Road trip loop: Explore America’s musical roots across five states

Note from 10Best: Check with individual businesses and attractions before going, because of sporadic closures due to COVID-19.

The transformative nature of a live music experience is singular. A Facebook Live performance of the New York Metropolitan Opera or YouTube videos of old Johnny Cash gigs are great, but they just don’t tickle serotonin receptors like the throb of drums and bass vibrating right through a body.


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Why not combine your appreciation of travel and music born and bred in the USA with a five-state road trip loop that transports you through blues and rock to country, bluegrass, soul and the Great American Songbook? Launch your symphonic road trip at any point in the loop that visits Chicago, St. Louis, Memphis and Nashville, Kentucky and Indiana.

Drive times between cities are eminently doable in one pass, but there are places to stop to stretch the legs and have a regional bite in between. Count on museums stocked with magical musical archives; retro, stylish and rustic places to recharge; and dishes Elvis, Bill Monroe, Chuck Berry and Loretta Lynn would approve. Because what makes people happier than music and food? Call ahead about live performance possibilities.

In total, this trip will cover a little more than 1,300 miles and include about 22 hours of driving, however, we have a few suggestions that take you off the interstate to slow the pace and experience some of the South, too.

Part 1: Chicago, Illinois to St. Louis, Missouri

4.5 hours, 297 miles on I-55

Music to download for the ride: “(Get Your Kicks on) Route 66” by Nat King Cole and tunes by St. Louis natives Nelly, Chuck Berry, Fontella Bass, Miles Davis, Uncle Tupelo or John Hartford

You can plow right through the 4.5-hour drive from Chicago (the longest drive on this road trip) or stop about halfway in central Illinois’ Bloomington/Normal. See the historic Sprague Super Service Station in Normal and peruse the Route 66 Visitor Center in downtown Bloomington.

Back onto 55, exit into tiny McLean (about 20 minutes away) and refuel at a famous old Route 66 eatery, The Dixie Family Restaurant. The truck stop began as a mechanic’s shop/sandwich stand in 1928, and today, locals and travelers go for the inexpensive country cooking, all-day breakfast and tempting buffet.

St. Louis calls itself “the birthplace of the blues,” but its rock ‘n’ roll pedigree ain’t too shabby either. Stroll along the Delmar Loop, where city natives have stars on the St. Louis Walk of Fame, including Chuck Berry whose statue is nearby.

Enjoy a drink, burger or vegan options at Blueberry Hill Restaurant & Music Club, a St. Louis landmark where Berry duck walked across the stage more than 200 times. Its Duck Room offers live music several nights per week and the venue includes scads of the Father of Rock & Roll’s memorabilia. Nearby music halls, such as The Pageant and Delmar Hall, host rock, roots, country and indie artists.

Music fans won’t want to miss the compact yet immersive National Blues Museum. In addition to highly interactive exhibits (like creating your own blues riff in a mixing booth) and fascinating artifacts, the museum frequently hosts live music. Jack White made a financial contribution which funded the “MIX IT UP” creative Blues experience within the museum.

For dinner and a show, BB’s Jazz, Blues & Soups and Broadway Oyster Bar are the focal points of St. Louis’ Blues Triangle. Broadway Oyster Bar serves Cajun classics plus nightly live music and a buzzing outdoor patio. Take in jazz, blues and swing shows with cabaret-style seating and a Southern menu at BB’s Jazz Blues Soups.

Venice Cafe is a cash-only bar/performance venue adorned with folk art mosaics outside and in. Hit up 1860’s in Soulard for live music in the saloon that boasts a 100-plus-year-old back bar. Soulard is listed on the National Register of Historic Places and is the oldest thriving residential neighborhood in St. Louis.

Before you head out of town, check out Vintage Vinyl, considered one of the 10 best record stores in the country.

Stay at the trippy Moonrise Hotel right in the Delmar Loop neighborhood. Expect iridescent lobby walls, a multi-colored lighted staircase, lots of art and an indoor/outdoor rooftop venue with outstanding views.

If the Moonrise isn’t your scene, Hotel Saint Louis is an 1893 historic landmark and one of only 30 Louis Sullivan-designed buildings left in the world. Each room has a record player and a selection of records. Budget lodging includes any of the Drury Hotels, offering free breakfast, happy hour and Wi-Fi.

St. Louis-centric bites to sample include regional pizza that uses Provel cheese (Imo’s is a good bet); frozen custard at Ted Drewes; toasted ravioli; St. Louis-style ribs; an inexpensive St. Paul sandwich available at Chinese restaurants (it’s an egg foo young patty sandwiched between white bread and topped with mayo, pickles and lettuce); and sinful gooey butter cake.

The St. Louis Slinger, served at diners, consists of a couple of eggs, hash browns and a hamburger patty smothered in chili, cheese and onions – something you might not want to digest on your way to Memphis unless you can keep the windows open.

Part 2: St. Louis, Missouri to Memphis, Tennessee

Around 4 hours, 284 miles on I-55

Music to download for the ride: “Five Feet High and Rising” by Johnny Cash and “Graceland” by Paul Simon. Tunes by Elvis Presley, Roy Orbison, John Lee Hooker, Sam & Dave, Booker T and the MG’s, Otis Redding and ZZ Top.

About 45 minutes before reaching Memphis, consider a stop at the childhood farmhouse of Johnny Cash just outside of Dyess, Arkansas (it’s just eight minutes off of I-55 on exit 41). You might recognize it from the 2005 film “Walk the Line” or in Cash’s song, “Five Feet High and Rising.”

Drive by the home or buy tickets at the Dyess Colony Museum, then take a shuttle bus to the farmhouse for a tour. For local flavor, stop at Clara’s Midway Cafe and try to decide between family recipes of fried catfish, chicken and dumplings or a slice of homemade coconut cream or pecan pie.

Don’t just fill up your tank and take off – some local gas stations serve items like pimento cheese sandwiches, fried chicken and plate lunches.

Once you arrive in Memphis, drop your gear at the Priscilla Presley-designed Guest House at Graceland (steps from the Graceland Mansion) or the Central Station Hotel in downtown. It’s still an active train station with connections to Chicago and New Orleans.

The listening lounge bar offers a curated playlist and live DJ playing music with a Memphis connection. There’s also a small listening room behind the bar where you can choose among over 2,000 records.

There is so much music and musical history to discover in Memphis, you can’t do it all in one day. Choose from touring any of the following:

By now, you’ll be itching to hear some live tunes, so head to the Historic Beale Street Entertainment District. The National Historic Landmark was declared the “Home of the Blues” by an act of Congress and has witnessed the likes of Louis Armstrong, Muddy Waters and B.B. King.

Stroll the street with music and jam sessions echoing from restaurants and clubs. If you’re like me and don’t warm to following the crowds, go beyond Beale with this list of local hangouts, dive bars, patios, songwriter nights, music halls and late-night hotspots.

Memphis is home to over 100 barbecue restaurants, but if time is not on your side, try Charlie Vergos’ Rendezvous – it’s easy to find (just across the street from the Peabody Hotel Memphis) and its famous dry rub seasoning has been delighting diners since 1948.

Old-timey Cozy Corner attracts barbecue fans from all over the world (try smoked bologna sandwiches, petite Cornish game hens and tangy ribs).

Historic Four Way Grill in the Soulsville neighborhood was a favorite of Dr. Martin Luther King, Jr., B.B. King, Elvis and Aretha Franklin. Try the fried green tomatoes, platters of vegetables, salmon croquettes, smothered pork chops or make a meal from a roster of sides – it’s all good.

For southern breakfast or brunch, head to the oldest restaurant in town, The Arcade (circa 1919). It made cameo appearances in films like “Great Balls of Fire,” “Walk the Line” and “Elizabethtown.”

Part 3: Memphis, Tennessee to Nashville, Tennessee

3 hours and 15 minutes, 212 miles on I-40

Music to download for the ride: “Nashville Cats” by The Lovin’ Spoonful; “Down on Music Row” by Dolly Parton; “Wrong Side of Memphis” by Trisha Yearwood; “Sundown In Nashville” by Marty Stuart; “Crazy Town” by Jason Aldean; and “Nashville Bum” by Waylon Jennings.

There’s so much awaiting music fans in Nashville, we suggest sailing down I-40 straight away to get to Music City. However, you could detour to Loretta Lynn’s Ranch (seven miles north of I-40 on Highway 13, around 75 miles west of Nashville) in Hurricane Mills, Tennessee.

Tour an exact replica of Lynn’s Butcher Holler, Kentucky home; browse the shops and museums; or even camp or get a cabin onsite for the night. It’s touristy, to be sure, so weigh your timetable.

Nashville has become the Disney World of music venues and museums, so like a trip to a theme park, you should have a plan. Settle on at least two days in Nashville to see and hear just some of what tickles your neurons.

Who’s your favorite country artist? There’s a museum for him/her: the wonderfully quirky George Jones Museum which also has a bar and smokehouse; Johnny Cash Museum; Patsy Cline Museum; and the Glen Campbell Museum.

But that’s not all. There are so many other country music attractions to check out:

Check the calendar and purchase tickets in advance to the BlueBird Cafe, one of the sweetest venues to hear live music in an intimate space. In addition, the 50-year-old, family-owned Exit/In has welcomed artists from Etta James and Linda Ronstadt to Talking Heads, Kings Of Leon, Lucinda Williams and Cage The Elephant. The venue is across from Vanderbilt University in the heart of the historic “Rock Block.”

Celebrating 100 years, Springwater Supper Club & Lounge is the oldest continuously open bar in Tennessee and it hosts live music seven nights a week. Alternatively, nearly every night of the year, locals and visitors can experience live bluegrass, Americana and Roots at The Station Inn.

Nashville offers every level of accommodations from the casual Moxy and Graduate to the Grand Hyatt and Virgin Hotel located on Music Row. Think about holing up at one of the half-dozen boutique hotels in historic Printers Alley – it’s downtown, an easy walk to attractions and has plenty of choices for food and drink.

The Dive Motel is a fun, heavily wood-paneled place to snooze with 23 one-of-a-kind rooms, an outdoor pool and a dive-y lounge (natch).

Don’t leave town without trying Nashville Hot Chicken (Hattie B’s if you don’t mind a wait). Swett’s is a must for southern food served cafeteria-style since 1954. Arnold’s Country Kitchen is a favorite for “meat and three” platters.

Elliston Place Soda Shop is an 80-plus-year-old soda shop and southern meat-and-three eatery that doesn’t disappoint. The banana pudding and Chess pie are bites you may covet for the rest of your life.

Part 4: Nashville, Tennessee to Owensboro, Kentucky

About 2 hours, 134 miles on I-65 and I-165

Music to download for the drive: Bluegrass music, especially by Bill Monroe, Doc Watson, Alison Krauss and Union Station, Flatt & Scruggs, and the Nitty Gritty Dirt Band.

After the sensory overload of Nashville, a leisurely two-hour drive takes you to Owensboro, Kentucky, known as the birthplace of bluegrass. Soak in exhibits, live performances, art, costumes and films about the Kentucky art form at the Bluegrass Music Hall of Fame and Museum.

The venue’s outdoor stage hosts live concerts in a pastoral area overlooking the Ohio River. The annual ROMP Festival featuring the best in bluegrass leaves visitors pickin’ and grinnin’ (typically held in June, but moved to September for 2021). Bring your instrument if you play because there are jam sessions and artist-led workshops.

Pencil in a stop at the birthplace of the Father of Bluegrass, Bill Monroe (a guided tour may be given by someone who knew Bill and his family).

Milligan’s Bar promises live music most nights, and this is bourbon country after all, so stop into one of the oldest bourbon distilleries in the world, Green River Distilling Company to taste or tote some back home. Then, take a picture of yourself near the largest known Sassafras tree in the world – it’s around 300 years old.

For southern comfort food, check out casual diners like Madewell’s Corner Cafe and Dee’s Diner. There are a handful of old-fashioned drive-ins for burgers and shakes. Barbecue also abounds at Ole South Barbeque, while six generations of meat men stoke the fires at Old Hickory Bar-B-Q.

The city offers many mid-priced chain hotels, some on the riverfront, as well as pristine campgrounds including Windy Hollow Campground and Diamond Lake Resort, which offers campsites and cottages.

Part 5: Owensboro, Kentucky to Carmel, Indiana

Around 3.5 hours, 230 miles on I-64 and I-65

Music to download for the drive: Streaming services like Spotify have playlists of the Great American Songbook. Otherwise, music by Duke Ellington, Irving Berlin, Harold Arlen, Cole Porter, Hoagy Carmichael, Ella Fitzgerald and Frank Sinatra.

Why are we driving to Carmel, Indiana? The town just north of Indianapolis has an impressive art scene, a plethora of walking and biking trails, and plenty of tasty, local food options. And music lovers are keen to visit to better understand the rich cultural basis for American pop.

The Hotel Carmichael pays tribute to Michael Feinstein, the singer, pianist and preservationist renowned for his founding of The Great American Songbook Foundation.

The property braids musical influences throughout with framed sheet music, playbills and paintings of musicians punctuating the walls. And the grand piano in the lobby bar plays songs from the Great American Songbook (4pm-11pm, seven days a week). Expect live music Thursday-Saturday from 7pm-10pm, too.

The hotel will be home to the second site of Michael Feinstein’s Cabaret (similar to Feinstein’s 54 Below in New York), featuring dining and live music. In addition to chandeliers, every room is outfitted with devices allowing guests to request songs or composers from the Great American Songbook so you can really steep in the music.

Hotel Carmichael is located directly next to The Palladium, also known as The Center for the Performing Arts, a world-class performing arts center that houses the Great American Songbook museum. Browse the Songbook Exhibit Gallery’s rotating installations of images, many of which come from the Foundation’s vast Songbook Archives & Library.

Admission is free and a friendly docent will tell you about the exhibits. The Center presents about 50 performances a year: classical, jazz, pop-rock, country, Great American Songbook, international music and even standup comedy.

Browse Carmel’s Arts & Design District, home to art galleries, restaurants, antique stores and showrooms at the Indiana Design Center. Stop in Books & Brews: there’s a bookstore in the front and a bar in the back of the shop where you peruse a collection of craft beers all named after literary characters.

When you’re hungry, look for the Cake Bake Shop (it made Oprah’s Favorite Things List two years in a row) for breakfast, lunch, dinner and exquisite sweet treats. While in Indiana, hunt for the state’s famous pork tenderloin sandwich – a colossal hand-breaded tenderloin that hangs over the bun, topped with lettuce, tomato, pickles, onion and mayo. Rosie’s Place offers it, as well as all-day breakfast and lunch items.

Part 6: Carmel, Indiana to Chicago, Illinois

3 hours, 181 miles on I-65 and I-90

Music to download for the drive: “Chicago” by Sufjan Stevens, “Pulaski at Night” by Andrew Bird, “Born in Chicago” by Paul Butterfield Blues Band, “Chi City” by Common and Kanye West, and any tunes by Buddy Guy.

In three hours, you’re either home in Chicago or back to visit this amazing city. Entire books have been written about the Chicago sound in jazz and blues, the mid-century folk music scene and house music, among others. Choose Chicago is the resource for visitors who want to explore the city’s rich musical heritage and where to experience it.

For hotels, museums, events, attractions and restaurants, hit up the USA TODAY 10Best guide.

10Best is a part of the USA TODAY Network, providing an authentically local point of view on destinations around the world, in addition to travel and lifestyle advice.

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