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Rural Road Trips

Hit the Backroads and Visit These Six Small Southern Towns This Summer

Small towns are charming—there’s no question about that. Sequestered miles away from big city living, small towns are places where neighbors lend sugar to neighbors and kids run wild and free. But are these sleepy-eyed hamlets summer vacation material? 

BRO decided to find out. So, we packed our bags, hit the Southern highways, and ventured to six of the tiniest, most rural communities we could find in the region. 

Photo: After hiking, refuel at the Pumpkintown Mountain Opry. Photo courtesy of Jenny Aartun

Pumpkintown, South Carolina

Population: Unknown 

In the 1700s, a voyager passed through South Carolina’s Oolenoy River Valley. He saw emerald green brooks, groves of loblolly pines, and sheer granite faces. But what impressed him the most? Fields of large, yellow pumpkins.

“That’s where the name came from,” says Jenny Aartun, a Pumpkintown native. 

Nestled in Pickens County, Pumpkintown is an unincorporated community with a single blinking red light and an old-school general store. Though this place may seem uneventful, locals argue otherwise. 

WHAT TO DO: Start your stay off by hiking an 8.4-mile stretch of the Foothills Trail from Highway 178 to Sassafras Mountain, the highest point in South Carolina.     

WHERE TO EAT: Refuel at the Pumpkintown Mountain Opry, an eatery owned by the Aartun family. The cafe does a little bit of everything, from homemade banana pudding to salads with local microgreens. 

WHERE TO STAY: Though you won’t find a Holiday Inn or Marriott in Pumpkintown, you will find more creative accommodations. At Branches Up Tree Houses, Mason and Ben Sanders host guests in a multi-story treehouse. 

Photo: The Toe River meanders through downtown Bakersville. Photo by Christy Thrift

Bakersville, North Carolina

Population: 439 

Bakersville was once known as the “Wild West of the East.” In the late 1800s, it was known for bootlegging and larceny. It was also home to outlaws Will, Dick, and Tom Whiston, says Christy Thrift, owner of N.C. Outdoor Adventures.

More than 100 years later, this High Country town is now a family-friendly escape better suited to hikers than outlaws. But with sun-parched summits to explore and rivers to raft, Bakersville still feels pretty wild. 

WHAT TO DO: Spanning from Sugar Gap to the Black Mountains, the Toe River is said to be one of North Carolina’s most pristine waterways. You can explore the river during a whitewater tubing or kayaking trip with N.C. Outdoor Adventures.  

WHERE TO EAT: Before loading up the kayaks, grab some healthy snacks at Just Local Market on North Mitchell Avenue. 

WHERE TO STAY: Bakersville offers little in terms of traditional accommodations. However, visitors can set up camp at the Root Cellar Tiny House, an itsy cabin situated on a 19th-century tobacco farm.    

Photo: Warm mineral waters flow from the springs at Berkeley Springs State Park. Photo courtesy of the West Virginia Department of Tourism

Berkeley Springs, West Virginia 

Population: 587

In 1748, at the ripe old age of 16, George Washington traveled to Berkeley Springs to take a bath. There, the soon-to-be president soaked in 74-degree mineral water, which was thought to have curative properties. 

Today, you can still visit Washington’s bathtub, a relic in the heart of downtown. You can also try out “ye famed warm springs” for yourself.   

WHAT TO DO: Start your stay with a mineral soak at Berkeley Springs State Park. Then go horseback riding with Triple C Outfitters. These hour-long rides meander through the dogwood-lined trails of Cacapon Resort State Park.

WHERE TO EAT: After your trail ride, nurse an apple butter ale and boozy brisket sandwich at Berkeley Springs Brewing Company. 

WHERE TO STAY: For a truly authentic experience, stay in the Bath Keeper’s Cottage. Located on land previously owned by bathkeeper John Davis, this tiny guest house is perfect for two people.

Photo: Helen is an angler’s paradise. Photo courtesy of

Helen, Georgia

Population: 593

Despite being a transatlantic flight away from Germany, the town of Helen looks like a Bavarian alpine village. Cobblestone streets are lined with gingerbread-esque chalets and there’s spätzle on every corner. 

The European ambiance is endearing, sure. But there’s a lot more to do than sip hefeweizen and munch on soft pretzels. According to Jake Darling, manager of Unicoi Outfitters, this old-world borough is the perfect basecamp for outdoor adventuring. 

WHAT TO DO: With 180 trout streams in the area, Helen is a fly-fishing haven. To help you find the best honey hole, Unicoi Outfitters guides trips on private and public waters. The shop also offers a basic fly fishing course called the “Gilligan Special.” 

WHERE TO EAT: Darling recommends eating at Cowboys and Angels, a southern steakhouse about five minutes from the fly shop. Try out the Pickled Peach, a ground chuck burger with house-pickled peaches and spicy pepper jack cheese. 

WHERE TO STAY: When you stay at the Biscuit Inn, there’s no need to leave Fido at home. Located four miles outside of downtown, this pet-friendly motel is the perfect place to crash when you’re dog-tired. 

Photo: At 34.3 miles long, the Virginia Creeper Trail is a mecca for cyclists. Photo by Michael Wright

Damascus, Virginia 

Population: 757 

Damascus is a quirky trail town with a carefree attitude. “You never know what the hell you’re going to see,” says Michael Wright, owner of Sundog Outfitter. Case in point: “Just last week, a dude was hiking with a goat.”

Wright credits the area’s off-beat vibe to the Appalachian Trail, which runs right through downtown and attracts a motley crew of nomads. There’s also the Virginia Creeper Trail, which is a popular destination for families visiting from more urban areas.

“It’s a weird place, but friendly,” Wright explains. “Everyone smiles and waves.”

WHAT TO DO: Want to experience the Virginia Creeper Trail without all the huffing and puffing? Rent a bike from Sundog Outfitter and let them shuttle you to Whitetop Station. From there, enjoy a 17-mile downhill ride to Damascus.  

WHERE TO EAT: Breakfast is the most important meal of the day, especially when adventure is afoot. Fuel up with a banana strawberry smoothie and latte from Mojo’s Trailside Café.  

WHERE TO STAY: Sure, you could rent a hotel room in Damascus. Or, you could pitch a tent at Grindstone Campground and access a bounty of pristine terrain in the Mount Rogers National Recreation Area.       

Photo: Kayaking in the Big South Fork National River and Recreation Area is a popular pastime in Stearns. Photo courtesy of Sheltowee Trace Adventure Resort

Stearns, Kentucky

Population: 1,190

In 1902, Justus S. Stearns bought 30,000 acres of virgin timberland in southern Kentucky. Coal was discovered not long after, and the area emerged as a hub of industry. 

A lot has changed since then. Namely, the logging and mining empires have wilted. But in the wake of this change, Stearns is gaining recognition for its other natural resources: limitless sunshine and thousands of acres of public land.   

WHAT TO DO: For a taste of what once was, ride the Big South Fork Scenic Railway to Barthell Coal Camp for a historic tour. If you’re not much of a history buff, go canoeing or kayaking in the Big South Fork National River and Recreation Area with Sheltowee Trace Adventure Resort.

WHERE TO EAT: In keeping with the railroad theme, eat some fried pickles and catfish at The Whistle Stop. End with a decadent slice of peanut butter pie.  

WHERE TO STAY: Spend the night at Barthell Coal Camp in a “Company House.” These cabins were inspired by those built in the early 1900s by Stearns Coal and Lumber Company. 

Cover Photo: Photo courtesy of Getty Images

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