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Before the U.S. had a national highway system (courtesy of President Eisenhower in 1956), the “Dixie Highway,” now known as US-41, became one of the country’s first to guide travelers on interstate road trips. Built in 1915, it became the easiest way to travel from Chicago to Miami, with motels and souvenir stands popping up along the route.
Like other iconic roadways of the era, its heyday has come and gone. The more-efficient I-75—which runs alongside much of the US-41—opened in the 1970s, causing many of the aforementioned businesses to close as they were no longer on the main route. But driving the highway today promises a quieter, nostalgia-steeped experience.
If you want to see this route as generations before did, follow the traditions of “auto camps” by parking at one of the campgrounds along the way, or check into one of the remaining roadside motels—from Chicago’s circa-1960 Ohio House Motel, to Nashville’s Dive Motel and Miami’s Vagabond Hotel—which also promise updated decor and modern conveniences.
Below, we cover highlights along this nostalgic road, as it takes the form of rural backroad and major city thoroughfares through seven states. Consider it inspiration for a multi-day drive of your own.
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Chicago, Illinois to Evansville, Indiana (292 miles)
US-41 starts in the north, not far from Route 66, and follows along Chicago’s Lake Michigan shoreline. You can pop in for a drink at The Green Mill, a watering hole beloved by gangster Al Capone, catch a game at Wrigley Field, and grab a slice of deep dish pizza.
In Indiana, the road winds south through the Chicago suburbs before opening up into farmlands in the western edge of the state. Roadside stands offer produce like tomatoes, blueberries, and corn, depending on the season.
Stop in Morocco to see bison roam the prairie at the Kankakee Sands nature preserve. Open from 7 a.m. to dusk, it includes over 8,000 acres owned by the state chapter of the Nature Conservancy.
Between Veedersburg and Terre Haute, you can detour to dozens of covered bridges that bring New England to mind. In Bruceville, stretch your legs and enjoy a photo op at the Big Peach, a large replica of the fruit in front of a store selling locally made baked goods and gifts.
Evansville, Indiana to Guthrie, Kentucky (108 miles)
Cross the Ohio River into Henderson, which is a significant location because it was where John James Audubon lived in the 1810s, doing research on the animal species there. It’s now Audubon State Park, a 700-acre site encompassing hiking trails through an old growth forest. His former home is now the Audubon Museum & Nature Center, featuring his early paintings.
