How To Take the Perfect Music, Culture, and Food-Filled Road Trip Through Northern Mississippi

If you aren’t a fan of hot weather, you might want to skip a Mississippi road trip in the height of summer in order to make the most of the outdoors on cooler, less humid days. Otherwise, there’s not a bad time to visit.

The best way to experience the beauty of the state, and to stop in as many cities as possible, is a road trip. Bicycling trips are also options for those who want to tackle the historic Natchez Trace Parkway and nearby cities. Amtrak serves many Mississippi cities well. And Gulf Coast Amtrak service is likely to return to Mississippi in 2023 for the first time since Hurricane Katrina.

While the state isn’t particularly big (in terms of land mass, it’s 32nd in size) or population (35th overall), the best road trips allow for a little meandering and serendipity along the 350 or so miles from the northern border with Tennessee to the southern edge along the Gulf of Mexico. If you don’t have weeks to devote to a single trip filled with thoughtful museums, fragrant gardens, and tasty tamales, it’s easy to divide your adventures into several road trips.

Start with a focus on the rolling hills of north Mississippi (aptly called the Northern Hills) on a tour that includes one of the state’s favorite sons (that would be Elvis Presley), a Nobel Prize-winning author (William Faulkner), a former president (Ulysses S. Grant), and some of the best tailgating in the SEC.

Start in Tupelo

Photo: Visit Mississippi

Tupelo is a charming town 80 miles from the Mississippi-Alabama border. The city is best-known for being the birthplace of Elvis Presley, though Tupelo has much more to do than visit the King’s childhood home. And while all things Elvis are part of the city’s charm, the city is chockful of interesting attractions, fun facts, delicious food and drink, and access to the great outdoors.

As you are driving around town, neon-lovers will appreciate the iconic arrow-shaped city sign. It commemorates Tupelo being the first city to buy hydro-electric power from the new Tennessee Valley Authority in 1934. This move changed the lives of folks in the rural South. Grab a cup of coffee from Strange Brew Coffeehouse near the sign before heading the one mile downtown.

Photo: Hotel Tupelo

Nowhere in Tupelo is very far away, quick drives and easy walks are the hallmark of visiting town. Park downtown at the Hotel Tupelo on Main Street. This boutique will be your homebase for your stay. If you prefer exploring on two wheels, borrow a free bicycle from the hotel before setting out to explore downtown’s many shops and restaurants.

Reed’s Department Store has been a fixture in Mississippi since 1905 and is the place to look for shoes, clothing, and gifts to take home. Reed’s GumTree Bookstore, connected to the department store, features books by local authors as well as your favorite bestsellers. The streets are dotted with murals and small guitar sculptures (part of Elvis’ Guitar Trail), offering lots of opportunities for fun photos. Duck your head into the various shops, including Tupelo Hardware. A hardware store might not be on your typical vacation route, but this one is different. This is the place where Elvis’s mother bought him his first guitar. He wanted a BB gun, and she redirected his energy. Snap a picture in front of the neon-bedecked marquee of the nearby historic Lyric Theatre before heading out.

Photo: Visit Mississippi

From there, dive into Elvis’s past at the Elvis Presley Birthplace. This site includes a museum, his childhood home, and the chapel where he first sang before an audience. You’ll get guided tours to tell you about how the King found his voice, and how his family supported him in doing so. The site includes bucolic walking trails dotted with sculptures of Elvis and even one of his classic cars. You can continue your Elvis-themed exploration by having lunch at Johnnie’s Drive-In, a favorite fast-food spot during Elvis’ youth. You can even have your photo taken in his booth.

Photo: Queens Reward Meadery

For more substantial fare, book dinner at Park Heights Restaurant, a bright welcoming restaurant with a menu of Southern-inspired dinners. Or enjoy surf-style dishes at Jobos in the light-filled Hotel Tupelo. Stop by Queen’s Reward Meadery for a sample of honey-based drinks from Mississippi’s first meadery — the space has board games and a lovely outdoor space where you can hang out as you sip.

Before heading to Oxford, swing by Connie’s Fried Chicken for one of its famous blueberry doughnuts to eat in the car. Then, for the next stop on your Mississippi road trip, take a detour to the Natchez Trace Parkway Visitors Center. The Trace is a 444-mile historic route maintained by the National Park Service. Much of the Trace runs through Mississippi and includes battlefields, Indigenous mounds, and scenic vistas. The Visitors Center has a small museum and shows a film that gives you an overview of the Trace, so you can decide which sections you want to visit as you explore.

Head to Oxford

Photo: Greetings Tour

It’s just an hour’s drive west to get from Tupelo to Oxford, best known as the home of the University of Mississippi. If you’re a football fan, you’ll want to plan ahead (very ahead) to come to town on game days when Ole Miss plays at home, as hotels and tailgating space is at a premium. If you’re not, there is no shortage of other things to do in Oxford.

Photo: Square Books

The Square is Oxford’s picturesque downtown and is filled with boutiques, bars, restaurants, and music venues. It’s eminently walkable, so leave the car at The Graduate Oxford, an easy home away from home while in town. The colorful, welcoming hotel has plenty of space for lounging in the lobby, and Ole Miss-colored bicycles can be borrowed if you want to see the city at a faster pace. Square Books, open since 1979, has four locations on the Square, housing first-editions, children’s books, cookbooks, and pretty much anything else available on paper. End of All Music is the go-to for folks who like their tunes on vinyl.

Photo: Visit Mississippi

While wandering the streets you’ll see red phone booths, evocative of those from Oxford’s namesake across the pond. And, yes, they work for local calls. Go in and dial up a restaurant to make a reservation. Best bets include the first location of Big Bad Breakfast, for a hearty breakfast or lunch of Southern staples, and Emily Blount’s Saint Leo, a James Beard Award-winning semi-finalist thanks to its menu of wood-fired Italian treats.

Photo: Rowan Oak

Oxford’s other claim to fame is Rowan Oak, the former home of Nobel Prize-winning author William Faulkner. Located adjacent to the Ole Miss campus, Rowan Oak offers a look into the mind of the man who lived here for more than four decades. The walls include outlines for some of his works (this was before the days of the Post-It note) and insight on how the Mississippi landscape influenced him. Leave enough time to wander the grounds after your tour. You can walk across the street, too, to Oxford Memorial Cemetery, Faulkner’s final resting place. It is not unusual to see a fan has left Faulkner a bottle of whiskey to enjoy.

Head south to Starkville

Photo: University of College/Shutterstock

Mississippi’s other favorite college town, Starkville, is two hours south of Oxford. Home to Mississippi State University, Starkville is surrounded by wide-open expanses of farmland (great for catching some of the state’s best sunsets), while being home to a charming downtown and thriving university neighborhoods. Blues music fans should make a quick detour en route to West Point, which is home to Howlin’ Wolf Blues Museum.

Once in Starkville, you’ll want to park your car and walk through the MSU campus, a leafy oasis with sculptures of bulldogs, the school’s official mascot. (Cowbells optional unless you are planning on attending a football game.) The campus also houses the Ulysses S. Grant Presidential Library, an in-depth and informative look at the 18th president of the United States. The museum features interactive displays, life-size sculptures, and areas for scholarly research. The museum is in the school library building, which also houses the Charles H. Templeton, Sr. Music Museum, stocked with instruments and sheet music, and the John Grisham Room — both worth a look while on campus.

Photo: Visit Mississippi

There are three hotels near the Mill Conference Center at MSU. Nab a room at one of them and then spend some time checking out the renovated space in the former cotton mill. If you like historic buildings, eat at The Central Station Grill, housed in a former Borden dairy plant. The free Oktibbeha County Heritage Museum will give you a great overview of this city and the way in which the community grew to be what it is today.

Swing through downtown, with its boutiques, bookstore, and restaurants before continuing on your road trip. Starkville Café is a classic diner; a great place for breakfast before hitting the road (as well as a place to get the town gossip).

End the tour in Jackson

Photo: Sean Pavone/Shutterstock

Jackson is Mississippi’s state capitol and soul music center. It’s a little more than a two-hour drive from Starkville along a road surrounded by lots of greenery though the Tombigbee National Forest. This is another opportunity to get on a portion of the Natchez Trace Parkway, and that’s highly recommended if you have the time to take the scenic route. If you come to town from the Trace, stop at the Bill Waller Craft Center and peruse art from artists from across the state. If you are in town long enough, sign up to take a workshop and get your hands dirty.

As would be expected of Mississippi’s largest city, it’s easy to keep yourself busy. Make sure you come with enough time for museums, music, and food (not necessarily in that order). Jackson is a museum town, with some world-class opportunities. The Mississippi Civil Rights Museum is worth a trip to Jackson alone. It’s a thoughtful, difficult look at the fight for justice and civil rights in the United States. The interactive displays are well-marked, so visitors can make decisions about what kinds of material are appropriate for them. Plan on spending several hours here and then taking a break to decompress before your next activity. A trip to the Medgar and Myrlie Evers Home, now managed by the National Park Service, is a good companion experience to the Civil Rights Museum. The first public school for Black students in Jackson is now home to the engaging Smith Robertson Museum and Cultural Center. The Mississippi Ag Museum is a good place to get outside, stretch your legs and see how Mississippi’s farmers shaped the state.

Photo: Chad Robertson Media/Shutterstock

If you spent time at Rowan Oak in Oxford, you’ll want to explore the Eudora Welty House and Garden in Jackson. The author’s former home has been preserved so it feels like she just stepped out for a minute, with piles of books she intended to read on the chairs and sofas. The gardens, which she built with her mother, are an explosion of color.

Photo: Elvie’s

After all the edification, you’ll need some sustenance. The all-day café Elvie’s from James Beard Award semifinalist Hunter Evans provides modern takes on classic Southern dishes and is just a few blocks from the Welty home. Or, head to the Fondren neighborhood where you can eat at a classic old-fashioned soda fountain at Brent’s Drugs. If you’re not full from a post-meal milkshake, walk across the street to Campbell’s Bakery, which has served the city’s favorite tea cakes and petit fours since 1962.

Take a break by checking into the Westin Jackson, a new shining star in downtown. You can relax at the spa or take a dip in the pool or just catch views from your modernly appointed room. Then, walk over to Hal and Mal’s. This second-generation restaurant is a friendly spot to catch Jackson’s signature sound: live music. If you want to keep the toe-tapping going, head to the Iron Horse Grill for more music and libations.