Get ready for an unforgettable road trip through Illinois’ Great Rivers & Routes region, where charming river towns, scenic views, and iconic Route 66 landmarks come together for one incredible adventure.
“They started paving Route 66 in 1926 as a way to go from east to west. It is also what formed all of these small towns,” explains Casey Claypool, executive director of Illinois Route 66 Scenic Byway, as well as the owner of Docs Just Off 66. “It was bringing travelers; people were able to go out and have road trips. That’s where the [term] ‘road trip’ came from.”
This itinerary is packed with hidden gems and can’t-miss experiences.
The Great River Road
First stop: Elsah, Illinois
Situated between limestone bluffs, Elsah is a storybook village where time seems to stand still. Walk cobblestone streets lined with preserved 19th-century buildings, browse charming shops, and soak in the peace of this historic Mississippi River town. If you have time, visit the historic Village of Elsah Museum or dine at State Street on LaSalle.
Next stop: Grafton, Illinois
Just down the road, Grafton offers one of the best views in the Midwest at Aerie’s Resort. Take in the river valley from the sky deck, enjoy a wine tasting, or zipline through the treetops for an adrenaline rush.
Pair your river views with live music, food, and fun at The Loading Dock. Book a river cruise, or unwind by the water with a drink in hand. For a closer look at the river, rent a tri-toon boat from Grafton Harbor, and venture down one of the most iconic waterways in America.
Route 66 Highlights
Next stop: Girard, Illinois
Start your Route 66 journey with a classic at Docs Just Off 66, a retro soda fountain with malts, burgers, and small-town charm. Deck’s Drugstore began in 1884 and remained a beloved fixture in Girard after more than a century. Known for its iconic white storefront and old-fashioned soda fountain, it was a central gathering spot for the community. It was operated by three generations of the Deck family. When the most recent generation retired in 2001, the building changed hands, eventually becoming home to Docs Soda Fountain and, later, Docs Just Off 66. Today, the renovated restaurant honors its roots by preserving the original artifacts, blending local history with a fresh, modern experience.
“I have their original registers from 1884. I have prescriptions dating back to the early 1900s. All of the medicine that’s on display, the contents are real,” Claypool says. “The soda fountain is in its original location.”
Next stop: Litchfield, Illinois
Make time to visit one of the oldest restaurants on Route 66, Ariston Café, serving travelers since 1924. Litchfield’s roots run deep in Illinois farmland. When nearby Hardinsburg lost its bid for the railroad, determined settlers moved their entire town—buildings and all—to what became Litchfield. Today, the city thrives with manufacturing, recreational amenities, a scenic lake, and a strong educational and health care system. Amid the growth, the historic Ariston Café still stands as a proud symbol of the town’s legacy, serving up beloved American, Greek, and Italian dishes.
End the evening with a double feature under the stars. The Route 66 Skyview Drive-In is now in its 75th consecutive season and has been a beloved destination for big-screen entertainment since it first opened in June 1950. It holds the distinction of being the only original drive-in theater in the country still operating on the iconic Mother Road.
Next stop: Edwardsville, Illinois
Catch a concert or show at the Wildey Theatre, a beautifully restored venue. For more than a century, the Wildey Theatre has been a go-to entertainment hub in downtown Edwardsville. Located on Main Street, it also offers event space for private gatherings and is easily accessible, whether you’re local or visiting from the St. Louis or Springfield area. Be sure to stop at the West End Service Station, a lovingly preserved Route 66 relic-turned-interpretive center. From 1927 to 1964, the building at 620 St. Louis Street operated as a fuel stop and service center—until Route 66 bypassed Edwardsville. It then transitioned into a dental office, serving the community for 55 years, until 2019. In 2022, the City of Edwardsville and the Great Rivers and Routes Tourism Bureau teamed up to purchase and restore this historic Route 66 site. The space reopened in June 2023 as a Route 66 interpretive center, offering visitors a nostalgic journey through the highway’s local history with stories, photos and memorabilia. And before you leave town, be sure to enjoy dinner at 1818 Chophouse.
Next stop: Collinsville, Illinois
A must-visit site is Cahokia Mounds, the largest pre-Columbian mound system found outside of Mexico. Once spanning 4,000 acres, with 120 mounds, Cahokia Mounds had a population of nearly 20,000 at one time—larger than London at the time. Today, Illinois preserves 2,200 acres of this historic site, including 72 of the remaining mounds. Recognized as a U.S. National Historic Landmark in 1965, it became a UNESCO World Heritage Site in 1982.
You can also find the World’s Largest Catsup Bottle in Collinsville. Built in 1949 for the G.S. Suppiger catsup plant, the 170-foot-tall World’s Largest Catsup Bottle is a quirky roadside icon that’s perfect for a quick photo op. Saved from demolition and restored in 1995, it’s celebrated as a classic piece of 20th-century Americana. In 2002, it was added to the National Register of Historic Places and continues to draw visitors from near and far.
Final stop: Granite City, Illinois
At the It’s Electric Neon Sign Park, restored neon signs from Hudson Jewelers, Reese Drug Store and Washington Theatre shine once again. This nostalgic stop along the last 100 miles of Illinois Route 66 also features vibrant murals and a Chain of Rocks Bridge model. Open from dusk to dawn, it’s a perfect photo op and a charming tribute to Granite City’s past.
Finally, treat yourself at the long‑standing Mr. Twist Ice Cream and Sherbert. This family‑owned favorite has delighted generations with its creamy, generous sundaes and classic soft‑serve. Open for more than 45 years, it feels like stepping inside a nostalgic local gem. Whether you’re craving a twist cone at the window or lingering over a delicious sundae with friends and neighbors, Mr. Twist offers warm hospitality and sweet memories.
This journey through Illinois’ Great Rivers & Routes region is the perfect mix of scenic landscapes, local flavor, and retro Americana. Whether you’re cruising the bluffs or reliving the glory days of Route 66, each stop invites you to slow down and savor the ride.
And don’t miss the centennial celebrations in 2026, when Route 66 turns 100 years old. “Route 66 goes through eight states. Individual towns will have [centennial] celebrations all year long,” Claypool says. “My organization is having a huge event in November, and we expect travel to be at an all-time high in 2026.”
This post was created by SLM Partner Studio on behalf of Great Rivers & Routes. For more information about Great Rivers & Routes of southwest Illinois, visit riversandroutes.com.
