8 Prettiest Towns to Visit in Mid-South
Known for its rolling hills, farmlands, and historic towns, the Mid-South is a place where tradition meets modernity. From the vibrant and intoxicating music scene of Nashville to the riverside views along the Mississippi, this region offers travelers a diverse range of experiences. Beyond its more well-known cities, the Mid-South is also home to some of the prettiest small towns in the country. These eight pretty towns, from Arkansas to Kentucky, ought to be at the top of your itinerary.
Eureka Springs, Arkansas
In the Ozark Mountains, Eureka Springs 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 town’s steep, winding streets and preserved historic buildings give it a unique charm that feels like stepping back in time.
Visitors to Eureka Springs should explore the town's arts community by visiting its numerous galleries. Studio 62 Eureka Springs and Zarks-A Fine Design Gallery are great options. The historic Crescent Hotel is often called "America's most haunted hotel." It gives both a glimpse into the past and a chance to hear spooky tales. Nearby, the 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, perched on the bluffs of the Mississippi River, was founded in 1716. It is one of the oldest European settlements on the Mississippi River, and its well-preserved antebellum homes tell the story of a bygone era. The town’s tree-lined streets and historic districts are filled with architecture that reflects its deep roots in American history.
A tour of the historic homes is a must for visitors to Natchez. Longwood, the largest octagonal house in the United States, is highly recommended. Its unfinished interior provides insight into the Civil War era. The Natchez Trace Parkway, which begins in Natchez, is a scenic drive with opportunities to explore historic sites and enjoy the region's natural beauty. For those interested in the town’s cultural heritage, the Natchez National Historical Park provides a comprehensive look at the area's history, from Native American settlements to the Civil War and beyond.
Hermann, Missouri
Hermann, a small town with a population of around 2,400, is nestled in the heart of Missouri Wine Country along the banks of the Missouri River. Known for its strong German heritage, Hermann is most known for its wineries, historic buildings, and festivals, like the Hermann Harvest Festival, which occurs every September.
A visit to Hermann should include a tour of one of the town’s many wineries, such as Stone Hill Winery, one of the country's oldest and most acclaimed wineries. For outdoor enthusiasts, the nearby Katy Trail provides a route for biking and hiking along the Missouri River. The town is known for its Oktoberfest celebrations, where visitors can enjoy traditional German food, music, and dancing.
Oxford, Mississippi
Oxford, known for its deep literary roots and Southern charm, is a small town in Mississippi. Founded in 1837, it quickly became a hub for education and the arts, largely due to the presence of the University of Mississippi, also known as Ole Miss. The town's courthouse square, lined with historic buildings, is the center stage of the 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 its beautiful architecture and significant historical landmarks, including the Lyceum, the oldest building on campus. For book lovers, Square Books, one of the South's most beloved independent bookstores, is a spot to browse and soak in the literary culture of the town.
Mentone, Alabama
Mentone, Alabama, is a mountain town located 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 peaceful retreat. The town’s views of the Appalachian Mountains make it a well-known getaway in the Mid-South.
Visitors to Mentone can enjoy the DeSoto Falls, a 104-foot waterfall, one of the most photographed spots in Alabama. The nearby DeSoto State Park has miles of hiking trails and opportunities for camping, fishing, and rock climbing. Mentone is also home to an arts community, with local galleries, like the Mentone Arts Center, and craft shops, including Orbix Hot Glass, showcasing the work of regional artists.
Bardstown, Kentucky
Bardstown, often referred to as the "Bourbon Capital of the World," is a small town with a long history. Founded in 1780, it’s one of Kentucky’s oldest towns known for its deep ties to the bourbon industry. The town has a pretty downtown area, where visitors can stroll through streets lined with Federal-style architecture.
A trip to Bardstown wouldn't be complete without a visit to one of its famous distilleries, such as the Maker’s Mark Distillery, where you can tour the grounds and learn about the bourbon-making process. The My Old Kentucky Home State Park, featuring the mansion that inspired Stephen Foster's famous song, has guided tours and gardens. For history buffs, the Civil War Museum provides insights into the town's role during the conflict and its impact on the region. Bardstown’s annual Kentucky Bourbon Festival 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. Located in the infamous Appalachian Mountains, this town is known for its historic buildings and its role as the storytelling capital of the world. The brick-lined streets and beautifully restored homes make Jonesborough a picturesque destination that feels like stepping back into the 18th century.
For those visiting Jonesborough, the International Storytelling Center is a must-see. This center hosts the annual National Storytelling Festival, attracting storytellers from around the globe. 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 importance in Tennessee's history. The town’s location in the Appalachian region also makes it an excellent base for exploring the surrounding natural beauty, with opportunities for hiking at the Lone Oak Trailhead.
Frankfort, Kentucky
Frankfort, a capital city along the Kentucky River, was founded in 1786. It is known for its role as the heart of Kentucky’s government. The town’s compact, walkable downtown area features Federal-style architecture.
Visitors to Frankfort should not miss the Kentucky State Capitol, an architectural marvel set amid landscaped grounds. The Old State Capitol, a Greek Revival masterpiece, has guided tours that delve into the state’s history. The Salato Wildlife Education Center, located just outside the town, allows one to explore Kentucky’s natural habitats and see native Kentucky wildlife up close. For a taste of local culture, visitors can explore the Bourbon Trail, with several distilleries located near Frankfort, including Buffalo Trace, one of the oldest in the state.
The prettiest towns in the Mid-South capture the essence of Southern living. Towns like Bardstown, known for its bourbon heritage, and Franklin, with its deep Civil War history, offer glimpses into the past with preserved architecture and historic sites. Mentone's mountain views provide a serene escape, while Hermann's German roots add a distinctive cultural flavor to the region. These towns, along with others like Oxford and Natchitoches, showcase the beauty of the Mid-South, making them must-visit destinations.
