Kentucky's Picturesque Town Set Between Mountains And A River Is Home To Folklore, Festivals, And Trails

In the late 1700s, settlers were just starting to explore the land we today call Kentucky. To get there, they'd take the Wilderness Road across the Cumberland River at a shallow point just past a gap in Pine Mountain known as The Narrows. In 1781 a permanent settlement called Cumberland Ford was built on the narrow piece of land separating the Cumberland River from Pine Mountain, one of the first to be established in Kentucky.

That settlement today is known as Pineville, and, despite the name change, it remains the oldest town in Bell County (and one of the oldest in Kentucky). The Courthouse Square Historic District is a good place to start if you want to learn more about this history. Listed on the National Register of Historic Places, this is where you'll find landmarks such as the 1930s Art Deco Bell Theater, an official stop on the Kentucky Artisan Heritage Trails.

Surrounded by historic national parks, Pineville has also retained its close connection to the land. The majestic views of Cumberland Gap National Historic Park are about 20 miles south, with Cumberland Falls State Resort Park (also known as the Niagara of the South) about 50 miles west. Yet as removed as Pineville feels from modern, urban life, it's only a two-hour drive from Knoxville or Lexington. This makes it a charming and accessible home base for visitors who want to explore the beautiful landscapes and unique culture of Eastern Kentucky.

Every Memorial Day weekend, Pineville transforms from a quiet town of about 2,000 people to the bustling setting for the Kentucky Mountain Laurel Festival. It's the second-oldest festival in Kentucky, first celebrated in 1931 as a tribute to Thomas Walker, the first European explorer to set foot on the present site of Pineville. Pageantry is the festival's main draw, culminating in the festival Queen's coronation at Laurel Cove Amphitheater and the Grand March to the Queen's Ball that follows. It's not all curtsies and taffeta, though, with vendor booths, live music, and carnival rides among the weekend's other activities.

If you're more into music than parades and galas, then the Laurel Cove Music Festival is likely to be more your speed. First held in 2019, it typically spans three days in early June — though you'll want to get your tickets early if you plan to attend. Per the Lexington Herald Leader, the 1,500 tickets available each year often sell out before the bands are even announced, and it's easy to see why. Not only does the lineup feature a slew of talented Appalachian musicians but it happens inside Pine Mountain State Resort Park. The combination of great jams and the picturesque backdrop of laurel blossoms and hemlock trees has earned the festival the nickname "Kentucky's Red Rocks."

On the other side of summer, Pineville hosts the Bell County Fair in August. This four-day fair offers affordable all-ages entertainment, with tickets typically ranging from $5 to $15 depending on the night. That entry fee gets you unlimited carnival rides, along with a seat for the night's entertainment, which includes live music, a rodeo, and a monster truck show. Classic car enthusiasts will want to hit the fair Saturday morning for the free car show.

Pine Mountain State Resort Park is known for its stunning Appalachian mountaintop views. Staying at the on-site Herndon J. Evans Lodge is a great way to enjoy the vistas since each room has its own private balcony or patio. This AAA 3-Diamond rated lodge also houses the Mountain View Restaurant, where you can marvel at the landscape while enjoying local Kentucky wines and fare like fried catfish or Kentucky Hot Brown. 

At the top of the park's Laurel Cove Trail is a must-see piece of folklore dating back to just after Pine Mountain opened as the first state park in Kentucky in 1924. Near the trailhead is a massive boulder attached to an equally gargantuan chain — 101 feet long and so heavy it took a four-mule team two trips to get it up the mountain. Per the Appalachlian Voice, it's been said that the Pineville Kiwanis Club installed the chain to keep people from worrying about the possibility of the boulder rolling loose and wreaking havoc. Whether or not it serves that functional purpose, the Chained Rock has become a notable landmark. The Laurel Cove Trail is challenging, with an 1,100-foot elevation change and obstacles like fallen trees and rock steps, but there's also a shuttle to the top if you want to see Chained Rock without breaking a sweat.

Less challenging trails wind through the 1,700-acre park, too. Among the most popular is Honeymoon Falls Trail, a 1.5-mile loop that passes through old growth forest on its way to the park's largest waterfall. The Lost Trail is ideal for spotting the more than 130 bird species and other wildlife that call the park home. It passes through a ravine and up the back slope of Pine Mountain, going past diverse habitats and the sandstone overhang known as Turtlehead Rock. Each of Pine Mountain's 10 named trails has unique sights to offer, one reason naturalist Dean Henson told the Appalachian Voice it's "one of Kentucky's last great natural places."