Known for its rolling hills, farmlands, and historic towns, the Mid-South is a place where tradition meets modernity. From Nashville’s vibrant and intoxicating music scene to the riverscapes along the Mississippi, this region offers travelers a variety of experiences. In addition to its more well-known cities, the Mid-South is also home to some of the most beautiful small towns in the country. These eight pretty towns from Arkansas to Kentucky should be at the top of your itinerary.
Eureka Springs, Arkansas
Eureka Springs, located in the Ozark Mountains, is known for its Victorian architecture and natural springs. Founded in 1879, the town quickly became a destination for those seeking the healing powers of its waters. The steep, winding streets and preserved historic buildings give the town a unique charm that feels like stepping back in time.
Visitors to Eureka Springs should explore the city’s art scene by visiting the numerous galleries. Studio 62 Eureka Springs and Zarks-A Fine Design Gallery are great options. Often called “America’s Most Haunted Hotel,” the historic Crescent Hotel offers both a glimpse into the past and the chance to hear spooky stories. The nearby Blue Spring Heritage Center is a must-see. Its crystal-clear spring has been a sacred site for Native American tribes for centuries. Gardens and walking trails complement the spring’s natural beauty.
Natchez, Mississippi
Natchez, situated on the cliffs of the Mississippi, was founded in 1716. It is one of the oldest European settlements on the Mississippi, and its well-preserved antebellum homes tell the story of a bygone era. The city’s tree-lined streets and historic neighborhoods are filled with architecture that reflects its deep roots in American history.
For visitors to Natchez, a tour of the historic homes is a must. Longwood, the largest octagonal house in the United States, is highly recommended. Its unfinished interior offers insight into the Civil War era. The Natchez Trace Parkway, which begins in Natchez, is a scenic drive with the opportunity to explore historic sites and enjoy the region’s natural beauty. For those interested in the city’s cultural heritage, Natchez National Historical Park offers a comprehensive look at the region’s history, from Native American settlements to the Civil War and beyond.
Herman, Missouri
Hermann, a small town of about 2,400 residents, is located in the heart of Missouri Wine Country on the banks of the Missouri River. Hermann is known for its strong German heritage and especially for its wineries, historic buildings and festivals such as the Hermann Harvest Festival, which takes place every September.
When visiting Hermann, be sure to take a tour of one of the city’s many wineries, such as Stone Hill Winery, one of the oldest and most renowned wineries in the country. For outdoor enthusiasts, the nearby Katy Trail offers a route for biking and hiking along the Missouri River. The city is known for its Oktoberfest celebrations, where visitors can enjoy traditional German food, music and dancing.
Oxford, Mississippi
Known for its deep literary roots and Southern charm, Oxford is a small city in Mississippi. Founded in 1837, the city quickly became a center for education and the arts, thanks largely to the University of Mississippi, also known as Ole Miss. The city’s courthouse square, lined with historic buildings, is the center of town.
Visitors to Oxford should start with a visit to Rowan Oak, the former home of Nobel Prize-winning author William Faulkner, where you can explore the grounds and gain insight into his life and work. The University of Mississippi campus is another must-see, with beautiful architecture and significant historical sites, including the Lyceum, the oldest building on campus. For book lovers, Square Books, one of the South’s most popular independent bookstores, is a place to browse and soak up the city’s literary culture.
Mentone, Alabama
Mentone, Alabama is a mountain town atop Lookout Mountain with a population of just over 400. Known for its nature, Mentone is a destination for outdoor enthusiasts and those seeking a quiet retreat. The views of the Appalachian Mountains make the town a popular Mid-South destination.
Visitors to Mentone can enjoy DeSoto Falls, a 104-foot waterfall that is one of the most photographed locations in Alabama. Nearby DeSoto State Park offers miles of hiking trails and opportunities for camping, fishing and rock climbing. Mentone is also home to an arts scene, with local galleries like the Mentone Arts Center and craft shops like Orbix Hot Glass showcasing the work of regional artists.
Bardstown, Kentucky
Bardstown, often called “Bourbon Capital of the World“,” is a small town with a long history. Founded in 1780, it is one of Kentucky’s oldest towns, known for its close ties to the bourbon industry. The town has a lovely downtown area where visitors can stroll the streets lined with Federal-style architecture.
A trip to Bardstown wouldn’t be complete without a visit to one of the famous distilleries, such as Maker’s Mark Distillery, where you can tour the grounds and learn about the bourbon-making process. My Old Kentucky Home State Park, featuring the mansion that inspired Stephen Foster’s famous song, offers tours and gardens. History buffs can gain insight into the town’s role during the conflict and its impact on the region at the Civil War Museum. The annual Kentucky Bourbon Festival in Bardstown is a highlight for many, celebrating the town’s rich bourbon heritage with tastings, events and entertainment.
Jonesborough, Tennessee
Jonesborough is the oldest town in Tennessee, founded in 1779. Nestled in the infamous Appalachian Mountains, the town is known for its historic buildings and its role as the storytelling capital of the world. Brick-lined streets and beautifully restored homes make Jonesborough a picturesque destination that feels like you’ve stepped back in time to the 18th century.
A must-see for visitors to Jonesborough is the International Storytelling Center. This center hosts the annual National Storytelling Festival, which attracts storytellers from around the world. The Chester Inn Museum, located in the heart of downtown, offers a glimpse into the town’s past with exhibits detailing its early days and its importance in Tennessee’s history. The town’s location in the Appalachian region also makes it a great base for exploring the surrounding natural beauty. Hiking is available at the Lone Oak Trailhead.
Frankfort, Kentucky
Frankfort, a capital city on the Kentucky River, was founded in 1786. It is known as the center of Kentucky’s government. The compact, pedestrian-friendly city center features Federal-style architecture.
Visitors to Frankfort shouldn’t miss the Kentucky State Capitol, an architectural marvel set in manicured grounds. The Old State Capitol, a Greek Revival masterpiece, offers tours that delve deeper into the state’s history. The Salato Wildlife Education Center, located just outside of town, allows visitors to explore Kentucky’s natural habitats and get up close and personal with Kentucky’s native wildlife. To get a taste of local culture, visitors can explore the Bourbon Trail, with several distilleries near Frankfort, including Buffalo Trace, one of the state’s oldest.
The most beautiful towns in the Mid-South capture the essence of Southern life. Towns like Bardstown, known for its Bourbon heritage, and Franklin, with its long Civil War history, offer glimpses into the past with preserved architecture and historic sites. Mentone’s mountain views offer a tranquil retreat, while Hermann’s German roots give the region a distinctive cultural flair. These towns, along with others like Oxford and Natchitoches, showcase the beauty of the Mid-South, making them must-sees.
