Pink Elephant Antique Mall became the biggest surprise of what was supposed to be a simple driving day to St. Louis.
Route 66 Roadside Attractions, Murals & Unexpected Adventures on the Way to St. Louis
Our first day of a nine-day Midwest road trip took us from Richmond, Kentucky to St. Louis through Indiana and Illinois—with Route 66 roadside attractions, 33 murals, giant roadside oddities and one stop that unexpectedly consumed almost four hours.
Day 1 result: 33 murals photographed, 484 photographs taken and far more stops than we expected from what was supposed to be a travel day.
What Can You See on a Road Trip From Kentucky to St. Louis?
Much more than I expected.
Our route from Richmond, Kentucky to St. Louis included murals in Indiana and Illinois, the Brooks Catsup Bottle Water Tower, Pink Elephant Antique Mall, Luna Cafe, Granite City roadside attractions and the historic Old Chain of Rocks Bridge.
A road-trip travel day does not have to feel like wasted time. Researching stops in advance while remaining willing to pull over when something caught our attention made the drive part of the destination.
This story is Day 1 of my nine-day, eight-state Midwest road trip. For the complete route and all supporting destination guides, start with The Ultimate Midwest Road Trip →
Day 1 at a Glance
What began as the drive to our first overnight destination quickly became a full day of Route 66 history, public art and roadside discoveries.
This article reflects our firsthand June 2026 road trip. Always verify current hours, access and operating information before visiting individual attractions.
What Was Supposed to Be a Driving Day
After a month of planning, outreach and anticipation, June 13 had finally arrived.
At 8:00 a.m., my brother Craig and I pulled out of Richmond, Kentucky, officially beginning our 2026 Midwest Road Trip.
St. Louis was our destination for the day, but it didn’t take long to realize Day 1 was going to involve much more than simply getting from Point A to Point B.
Several Route 66 stops were already on the itinerary, while other discoveries appeared simply because something caught our attention along the road.
By the time we reached St. Louis, I had photographed 33 murals and taken 484 photographs.
Not bad for what was supposed to be a driving day.
A mural in Lebanon, Indiana became the first of 33 murals I photographed during Day 1.
One Mural Became Thirty-Three
One of the first surprises came before we ever reached Illinois.
A sign for Lucas Oil Golf Course caught our attention and prompted a quick detour to check it out for a future trip. Although the golf course wasn’t part of the original plan, it became the first example of how curiosity would shape the road trip.
Not long afterward, a mural in Lebanon, Indiana caught my eye.
As someone who actively searches for murals when I travel, I rarely pass up an opportunity to stop for public art.
That first mural set the tone for what happened next.
Route 66 Murals Along the Way
By the time we reached Collinsville, Illinois, the mural count was growing quickly.
I had mapped several pieces in advance, including the Route 66, Postcard Trail, Bull Durham and Let’s Twist murals.
Seeing them in person was far more impressive than simply viewing photographs online.
Each mural brought a different mix of color, detail and local personality to the drive.
Travelers who enjoy building trips around public art can also explore my Street Art Maps and Photo Spots by Destination →
Collinsville provided several planned mural stops during our Illinois Route 66 drive.
Finally Seeing the Brooks Catsup Bottle
The massive Brooks Catsup Bottle Water Tower had been on my Route 66 bucket list for years.
One of my long-awaited Route 66 stops was the World’s Largest Catsup Bottle in Collinsville.
Photographs don’t fully communicate how large this roadside landmark really is.
The 170-foot water tower had been on my Route 66 bucket list for years, and finally standing beneath it was a reminder of why I enjoy road trips so much.
Roadside oddities can be every bit as memorable as major attractions.
Its size made photographing it a little challenging, but the stop was absolutely worth it.
The Stop That Stole Day One
We intended to stop at Pink Elephant Antique Mall for lunch. Nearly four hours later, we finally left.
From the moment we pulled into the parking lot at Pink Elephant Antique Mall, I knew this wasn’t going to be a quick stop.
Quirky statues, Route 66 memorabilia and colorful roadside attractions filled the lawn.
Its playful entrance immediately pulled us inside, and before long we were sitting at the diner counter enjoying lunch.
Craig ordered a Philly cheesesteak and fries while I chose a burger and onion rings. We added milkshakes—a chocolate peanut butter shake for Craig and salted caramel for me.
Both were fantastic.
Disclosure: Pink Elephant Antique Mall hosted portions of our visit, including lunch and a preview of the Haunted School. As always, the experiences and opinions shared here reflect my firsthand visit.
Pink Elephant Antique Mall became the most memorable stop of Day 1.
A lunch stop quickly became part of a much longer Pink Elephant experience.
Lunch, Route 66 Treasures and Family Hospitality
During lunch we met co-owner Tonia, who welcomed us like old friends and shared stories about the business.
Afterward, we explored the antique mall and eventually left with a few Star Wars and Route 66 treasures of our own.
The antiques were memorable, but they weren’t the biggest surprise.
Neither the diner nor the milkshakes ended up defining the visit either.
What happened next turned a good Route 66 stop into one of the funniest memories of the entire road trip.
Then the Visit Took a Completely Different Turn
When Tonia offered to show us the Haunted School attraction, I assumed we would get a quick walkthrough with the lights on.
Nope.
Instead, we received a full scare-filled preview.
What followed became one of the funniest moments of the entire road trip.
As Craig jumped, screamed and tried to survive the experience, I found myself laughing while Tonia, her husband and their son appeared to be having the time of their lives terrifying him.
Creativity impressed me more than any single room or prop.
The layout kept us guessing what might happen next, and the attraction felt unlike haunted experiences I had visited before.
I won’t give away the best details because the surprises are part of the experience.
A private preview of the Haunted School became one of the funniest memories from the road trip.
Luna Cafe added another piece of Route 66 history to the afternoon.
The Discoveries Continued
The Route 66 stops continued after we finally left Pink Elephant.
We visited historic Luna Cafe, where its neon sign and vintage character offered another glimpse into Route 66 history.
I also learned that the neighboring historic home is more than 100 years old, adding another layer of character to the area.
A little farther down the road, Granite City delivered several more surprises.
Muffler Men, Murals and a Literal Fork in the Road
Earl the Muffler Man made an appearance, along with a giant tire that was impossible to resist photographing.
Nearby Mural Park contributed even more color to the day and helped bring the final mural count to 33 before we reached St. Louis.
An actual Fork in the Road supplied the perfect bit of roadside humor before we continued west.
Those kinds of places are exactly why I prefer having extra time built into driving days.
Earl the Muffler Man was another unexpected roadside photo stop before reaching St. Louis.
A literal Fork in the Road added a little roadside humor to an already packed afternoon.
The Places That Never Make the Original Itinerary
Not every stop needs to be famous or historically significant.
Part of the fun of a road trip is pulling over for something simply because it makes you smile—or because you know it will make a good photograph.
That willingness to investigate small discoveries became one of the recurring themes of the entire nine-day journey.
Walking Across Route 66 History
The Old Chain of Rocks Bridge provided one of the classic Route 66 moments of Day 1.
One of our final major stops before reaching St. Louis was the historic Old Chain of Rocks Bridge.
Despite the warm afternoon temperatures, we walked all the way to the bridge’s famous bend.
Visitors were spread across the bridge, but the Mississippi River views made the walk worthwhile.
Looking toward St. Louis, spotting the Gateway Arch in the distance and walking across a historic piece of Route 66 created one of those road-trip moments that feels almost timeless.
The repeating geometric structure of the bridge also produced some of my favorite photography opportunities of the day.
A Giant Amoco Sign and a James Bond Ending
By the time we reached St. Louis, I thought the day’s surprises were winding down.
Our arrival at The Cheshire immediately proved otherwise.
Before I even focused on the hotel, the enormous vintage Amoco sign next door caught my attention.
Stepping inside brought another surprise.
Having recently returned from London, the hotel’s British literary atmosphere immediately felt familiar.
Even our arrival in St. Louis produced one more unexpected roadside landmark.
The James Bond Suite at The Cheshire became our home for the St. Louis portion of the road trip.
Our St. Louis Story Was Just Beginning
We were staying in the James Bond Suite, one of The Cheshire’s themed novelty suites.
The room was larger than anticipated, its details were thoughtfully executed and the whole experience felt playful and distinctive.
Later that evening, we visited Fox & Hounds Tavern and took a quick drive through nearby Forest Park.
Even from the car, it was obvious Forest Park deserved much more than a brief visit.
After everything we had already experienced that day, arriving at a British-inspired hotel felt like the perfect final surprise.
What Day 1 Taught Me
Day 1 may have been scheduled as a travel day, but it never felt like one.
Instead, it became a day built around discoveries.
A golf course sign led to an unexpected stop, while one mural eventually became thirty-three.
Our planned Route 66 antique-mall visit turned into a nearly four-hour adventure, and the Haunted School produced one of the funniest memories of the trip.
By the time we checked into our hotel, even the night’s British-inspired setting was reminding me of our recent London trip.
The lesson: Research enough to know what is around you, but leave enough room in the schedule to follow your curiosity.
Public art became one of the recurring visual themes of the entire Midwest road trip.
Go Deeper Into the Journey
Day 1 connects the larger Midwest itinerary with detailed guides to the stops and themes that shaped the experience.
The Ultimate Midwest Road Trip
See the full nine-day route through eight states, including St. Louis, Wichita, Oklahoma City and Little Rock.
Pink Elephant Antique Mall
Go inside the antique mall, diner and Haunted School that turned one planned stop into nearly four hours.
Street Art & Photo Spots
Explore more murals, public art and photography locations from destinations I’ve experienced firsthand.
From Route 66 Into St. Louis
Day 1 ended at The Cheshire, but our St. Louis portion of the road trip was only beginning.
Back to the Master Trip
See how Day 1 fits into the complete nine-day Midwest route.
Explore Pink Elephant
Take a closer look at the attraction that completely changed the schedule for Day 1.
Continue to St. Louis
Step inside the British-inspired hotel and James Bond Suite where we ended our first day.
About Angela
Angela Addington is the travel photographer and writer behind Lenses & Latitudes. She shares firsthand destination guidance and practical photography advice for independent and solo travelers, women over 50, road-trippers and weekend explorers. Learn more about Angela.
Pingback: Pink Elephant Antique Mall: A Must-Visit Route 66 Attraction in Illinois - Lenses and Latitudes
Pingback: Top Cow in Glen Ellyn, Illinois: Quirky Roadside Attraction