Extended Weekend Getaways 
Somewhere between encountering a giant pink elephant and standing in Lincoln’s family home, Route 66 became America’s most entertaining history lesson.
Few road trips capture America’s story as vividly as Route 66 across Illinois. As the nation approaches its 250th birthday, I joined fellow travel writers for a four-day journey from St. Louis to Chicago. Along the way, we explored the Mother Road’s historic towns, encountered quirky landmarks, and traced Abraham Lincoln’s enduring legacy.
This stretch of Illinois marks the first chapter of the highway’s story. Driving north from St. Louis to Chicago, Route 66 offers a rich look at people, places, and stories that shaped the American experience.
Giant Bottles and Roadside Legends
Pink Elephant at the Pink Elephant Mall
After marveling at the highway’s quirks, we quickly discovered Route 66’s flair for the wonderfully weird.
In Collinsville, we stopped at the towering World’s Largest Catsup Bottle. This water tower, built in 1949, looks exactly like a giant ketchup bottle. It stands above the buildings, a cheerful reminder that Route 66 never took itself too seriously.
World’s Largest Catsup Bottle
Nearby, we also visited the giant pink pachyderm at Pink Elephant Antique Mall. The massive statue stands outside the shop like a whimsical sentinel guarding a trove of Route 66 nostalgia.
Bunyon Giant along Route 66 -Photo Robin O’Neal Smith
Further north, towering roadside giants continued the theme. The famous Gemini Giant stands proudly holding a rocket. This classic “Muffler Man” has greeted travelers since the highway’s heyday.
At the American Giants Museum, we learned about the history of these fiberglass titans and met another legend: Paul Bunyan, towering above the roadside.A Route 66 historian at the museum told us, ‘These roadside giants weren’t just advertising, they were storytelling tools.
Each stop reminded me that Route 66 has always blended imagination with marketing flair. These landmarks weren’t just roadside gimmicks. They were invitations for travelers to pause, laugh, and explore.
Unexpected Stops and Surprises Along the Road
Cahokia Mounds State Historic Site. Photo Robin O’Neal Smith
Our journey also included places that told deeper stories about the region.
Cahokia Mounds State Historic Site was one of the most fascinating stops. As a UNESCO World Heritage Site, it preserves the largest pre-Columbian Native American city north of Mexico. When you stand atop the massive earthen mounds, you can’t help but feel humbled by the ancient civilization that once thrived here—long before Route 66.
The author in a cell at the Cannonball jail. Photo Robin O’Neal Smith
Not all of our stops were quite so ancient. At Cannonball Jail, we discovered one of the most unusual jails in America. The circular stone structure once held prisoners in wedge-shaped cells arranged like pie slices. It’s a peculiar building, but like many Route 66 landmarks, it comes with stories that linger.
A Route 66 sign at the WWT Raceway Photo Robin O’Neal Smith
Our group also visited World Wide Technology Raceway, where the roar of engines offers a modern counterpoint to the vintage highway nearby. Later, at Motorheads Bar, Grill, and Museum, we stepped into a vibrant celebration of classic cars, motorcycles, and the golden era of American road travel.
Dining on the Mother Road
A bottle of Horseradish Vodka. Photo Robin O’Neal SmithNo Route 66 road trip would be complete without stopping at one of the highway’s historic eateries.
In Litchfield, we stopped at the legendary Ariston Café, a staple of Route 66 since 1924. Known as one of the oldest continuously operating restaurants on the Mother Road, it still fills its booths with hopeful Route 66 dreamers nearly a century later.
But perhaps the most memorable culinary moment of the trip happened at Old Herald Brewery & Distillery.
Someone suggested the horseradish-flavored vodka. Glasses lifted confidently. Then came the faces. If laughter were a spirit, it would have filled the room.
Experiences like the horseradish vodka toast underscore Route 66’s ability to surprise, making everyday moments part of a larger story. These small joys, woven into the trip, reinforce the arc of discovery that defines a true journey along the Mother Road.
Springfield and the Legacy of Abraham Lincoln
Abraham Lincolns home in Springfield, Illinois. Photo Robin O’Neal Smith
Springfield may be the emotional heart of Route 66 in Illinois, thanks largely to its connection to one of America’s most influential presidents.
Our visit to Lincoln Home National Historic Site gave a fascinating look at Abraham Lincoln’s life before the presidency. Walking through the preserved neighborhood felt like stepping into the mid-19th century.
Inside, small details brought Lincoln’s family life into focus. Lincoln’s enormous size-14 boots sit near the entryway. They remind visitors of the towering man who once paced these floors. We learned something surprising: Mary Todd Lincoln owned one of the earliest seated chamber pots.
What struck me most, however, was learning about Lincoln as a father. I had always assumed he lived in poverty until becoming president. Instead, I discovered that as an adult, he was fairly well off and even enjoyed buying expensive gifts for his children.
He was also known as a remarkably lenient parent. The Lincoln boys roughhoused freely throughout the house. Sometimes, they even wrestled on the floor with their father joining in. As long as no one got hurt, the chaos was allowed.
That glimpse of Lincoln’s family life made him feel far more human.
The Lincoln Family in the Lincoln Presidential Library and Museum. Photo Robin O’Neal Smith
The story continued at the Abraham Lincoln Presidential Library and Museum. The museum’s immersive exhibits trace Lincoln’s life from humble beginnings to the presidency and the Civil War.
As you walk through the galleries, you feel the emotional weight of Lincoln’s story. The exhibits do more than simply display artifacts, for they tell a deeply human story—one of leadership, sacrifice, and a nation struggling to define itself.
For many of us on the trip, it was the most powerful stop along the entire journey.
Murals, Museums, and the Spirit of Route 66
A Route 66 Mural in Pontiac, Illinois. Photo Robin O’Neal Smith
As we continued north, Route 66 delivered even more glimpses into its colorful past.
In Pontiac, we admired the vibrant Route 66 Mural, a massive painting that celebrates the road’s history. Just steps away stood the Route 66 Association of Illinois Hall of Fame and Museum. Inside, stories from travelers, businesses, and dreamers who made the highway famous are carefully preserved.
Other memorable stops included the beautifully restored Ambler’s Texaco Gas Station. It is a charming reminder of the era when service stations were architectural landmarks.
Route 66 Slides at the Illinois State Fairgrounds. Photo Robin O’Neal Smith
At the Illinois State Fairgrounds, we explored the Route 66 Experience—a collection of exhibits celebrating the culture and history of the famous highway. We also took a thrill ride down the huge yellow slides.
Every stop added another layer to the story.
The Road That Tells America’s Story
Our group in front of the Route 66 Sign in Edwardsville, Illinois. Photo Robin O’Neal Smith
As our bus rolled toward Chicago, our notebooks brimmed with roadside legends, historical insights, and stories of shared laughter among fellow travel writers.
There was only one small disappointment. Instead of visiting the official “End of the Trail” sign in Chicago, our schedule delivered us directly to the airport. The journey ended not beside a Route 66 marker but at a departure gate.
After exploring dozens of stops along historic Route 66, I’ve discovered that Illinois offers one of the most entertaining stretches of the Mother Road.
From ancient civilizations at Cahokia to Lincoln’s family home, from giant roadside figures to laughter over horseradish vodka, this stretch of highway captures the playful, complicated, and endlessly fascinating character of America.
Route 66 may be famous for its roadside attractions, but along this stretch of Illinois, it also tells a deeper story about the people who built the nation.
And like any great road trip, it leaves you wanting to return and explore just a little bit more of the story waiting down the road.
If You Go: Route 66 Across Illinois
Mural at Legends & Landmarks in Springfield, Illinois. Photo Robin O’Neal Smith
Start:
Cross the Mississippi River from St. Louis into Illinois and begin your journey along historic Route 66.
Must-See Stops
Legends-Park-on-Route-66-Photo-Credit-Robin-ONeal-Smit
- Cahokia Mounds State Historic Site – A UNESCO World Heritage Site and the largest ancient Native American city north of Mexico.
- World’s Largest Catsup Bottle – One of Route 66’s most iconic roadside landmarks.
- Ariston Café – A Route 66 dining legend serving travelers since 1924.
- Lincoln Home National Historic Site – The only home Abraham Lincoln ever owned.
- Abraham Lincoln Presidential Library and Museum – Immersive exhibits telling Lincoln’s life story.
- Route 66 Association of Illinois Hall of Fame and Museum – A must-stop for Route 66 enthusiasts.
- Gemini Giant – One of the most famous “Muffler Man” statues on the highway.
Quirky Photo Stops
- Pink Elephant Antique Mall
- American Giants Museum
Best Time to Visit
Late spring through early fall offers the best weather for exploring roadside attractions and historic towns along the Mother Road.
All photos by Robin O’Neal Smith
