Day 3: Crossing the Mississippi and Into the Heart of Route 66

Day three began early at Charlie Parker's Diner in Springfield, one of the Route 66 corridor's most beloved breakfast stops. Housed in a distinctive World War II-era Quonset hut, the diner has been serving travelers and locals since the early 1990s and has become famous for its massive 16-inch pancakes and Springfield's signature Horseshoe sandwich. National attention arrived in 2008 when Guy Fieri featured Charlie Parker's on Diners, Drive-Ins and Dives, introducing audiences across the country to this Route 66 favorite and the unique flavors of central Illinois.

Over a hearty breakfast, we looked ahead to a day packed with roadside attractions, engineering marvels, and one of the most famous landmarks on the entire Route 66 corridor.

Our first stop was the legendary Cozy Dog Drive In, birthplace of the original Cozy Dog, a Route 66 icon that helped put Springfield on the roadside dining map.

We also stopped to see the Lauterbach Giant, one of the remaining fiberglass "Muffler Men" that once stood proudly along highways across America, welcoming travelers with oversized roadside charm.

Next, we made our way to the Pink Elephant Antique Mall in Livingston. Route 66 is famous for quirky roadside attractions, and a giant pink elephant certainly qualifies. It was the kind of place that makes you smile before you've even stepped out of the car.

Continuing south, we stopped in Collinsville to see the World's Largest Catsup Bottle. Rising above the surrounding neighborhood, this unusual water tower is one of those wonderfully odd landmarks that perfectly captures the spirit of the Mother Road.

Just a few miles away, we visited Cahokia Mounds, one of the most significant archaeological sites in North America. Walking among the massive earthworks was a reminder that this land had been an important crossroads for centuries, long before Route 66 connected travelers across the country.

Soon afterward, we crossed into Missouri and arrived in St. Louis, where the Mississippi River marked another milestone on our westward journey. Before exploring downtown, we took a walk across the historic Chain of Rocks Bridge. Once a key part of Route 66, the bridge's distinctive 22-degree bend over the river makes it one of the most recognizable crossings on the entire highway.

No stop in St. Louis would be complete without visiting the Gateway Arch.

Riding the tram to the top was a unique experience in itself, and the views were spectacular.

From 630 feet above the city, we could see the Mississippi River winding through the landscape, downtown St. Louis stretching in every direction, and the route that lay ahead. It felt like standing at the gateway to the American West, exactly as the monument was intended.

After our visit to the Arch, we made a pilgrimage to another St. Louis institution: Ted Drewes Frozen Custard. Route 66 veterans will tell you it's a must-stop destination, and after one taste of the famous frozen custard, it was easy to understand why. Some traditions survive because they're good. This one survives because it's exceptional.

Leaving the city behind, we followed Route 66 through the rolling hills of Missouri toward Meramec Caverns. For decades, painted barn advertisements encouraged travelers to "See Meramec Caverns," and today we finally did.

Descending underground revealed an incredible world of massive chambers, colorful formations, and natural beauty. The scale of the caverns was difficult to comprehend, and the guided tour offered a fascinating glimpse into one of Route 66's most enduring attractions.

As evening approached, we arrived in Sullivan, Missouri, and checked into the beautifully restored Shamrock Court Motel. With its classic neon sign and vintage Route 66 charm, it felt like stepping back into the golden age of American road travel.

Dinner was at Rich's Famous Burgers, where we enjoyed a simple, satisfying meal while reflecting on the day. In just a few hours, we had explored ancient civilizations, crossed the Mississippi River, stood atop one of America's most recognizable monuments, enjoyed a legendary Route 66 treat, and ventured deep underground into one of the country's most famous cave systems.

Not every day on Route 66 can be this packed with iconic stops, but that's part of what makes the journey so special. Every mile reveals another story, another piece of history, and another reason why this highway continues to capture imaginations nearly a century after it was built.

Tomorrow, we continue west.