How cool is it to do a Mississippi road trip visiting multiple unique towns along the way? That is how Southern TravelingMom Melody and several other travel writers set out to explore the state of Mississippi. Beginning in Oxford and ending in Hattiesburg, see what these small-town Mississippi cities had to offer.

Mississippi Road Trip: 5 Mississippi Cities with Small-Town Charm

1. Oxford: The High-Brow College Town
2. New Albany, The Sweetest Town in Mississippi
3. Tupelo, Synonymous with Elvis Presley
4. Columbus, A Town With Hundreds of Historical Homes
5. Hattiesburg, A Place To Revisit

I’m always eager to venture out to new places and see new things, which is just what we did on our Mississippi road trip. We discovered historical landmarks, decadent Southern eats, and walked in the footsteps of famous Americans. Here is how our up-close-and-personal trip unfolded.

1. Oxford: The High-Brow College Town

Our road trip began in Oxford, Mississippi, a bittersweet destination for me. My daughter, Taylor, went to college in Oxford at the University of Mississippi (Ole Miss). I have great memories of visiting Oxford to see her.

Any road trip to Oxford should include a drive-through Ole Miss’ campus to admire the Greek architecture, magnolia and oak-lined streets, and The Grove, where the best football tailgating in America takes place.

While on campus, we stopped at the University of Mississippi Museum. It is chock full of interesting artifacts, my favorite being the 19th-century scientific instruments. Admission to the museum is free.

Built around the stately courthouse, The Square is the center of downtown Oxford, and it is home to boutiques, stellar restaurants (Ajax Diner is my fave!), and the South’s oldest department store, Neilson’s. The Square features one of the most renowned independent bookstores in the country, Square Books. When I visited my daughter at Ole Miss, we always ate and drank around The Square, which is the heart of Oxford’s nightlife.

We were hosted at The Graduate, one of Oxford’s favorite hotels for our overnight accommodations. The hotel has cool and whimsical decor, an eclectic lobby, and a fun rooftop bar.

2. New Albany, The Sweetest Town in Mississippi

The next stop on our road trip was New Albany. Unless you read Southern Living or other food magazines, you might not be familiar with New Albany.

Since I read those magazines, I immediately knew that Sugaree’s Bakery was in New Albany. This drool-worthy shop is famous for caramel or strawberry layered cakes, which can be shipped to your door. The charming small batch bakery has an arsenal of homemade treats, too. From tasty cupcakes, kolaches, cookies, and other baked goods, this is a sweet lover’s paradise. I was smitten with everything, from the romantic chandeliers to the vintage apron collection. Luckily nobody judged me for the number of samples I tried.

New Albany is on the Hallelujah Trail, showcasing 65 churches, some even 100 years old. The town has cool street art including a retro Coca-Cola sign (great for selfies!), cute boutique shops, and Van Atkins Jewelers, the state of Mississippi’s #1 estate jeweler. We stopped by and oohed and aahed over the gorgeous pieces on display.

3. Tupelo, Synonymous with Elvis Presley

Our third stop was in Tupelo, the birthplace of Elvis Presley. At the Elvis Presley Birthplace & Museum, his childhood home, the church he sang in as a boy, and a museum offer a look into his life for the millions of fans who visit annually. Take time to see the film; it illuminates his life well.

We chatted with Guy Harris, a childhood friend of Elvis who shared some personal photographs of the two boys together. Sweet Tea and Biscuits furnished our tasty lunch with Fried Green Tomato BLTs (with pimento cheese!) and Momma’s Famous Chicken Salad Sandwiches. Yummy!

I picked up a souvenir t-shirt at Tupelo Hardware, where Gladys Presley bought Elvis his first guitar at a mere price of $7.95.

Our evening concluded with a private function at the Tupelo Car Museum. The museum hosts a 100+ car collection that spans 150 years in the automobile world. It is definitely one of the best car museums in the nation. Don’t miss the $3 million 1948 Tucker, the most valuable car in the collection. It was very Leo Dicaprio meets Great Gatsbyish.

4. Columbus, A Town With Hundreds of Historical Homes

Next, we visited the city of Columbus. I was unfamiliar with this one but won’t be a stranger in the future. The Columbus tourism board planned a fun-filled day for us, including sightseeing on their European red double-decker bus.

The tour showcased a portion of the 650+ homes listed on the National Historic Register, a huge number for a town this size. I’m obsessed with visiting places on the National Historic Register, so New Albany was definitely a place for me. From the enormous mansions with decorated porches to quaint and charming bungalows with fun outdoor yard ornaments, they all oozed Southern charm.

Columbus, Mississippi is the birthplace of Tennessee Williams, the most prolific American playwright and writer. Some of Williams’ best-known works are Cat on a Hot Tin Roof, The Glass Menagerie, and A Streetcar Named Desire. See some of Williams memorabilia at this Literary Landmark.

For Sunday brunch, a charming local couple opened their beautiful historic home (Whitehall) to a catered reception in our honor. What a treat! A jazz band on the porch greeted us along with cocktails and a bounty of delicious catered Southern foods. Mississippi knows how to put on the dog!

5. Hattiesburg, A Place To Revisit

Our Mississippi road trip concluded in Hattiesburg. Here, we were treated to a private meal from perhaps the most famous chef in Mississippi.

Chef Robert St. John, a Mississippi culinary legend, greeted us at Purple Parrot Seafood & Steaks, one of his six restaurants. We indulged in a decadent Corn & Crab Bisque and Shrimp and Grits brunch. The Purple Parrot just received its 6th Four-Diamond rating from the AAA Travel Guide.

We met with Chef Robert who chatted with our group presenting each of us with a signed copy of his newest cookbook, A Mississippi Palate. I will gladly add his new cookbook to the other three of his that I already have at home. Awesome recipes AND stunning watercolor artwork by Wyatt Waters are both featured in Chef Robert’s cookbooks.

The Residence Inn by Marriott provided accommodations for our stay with super comfy beds, free breakfast,  and free Wi-Fi.

Discover Southern Traditions in the Magnolia State

Our Mississippi road trip was a visual and tasty delight. It afforded us a chance to intermingle with fabulous and friendly people who are grateful to share their history and towns with you. As I did, I’m sure you will discover a little something special in each of these adorable Mississippi cities.