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Route 66 attractions you shouldn’t miss

The iconic Route 66 runs for nearly 600 miles (965km) through Illinois and Missouri and takes travelers through history and culture of America.

Pontiac on Route 66
Route 66 in Pontiac, Illinois (Credit: Adam Alexander / Illinois Office of Tourism)

Explore the Mother Road in Mississippi River Country—legendary Route 66 runs for nearly 600 miles (965km) through Illinois and Missouri in America’s Midwest and takes travelers through the iconic history and culture of America. Route 66 isn’t one road in these destinations, but rather a collection of state highways and federal highways and interstates that approximate the route of the former highway. Here are a few iconic stops along the route.


Route 66 sign, Chicago

There’s some debate about where Route 66 actually “starts”–some say it’s at the shores of Lake Michigan, others say it’s at Lou Mitchell’s diner farther west in downtown Chicago–but one thing’s for sure: pretty much everyone interested in the road takes a picture of the “Route 66 Begin” sign near the corner of Adams Street and Michigan Ave in Chicago. The sign, put up by the Chicago Department of Transportation is for traffic heading west, so it’s on the south side of the street. (It also routinely gets so covered with stickers that it has to be replaced.) There are also a couple of older brown signs in the area and a newer sign at a park at Adams Street and Wabash Avenue.

Route 66 Association Hall of Fame & Museum

Follow Route 66 southwest out of Chicago (along Interstate 55) for about two hours and you’ll arrive in the charming town of Pontiac, Illinois—home to the Route 66 Association Hall of Fame & Museum. This unique museum features thousands of pictures, posters, signs and other memorabilia related to Route 66, including the bus and van of famous Route 66 explorer and artist Bob Waldmire. Don’t miss the photo op of the Route 66 shield mural on the back of the building. Walk around Pontiac’s town square to see other murals and unique attractions like the Pontiac Oakland Auto Museum and the International Walldog Mural & Sign Art Museum.

Cozy Dog Drive-in, Springfield

Another hour or so down I-55 will take Route 66 riders to the famous Cozy Dog Drive In, a famed stop along Route 66 in Illinois’ capital city. This classic diner was the birthplace of the “hot dog on a stick”—also known as the corn dog—in 1949, and it’s been serving up this quintessentially American treat ever since. The Cozy Dog also houses a large collection of Route 66 memorabilia and an on-site shop so you can commemorate your visit.

Learn more about Route 66 in Illinois.


Chain of Rocks Bridge, St. Louis

This historic bridge, which spans the Mississippi River between Illinois and Missouri, was a significant landmark for visitors traveling Route 66. The name comes from the 17-mile (27km) stretch of rocky rapids along the river that starts north of St. Louis (a low-water dam built in the 1960s hides the rocks from observers now). The iconic bridge, which sits 60 feet above the Mississippi River, also has a 30-degree turn midway through, thanks to technological and geological issues encountered by engineers. The Chain of Rocks Bridge closed to auto traffic in 1968 but reopened as a biking and walking path in 1999 and was named to the National Register of Historic Places in 2006.

National Museum of Transportation

What would a trip along Route 66 be without a chance to see some classic cars? The National Museum of Transportation in the St. Louis suburb of Kirkwood has a special collection dedicated to Route 66. The museum isn’t just focused on cars, though; among its collection of more than 300 vehicles are steam locomotives, freight cars, streetcars, buses, aircraft and boats.

Route 66 Museum, Lebanon

Located in the Lebanon-Leclede County Library, this self-guided museum features recreations of a 1950s gas station and a classic diner travelers would have encountered on Route 66, as well as displays of antique cars and Route 66 books, magazines and videos.