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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.
The Trail of Tears Commemorative Park in Hopkinsville acknowledges the government-led effort in the 1800s to remove Indigenous people from their ancestral lands. The site was home to one of the many camps on the route from the Southeast to Oklahoma.
Before crossing the state line, continue south to Guthrie, birthplace of All the King's Men author Robert Penn Warren. His home is open for tours by appointment.
Guthrie, Kentucky to East Ridge, Tennessee (195 miles)
In Tennessee, US-41 follows the Red River where outdoors lovers can rent canoes to paddle the waterway—the courageous can explore the spooky Bell Witch Cave, home to rumors of supernatural activity.
It’s a short drive into energetic Nashville, known for its country music legacy. It’s easy to spend days here, but if you’re short on time, the Country Music Hall of Fame is your must-see, plus the famous hot chicken from Prince’s.
Catch a live music act at The Caverns, an underground venue in Pelham, or stop by one of the many distilleries on the Tennessee Whiskey Trail. After a hike to Monteagle’s Old Stone Fort, a park filled with massive boulders, settle in to a meal at the Smoke House in Monteagle, a restaurant from 1960 that is again operational after a 2021 fire. It also has motel rooms and cabins.
Near Chattanooga, you’ll start to see remnants of the highway’s heyday, specifically the Rock City advertisement barns painted on rural structures to bring visitors to the quirky mountain top attraction with its fairy village and scenic viewpoints.
East Ridge, Tennessee to Macon, Georgia (206 miles)
The Georgia section of US-41 has stretches of rural pasture and suburban Atlanta sprawl. In the northwest corner of the state, the drive passes through Dalton, where the chenille quilts sold on the highway’s roadside stands in the 1930s inspired the modern carpet industry.
Visit New Echota State Historic Site in Calhoun, a reconstructed village where the treaty was signed that led to the Cherokee removal on the Trail of Tears. The site hosts regular events that feature Indigenous artisans.
In the town of Cartersville, the Booth Museum of Western Art is not just a highlight of the town but of the region, with an incredible array of paintings, sculpture, and artifacts of the American West.
US-41 also cuts through Atlanta, another big destination with no shortage of things to do. But if you're passing through quickly, don’t miss the Trap Music Museum on the west side of the city. It focuses on the genre of hip-hop popularized by A-Town, with items from notable music videos and a bar for a post-tour cocktail.
Macon, Georgia to Dunellon, Florida (294 miles)
Driving south out of Atlanta the next big city is Macon, which attracted Southern rock acts like the Allman Brothers Band in the 1960s (not to mention their song “Ramblin Man,” which mentions the highway). But it’s also home to the Ocmulgee Mounds National Historical Park, an aspiring national park with Indigenous mounds dating back thousands of years.
Crossing into Florida, it feels like you’re in the heyday of the highway. While many of the classic roadside attractions have come and gone, many still remain like Weeki Wachee, a natural spring with a famous mermaid show, which is well worth the detour. Closer to the highway, Devil’s Den is a privately-owned spring for cave diving.
White Springs is a look into Old Florida, with its old-fashioned hardware store and charming Victorian homes. The Stephen Foster Folk Culture Center State Park is named for the composer and has miles of trails and river access for kayaking, plus a museum of dioramas inspired by his songs.
Dunnellon to Miami, Florida (309 miles)
Central and south Florida are where you’ll find plentiful ranches and farmland with stands to pick up your favorite citrus products. Driving into Tampa, you can’t miss the city’s Cuban restaurants like Brocato’s Sandwich Shop, where you can have one of the famous sandwiches without a detour. If you have time, tour the Ybor City neighborhood and its converted cigar factories.
The Showmen’s Museum in Riverview and the Ringling Museum in Sarasota honor the region’s longstanding history of carnivals and circuses. In Fort Myers, see where American inventors vacationed next door to one another at the Ford Edison Winter Estates, where the Model T brings to mind early American road trips.
In South Florida, US-41 is called the Tamiami Trail, an alternative to the stretch of I-75 nicknamed “Alligator Alley," which cuts through the Everglades and Seminole tribal land. The tribe runs its own attractions, including swamp tours and buggy rides through the forest. The small town of Ochopee and the Skunk Ape Headquarters, a nod to Florida’s version of Bigfoot, are funky detours.
The last stop on US-41 is the Little Havana neighborhood of Miami, where it’s the main thoroughfare. You’ll see famous landmarks of the Cuban neighborhood, including the famous Versailles Restaurant, open since 1971, and Maximo Gomez Park, where you’ll find locals playing dominoes. The highway ends on Brickell Avenue, where you can spend many more days soaking up sunshine—or continue further south to the Florida Keys.
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