The Tomato Place  

*This stop will work with your trip if you are an upper-Louisianan and have to take Interstate 20 across to Mississippi before heading up to Chattanooga.

To me, this is the quintessential roadside stop. It has mismatched tables, a kaleidoscope of produce, and as they profess themselves, a “southern grandma’s back porch” atmosphere.  Not only did I enjoy sitting in the sunshine, bathing in the scent of ripening fruits and vegetables, but the Fried Green Tomato BLT was bursting with perfection. It is definitely worth the huge detour. 

Majestic Caverns 

Majestic Caverns in Alabama is an underground cave system located in Childersburg. There are breathtaking formations, including massive stalactites, stalagmites, and other mineral deposits paired with a fun and interesting history. The tours range from more accessible ones to deeper, more adventurous explorations, catering to all levels of interest. That is just the beginning – this spot offers gemstone panning, crystal find, axe throwing, goat yoga, and a Cave Café. 

Amore Ristorante Italiano  

This restaurant is all from scratch Italian and it practically saved my long-distance relationship when we needed a meet-in-the-middle spot for the weekends. The lasagna and cannoli are spectacular. The meatballs are perfect. It is not your typical roadside spot, but it is worth brushing off some crumbs and tucking in your shirt for.  

Noccalula Falls Park and Campground 

This is the ultimate in quick waterfall access – you very literally park and walk up a path for less than 5 minutes and you are at the falls. It has a little more of an “attraction” feel – there will be other people visiting, manicured grounds etc. On one side of the creek, there is a family campground and on the other you can explore a garden, check out historic buildings, and ride a miniature train. Afterward, hike the Gorge Trail to the cavern behind the falls. 

Little River Falls 

This is one of the first waterfalls I ever stopped at on my way to Chattanooga. It is not little. It is a stunning, thundering falls (depending on waterfall season), there are paved trails leading up to the falls, and several spots to splash into the water. For full submersion, there is a blue hole just up the road.  Wear your suit, set aside some time to picnic and bask, and tell your Chattanoogan friends you will be a little late getting in.   

Cloudland Canyon & Trading Post Smokehouse 

Cloudland Canyon is one of those places that takes your breath away the moment you step out of the car – but this is a detour that could last days. Just across the Georgia state line, it’s packed with stunning views, rugged cliffs, and waterfalls you can’t help but stop and stare at. Choose your level of difficulty here – there are hikes around the canyon rim, yurts to camp in, or a seemingly infinite stairway down to a waterfall. After your hike, you must get a pulled pork sandwich from Trading Post Smokehouse because nothing pairs with hard earned muscle fatigue quite like smoky BBQ.  

The Pocket Shirley Miller Wildflower Trail 

This trail takes about an hour to complete. You will take a pretty pockmarked dirt road (Hog’s Jowl) to get to the parking lot. The path starts off as a boardwalk, which is very accessible - in the spring, the area around the boardwalk erupts in a cacophony of bluebells and buttercups. The boardwalk ends and you will have to content with a few steep spots and downed trees on the dirt trail. It is worth it - it ends in a waterfall with natural stone steps you can climb to access a small cave behind the falls. 

Rattlesnake Saloon 

This is a tavern that is in a cavern – a saloon in a cave. Since 1916, the Foster family has transformed the land from a humble farm into a dynamic destination for hunting, trail riding, and adventure, with the iconic Rattlesnake Saloon emerging from what was once a simple hog pen. Because of its unique construction, the Saloon quickly became a top attraction, drawing visitors from all 50 states and over 30 countries. And you don’t have to risk driving after a fun night enjoying live music at the bar - there are campgrounds and cabins, as well as the Seven Springs Lodge, if you want to stay the night. 

Walls of Jericho 

The Walls of Jericho in Alabama is a stunning natural wonder located near the Alabama-Tennessee border. It’s a massive limestone canyon that feels like a hidden sanctuary, surrounded by towering cliffs and lush forest. To reach it, you have to take a fairly challenging 7-mile round-trip hike, but the payoff is worth it. It’s a spot that feels remote, perfect for adventurous hikers looking for something a bit off the beaten path. 

Haunted Old South Pittsburg Hospital Paranormal Research Center 

Sick of hiking but want to keep your heart rate up? The Old South Pittsburg Hospital Paranormal Research Center in Tennessee is a renowned hotspot for paranormal activity. Originally built as a hospital in 1959, it’s now a destination for ghost hunters and thrill-seekers. Visitors have reported eerie encounters, strange noises, and sightings of apparitions, said to be spirits of former patients and staff. The hospital offers tours, investigations, and events for those curious about the supernatural, making it a perfectly odd and quirky place to explore. 

Nickajack Lake

Formed by the Tennessee River and nestled in the Sequatchie Valley, it’s surrounded by scenic mountain views that are perfect for soaking in from a boat or the shoreline. It’s a great spot for kayaking, fishing, or just relaxing by the water. Plus, the lake is home to Nickajack Cave, which is famous for housing thousands of bats—you can watch them fly out at sunset (highly recommended: booking a tour with Chattanooga Guided Adventures) which is a pretty surreal experience. The lake combines natural beauty with a sense of adventure, making it a favorite for locals and road trippers alike. 

Tri-State Corner 

For a quick excursion by Nickajack lake, you can hike to the Tri-State Corner. It’s a relatively short, moderate trail that winds through the woods and offers some great views of the surrounding landscape, including glimpses of the Lake. The real highlight is reaching the Tri-State Corner marker, where you can literally be in three states at once (Alabama, Georgia, and Tennessee). This is a great stop for anyone who loves quirky, offbeat experiences and wants to combine some hiking with a cool photo-op! 

Rock Island State Park

Instead of sticking to Highway 24, take Highway 70—it'll add an hour to your trip, but reward you with endless scenic views. Midway through, stop at Rock Island State Park, countless cascading waterfalls converge. You’ll feel the thunder of the falls in your chest, and if you’re up for it, there are some great hiking trails to explore around the area. 

George Dickel Distillery 

Visit a piece of the Tennessee Whiskey Trail! Cascade Hollow Distilling Co., home to George Dickel whiskey, offers a fun, intimate tour experience with knowledgeable guides. Visitors can enjoy tastings of exclusive spirits and pick up bottles from the gift shop – this is a great pit-stop if your passengers are whiskey lovers! 

The Caverns 

If you manage to synch your trip with a show and overnight at The Caverns, you've hit the road trip jackpot. Nestled in the hills of Pelham, TN, The Caverns is an underground music venue that feels more like a natural cathedral than a concert hall. With rock walls that hum along with the music, this cave-based venue brings you closer to the earth. Beyond the shows, The Caverns also invites you to step into the depths with daily Guided Cave Tours. For true cavers, the Big Room Adventure Tour offers some heart-pounding moments as you navigate tight spaces and climb through rugged passages. Whether you're a hiker, cavern, or just someone who loves good jam, The Caverns offers a blend of adventure, music, and nature that sticks with you long after your eyes re-adjust to the daylight. 

Mountain Goat Market   

Grab a sandwich for your picnic at Denny Cove Falls. This charming café and market offer a mix of sandwiches, salads, pizzas, and baked goods and is known for its eclectic, cozy atmosphere. With its quirky decor and friendly vibe, Mountain Goat Market is the perfect place to grab a bite. 

Denny Cove Falls 

Denny Cove, located in Sequatchie County, TN, is a stunning outdoor spot and one of my favorite hikes. The trail to Denny Cove is a 2-mile, moderate hike that leads you through beautiful, forested landscapes and rewards you with a stunning waterfall. I recommend checking out the scenic views at the end of the hike, which are a short hike from the trail head.

Lodge Caste Iron Museum 

The Lodge Cast Iron Museum in South Pittsburg, Tennessee, is a fun dive into the history of one of America’s favorite kitchen brands. From its 1800s beginnings to its modern-day success, you’ll see cool exhibits about how Lodge cookware is made and its impact on cooking. It’s a must-see for food lovers and anyone curious about the iconic cast iron skillet! 

Dam Whiskey at Hales Bar Dam  

Hales Bar Dam in Marion County, TN, is a historic site with a haunting past. Built in 1905 to control the Tennessee River, it faced floods, financial woes, and fatal accidents. Though replaced by Nickajack Dam in the 1960s, the original powerhouse remains a hotspot for eerie encounters. The best way to experience all this is with the “Distillery plus History Tour” at the Dam Whiskey distillery, which takes you inside the Dam. Sip local spirits while uncovering the dam’s mysterious lore. 

The Gray Fossil Site and Museum

In the top corner of East Tennessee is the town of Gray, where an abundance of fossils was unearthed in late May of 2000 during a TDOT construction project. The Gray Fossil Site is situated around a sinkhole, which has preserved fossils from around 200 species of plants and animals, including tapirs (so. Many. Tapirs.), rhinos, alligators, and mastodons, and more. On their tours, you follow guides down a boardwalk where you can watch archeologists excavate its contents live and in person and peer into a paleontology lab. Hands On! Discovery Center in the museum has lots of activities for kids. Conveniently, it’s just a quick drive off Interstate 26. 

The Town of Rugby, TN  

Rugby, founded in 1880 as a utopian colony by English author Thomas Hughes, is a unique blend of history and charm. Though the original experiment ultimately failed, preservationists stepped in the the 1960s, and now Rugby thrives as a unique destination with Victorian architecture, guided tours of restored landmarks, and beautiful hiking trails. Visitors can explore the first free public library in the South, enjoy a film on Rugby’s story, and take part in fun activities like Irish Road Bowling. For adventure lovers, there are trails leading into the Big South Fork National River, and spooky after-dark haunted tours. With historic lodging options and interesting architecture, Rugby is a great detour on your trip. 

The Lost Sea Adventure

I must be honest—if there’s a chance to explore something mysterious, I’m there. Hidden in Craighead Caverns, there is the largest underground lake in the U.S. The cool, mysterious air pulls you in the moment you enter.  At the entrance, a bright yellow tube stretches into the abyss. You’ll take a guided tour down into the caverns, learning about its history, and then hop on a boat to glide across the lake’s crystal-clear water. It’s a surreal experience and an easy stop if you’re road-tripping through the area. Wear good shoes – the hike down is steep and slippery – strollers/heavy bags are not recommended.  

Shipley Hollow 

My adoration of all creepy things could fill a whole other blog (and it has), but here is a fun spot of note. North of Chattanooga lies Sale Creek, and beyond it, Shipley Hollow, a secluded area with a long-standing eerie legend. For nearly two centuries, locals have reported encounters with a mysterious entity nicknamed the "Pity Pat." There are reports of legends, lights, and spooky sound – pull over if you dare! 

*Full disclosure: this stretch contains my favorite roads in the country. These are the roads that catch your breath mid-sentence, that make your heart well up with a sense of something vast and eternal. Driving west on US 64 or 74, leaving behind the heights of North Carolina, the world unfurls into flower-freckled forests, streams, and valleys, while your car shoulders the curves of charming creeks and thundering rivers. You feel the pulse of the earth beneath your tires, try to decipher old rock songs through the static of the radio, and you remember, with a deep ache of gratitude, how America fell in love with the road. 

Andrews Valley Rail Tours 

Andrews Valley Rail Tours, based in Andrews, North Carolina, offers a fun, scenic adventure on pedal motor-assisted Rail Bikes. The 8.5-mile round trip takes you along old railroad tracks, through the Valley River Tunnel, offering scenic views of the landscape. Tours run Wednesday through Sunday at 9 AM, 12 PM, and 3 PM, and each Rail Bike accommodates up to four people. It’s a unique way to explore the area, combining history, nature, and a bit of exercise!  

Copperhill, TN 

Copperhill, Tennessee, is a darling roadside town to investigate- it combines charm, history, and great scenery all in one spot. Nestled right at the border between Tennessee and Georgia, it offers a relaxed vibe with fun shops, breweries, and restaurants. I loved the river view and frozen creamsicle at the Waterfront Bar and tooling around the walkable downtown. 

Chilhowee Mountain Overlook 

On the way to Benton Falls, you’ll pass the Chilhowee Mountain Overlook, which just happens to be my absolute favorite view in Tennessee. It’s one of those places that instantly restores your faith in the beauty of the outdoors. I’ve taken so many people there, and it never fails to leave them in awe. The best part? It’s just a quick drive off of Highway 411, so it’s easy to stop and soak in the breathtaking views of the mountains and valleys. Always worth the detour. 

Benton Falls 

Benton Falls, located in the Cherokee National Forest near Benton, Tennessee, is a stunning, 65-foot waterfall that’s easily accessible via a short, 1.5-mile hike. The trail is scenic and well-maintained, offering beautiful views of the surrounding forest.  

Ocoee Riverside Farm 

Have you ever considered a sloth sleepover? At this quirky farm, you can snuggle sloths, kangaroos, and bottle feed Scottish Highland calves. For lodging, you have the choice of bunking down in covered wagons, riverside cabins, or a condo that sits above the exotic animal barn. Are you curious but need to know more? They host livestreams daily – visit Ocoeeriversidefarm on YouTube! Whatever animal you choose to cuddle with, this will definitely add some whimsey to your adventure. 

Red Top Mountain State Park 

Red Top Mountain State Park, located on the shores of Lake Allatoona in Georgia, features scenic hiking trails that lead to beautiful, swimmable inlets on the lake! Visitors can enjoy fishing, boating, and swimming in the clear waters, or relax at one of the park’s campsites or cabins. With its rich history, including iron mining remnants, and diverse wildlife, Red Top Mountain offers a peaceful retreat for a quick swim! 

The Jerks of Cartersville  

Cartersville, Georgia, is known for its abundance of museums, including the Tellus Science Museum and the Booth Western Art Museum.  On a drive from Chattanooga to Atlanta, you could spend more than just an afternoon exploring! The Jerks of Cartersville is an old-fashioned soda shop in downtown Cartersville, where you pick your syrup flavor and add carbonation for a truly retro refreshment. This unique stop offers an extensive menu of sodas, shakes, malts, and treats. 

The Rock Garden  

This checks the box for a quirky, roadside stop and will whet your appetite for Rock City in Chattanooga. The Rock Garden in Calhoun, GA, is a tiny, whimsical, hand-crafted garden filled with miniature stone castles, churches, and other intricate structures. Tucked behind a local church, visitors can explore the peaceful pathways, admire the detailed craftsmanship of the miniature buildings, and get back on the road post haste! 

Grumpy’s Antiques 

This multi-level building is loaded with vintage finds, and the unassuming 3rd floor is the definition of an emporium! If you are a thrifter, you MUST stop here on your drive to Chattanooga. You can easily spend several hours wandering through this maze of bizarre collectibles and antiques.