8 Most Overlooked Kentucky Towns For 2025
The next time you plan a road trip in Kentucky, skip the Louisville or Lexington tourist attractions and head to the real heart of Kentucky. They may be slightly off the beaten path, but the journey through the winding roads and bluegrass fields of Kentucky is half the fun! From the geological wonders of Carter Caves in Olive Hill to the farm-to-table homestyle meals of the Shaker Village of Pleasant Hill in Harrodsburg, these communities are overlooked. When you are ready for a memorable trip in 2025 to Kentucky’s hidden treasures, the open road is waiting!
Olive Hill
In eastern Kentucky in the foothills of the Appalachian Mountains, Olive Hill is considered a Kentucky Trail Town, due to its proximity to some of the best trail systems and outdoor adventures in the state. Visiting Olive Hill is like a huge outdoor playground for nature lovers. One of the best places for exploration is Carter Caves State Resort Park. The air is always a little cooler in the underground caverns of Carter Caves, with a stunning 30-foot waterfall, giant stalactites, and the Saltpeter Cave that used to be a source of gunpowder during the War of 1812. Above ground, there are over 30 miles of scenic hiking trails with naturally occurring bridges like Smokey Bridge, Fern Bridge, and Raven Bridge, some standing 90 feet tall!
Grayson Lake State Park is another must-see for visitors to Olive Hill, with stunning lake views. This over 1,500-acre park has 74 miles of shoreline along Grayson Lake that is great for swimming, boating, or fishing on its calm waters. The park also has the Beech‑Hemlock Nature Trail and the Lick Falls Loop, which takes you through the lush scenery of the foothills of the Appalachian Mountains. After a long day of exploring the natural wonders of Olive Hill, you can stroll through the sleepy downtown streets and stop in for a filling meal at Walker's Restaurant.
La Grange
In La Grange, you might be savoring a meal at One Nineteen West Main when, just outside the window, a freight train rumbles right down Main Street. That is quite a common experience in La Grange, where passing freight trains rumble the windows of local shops 20 times a day, echoing the spirit of the community 100 years ago. To learn more about the railroad history of La Grange, the La Grange Railroad Museum's century-old train depot details the evolution of the railroad industry, and even has a restored 1929 dining car and caboose available to rent for parties.
You don’t have to leave La Grange’s city limits to enjoy its natural beauty. Wilborn Park is a lovely green space along the banks of L and N Lake. The lake was once a Limestone Quarry while the community built the railroad tracks, and was later flooded and transformed into a recreational area. It’s even named after the L&N (Louisville and Nashville) railroad! It’s a wonderful place to fish or just relax along its calm waters.
Augusta
Along the banks of the Ohio River in northern Kentucky is Augusta, an area that seamlessly blends natural beauty and history. The best way to take in the views of Augusta is aboard the Augusta Ferry. It is one of the oldest ferry services still in operation on the Ohio River, shuttling passengers from Augusta to Higginsport, Ohio, since 1798! While the views aboard the ferry are amazing, strolling through historic downtown Augusta is just as charming.
Augusta is home to hidden treasures, like the Rosemary Clooney House, which transports you back to the days of old Hollywood without leaving the Midwest. The museum has a collection of memorabilia, including the largest collection of mementos from White Christmas anywhere in the world. One of the best ways to end a day exploring the natural and historical sites of Augusta is by popping in for a brew and tasty dinner at the Augusta Pub.
Pineville
On the southern edge of Kentucky, not too far from the Tennessee border, is Pineville, aka the Gem City of the Cumberlands. Nestled on a strip of land between the Cumberland River and Pine Mountain, it is a hidden community that you would never stumble upon by accident. The most amazing views in Pineville overlook the Cumberland River, like the famous Chained Rock. Chained Rock is a bit of a local legend in Pineville. The rock formation has a long chain drilled into it, and the legend says that the chain keeps the rock from tumbling down into the town. In reality, the chain was installed in 1933 as a tourist attraction to draw visitors to Pineville during the Great Depression.
Not too far from Chained Rock is the Pineville Overlook within Pine Mountain State Resort Park. The overlook not only provides breathtaking views of the rolling mountains and Cumberland River below, but also of the entire community of Pineville. While central Pineville has a few diners and cafes, nothing beats the dining experience of the Mountain View Restaurant at Herndon J Evans Lodge. Situated southwest of Pineville, the restaurant is located in a remote, wooded setting, with superb buffets, seasonal entrees, and the most amazing views.
Cadiz
On the southwestern edge of Kentucky is Cadiz, the perfect destination for a long weekend of fishing, hiking, and outdoor adventures. Cadiz is known as the Gateway to Land Between the Lakes, which is so much more than a beautiful national park. The park encompasses over 170,000 acres between Lake Barkley and Kentucky Lake (hence the name Land Between the Lakes). There are hiking trails, like Honker Lake Trail, or the Homeplace Working Farm and Living History Museum (just across the border into Tennessee), which transports you back to the early days of Cadiz.
The Land Between the Lakes may be the biggest draw to Cadiz, but its friendly downtown area is just as charming! Strolling down the picturesque Main Street offers delightful stops like the Janice Mason Art Museum or the Cadiz Antique Mall. As a community centered around lakes and waterside attractions, the best place to grab a bite to eat is the Fishin' Hole Restaurant, known for its locally sourced catfish.
Pikeville
Life is quite peaceful these days in the eastern Kentucky town of Pikeville — but it hasn’t always been that way. It was once home to the notorious feud between the Hatfields and McCoys in the late 1800s. Many of the feuds took place in Pikeville, and you can visit some of the locations like the McCoy homeplace, Hog Trial Cabin, and the final resting place of Randolph McCoy at Dils Cemetery via the Hatfield-McCoy Historic Feud Driving Tour.
One of the most spectacular views in Pikeville is the Pikeville Cut-Through, a massive excavating project of the 1980s that removed over 18 million cubic yards of rock and soil to prevent flooding of the region and opened up the area for more parks and public spaces. From the Cut-Through Overlook at Bob Amos Park, you can see the layers of exposed rock faces. But if you want to experience the real fun of Pikeville, one of the best times to visit is in the spring during the annual Hillbilly Days Festival! Expect carnival rides, live music, great southern food, and a hillbilly-themed parade.
Stearns
In the early 1900s, Stearns was a booming coal and lumber community. The Stearns Coal and Lumber Company built the entire town, from housing to general stores. However, in the 1950s, when demand for coal waned in Kentucky, many of the mining and coal operations shut down. While Stearns suffered the demise of its mining operations, it entered its new era as a trail town, offering hikers a humble retreat from amazing nearby trails.
Stearns is considered a Gateway to the Big South Fork National River and Recreation Area, just on the other side of the border into Tennessee. It is a great place to hike the trails, raft down the Big South Fork of the Cumberland River, or explore the mining ruins of the Blue Heron Mining Community. If you want to travel through the lush forests, taking the same paths as the miners all those years ago, be sure to hop aboard the Big South Fork Scenic Railway! When you are ready to learn more about the history of Stearns, the McCreary County Museum is right next door to the train depot.
Harrodsburg
In central Kentucky is Harrodsburg, Kentucky’s oldest permanent English settlement west of the Allegheny Mountains. You can sense Harrodsburg's deep-rooted history in every corner of the community, from the Victorian-inspired architecture lining the streets with quaint establishments like The Local ice cream parlor or Granny’s Diner. Old Fort Harrod State Park, located in central Harrodsburg, is part green recreational area, part historical attraction. It has a full-scale replica of the original 1770s fort, the Mansion Museum, and Pioneer Cemetery.
The Shaker Village of Pleasant Hill, located not too far from the lovely Fulling Mill Falls, was at one time the third-largest Shaker settlement in the country. Self-guided tours of the sprawling farm nestled on almost 3,000 acres take you through restored buildings and live demos of soap making and basket weaving. There is even a restaurant called the Trustees’ Table, serving up homestyle farm-to-table Kentucky cuisine in a historical setting.
Discover the Best Kept Secrets of the Bluegrass State
Kentucky may be known for bourbon and bluegrass, but its quiet backroads tell the best stories. Whether it is the story of the original European settlers of Harrodsburg or the tale of the old mining operations of Stearns, the true heart of Kentucky lies in hidden communities scattered throughout the fields of bluegrass. The next time you find yourself in Kentucky, take a detour off Interstate 65 and travel the backroads. It is where you will find a good homestyle meal and friendly locals who make it feel like home.
