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Road Tripping from Chicago to the Great Smoky Mountains

A road between the mountains
Fall colours

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.

Do this road trip in an RV to stay close to nature or opt for your own car/car rentals. Either way you won't regret going on this 5N/6D trip!

START: Day 1:- Chicago

Picture of the bean, Chicago
The Bean by @anish.kapoor

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 mesmerising 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.

You can cover all of this on 1 day, if you start early.

Day 2:- Louisville, Kentucky

Kentucky Club Mixture
Kentucky Derby

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.

KFC ball

The state is also home to the globally famous KFC (Kentucky Fried Chicken). KFC was founded by Colonel Harland Sanders (1890–1980), an entrepreneur who began selling fried chicken from his roadside restaurant in Corbin, Kentucky, during the Great Depression. Day 3:- Nashville, Tennessee

Night time picture of Nashville
Downtown Nashville

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 honour 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 recognise 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).

Day 4 & 5:- Gatlinburg, Tennessee

River flowing in the middle of the forest
The Great Smoky Mountains

Gatlinburg 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, distilleries, village squares, 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.

Best time to go on a road trip from Chicago to the Great Smoky Mountains National Park

The road trip from Chicago to the Great Smoky Mountains will be memorable whichever time of year you decide to go, which is all dependent on your preferences for the weather and the season.

If you choose to visit during spring, the crowds will be significantly smaller and hotel prices relatively low. Do bear in mind some attractions may be closed as they transition from winter.

The period between June and August is an excellent time to go on a road trip from Chicago to the Great Smoky Mountains. Expect to see lush greenery as you drive down the route and hit the mountains.

Summer has temperatures reaching as high as 80 degrees Fahrenheit, but in the mountainous environment of the Smokies, the uneven topography can see it drop to 20 degrees.

If you appreciate the beauty of foliage in the fall season, making the trip in autumn is for you. You can also catch Oktoberfest at Ober Gatlinburg, a festival of Bavarian food, drink, and music accompanied by the fabulous Smoky Mountains Oompah band.

Making the trip in the winter months will make for stunning viewing with the mountain peaks covered in snow. It's a popular time for winter sports lovers and skiing enthusiasts and the local Christmas markets make it extra special at this magical time of year

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