Aerial view of Jonesborough, Tennessee.

8 of the Most Charming Small Towns to Visit in the Mid-South

The Mid-South is a unique region of the United States both historically, geographically, and culturally. It encompasses several states, including Kentucky, Tennessee, West Virginia, Maryland, North Carolina, South Carolina, and parts of other nearby states. Known for hot summers and mild winters, the Mid-South is ideal to travel in at just about any time of the year. Whether it is hiking or winter festivities you are after, you can't go when you choose this area for your next road trip. Take a deeper dive into the Mid-South by visiting these eight must-see towns packed with regional charm.

Hot Springs, Arkansas

Aerial view of downtown Hot Springs, Arkansas.
Aerial view of downtown Hot Springs, Arkansas and surrounding forests.

As the name implies, Hot Springs, Arkansas, is renowned for its natural thermal springs, a defining feature of the town within Hot Springs National Park. Bathhouse Row, a designated National Historic Landmark District, allows visitors to explore the historic bathhouses. One can also take a dip for themselves and have a traditional therapeutic bath or take a guided tour to learn about the area's unique history.

Hot Springs has more than just baths; this town has an array of fun amenities, such as art galleries, studios, and theaters that host a variety of events, from live music to stage performances. The Hot Springs Arts District is a hotspot for creativity, with local artists attending. Hot Springs is also home to the World's Shortest St. Patrick's Day Parade each year, just in case you're on a time crunch.

For those looking to stretch their legs in nature, nearby trails that wind through the Ouachita Mountains offer majestic hikes and mountain biking. For a more laidback experience, the Garvan Woodland Gardens, a botanical garden with a Japanese garden and beautiful chapel, is a must-visit.

Bardstown, Kentucky

The town square in Bardstown, Kentucky.
Historic buildings in the town square of Bardstown, Kentucky. Editorial credit: woodsnorthphoto /

Bardstown, Kentucky, known as the "Bourbon Capital of the World," is a whiskey lover's dream with deep roots in the history of bourbon whiskey. Located in the heart of the Kentucky Bourbon Trail, Bardstown is a prime destination for bourbon enthusiasts and those interested in exploring the heritage of this iconic American spirit.

While in Bardstown, visitors should explore the Heaven Hill Bourbon Experience, which provides comprehensive tours and tastings, providing insights into the history and production of the bourbon that has made this area famous. As most assume, this town is home to several well-known distilleries, such as Willett and Barton 1792, each holding gift shops and tours of their own. The annual Kentucky Bourbon Festival, held in September, draws bourbon lovers from across the globe for a week of tastings, music, and other festivities. Beyond bourbon, Bardstown has The My Old Kentucky Home State Park, a popular attraction featuring Federal Hill, the mansion that inspired the state song "My Old Kentucky Home."

Oxford, Mississippi

Downtown buildings in Oxford, Mississippi.
Downtown buildings in Oxford, Mississippi.

Oxford, Mississippi, is most notable for being the home of the University of Mississippi (Ole Miss). A must-visit place if you are interested in the academic history of this town is Rowan Oak, the former home of Nobel Prize-winning author William Faulkner. This historic site provides insight into Faulkner's life and work, set in a landscape of ancient oak trees and gardens.

The historic downtown Square is the beating heart of Oxford, filled with iconic shops like Square Books, a bookworm's dream with a massive selection for sale. This beloved bookstore has been a gathering place for book lovers and hosts frequent author readings and literary events. Oxford is also renowned for its music scene, with live performances at various venues throughout the week. One can also get outdoors and see the nearby Sardis Lake, a vast lake with many viewpoints and a fun boating, fishing, and hiking spot.

Midway, Kentucky

View of buildings on Main Street in Midway, Kentucky.
Buildings and businesses lined along Main Street in Midway, Kentucky. Editorial credit: Alexey Stiop /

Midway is a small town in the center of Kentucky's Bluegrass region, best known for the aptly named bluegrass genre of music (like a blend of country and folk) and the country/equestrian culture that goes hand in hand with it. The Midway Bourbon and Blues Festival is certainly an event to see to get a taste of not only some local musical talent but also the beverage that the state of Kentucky is most famous for. Come for the live performances and stay for the bourbon many tastings available around every corner. The annual Midway Fall Festival is a highlight, featuring arts and crafts, live music, and local food vendors.

Midway is surrounded by many notable horse farms, and visitors can tour local stables to see thoroughbred horses up close. If this interests you, definitely visit the Keeneland Racecourse and the Kentucky Horse Park nearby.

Franklin, Tennessee

Aerial view of downtown Franklin, Tennessee.
Aerial view of downtown Franklin, Tennessee.

Located just south of Nashville, Franklin was established in 1799 and has since become a destination for travelers who want to get out of the big city and experience a slower pace of life. For fans of Civil War history, the conflict is commemorated in several Civil War sites like the Carnton Plantation and the Carter House. Learn more at museums like the Lotz House Museum, a well-preserved example of a home from the Civil War era, and the Battle Of Franklin Civil War Museum. All great spots to take the family that are also within walking distance of the downtown core.

The nearby Natchez Trace Parkway, a 444-mile recreational road, provides scenic drives and hiking opportunities. Several notable trails, like the Natchez Trace National Scenic Trail, are located at various stops along the way.

Hendersonville, North Carolina

Aerial view of downtown Hendersonville, North Carolina
Aerial view of downtown Hendersonville, North Carolina with towering mountains in the background.

Hendersonville, North Carolina, is located in the iconic Blue Ridge Mountains. Just south of much more populous Asheville, It offers a great mix of small-town living and easy access to outdoor adventures in the nearby Pisgah National Forest and DuPont State Recreational Forest.

This town also has a strong connection to the arts, with the Flat Rock Playhouse, North Carolina's State Theatre, offering regular performances from Broadway-style productions to original plays. Hendersonville also hosts the annual North Carolina Apple Festival, a four-day event celebrating the region's apple-growing heritage with parades, music, and, of course, plenty of apples, both fresh and prepared in a number of delicious ways. After the event, one can take advantage of the town’s burgeoning craft beer scene, with several local breweries serving unique beers from inviting taprooms. Visitors adore the local craft beer trail through, sampling a variety of styles from different breweries.

For those interested in history, the Historic Johnson Farm is a homestead that gives all who visit it a look into rural life in the late 19th and early 20th centuries in this southwestern region of the state. The farm offers guided tours and educational programs for all ages.

Jonesborough, Tennessee

Historic buildings along a street in Jonesborough, Tennessee.
Historic brick buildings along a street in Jonesborough, Tennessee. Editorial credit: Dee Browning /

Jonesborough, Tennessee, is the state's oldest town, having been incorporated in 1779. Located in the foothills of the Appalachian Mountains, Jonesborough is known for its natural beauty and laid-back country vibe. It is away from any major cities, the closest being Knoxville or Ashville, each over an hour’s drive away.

Jonesborough is often called the "Storytelling Capital of the World," and it's home to the International Storytelling Center, which hosts the annual National Storytelling Festival. This three-day event attracts storytellers from around the globe, sharing tales that range from traditional folklore to contemporary narratives. The festival is a significant draw for visitors and contributes to the town's unique cultural identity. In addition to its storytelling heritage, Jonesborough offers a variety of other cultural experiences. The town has several museums, including the Chester Inn Museum, which provides insights into the area's long-standing history, and the Jonesborough-Washington County History Museum, which covers the region's broader history. Jonesborough is also near the Cherokee National Forest and the Pisgah National Forest, both fantastic destinations for camping, hiking, and sightseeing.

Lewisburg, West Virginia

Buildings along a street in Lewisburg, West Virginia.
Martin Luther King Day celebrations in Lewisburg, West Virginia. Editorial credit: /

Located in the scenic Greenbrier Valley, Lewisburg is a great place to travel to get a dose of laid-back Appalachian living. But don't be fooled by the slower pace of life here; this town is filled with cool and interesting things to see and do. Lewisburg has a strong connection to the arts, with venues like the Greenbrier Valley Theatre playing regular performances, from musicals to plays and concerts. Another venue, Carnegie Hall, one of the oldest of its kind in the United States, serves as a hub for the arts, hosting concerts, exhibits, and workshops throughout the year. This town also hosts the annual Lewisburg Literary Festival, attracting authors and readers alike from across the region.

Lewisburg's location in the Greenbrier Valley provides ample activities for anyone looking to get outdoors. The nearby Greenbrier River Trail is a popular place for hiking, biking, and horseback riding, with its unobstructed views of the river and lush landscapes. The Greenbrier State Forest is another outdoor destination, with trails for hiking and areas for camping and picnicking.

Be Charmed by the Mid-South This Summer

The Mid-South and surrounding regions have an array of charming small towns, each with its unique character, history, and attractions. Whether drawn to the therapeutic hot springs of Hot Springs, the storytelling tradition of Jonesborough, or the historic streets of Shepherdstown, visitors can't go wrong with a weekend road trip in this expansive region. No matter which town you choose to visit, you're sure to find a captivating experience showcasing the best of what the Mid-South offers.

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