People seated at a sidewalk table taking a picture in front of the 'Downtown Sweet' coffee shop in Jonesborough, Tennessee. Editorial credit: Nolichuckyjake / Shutterstock.com

9 Picturesque Towns in Tennessee for a Weekend Retreat in 2024

The Mid-South state of Tennessee has a reputation for country music, mountainous geography, and good old-fashioned hospitality. First admitted to the Union in 1796 as the 16th state, Tennessee has a long history, including its time as a Confederate state during the American Civil War. Beyond its history, the state has many beautiful landscapes in both the rolling hills of Western Tennessee and the picturesque mountain towns in the Appalachian Mountains. In these towns, you'll find historic distilleries, the sites of major American trials, picturesque mountaintop views, natural bridges, and much more. If you're looking for a great weekend getaway, these nine picturesque Tennessee towns will be right up your alley.

Lynchburg

Lynchburg Hardware and General Store, along with the Jack Daniels and Barrel Shop, located in the traditional commercial block near the Jack Daniels Distillery in Lynchburg, Tennessee.
Lynchburg commercial block in Lynchburg, Tennessee. Editorial credit: Paul McKinnon / Shutterstock.com

Lynchburg was first settled in the early 1800s by Thomas Lynch. The area quickly became a hub for corn and barley farming, which set the stage for its history as a whiskey town. The Jack Daniels Distillery was established in 1866, with its water coming from Cave Spring. Today, the Jack Daniel's Distillery is a great place to tour and try out the locally made spirits. There are several other spots in town for explorers, including the old Moore County Jail and Courthouse from the late 1800s and the Lynchburg Hardware and General store, which sells a great deal of local souvenirs. Don't forget to visit Jack Daniels's grave while you're there. For places to stay, consider trying out a local bed and breakfast at Lynchburg Valley Inn.

Tullahoma

View of Jackson Street (U.S. 41A) in Tullahoma, Tennessee, with the First United Methodist Church on the left.
Jackson Street in Tullahoma, Tennessee. By Brian Stansberry, CC BY 3.0, Wikimedia Commons

This small town of just over 20,800 people was founded in 1852 and would play a major role in the American Civil War when Union General William Rosecrans drove out the Confederate Army in the Tullahoma Campaign. History lovers will enjoy learning about this history by exploring the Tullahoma Campaign Civil War Trail and checking out Beechcraft aircraft at the Beechcraft Heritage Museum. Tullahoma also has several great hiking spots, such as the Short Springs Natural Area, which features the Machine Falls, and Tims Ford State Park, which has a picturesque lake and hiking trails. Lastly, you can enjoy a good show at the South Jackson Performing Arts Theater or try out whiskey at the George Dickel Distillery. There are several hotels you can stay at, including Hampton Inn Tullahoma and The Grand Lux Inn.

Winchester

The old Bank of Winchester building, originally home to Farmers National Bank and now housing the San Miguel Coffee Company, in Winchester, Tennessee.
The San Miguel Coffee Company, in Winchester, Tennessee. By Brian Stansberry, CC BY 3.0, Wikimedia Commons

Home to just under 10,000 residents, Winchester has a long history. It was founded in 1809 and named after General James Winchester, who served in the American War of Independence. Today, the town is home to several unique landmarks, including the Franklin County Courthouse, an Art Deco-style structure, and The Old Jail Museum, which has many local exhibits. Much like Tullahoma, it is located close to the Tims Ford Lake, which offers boating, hiking, and fishing opportunities. Also close to town is the Sewanee Natural Bridge, a sandstone structure that you can easily hike to. There are many local shops in the area that are great for finding a nice souvenir, ranging from The Lake Store to About Town Apparel and Meshed. For spots to stay at, consider the County Manor Bed & Breakfast.

Dayton

The Bryan College campus in Dayton, Tennessee, featuring academic buildings and well-maintained grounds in a scenic setting.
The Bryan College campus in Dayton, Tennessee. By Harrison Keely, CC BY 4.0, Wikimedia Commons

Originally known as Smith's Crossroads, it would be renamed as Dayton in the 1870s, the same as the city in Ohio. History and science enthusiasts will definitely want to visit Dayton as it was the home of The Scopes Trial in the 1920s, which pit a teacher who taught evolution in schools against the state in a trial that would come to be known as the Monkey Trial. You can learn about this trial at the Scopes Trial Museum housed within the basement of the picturesque Rhea County Courthouse, built in 1891. Dayton also has a rich fishing tradition, which earned it the nickname of The New Bass Fishing Capitol in the South. You can fish for bass yourself at nearby Lake Chickamauga. Also in town is the charming Lorenzen Flower Farm, where you can snap a photo or pick a flower of your own. For places to stay, consider the Blue Water RV Resort and Marina on the shores of Chickamauga Lake or the Sleep Inn and Suites in town.

Rogersville

Rogersville, Tennessee, settled in 1775 by the grandparents of Davy Crockett.
Street view in Rogersville, Tennessee. Editorial credit: Dee Browning / Shutterstock.com

This historic Tennessee town is the second oldest in the state and, as a result, has some of the oldest spots in Tennessee to explore. In Rogersville, you can see the site of the first newspaper in Tennessee at the Tennessee Newspaper and Printing Museum. Other historic sites in town include the Hawkins County Courthouse and Hale Spring Inn, which held guests such as Andrew Jackson and Andrew Johnson. You can also explore the birthplace of the famous performer Archie Campbell at the Archie Campbell Museum. There are also great parks to visit, such as Crockett Springs Park and Laurel Run Park. The Hale Spring Inn still operates as an inn, which makes it an ideal spot to stay.

Greeneville

The historical district of Greeneville, Tennessee, featuring the General Morgan Inn, originally built as the Grand Central railroad hotel in 1887.
The historical district of Greeneville, Tennessee. Editorial credit: Dee Browning / Shutterstock.com

Located in East Tennessee, Greeneville gets its name from Nathanael Greene, a general in the American War of Independence. This quiet mountain town was a part of North Carolina in 1783 before being integrated into the state of Tennessee. Today, there are several unique sites and experiences in town. One of the most interesting ones is The Wandering Llamas business, which allows you to hike the mountains of the Appalachian with a Llama at your side. You can also see the picturesque Margaret Falls or The Bible Covered Bridge; one of the few remaining covered bridges in the state is the Bible Covered Bridge. For Presidential history buffs, you'll definitely want to visit the Andrew Johnson National Historic Site, where the 17th president was born. For places to stay in town, the Nolichuckey Bluffs Bed & Breakfast Cabins are an ideal spot.

Jonesborough

Aerial view of Jonesborough, Tennessee, the state's oldest town, founded in 1779. It once served as the capital for the short-lived 14th state of the U.S., known as the State of Franklin.
Aerial view of Jonesborough, Tennessee, the state's oldest town, founded in 1779.

Jonesborough is the oldest town in the state, with the first settlers showing up in 1779. With this long history, the town has a lot of stories to tell, which is reflected in its International Storytelling Center and the annual National Storytelling Festival in October. You'll have many stories to tell after visiting Jonesborough, especially after exploring the many sites, such as the Chester Inn State Historic Site and Museum, Jonesborough-Washington County History Museum, and Old Jonesborough Cemetery. The town is near several magnificent parks, such as the Davy Crockett Birthplace State Park, Cherokee National Forest, and the Wetlands Water Park. While you're in town, you can stay at the Historic Eureka Inn, first built in 1797, or the Blair-Moore House.

Franklin

Memorial to the Confederate soldiers of the American Civil War along Main Street in Franklin, Tennessee, a small town south of Nashville.
Memorial of the American Civil War in Franklin, Tennessee. Editorial credit: Fotoluminate LLC / Shutterstock.com

Renowned as a charming town, it's easy to see why Franklin has one of the best main streets in the country. In fact, its downtown area has been named a Great American Main Street for its boutique shops and historic buildings, such as Mercantile 1858 and the Lotz House Museum. There are numerous rich historic sites to explore in Franklin, such as the Rippa Villa plantation, the Williamson County Archives & Museum, and Carnton. Franklin stands at the intersection of several unique parks, such as the Natchez Trace Parkway, built on ancient Native American roads, Wilkins Branch Mountain Bike Park, and Marcella Vivrette Smith Park, which contains the 1825 Ravenswood Mansion. For a relaxing place to stay, try out The Harpeth Hotel downtown or the Whispering Woods Lodge in nearby Leiper's Fork.

Gatlinburg

Gatlinburg, Tennessee, showcasing the unique architecture of this popular tourist destination, known for travel, shopping, and scenic mountain views.
The unique architecture of Gatlinburg, Tennessee. Editorial credit: Kosoff / Shutterstock.com

Gatlinburg is one of the most beautiful places, not just in Tennessee but also in the entire Mid-South region. It's the entry to the Great Smoky Mountains National Park, a vast place with trails, caves, waterfalls, and black bear populations to see and explore. Within the park, you can also see more than 90 historic buildings, such as the Jim Bales Cavin and Smokemont / Oconaluftee Baptist Church. The town itself has a lot of places to explore, ranging from the Arts and Crafts Community to the Hollywood Star Cars Museum. You can get a great view of Gatlinburg from the SkyBridge, a 680-foot-long pedestrian glass floor sky bridge 140 feet in the air. Lastly, the town is close to Pidgeon Forge, the home of Dollywood and other great mountain attractions. There are several hotels you can stay at in town, or you can rent a cabin with Big Smoky Mountain Cabins.

Discover Tennessee's Hidden Highlights for Your Next Retreat

Tennessee is a wonderful state to explore for several reasons, but the biggest one is its high-quality small towns. The towns have quaint and charming main streets, picturesque mountain views, and more. By visiting these towns, you can learn about the American Civil War, the struggle over science that continues today, and American President Andrew Johnson. And while you're at it, you can catch a great story from residents of towns like Jonesborough. The next time you're in the Mid-South, consider renting a hotel or cabin in one of these nine towns.

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