On November 11, 1926, a numbered highway was born, running 2,448 miles from Grant Park in Chicago to the Pacific at Santa Monica. A century later, Route 66 is less a road than a story America tells about itself — and in 2026, Illinois is throwing the birthday party.

Here’s the thing most travelers miss: the Mother Road starts here. The first hundred miles run from downtown Chicago through the southwest suburbs — straight down Joliet Road, past our front door in Countryside — before rolling on toward Springfield and St. Louis. If you want to celebrate the centennial where the road begins, this is the guide.

And yes, we’re biased. The William Tell Hotel has stood on this alignment of Route 66 for more than fifty years. Read our story here. The centennial is personal.

The Big Dates Still Ahead in 2026

• Illinois State Fair Route 66 Experience — August 13 to 23, Springfield. The fairgrounds put the road at center stage this year, including the Legends Neon Sign Park, a permanent collection of restored roadside neon.
• International Route 66 Mother Road Festival — September 25 to 27, Springfield. The state’s signature Route 66 weekend: thousands of vintage cars, live music, and three days of unapologetic Americana.
• Last 100 Miles Festival — October, southwest Illinois. Community celebrations across the towns that carry the route to the Mississippi.
• Miles of Possibility Conference — October, Springfield. For the true roadies: historians, preservationists, and tourism folks comparing notes on the road’s next century.
• The Centennial itself — November 11, Springfield. A full-day conference capped by the Epic Centennial Celebration and awards gala. One hundred years to the day.

Check the state’s official listings before you travel, as details firm up through the year, via the Enjoy Illinois Route 66 events page and the route66centennial.org Illinois calendar.

The First Hundred Miles: What to See Near Chicago

You don’t need to drive to Springfield to touch the centennial. The stretch between Chicago and Joliet has quietly become one of the best-curated sections of the entire route:

• Route 66 Shield Monuments. Sixteen communities along the first hundred miles are installing permanent centennial shield monuments — including right here in Countryside, alongside Berwyn, Willowbrook, Joliet, Pontiac, and more.
• Old Joliet Prison. The gates made famous by The Blues Brothers now welcome photographers instead of inmates, and Joliet’s Broadway Greenway adds restored neon and murals nearby.
• The Gemini Giant. Wilmington’s beloved 30-foot spaceman has a new home at South Island Park, with The Landing Pad souvenir shop close by.
• The Illinois Rock and Roll Museum. In Joliet, under a 24-foot guitar-shaped sign they call the Gigantar.
• Ogden Avenue wayfinding. New signage through the near-west suburbs marks the historic alignment for the centennial.

Make a day of it: start at the Begin Route 66 sign in downtown Chicago, follow Ogden and Joliet Road southwest, and count the shield monuments as you go. The first one after the city limits? You’ll pass our corner at La Grange Road.

You’ll sleep in a landmark that has watched this road for half a century, eat at Tell’s Tavern downstairs, and start the next morning already on the route. Let the past meet your present. Check availability.

Traveling with family? Brookfield Zoo is ten minutes away.