restore it.
Today, under the care of Okura’s son Kyle, the gas station is again operational with its neon sign lighting the desert sky. The town’s stark desert setting makes it a must-see for anyone intrigued by the haunting beauty of America’s forgotten places. In the silence of the Mojave, Amboy is a reminder that even ghost towns have stories left to tell.
Time to hit the dusty, and possibly haunted, trail
Whether you’re a thrill-seeker, a history buff or just someone who likes road trips with a side of goosebumps, these spooky stops along Route 66 will surely make your journey unforgettable. Just don’t blame me if you need to sleep with the lights on afterward.
Sage Scott was bitten by the travel bug as a preschooler when her family moved abroad for the first time. Now settled in America’s Heartland, Sage is a travel writer, world wanderer and photographer whose favorite color is golden hour. Follow her adventures at Everyday Wanderer.