When the U.S. Bureau of Public Roads created the first federal highway system in 1926, all eyes were on Route 66, the 2,448-mile thoroughfare connecting Chicago to Santa Monica. Known as the Mother Road, Route 66 was a symbol of freedom and discovery, emblematic of road tripping’s golden age and, to this day, deeply embedded in Americana culture.
Celebrate the route’s centennial this year by traversing it firsthand along the 301 miles in Illinois, the state where it all began. Kick off at its official starting point at Chicago’s Navy Pier, roll down the windows, turn up the volume, and enjoy the towns that helped shape “America’s Main Street.”
See street art in Pontiac
Pontiac, Illinois
Courtesy of Enjoy Illinois
Begin your journey in Chicago. Take in some of the Second City’s skyline views, then hit the road, cruising west towards Pontiac. This charming town is home to the Route 66 Association of Illinois Hall of Fame & Museum, where you can explore the history of the Mother Road through memorabilia, stories, and photo ops.
Enjoy downtown’s eye-catching murals and dedication to the arts (in warmer months, see if you can spot the 15 miniature cars, including 10 replica ‘57 Chevys). When hunger strikes, fuel up at Acres Inn, a local favorite for burgers and hearty chicken sandwiches.
Discover state history in Springfield
The Old State Capitol in Springfield, Illinois
Courtesy of Enjoy Illinois
Continue your drive to Springfield, and upon arrival, check in for the evening at the Pasfield House, a historic mansion and boutique hotel just steps from the town’s top attractions. Settle in before dinner at Luminary Kitchen & Provisions, known for its in-house charcuterie program and thoughtful cocktails.
Come morning, grab a latte from Custom Cup Coffee and explore the sights, including Lincoln Tomb, the Abraham Lincoln Presidential Library and Museum, and the Old State Capitol State Historic Site. On your way out of town, stop for a bite at Cozy Dog Drive In—the perfect fuel for the trip.
Go antiquing in Livingston
Soft serve at the Twistee Treat Diner in Livingston, Illinois
Courtesy of Enjoy Illinois
Stop for a visit in the village of Livingston, known for its Pink Elephant Antique Mall. Discover an array of vintage finds, and its best-known items: large-scale, fiberglass statues. Take a break for burgers and fries at the Twistee Treat Diner, then try the fudge and saltwater taffy at Mother Road Fudge-n-Candy, a favorite for sweet souvenirs.
Enjoy the views in Alton
This small Mississippi River town has big history—it’s home to the world’s tallest man (Robert Wadlow) and jazz legend Miles Davis. Enjoy the views from Melvin Price Locks and Dam at the National Great Rivers Museum, and take in the Great Rivers and Routes region.
Here, the Mother Road meets the Great River Road, at the confluence of America’s three great rivers. It’s the only place in the U.S. where two of its great roadways come together alongside three of its great rivers. If you’re here during winter months, look up—Alton is in one of the best areas in the country to see bald eagles from December through early March.
Enjoy dinner and live music at Fast Eddie’s Bon Air and a stay at the historic Beall Mansion before making your way back to the Windy City or continuing wherever the road may take you.
