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6 Best Road Trips

Chicago to Nashville and Great Smoky Mountains Road Trip

Stop at a shiny bean, an underground corridor, a racetrack and a music mecca on your way to the national park.

Get ready for an incredible journey into the South’s top attractions and best-kept secrets in this road trip that begins in Chicago and leads you to the nation’s most visited national park, Great Smoky Mountains National Park.


Start: Chicago, Ill.

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Cloud Gate in Chicago's Millennium Park.
Cloud Gate in Chicago’s Millennium Park.Deposit Photos

What makes Chicago one of the best cities to visit is that it has a cosmopolitan feel with none of the attitude of similar-sized cities on the coasts. Its bustling energy is countered by the friendliness of the people, which can catch you off-guard if you are not from the Midwest.

Where’s the best place to start exploring this city that sits on the turquoise shores of Lake Michigan? Take an architectural boat tour to get a strong sense of the city’s past and present. The docents are super entertaining and informative. There’s few better ways to enjoy a hot summer day than to be on the water. Having said that, if the humidity is predicted to be really high, plan your boat trip for the morning before the sun gets too high in the sky.

Then head to the city’s celebrated Millennium Park downtown. A showcase of who’s who in architecture, this interactive park is an adult playground. As you wander around, be sure to see these three architectural attractions.

You’ll spot Cloud Gate, a kidney-bean-shaped sculpture that’s 66 feet long and 33 feet high, from a distance as its metal gleams in the sunlight. If you’ve ever seen a Tiffany’s bean necklace, this sculpture bears a striking resemblance. Made with polished stainless steel, the sculpture features an arch that enables you to walk under it and see your contorted reflection in the steel walls. It’s the first public outdoor work of British artist Anish Kapoor to appear in the United States.

If you are a music lover, head to a show at the Jay Pritzker Pavilion. Designed by architect Frank Gehry, this outdoor concert venue has 4,000 fixed seats and room for an additional 7,000 people on the Great Lawn. Bring a blanket to sit on and enjoy the tunes (and the excellent people watching).

Next, stop by the mesmerizing Crown Fountain, which features the faces of 1,000 Chicago residents on two 250-foot glass towers, each one at the opposite end of a shallow reflecting pool. Designed by Spanish artist Jaume Plensa, the towers feature water flowing out of an outlet, which gives the illusion that water is pouring out of the mouths of the faces appearing on each tower.

Louisville, Ky.

Horses at Churchill Downs in Louisville, Ky.
Horses at Churchill Downs in Louisville, Ky.Adobe Stock

Head south 4 hours and 45 minutes to Louisville, Ky. Long known for its legendary Churchill Downs, home of the Kentucky Derby and the longest continually running sporting event in the country. Churchill Downs officially opened in 1875, but the sport of horse racing can be traced back to 1789 in Kentucky.

An important thing to know is the city’s name is actually pronounced “Luhlville” by the locals and everyone else in Kentucky. To avoid being snickered at by locals, resist the natural impulse to pronounce the name as it appears [Loueyville]. It’s Luhville to you.

There are certain things you must do like experience the Kentucky Derby at Churchill Downs, if you happen to be in town April 29-May 5, 2017. You can also catch up on equestrian history at the the Kentucky Derby Museum.

The Mega Cavern underneath Louisville, Ky. Photo by H. Michael Miley via Flickr
The Mega Cavern underneath Louisville, Ky.Photo by H. Michael Miley via Flickr

But to truly experience Louisville, you need to go underground. Really. At Louisville Mega Cavern, you’ll have an adventure like none other, exploring some of the 17 miles of corridors beneath the city. Entertaining guides bring you deep into the cave for an up to 2.5-hour tour, explaining the geology and history of the cavern. There’s also six underground zip lines that make up the world’s only fully underground zip line course. The cavern is actually man-made and offers experiences for the whole family.

Nashville, Tenn.

Neon signs on Lower Broadway Area of Nashville
Neon signs on Lower Broadway Area of NashvilleDeposit Photos

After coming up for air, hit the road and point your wheels toward Nashville. Just two and a half hours southwest of Louisville lies Nashville, the country western capital of the country. A trip to Nashville is not complete without immersing yourself in its vibrant music scene. After all, the city boasts “free music all the time.”

See if you can catch a show at the legendary Grand Ole Opry where pop artists and country singers perform or head to a smaller venue like The Bluebird Cafe to see incredible live music in a really intimate space. Then, stretch your legs, head to the Music City Walk of Fame on Nashville’s Music Mile to see the names of accomplished artists with a Nashville connection of all musical genres.

It turns out you don’t have to head to Athens, Greece, to see the Parthenon, which was completed in 432 B.C. to honor the goddess of Athena. Nashville has its own replica of the Parthenon at the 132-acre Centennial Park and Gardens, which is located within walking distance from Vanderbilt University. If you saw the 1975 movie Nashville, you’ll recognize this iconic structure.

While in the park, see videos of different Nashville music artists talking about trees, how to take care of them and why they are important. The series is called “If Trees Could Sing,” and it’s the result of a Metro Parks and The Nature Conservancy partnership. Look for the tree signs around the park with QR codes and web addresses. Then use your smartphone to view the Nashville artists sharing tree stories.

Other attractions include The Johnny Cash Museum, National Corvette Museum and the Nashville Flea Market (held the fourth weekend of every month).

Pigeon Forge / Gatlinburg, Tenn.

Gatlinburg, Tennessee
GatlinburgDeposit Photos

Gatlinburg, Tenn, is the busiest, most touristy gateway to Great Smoky Mountains National Park. Chock-full of souvenir shops, craft stores, restaurants, and kitschy attractions (think Ripley’s Believe it or Not!), the bustling towns can be a sensory overload or a rollicking good time, depending on your perspective. Here you’ll find plenty of hotels, grocery stores, and gear shops.

But you can also get away from it all at a unique lodging option with Under Canvas. Glamping, short for “glamorous camping,” is a luxury experience in tents equipped with the creature comforts of home. And you can now go glamping near Gatlinburg, Tenn. Here are five reasons why you should.

Pink Adventure Tours at Newfound Gap in Great Smoky Mountains National Park
Newfound Gap Tour with Pink Adventure ToursPink Adventure Tours

Think Pink
When you board one of Pink Adventure Tours’ signature pink Jeep Wranglers, you’ll soak up more information than you thought possible on your Smoky Mountains tour. Catch a tour from Pigeon Forge.

Blount County, Tenn.

Sunrise at Cades Cove in Great Smoky Mountains National Park.
Sunrise at Cades Cove in Great Smoky Mountains National Park.Deposit Photos

Three hours east of Nashville, clocking in at 180 miles, make a pit stop in Knoxville. The city’s Market Square is a fantastic place to spend some time as the restaurants and shops lining the area are great.

From here you are just 18 miles from Maryville in Blount County, one of the gateway counties to Great Smoky Mountains National Park. In fact, the nearby park entrance at Townsend is closer to Cades Cove, a preserved pioneer community, than the Gatlinburg entrance (7.3 vs. 27 miles). Cades Cove is the most popular destination in the national park due to its plentiful wildlife and many historic buildings you can explore.

Nestled in the foothills of the Great Smoky Mountains, the county’s towns of Townsend, Maryville, Alcoa, Friendsville, Louisville and Rockford offer travelers a ton of things to do from regional dance and theater performances at the Clayton Center for the Arts in Maryville to in-depth history of the Smoky Mountains at the Great Smoky Mountains Heritage Center in Townsend. And history buffs will feel right at home with these historic treasures.

For an incredible scenic drive, take the two-lane Foothills Parkway located off Hwy. 321 just west of Townsend 18 miles up Chilhowee Mountain. Started in the 1960s, this parkway is still a work in progress with only sections of the 72 miles stretch completed.

Nonetheless, It offers a panoramic view of the park and is less visited than other roads in the area. Follow signs along the parkway for a picnic area, campground and Look Rock. Stretch your legs on the .5-mile observation trail that is 9.6 miles from the start of the parkway. It’s rated easy and offers visitors great scenery without having to exert themselves too much.

End: Great Smoky Mountains National Park

Enter the park at the Townsend entrance and follow Laurel Creek Road to Cades Cove. View our suggested park itineraries.