A centennial road trip through southwest Illinois connects a coal miner's filling station, a restaurant that followed the highway and the artists keeping roadside culture alive. This weekend's Last 100 Miles Festival gives travelers an especially good reason to slow down.
At Soulsby Service Station in Mount Olive, Illinois, the American road trip comes down to a small building with an outsized backstory. After an injury ended Henry Soulsby's mining career, he put his savings into a new livelihood: selling gasoline beside the highway coming through town. The station stopped pumping fuel in 1991, but its restored façade and vintage pumps still invite a closer look.
Such encounters make southwest Illinois a rewarding place to celebrate Route 66's centennial. From October 9 through 11, 2026, the Last 100 Miles Festival links communities through music, markets, art and roadside history. The pleasure lies in lingering long enough to discover who built these places and how they survived.
In nearby Litchfield, make time for the Ariston Café. Founded in Carlinville in 1924, the restaurant moved after Route 66 shifted east; its current building opened in 1935. When another realignment later sent traffic behind the restaurant, owner Pete Adam installed neon signs at the rear to lure motorists around to the entrance. Even the ceiling has a story: the original dining room retains its 1935 acoustical tiles. Lunch here comes with an unusually tangible lesson in roadside ingenuity.
Continue to Staunton for the Rabbit Roadside Art Crawl on October 9 and 10. Inspired by Henry's Rabbit Ranch, the event brings neon-making demonstrations, traditional sign painting and custom pinstriping into the centennial celebrations. The Macoupin Art Collective is a useful starting point for exploring participating downtown businesses. Watching the work take shape offers a fresh appreciation of the skill behind the highway's exuberant visual identity.
Farther south, Edwardsville's West End Service Station tells a preservation success story. The city and Great Rivers & Routes partnered to restore the building, which reopened in June 2023 as a Route 66 interpretive center. Admission is free, with regular hours Wednesday through Sunday. In Granite City, follow your appetite to Civic Park, where Sizzlin' on 66 pairs barbecue competitions with live music on October 9 and 10.
Allow a weekend rather than racing between landmarks, and check individual event schedules before setting out. For a Mississippi River finale, the Old Chain of Rocks Bridge offers a walk above the water, but plan carefully: Great Rivers Greenway currently lists access from Missouri only because construction has closed the Illinois approach.
Beyond the festival, these stops make a satisfying October journey. A meal, a conversation with an artist and a few minutes beneath an old filling-station canopy reveal how much life remains along a road turning 100.
Hero photo: Soulsby Service Station in Mount Olive, Illinois, photographed in 2008. Photo: Marcin Wichary / Flickr, CC BY 2.0.