6 of the Prettiest Small Towns in the South

For many travelers, Southern charm can’t be beat — especially when it comes to small towns. Whether you’re drawn to historic architecture, picturesque scenery, or a slower place of life, the following small towns have you covered. Add in fun community events and a healthy dose of Southern hospitality, and it shouldn’t be difficult to pick your next travel destination (or two, or three) from this list of six of the most beautiful small towns in the American South. 

Beaufort, South Carolina

Founded in 1711, Beaufort is not only one of the oldest towns in South Carolina, but also surely one of the prettiest. Beaufort’s historic downtown, filled with Federal-style mansions and Queen Anne cottages, is a reminder that when it comes to architecture, they just don’t make buildings like they used to. And with streets that ring with the clip-clop of horses and the rumbling of carriages, Beaufort feels almost like stepping back in time. 

The surrounding scenery of the South Carolina Lowcountry is just as pretty as the town itself. Within town limits, you can expect to find a mix of palm trees and live oaks dripping with Spanish moss, winding waterways such as the Beaufort River, and ample marshland filled with wildlife. Waterfront Park is the perfect place to take in the views, especially since it’s within easy walking distance to Beaufort’s many boutiques, restaurants, and art galleries.

Bay St. Louis, Mississippi

Named for King Louis IX of France and incorporated in 1818, Bay St. Louis and its eponymous bay are located on the Mississippi Sound. The town was once a resort destination for wealthy Southerners, and today it continues to draw all types of travelers with its laid-back coastal vibe, waterfront access, plentiful recreational opportunities, and strong sense of Southern hospitality.

Luckily, there’s plenty to do on land, too. Known for its vibrant art scene, the Old Town hosts Second Saturdays, a monthly event that features live music, shopping, and festive themes to draw the community together. Public art installations can be found throughout downtown, including the Angel Trees, which are elaborate wood carvings crafted from live oaks that were destroyed during Hurricane Katrina.

Fernandina Beach, Florida

Located on Amelia Island, a barrier island tucked off the northeast coast of Florida, Fernandina Beach isn’t your typical Southern town. With 13 miles of sandy beaches, a network of walking and biking trails, and a bustling Main Street, this beach town is equal parts active and relaxed. The island itself is filled with history, too. Originally inhabited by the Timucuan peoples, it has flown eight different flags since 1562. To celebrate Fernandina’s French, Spanish, English, and Mexican colonial roots, the town hosts the Isle of Eight Flags Shrimp Festival, which features live music, a parade, and plenty of shrimp to eat. 

The Amelia Island Museum of History details Fernandina Beach’s historic beginnings, while the island’s maritime past is evident at the Amelia Island Lighthouse, the oldest lighthouse in the state, and Fort Clinch State Park, which dates back to the Civil War. Fernandina Plaza Historic State Park in the Old Town provides views of the Pippi Longstocking House, a historic home that was used as the fictional Villa Villekulla in the 1980s film.

Bardstown, Kentucky

As the “Bourbon Capital of the World,” Bardstown, Kentucky, features 11 distilleries in a 16-mile radius. Situated on the Kentucky Bourbon Trail and host to the annual Kentucky Bourbon Festival, the small town is a favorite for those who sip whiskey or have an interest in the distillery process.

Teetotalers need not fear, though, for Bardstown has plenty more to do than imbibe. Its exceedingly charming downtown area is home to nearly 200 buildings listed on the National Register of Historic Places. Visitors can stay at the Jailer’s Inn, a former jail that housed prisoners for nearly two centuries, or attend a murder mystery dinner at My Old Kentucky Home, a 200-year-old estate. The Kentucky Railway Museum hosts weekend train rides, while the local monastery, Abbey of Gethsemani, offers peaceful walking trails that are open to the public. 

Middleburg, Virginia

About an hour’s drive from Washington, D.C., in the Piedmont region of Virginia, Middleburg has a bucolic feel, with rolling green hills, long stone walls, and horses grazing in wide pastures. Indeed, the town’s equestrian culture is its main claim to fame: Nicknamed the “Nation’s Horse and Hunt Capital,” Middleburg has hosted a weekly fox hunt since 1905, complete with foxhounds and specialty hunting attire.

Such traditions have also bred establishments like the Red Fox Inn and Tavern, which was founded in 1728 and remains a Middleburg mainstay for dining and lodging. Elsewhere in town, you’ll find well-preserved brick buildings, winding roads, and vast rural estates. Middleburg is a local wine destination, with 20 wineries in the surrounding area, and hosts the annual Middleburg Film Festival in October.

Jonesborough, Tennessee

Established in 1779, Jonesborough is Tennessee’s oldest town, and its rich history is visible everywhere you look. The town’s historic architecture includes a mix of Federal, Greek Revival, and Victorian homes. Red brick buildings (and sidewalks) line the immaculate downtown, which hosts historic walking tours in full period costume. Check out the Chester Inn State Historic Site and Museum to learn about the town’s frontier history and the former U.S. presidents who were guests.

Jonesborough, nicknamed the “Storytelling Capital of the World,” also hosts an annual National Storytelling Festival, an event that celebrates the art of oral communication through music, spoken-word poetry, and, of course, storytelling. The International Storytelling Center on Main Street is open year-round, offering performances, events, and community workshops to the public.