7 of the Most Beautiful Historic Towns in Tennessee

Several communities call Tennessee home, each with distinct histories and cultural heritages. From the Chickasaw and Cherokee tribes that originally occupied the territory to the waves of European immigrants that helped develop the land, these diverse cultural influences collectively shaped the Volunteer State as we know it today. The integration of all these heritages makes Tennessee a culturally rich destination, promising tourists a unique experience. 

However, these experiences will not be found in big cities such as Memphis or Nashville; instead, the small towns in Tennessee are the true heart and soul of the state’s cultural and historical heritage. Touring them presents a rare opportunity to discover iconic landmarks that have stood the test of time and experience local traditions passed through countless generations. So, set the stage for an engaging cultural rendezvous in these charming Tennessee destinations. 

Jonesborough

As the oldest town in Tennessee, Jonesborough boasts a storied heritage dating back several years before the state was established. It is an excellent example of Scottish-Irish cultural heritage and has done an impressive job preserving its historical sites. The Historic Jonesborough Visitors Center is the first stop for newcomers in town. Located within the historic district, it takes visitors on an incredible journey back to the 1800s, showcasing the state’s oldest city from its infant years to its current state. Some of the noteworthy landmarks in the neighborhood include the Chester Inn State Historic Site and Museum. This former hotel was opened in 1797 and has served as a museum chronicling Jonesborough’s history since its inception. 

At the Heritage Alliance, you can take a self-guided tour to explore the historical, cultural, and architectural heritage of the town. Browsing through artifacts in this iconic facility offers a sense of just how old Jonesborough really is. But if you want to relive this rich history and other exciting stories through the compelling words of a seasoned orator, you should stop by the International Storytelling Center. 

Columbia

This delightful Maury County community is famed for being the former home of President James K. Polk. It hosts the only remaining private residence of the 11th U.S. president, which dates back to 1816. The brick structure sports a lovely Federal style façade and houses period furnishings and other artifacts depicting the legacy of President Polk. But that is not the only historical gem in Columbia. At the National Confederate Museum at Historic Elm Springs, you can browse a collection of Civil War artifacts telling the story of when the historic  Army of Tennessee started its march to Nashville. 

Elsewhere, the Athenaeum Rectory is an excellent example of Moorish and Gothic architectural combo in the town. The historic building dates back to 1837, when it served the Columbia Female Institute as a rectory. After a long day of exploring the top sites, unwind by sampling sumptuous Southern-style dishes at the Southern Tre Steakhouse. 

Winchester

Winchester was named after James Winchester, the first speaker of Tennessee’s legislative house, who was also a soldier during the American Revolution. It has a rich legacy that involves serving as the capital of the state of Franklin at one point and is home to a couple of sites that will intrigue history buffs. Prominent among them is the Hundred Oaks Castle, a plantation farmhouse constructed by Benjamin Decherd in 1830. A tour of the expansive castle takes guests back to the town’s bygone eras, a symbol of Winchester’s resilience through the years. Meanwhile, the Old Jail Museum is a window into the area’s Civil War history, hosting an impressive collection of artifacts from the period. 

Exploring downtown Winchester exposes you to a bustling corridor with diverse points of interest. You can stop to admire the gorgeous Art Deco architectural style of the Franklin County Courthouse, built at the start of the 1900s. Those with an affinity for caffeine can walk into the Walnut Hill Coffee Company and enjoy a hot cup of coffee in a chill atmosphere. 

Greenville

Greenville’s claim to fame is the hometown of America’s 17th president, Andrew Johnson. This small Greene County community honors the legacy of its most famous son through several landmarks, none more prominent than the Andrew Johnson National Historic Site. The site preserves his homes, tailor shop, final resting place, and other structures related to the former president. Greenville is also one of the oldest towns in Tennessee and boasts a colorful legacy well preserved inside the Greenville Greene County History Museum. Housed inside is a vast collection of archives and artifacts, including Civil War memorabilia, documenting centuries of the town’s existence. 

The Dickson-Williams Mansion is another important historical site showcasing Greenville’s Irish heritage. It belonged to a wealthy Irish settler, William Dickson, who employed skilled Irish artisans to build the homestead in 1821. While exploring the historic district, stop by the Greenville Antique Market and peruse its impressive selection of antique items and collectibles from over 80 vendors at the venue. 

Lynchburg

If you are a fan of Tennessee whiskey, you’ll be intrigued to witness where the state’s rich whiskey culture took root. Jack Daniels, the founder, registered Tennessee’s most famous whiskey brand in 1866, which makes it the country’s oldest registered distillery. Visitors can learn more about it at the Jack Daniel’s Distillery Visitor Center. A behind-the-scenes tour of the facility takes you through the rigorous process of crafting the perfect whiskey, with an opportunity to sample the freshly distilled spirit. Furthermore, several artifacts present a look into the beginnings and growth of the iconic Jack Daniels whiskey. 

But there is more to Lynchburg’s heritage than Jack Daniels. The town also hosts the Moore County Old Jail Museum, the county’s only museum. The site was constructed in 1893 and hosts various artifacts, clothing, photos, and other memorabilia, preserving the town’s past for future generations. Finally, Lynchburg has another hidden gem worth checking out. Miss Mary Bobo’s Restaurant has been serving traditional Southern cuisine since 1908 and continues to do so. It is also listed on the National Register of Historic Places. 

Pikeville

This modest Bledsoe County hamlet boasts a rich historical heritage dating back to its founding in 1816. It played a vital role during the Civil War, and strolling through its vibrant downtown introduces you to various historic structures that witness the town’s storied legacy. The Bledsoe County Courthouse is one of the several gems to explore in the district. Sporting a classic red brick construction, it was completed in the early 1900s and included in the National Register of Historic Places in 1995. 

Also, the Pikeville Historic District hosts a mix of 19th-century homes, churches, and other structures currently housing different businesses. It presents a glimpse into the town’s past; exploring it feels like stepping into a time capsule. Meanwhile, the Old Pikeville Cemetery is another essential site and the final resting place of the earliest settlers and pioneers who helped build the town. When not absorbing Pikeville’s exciting history, explore the great outdoors and discover natural wonders at the nearby Falls Creek Falls State Park. 

Bell Buckle

The small town of Bell Buckle in Bedford County welcomes visitors with pleasant charm and warmth. It has a quaint Historic District listed on the National Register of Historic Places, and wandering through its pristine streets transports folks back in time. The neighborhood is lined with immaculately preserved Victorian buildings from another era, with many now housing quirky shops. The Bell Buckle Café is a must-visit and presents a sense of Americana nostalgia with a rustic atmosphere and classic comfort food. Next, you can browse a lavish collection of antique items at Blue Birds Antiques, featuring rows of fine china, furnishings, and other heirlooms from decades past. 

Bell Buckle is also known to host several small-town festivals throughout the year. One of the most popular is the RC-MoonPie Festival, which brings the community together for a day of old-fashioned fun and celebration. Families enjoy Southern dishes while listening to live bluegrass music.

A trip to any of these charming towns in Tennessee is an exciting journey back in time, allowing tourists to witness well-preserved history and culture. From listening to captivating local legends of pioneers who established Tennessee’s oldest towns to perusing unique artifacts and relics from landmark events in the country, like the Civil War, discover a rich experience and once-in-a-lifetime vacation in this storied state.