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Looking for Southern hospitality, unique shopping and stellar restaurants in Mississippi? Take a detour to one (or more!) of these charming small towns where you’ll be welcomed like family. You’ll be welcomed like family in any one of these five towns in Mississippi.
How cool is it to take a Mississippi road trip visiting multiple unique towns along the way? That is how I like to travel, filling several days with new cities and attractions. For this Mississippi road trip, I started in Oxford and ended in Coastal Mississippi, between Louisiana and Alabama, seeing places on each side of the state along the way. Here are 5 of the best small towns in Mississippi and what each has to offer.
Oxford: The High-Brow College Town
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 and watching the college town grow year after year.
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 occurs.
While on campus, stop at the University of Mississippi Museum. It is full of interesting artifacts, my favorite being the 19th-century scientific instruments. Admission 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, the heart of Oxford’s nightlife.
When staying in Oxford, The Graduate, one of Oxford’s favorite hotels always gets my vote. The hotel has cool and whimsical decor, an eclectic lobby and a fun rooftop bar. The textures, fabrics and furnishings alone are worth the visit.
I also recommend visiting the home of legendary William Faulkner at Rowan Oak. You can also visit his gravesite at Oxford Memorial Cemetery.
TravelingMom Tip: Tupelo is less than an hour away should you want to include a drive-through animal attraction, the Elvis Presley Birthplace, and Tupelo National Battlefield (Civil War site).
Cleveland: The Heart of the Delta
The Mississippi Delta is a juxtaposition of rich and poverty, but that in itself helps shape the landmark region that it is today. For out of such division came the birthplace of the blues, which you will find in the highest form from city to city throughout the Delta. Cotton plantations still grow in the Delta, and times have changed tremendously, but the Mississippi River Delta roots are still felt through its landscape, food and drink.
In Cleveland, where I like to stay at the Cotton House Hotel, you’ll be in the heart of the Delta. Before diving into soul food at The Senator’s Place, visit The GRAMMY Museum Mississippi, a unique attraction with world-class exhibits. Then, listen to music or play trivia while sipping an adult libation or craft beer at Hey Joe’s Burgers + Beer.
Shopping Along the Blues Trail
Downtown Cleveland has a bit of shopping (think clothing, accessories and seasonal merchandise), tasty restaurants and an adorable train museum at the railroad depot. You’ll also see many interpretive markers and sights on the Mississippi Blues Trail in the area, such as at Dockery Farms (Charley Patton).
Clarksdale is another Mississippi Delta favorite, 40 minutes north of Cleveland, where you may or may not run into Morgan Freeman in his hometown. You can also visit Ground Zero (owned by Freeman) for the fantastic music and explore the Delta Blues Museum.
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TravelingMom Tip: If shopping is your thing, be sure to pencil in the Canton Flea Market on your calendar.
The exciting GRAMMY Museum Cleveland. Photo credit: Melody Pittman
Tunica: A Gambling and Discount Shopping Mecca
While Tunica doesn’t get nearly as much attention as some of Mississippi’s other cities, it is a sweet little town for a day or two getaway. Tunica has several casinos worth visiting (six at last count) and the Tanger Outlets Southaven a few minutes away with 130+ stores, including H&M, Columbia, Converse, Vera Bradley and Tory Burch. Horseshoe and Gold Strike Casinos are my favorites for playing slots. Our kids are 26 and 29 years old, so this is our kind of place for a quick getaway. Tunica is said to be the third-largest gaming center in the country.
Things to Do Near Tunica: Memphis and More
Tunica is also an excellent place to stay for visiting the city of Memphis, Tennessee. You’ll be minutes away from this inspirational city with a fabulous music scene (visit Beale Street for this), National Civil Rights Museum and amazing bbq. Memphis is also home to Graceland, the only home that Elvis Presley ever owned.
Want more Civil War history? The Mississippi towns of Vicksburg and Corinth are both chock full. And the quaint town of Holly Springs is an hour east. Visit Walter Place Garden & Estate, where General Ulysses S. Grant’s wife Julia stayed during the Civil War.
Lunch buffet from Gold Strike Casino in Tunica. Photo credit: Melody Pittman
Columbus: A Town With Hundreds of Historical Homes
The old town of Columbus, Mississippi, circa 1821, is one I was unfamiliar with, but I won’t be a stranger in the future. I even got to see the town in the comfort and style of a European double-decker bus…red, of course.
My tour of Columbus was to showcase the 650+homes listed on the National Historic Register, a huge number for a town this size. Other points of interest on the tour were the incredible mansions, adorned with magazine-worthy porches and landscaping, to the quaint bungalows with amazing yard-art and ornaments. They all oozed Southern charm.
Birthplace of a Literary Legend
Columbus, Mississippi, is the birthplace of Tennessee Williams, the 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. Some of the noteworthy memorabilia on display include Playbills from his Broadway shows and awards. Note: This stop is a Literary Landmark.
I was privy to a specially hosted Sunday brunch at Whitehall (an 1843 antebellum historic house), with a catered reception for a small group of us travel writers. What a treat! A jazz band played music on the porch as we were greeted with craft cocktails. The Southern fare that was served buffet style was absolutely amazing. Mississippi knows how to put on the dog.
Rather than split hairs between the adorable small towns that make up the Coastal Mississippi region in the southern part of the state, I’ll just mention a bit about each of them. Then, you can decide which one tickles your fancy.
Bay St. Louis
Bay St. Louis is the furthest west of the region towards Louisiana, a charming little area on the Gulf Coast that offers great eateries, cute boutiques and a lovely beach. Shopping at Fleurty Girl, with all things New Orleans-inspired, is a must, as well as visiting the other unique shops.
A look at the restaurants and shops in Bay St. Louis from the waterfront. Photo credit: Melody Pittman
Next comes Pass Christian, with a killer coffee shop (Cat Island), chartered fishing tours and epic sunset views from Shaggy’s.
Best known for the excellent casinos (think Hard Rock, Beau Rivage, Island Vibe and more), but the fishing and beaches are also big draws in Biloxi. It is also home to the Native American Cueva Indians. Be sure to try the great biscuits from Greenhouse Biloxi while you are there, and the kids will love a boat ride to Ship Island or touring the Maritime & Seafood Industry Museum.
What makes Gulfport popular? It has the Gulf Islands Waterpark, Mississippi Aquarium and Lynn Meadows Discovery Center, one of Mississippi’s best children’s museums. Technically, both Gulfport and Biloxi have a larger number of residents to be classified as a small towns, but since they are in the area, you might as well visit both of these powerhouses, too.
In my opinion, Ocean Springs is the most upscale part of Coastal Mississippi, and with a darling downtown you won’t want to miss. It is a small town with a big city feel, minutes from Alabama. Boutique shopping is on point in Ocean Springs—you’ll find store after store of treasures. The Walter Anderson Museum of Art is an excellent stop for beautiful artwork and education before getting sweet treats from The Candy Cottage and toy shopping at Miner’s Big Stuff Doll & Toy Store.
The Mississippi Aquarium is uniquely built with part of the exhibits inside and out. Photo credit: Melody Pittman
Discover Southern Traditions in the Magnolia State
A state of Mississippi road trip was a visual and tasty delight. It afforded my family a chance to experience Southern hospitality and friendly people who are grateful to share their history and towns with you. I’m sure you will discover a little something special in each of these Mississippi small towns.