Cruise Into Celebrating the Route 66 100th Anniversary

Rev your engines for a ride along Route 66 as the iconic highway celebrates 100 years in 2026. Spanning eight states, including Illinois, the 2,400-mile route was once one of the most traveled roads in the country, earning it nicknames including “Main Street of America” and the “Mother Road.”

In Illinois, Route 66 began in Chicago and ran diagonally through the state, making history as the first hard-surfaced road that traveled from the Windy City to St. Louis. Largely replaced and decommissioned by Interstate 55 in 1985, its legacy is now maintained by cultural landmarks along the route, and several original segments were preserved as the Illinois Historic Route 66 Scenic Byway.

Today, visitors can reminisce about the olden days with stops in several cities along the original Route 66.

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Chicagoland Cruising

Start your journey in Chicago at the official Historic Route 66 Begins Here sign, located at 122 S. Michigan Ave. The spot features a large Route 66 shield and plaque, making for a great photo op. As you travel through Willowbrook outside of Chicago, Dell Rhea’s Chicken Basket is the perfect spot for lunch. This family-run business has been famous for its fried chicken since 1939 and was inducted into the Route 66 Hall of Fame in 1992.

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Puttering to Pontiac

Pontiacholds plenty of Route 66 history. On Howard Street, housed in a historic firehouse, the Route 66 Association Hall of Fame & Museum showcases thousands of significant artifacts and memorabilia. Guests can enjoy exhibits including Route 66 – A Photo Journal, Life in the 1940s and the Bob Waldmire Experience, which traces the artistic development of the iconic Route 66 artist. The experience even includes Waldmire’s famous Volkswagen van and Road Yacht, a 1966 school bus he converted into a traveling studio. The museum is also home to the largest Route 66 shield mural in the state, one of 23 outdoor murals throughout the city depicting its history.

Continue your education at the Pontiac-Oakland Automobile Museum and Resource Center on North Mill Street. Opened in 2011, the museum houses one of the world’s greatest collections of Pontiac and Oakland brand automobile artifacts.

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Lollygagging in Logan County

As you make your way into Logan County, don’t miss the Logan County Courthouse in Lincoln. Three courthouses have stood in this location: The first burned down, and the second served the town until 1903, when construction began on the present structure. The first two were active during President Abraham Lincoln’s time as a lawyer.

Along with the courthouse, Logan County has several unique roadside attractions, including a 19-foot-tall Paul Bunyan statue that features the folk hero holding a hot dog; the World’s Largest Covered Wagon, measuring 25 feet tall and 40 feet long; and a Smiley Face Water Tower with a bright yellow façade.

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Spring Into Gear

Stop by Funks Grove Pure Maple Sirup near Bloomington-Normal for farm-fresh maple syrup, fresh fruit, pure maple sugar, ice cream and more. Then head into Springfield for lots of Route 66 fun.

The Illinois Route 66 Experience at the state fairgrounds is an educational exhibit open year-round. Visitors can embark on a self-guided tour highlighting businesses in 92 communities along the highway, beginning in Chicago and ending in Madison. History lovers will appreciate the vintage billboards, drive-in movie theater, Legends Neon Sign Park and tribute to muffler men. Also at the state fairgrounds, a giant, 40-foot-high slide dons the Route 66 shield, so guests can literally “Slide Down 66.”

If you’re looking for a family-friendly nostalgic pastime, don’t miss Springfield’s Route 66 Twin Drive-In, open April through October for movies under the stars. Finally, the state capital includes the must-see Lauterbach Giant – a giant fiberglass “muffler man” standing in the parking lot of Lauterbach Auto Service. Erected as a beacon to America’s motorists, the statue originally featured the man holding a tire but now showcases an American flag.

Next up in Sangamon County, Auburn includes a rare, 1.4-mile preserved segment of the famed highway’s hand-laid bricks. Listed on the National Register of Historic Places, it gives a glimpse of what early American road travel was like. Along the curve of the road, you’ll find a grain bin with another stunning Route 66 mural.

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Other Roadside Attractions

Litchfieldis home to the Litchfield Museum and Route 66 Welcome Center, where visitors can learn about the town’s history and its impact on the wider world. Ariston Cafe, the oldest restaurant along Route 66, is another great stop. It opened in 1924 and still serves delicious food.

As you cruise through Livingston, stop by the Pink Elephant Antique Mall for treasures of the past, then take a photo at the World’s Largest Catsup Bottle roadside attraction in Collinsville.

Arcadia, which calls itself America’s Playable Arcade Museum, is located in McLean, featuring pinball machines, arcade games and more from the Route 66 heyday. McLean also has a Route 66 retro pinball-themed mural that stands five stories tall.

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