The Great Rivers & Routes region of Southwestern Illinois offers a one-of-a-kind journey through America’s past and present
Southwestern Illinois is a meeting point for three mighty American Rivers and two iconic routes. The only place in the US where scenic stunners converge with highway history.
Spanning 39 towns, you’ll find the merger of Route 66, aka the Mother Road, and the Great River Road and the joining of the Missouri and Illinois rivers into the Mississippi in what is called the Great River and Routes region: an area of people, places and things to do unique to this once-in-a-lifetime collision. On April 30, 2026, historic Route 66 turns 100. The anniversary of the Mother Road is eagerly anticipated and preparations to celebrate are already underway with an exciting revival of the iconic American highway. Here are some legendary Route 66 stops in Southwestern Illinois.
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Litchfield, Illinois Route 66 Attractions
Residing on two alignments of the Mother Road, Litchfield is a fine example of Route 66 preservation.
Route 66-era businesses like the Ariston Café, built in 1924 and the 1950 Litchfield Sky View Drive-In Theatre, which is one of the last remaining drive-ins left on Route 66, are still in operation in Litchfield. The Ariston Cafe opened its doors in 1924 and is one of the oldest continually operational Route 66 restaurants in existence. The café features a wide range of food including American, Southern, Italian and Greek fare along with a fully stocked bar. The original cafe was located on Route 4, the predecessor of historic Route 66. In 1929, the Cafe was relocated to Litchfield and moved into its present location on Route 66 in 1935. It is one of the oldest, if not the oldest, Route 66 restaurant.
Another great Route 66 stop is the Skyview Drive-In Theater, located on Historic Old Route 66. This famed drive-in is enjoying its 75th consecutive season of big-screen entertainment. Opened in 1950, the Litchfield Rt 66 Skyview is the only original drive-in nationwide, still located on the Historic Mother Road.
Route 66 Postcard Mural Trail in Illinois
Explore Route 66’s many charms by traveling the Route 66 Mural Trail, a collection of 11 Americana-themed murals dedicated to the southwest Illinois towns that landmark the route and honor the great American road trip.
The mural journey will take you to places like Virden, a stagecoach stop and deep-rooted coal-mining town, and Girard, where you will see original attractions like the 1940s Former Standard Station, a vintage Shell Station, and savor treats at the famous 1920s Doc’s Soda Fountain (now called Doc’s Off Route 66) or 1950s Whirl-A-Whip Restaurant.
Another popular stop is Staunton, which is home to several notable Route 66 attractions including the Route 66 Flea Market and Storage Giant Rocking Chair, Henry’s Rabbit Ranch- a whimsical Mother Road stop in the Route 66 Hall of Fame dedicated to Volkswagen rabbits, fluffy rabbits, and Route 66 memorabilia- and Country Classic Cars- a shop and museum unto itself dedicated to 20th century vehicles.
Be a part of the Route 66 renaissance by traveling the Route 66 Monument Trail, a set of eight larger than life Route 66 shields honoring the Mother Road and the great American road trip. Take a photo with each monument to celebrate 100 years of travel on this famous road.
Groups can make a stop in Carlinville, featuring one of the shields. Carlinville is also famous for the ‘Million Dollar’ Macoupin County Courthouse – one of the most extravagant courthouses in the country- and the Old Macoupin County ‘Cannonball Jail’– a slightly unorthodox prison allegedly structured with Civil War cannon balls in the walls to hinder escapees.
Another famed stop if Edwardsville, one of the largest cities of the Last 100 Miles of Route 66 in Illinois. Edwardsville has a slew of historic sites dating back to 1805. Among them are the legendary West End Service Station, which ran from 1927 to 1964 before becoming a dentist office until 2019. It was then purchased by the city and turned into a historic site and visitor center, in conjunction with Great Rivers & Routes Tourism Bureau.
West End Station is one of Edwardsville’s few remaining Route 66 landmarks and one of two original Route 66 service stations left in southwest Illinois, the other being Soulsby Service Station in Mount Olive.
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