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Home Road Trip The 5 Best Stops on Your Chicago to Nashville Road Trip

The 5 Best Stops on Your Chicago to Nashville Road Trip

by Staff

Biergartens, Indy race cars and probably more Tang dynasty art than you’d expect

Road-Tripping From Chicago to Nashville: The 5 Best Stops Along the Way

Road-Tripping From Chicago to Nashville: The 5 Best Stops Along the Way

Trading out deep dish pizza and Loop-bound trains for Nashville’s country music and BBQ this summer? Before you book that flight, consider turning it into a good, old-fashioned, All-American road trip. Filled with top-tier dining, Instagram-worthy photo stops and world-class art museums, this drive will prove that there’s more to the Midwest than just miles and miles of corn fields. (But don’t get us wrong — there will be plenty of corn fields, too.) 

The Purdue Bridge at Purdue University.

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Lafayette, Indiana 

Your first can’t-miss stop is Lafayette, Indiana — best known as the home of Purdue University, but there’s plenty of fun to be had outside throwing back a beer at the school’s frat houses. Grab a homemade rugelach at European Bakery Scones and Doilies, and then head over for a tour of the Samara House, a Frank Lloyd Wright-designed home that’s been named a National Historic Landmark. The incredible home just reopened after two years of renovations, and whether you’re an architecture buff or you can’t tell your atria from your vestibules, this is solid activity. 

Not quite ready to hit the road? Fill up at The Bryant Food and Drink Company, a locally owned spot featuring brisket, burgers and Indiana-brewed beer. (And be sure to leave room for one of their famous milkshakes…or two. We won’t judge.) 

Indianapolis, Indiana, USA skyline over Monument Circle.

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Indianapolis, Indiana  

Indianapolis is so jam-packed with things to do that you may just need to make a separate roadtrip there to fit it all in. Kick off your time in the Racing Capital of the World with some time behind the wheel of actual Indy 500 race cars at The Indy Racing Experience. (Not quite ready to drive over 65 mph yourself? You can also opt to be a passenger alongside one of the Indy Racing Experience’s expert drivers.) 

Spend your afternoon at The Eiteljorg, a museum focusing on the art, history and cultures of the Indigenous peoples of North America and the American West. 

For dinner, you can’t go wrong with The Rathskeller, a German restaurant that features a traditional dining room, as well as The Kellerbar (a cozy beer bar) and The Biergarten (an expansive beer garden that features live events on Wednesday through Saturday). 

When you’re ready to call it a night, head to Bottleworks Hotel, a luxury hotel located in a former Coca-Cola bottling plant. Be sure to stop by The Garage — the hotel’s unique food hall — before check-out. 

Jefferson Street and Town Square in Downtown Louisville Kentucky.

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Louisville, Kentucky 

Louisville may be on the famous Bourbon Trail (and if that’s your thing, check out Bourbon Hall’s Kentucky Urban Bourbon Trail Tour), but that doesn’t mean there’s nothing to do in the city for the designated drivers. 

Art lovers will want to visit the Speed Art Museum, with a possibly surprising amount of ancient world artwork (like “Foreign Man,” an eighth-century Chinese sculpture) and then spend the night in 21C Louisville, a combination art museum/hotel that’s also home to renowned restaurant Proof on Main. (Honestly, you might just be able to spend the rest of your vacation days wandering around 21C Louisville). 

And don’t leave Louisville without a stop at Please and Thank You, a chocolate chip cookie cafe. (Do Future You a favor and grab a few extra to get you through any unexpected traffic.)

Mammoth Cave National Park.

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Cave City, Kentucky 

You didn’t think we’d let you get through a road trip without the chance to take pictures next to giant statues of dinosaurs, did you?! Dinosaur World offers hundreds of dinosaurs throughout the park, plus a once-in-a-lifetime chance to picnic next to them. (Can we recommend bringing a treat from Cave City Coffee and Creamery to enjoy while you ogle the roadside attractions?) 

Plus it wouldn’t be a stop in the aptly named Cave City without the chance to visit an actual cave. Check out Mammoth Cave National Park, which offers ranger-led tours and abundant wildlife. Stay in the rustic but comfortable Mammoth Cave Lodge or — to put a little more space between you and nature — head up the road to the Grand Victorian Inn, a Victorian mansion with elaborate decorations and unique, themed rooms. 

Lower Broadway in Nashville is a renowned entertainment district for country music.

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You’ve finally reached Nashville! And it wouldn’t be a stop in the Music City without going to the Country Music Hall of Fame

Inspired to become a famous country music star yourself? Don’t miss Jack White’s own Third Man Records’ 1947 Voice-o-Graph Recording Booth, a vintage machine that records two minutes of your voice and dispenses your very own 6-inch phonograph of the sound. (Call ahead to make sure the machine is working that day.) 

Grab dinner at Pelican and Pig, an award-winning restaurant that serves up food cooked in a wood-burning hearth, and then cruise over to The Station Inn, one of the top bluegrass venues in the country. Before you hit the hay, head to Cross-Eyed Critters, a karaoke bar where you’ll have the chance to sing karaoke in front of an animatronic back-up band. It doesn’t get better than that.

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