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6 Most Memorable Small Towns in the Southern United States

by Staff

Consisting of a large swathe of the country including 16 states and the District of Columbia (home to Washington D.C.), the Southern United States has earned a solid reputation for its warm hospitality, its rich history, as well as its stunning landscapes – all traits that are seen in abundance in the region’s most attractive small towns.

From the rolling hills of the Blue Ridge Mountains of Virginia to the sun-soaked coasts of Florida, each of the six towns on this list has its unique personality that’s guaranteed to captivate the interest and imagination of all travelers. Find out more and be inspired by these most memorable small towns in the Southern United States.

Wytheville, Virginia

Historic brick buildings in Wytheville, Virginia, via Kristi Blokhin /

The most northerly of the small towns featured on this list, the small town of Wytheville, Virginia, might well be the best known. Located at the junction of the I-77 and I-88 highways and often overlooked by travelers heading south to Florida, Wytheville was founded in 1789 in the Iron Mountains, a part of the Blue Ridge Mountains that extends from here to Tennessee, and was named after George Wythe, one of the original signatories of the Declaration of Independence. The town’s attractive downtown core is home to the Edith Bolling Wilson Birthplace Museum, a historic site that celebrates the life and legacy of the wife of President Woodrow Wilson; it’s also notable as one of the few museums in the nation dedicated to a First Lady. 

Other must-visits include the Wytheville Training School Cultural Center, which provides insights into the region’s African American heritage in a heritage schoolhouse built in 1882; and the Thomas J. Boyd Museum with its artifacts and exhibits detailing the rich history of Wytheville and Wythe County. Outdoor enthusiasts will enjoy a visit to the Big Walker Lookout with its excellent views from the 100-foot-tall observation tower, the oldest and highest privately-owned attraction in Virginia. Nearby Crystal Springs Recreation Area is also popular for its hiking, picnicking, and mountain scenery. For a great night’s stay, check into the historic, centrally located Bolling Wilson Hotel, handily located within walking distance of most downtown attractions.

Blue Ridge, Georgia

Aerial view of Blue Ridge, Georgia.
Aerial view of Blue Ridge, Georgia.

The Appalachian Mountain community of Blue Ridge, Georgia, was founded in 1886 as a railroad town, a legacy that lives on to this day thanks to the Blue Ridge Scenic Railway. This heritage railroad offers a 26-mile scenic train journey along the Toccoa River to the border with Tennessee, providing passengers with stunning scenic views along the way. Part of the fun is seeing the train come and go from its depot located in the middle of the town, passing the town’s many quaint shops and galleries along the way. For a truly memorable stay, the historic Blue Ridge Inn B&B is steps away from the downtown area and was built in 1890 and was once the home of the railway’s founder, Sylvester Long.

For outdoor enthusiasts, the Aska Trails Area is a must-visit. This network of hiking and mountain biking trails offers various levels of difficulty, with paths meandering through the beautiful mountain terrain and offering spectacular views of the Blue Ridge Mountains and Lake Blue Ridge. This lovely reservoir is also fun to explore and offers fishing and swimming, while its marina provides rental services for pontoons and jet skis. 

Hilton Head Island, South Carolina

Harbor Town Hilton Head Island, South Carolina.
Harbor Town Hilton Head Island, South Carolina.

Although only officially established as a township in 1983, beautiful Hilton Head Island has a long and rich history that dates back even further than the building of the bridge that connected it to the mainland in 1956. The big draw in this slice of South Carolinian paradise is the incredible 10-mile stretch of Atlantic-facing beach that attracts over 2.5-million-day trippers and vacationers each year. The best-known waterfront area Coligny Beach Park, a lovely area with seating, change areas, ample parking, wheelchair access, and even Wi-Fi access that winds down to the soft sand and ocean.

Nature lovers will want to visit Pinckney Island National Wildlife Refuge, located between the island and the mainland. This refuge spans over 4,000 acres and is a prime spot for hiking, bird watching, and spotting wildlife such as deer and alligators in their natural habitat. Another must-do is the Coastal Discovery Museum with its interesting look into the island’s cultural history and natural environment, featuring indoor and outdoor exhibits, gardens, and walking trails.

St. Augustine, Florida

Aerial view of St. Augustine, Florida.
Aerial view of St. Augustine, Florida.

St. Augustine, Florida, has the distinction of being not just one of the prettiest towns in the South, it just so happens to be the oldest in the United States. Founded in 1565 by Spanish explorers, highlights include the Castillo de San Marcos, the oldest masonry fort in the continental USA. This massive stone fortress, now a National Monument, overlooks the scenic Matanzas Bay and features gun decks and spectacular views over the town and bay.

Other historical attractions include the St. Augustine Lighthouse & Maritime Museum. Built in 1874, this well-preserved lighthouse can be toured and provides spectacular ocean views; and the Cathedral Basilica of St. Augustine is a stunning example of Spanish colonial architecture that features beautiful frescoes, stained glass windows, and a charming courtyard. The cobbled streets of St. Augustine are a delight to explore, with St. George Street standing out as a pedestrian-only thoroughfare lined with quaint shops, galleries, and restaurants.  

Bardstown, Kentucky

Nicols County Courthouse in Bardstown, Kentucky.
Nicols County Courthouse in Bardstown, Kentucky.

As most whiskey (or whisky) fans will know, Scotland isn’t the only maker of this world-class beverage. Known as the “Bourbon Capital of the World,” Bardstown, Kentucky, is home to 11 distilleries and is an essential destination for anyone interested in the history and production of bourbon. Visitors can explore the famed Bourbon Trail, which includes legendary distilleries like Heaven Hill, Barton 1792, and the Willett Distillery, each offering a unique glimpse into the intricate process of bourbon making, from fermentation to aging, culminating in tastings and, if you fancy hanging around, gourmet meals.

Continue your exploration of Bardstown and bourbon at the Talbott Tavern, a historic inn built in 1779 and said to be the oldest surviving stagecoach stop in the country. You can even book a night’s stay here but be sure to book well ahead if you’re planning on visiting during events like the Kentucky Bourbon Festival or the Bardstown Arts and Crafts Festival. Bardstown is also home to the Women’s Civil War Museum which, along with Old Bardstown Village, provides a look into the life and times of 19th-century America.

Key West, Florida

Street view of the Main Strip in the Downtown City where all the bars are located in Key West, Florida
Street view of the Main Strip in the Downtown City where all the bars are located in Key West, Florida

The most southerly community on this list of must-visit towns in the South, Key West has the distinction of being the southernmost point of the United States. Famous for its laid-back atmosphere and unique Caribbean vibe, this island town is located at the tip of the Florida Keys and can be reached by air or a spectacular four-hour drive from Miami via the famous 113-mile long Overseas Highway. This tropical paradise not only attracts tourists with its colorful architecture, lively street scenes, and picturesque beaches, but also for its rich history and culture. Topping most lists of fun things to do in Key West is the Ernest Hemingway Home and Museum, a classy Spanish Colonial-style house where the famed author lived in the 1930s. In addition to artifacts and exhibits relating to the famed author, the museum is home to a unique colony of six-toed cats, descendants of Hemingway’s own pets.    

Other must-visit attractions include the Southernmost Point Buoy, a concrete buoy marking the southernmost point in the continental United States. It’s a popular selfie spot for visitors and symbolizes the end of U.S. Route 1 which stretches all the way to Maine; the Key West Butterfly and Nature Conservatory, a glass-enclosed habitat that’s home to hundreds of butterflies and exotic birds; and the famous Mallory Square, known for its fun Sunset Celebration.

The Final Word  

These six most memorable small towns in the Southern USA each represent the region’s diverse culture, heritage, and natural beauty.  From the historic downtown core of Wytheville and its presidential connections to the country’s southernmost community, Key West, these great places to visit in the United States offer a fascinating journey through time, boasting no end of unforgettable travel experiences along the way.

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