While you may expect Cleveland, Mississippi, to be a place of quiet streets, cotton fields, and small-town charm, you’ll be delighted to discover that it is also a destination for gourmet dining, eclectic shopping, and rich artistic expression. In the core of the Mississippi Delta, Cleveland is a vibrant college town with so many things to do.
It’s a place where Southern traditions meet modern flair.
History of Cleveland, Mississippi
Cleveland, Mississippi, may be small, with about 11,000 residents and less than 8 square miles, but its history is as rich as the “cotton dirt” clay-like soil of the Delta itself. Founded in 1869 by settlers drawn to the fertile land, one of its earliest residents, Moses W. Coleman, built the first home along the bayou. Initially known as Fontaine and later Coleman’s Station, the town became Sims in 1885, named after landowner Rueben T. Sims. In 1886, it was renamed Cleveland in honor of President Grover Cleveland and was officially chartered and recognized by the U.S. Post Office in 1887.
The arrival of the Louisville, New Orleans & Texas Railroad was a catalyst for Cleveland’s growth. The railroad ran through the town center, and some of those historic tracks remain today as a reminder of how rail transportation shaped the town’s economy and future.
By 1901, Cleveland had grown enough to be named the second county seat of Bolivar County, and the town was on the cusp of another transformation. The Mississippi State Legislature chose Cleveland for the Delta Teachers College due to its central location and existing railroad infrastructure. This school, now known as Delta State University, became a cornerstone that shaped the region’s educational and cultural landscape.
Things to Do in Cleveland, Mississippi
Cleveland may be small, but it’s packed with cultural experiences that leave a lasting impression. Whether you are interested in the deep roots of Delta blues, love history, or seek outdoor adventure, Cleveland offers something special for every traveler.
The Rhythm of Cleveland: Grammy Museum Mississippi and Dockery Farms
One of the highlights of Cleveland is its connection to music, and nowhere is this more evident than at the Grammy Museum Mississippi. As the only Grammy Museum outside of Los Angeles, it was built here to honor the Delta’s profound impact on American music. From soulful blues and country to energetic rock ‘n’ roll, the museum’s immersive, interactive experiences trace the artistic styles that shape the world’s musical landscape.
To delve into the origins of the blues music, take a short seven-mile drive from downtown Cleveland to Dockery Farms. This historic site was once home to Charley Patton, considered the father of Delta blues. The old gas station near the main highway pipes out audio recordings of bluesmen who worked and played here. The commentary teaches about this historic location in the context of how it influenced other Mississippi musicians like B. B. King and Elvis Presley.
On your self-guided tour, you’ll also find the cotton-processing station, a nod to the farm’s economic significance in the early 1900s. When I visited, the geographic diversity represented in the visitor log was fascinating. I observed signatures from Sweden, France, and Spain, along with those of guests from nearby Memphis, Cleveland, and Jackson.
Exploring Cleveland’s Culture and History
Faces of the Blues
Beyond music, Cleveland appeals to history lovers and art enthusiasts. The Delta State University’s “Faces of the Blues” exhibit showcases powerful facial expressions through life-cast sculptures. This wall display authentically captures the essence of the famous musicians who shaped the genre.
For train enthusiasts, the Martin and Sue King Railroad Museum demonstrates how the railroads fueled the expansive growth of the Delta. Inside the town’s historic depot, visitors explore displays of vintage railroad tools, memorabilia, and photographs that detail the development of the Delta’s economy.
The intricately designed model trains bring the railroad’s history to life as they travel through the various mountain tunnels, forests and small-town terrains. This interactive exhibit is a visual journey that appeals to train enthusiasts of all ages. There is even a miniature drive-in movie theatre that had a John Wayne movie playing on the screen when I visited.
What makes this attraction so compelling are the onsite train conductors, whose enthusiasm for railroad history is contagious. They are well-informed and skilled storytellers, eager to share insights about how the railroads shaped Cleveland’s growth and the broader Delta economy. Whether you’re a railroad aficionado or simply curious, this museum provides a fascinating insight into a transformative era.
Shopping in Cleveland
Cleveland’s charming downtown is a haven for boutique lovers and treasure hunters. Stroll along the boulevard streets, where the shops offer everything from local art and handmade crafts to stylish clothing and home goods. Vintage enthusiasts are eager to explore Moonstruck, which is only three blocks from the train depot. It’s the perfect way to take an authentic piece of the Delta home with you.
Outdoor Adventures and Festivals
If you’re craving outdoor activities, Cleveland has you covered. The scenic hiking trails such as the Crosstie Walk, also known as the Downtown Walking Trail, are ideal for soaking in the natural beauty of the Mississippi Delta.
And for those visiting in October, you’re in for a treat! Cleveland hosts the lively Octoberfest, and Delta Deep Roots, a festival that showcases local music talent. Both events deliver a vibrant mix of live music, local art, and mouthwatering food. These festivals present an authentic taste of Cleveland’s community spirit.
Places to Stay in Cleveland, Mississippi
Cleveland’s overnight accommodations are as charming as the town itself. The Cotton House Cleveland, part of the Marriott’s Tribute Portfolio, is a luxurious option in the downtown district. The rooftop patio, Bar Fontaine is ideal for cocktails or for light dining with city views. This boutique hotel beautifully blends modern amenities with the Delta’s rich cultural heritage. It’s an upscale experience with a distinctly local flavor.
Another excellent overnight option is the Lyric Hotel West End (Ascend Hotel Collection by Choice Hotels). This chic boutique hotel has a modern design that pays homage to the town’s musical roots.
With its comfortable rooms and convenient location less than a mile from the Grammy Museum and Delta State University, the Lyric Hotel is an ideal home base for your time in Cleveland. The hotel features a fitness room and an outdoor pool. The hotel’s warm, inviting ambiance and personalized service make it a perfect retreat after a day of exploring.
Where to Eat: Savor Southern Flavors
Cleveland boasts a diverse culinary scene with plenty of great places to eat. There are cozy cafes and upscale restaurants. Whatever your choice, your dining experience will be a delicious adventure.
For lunch, try The Warehouse. Located in a restored 1901 grocery warehouse on Sharpe Street, this restaurant has a rustic wood interior adorned with vintage signs, old doors, a traffic light, and movie posters. It’s known for its famous sandwiches, salads, pizzas, and soups. The laid-back atmosphere and friendly service make it a perfect place to relax.
For dinner, you can’t go wrong with Lena, where fresh, locally sourced ingredients meet bold flavors in their creative pizzas. Next door, Backdraft is yet another popular restaurant in Cleveland, Mississippi. With a lively, welcoming spirit and a firefighter’s theme, Backdraft serves up hearty dishes with steaks and seafood. The 8 West Grille in the West End District has live entertainment and a casual atmosphere. As a bonus, this restaurant is within walking distance of the Lyric Hotel. In fact, it shares the parking area!
Why Cleveland, Mississippi Should Be Your Next Destination
Cleveland, Mississippi, deserves a top spot on your Southern getaway list. With its impressive history, vibrant artist scene, and warm Southern hospitality, Cleveland delivers a travel experience that’s distinctive and unforgettable. The town’s natural connection to the blues and its modern attractions are the perfect blend of yesteryear and innovation.
Thanks to the wonderful folks at VisitClevelandMS and Grammy Museum Mississippi for assistance and hosting me. All opinions are my own.
