East Pinnacle lookout near Berea, Kentucky.

8 Of The Most Captivating Small Towns In Kentucky

What is the difference between a stopover and a worthwhile destination? That is to say, what are some of the things that make you never want to leave? A lot of cars pass through Kentucky on their way to other southern states, but aside from its world-class franchises, the Bluegrass State has a few gems that are often overshadowed. Before the name became so famous, this bountiful land was home to hunter-gatherers, over 10,000 years ago. Today, some of the most captivating small towns are hidden away among the tulips. Whether you are looking to explore Mammoth Cave National Park, attend the Kentucky Derby, or visit bourbon distilleries on the Bourbon Trail, you will soon find that there is a lot more to this state than you may have heard. Here are eight of the most captivating small towns in Kentucky. Find out what makes them so memorable.

Bardstown

Bardstown, Kentucky.
Bardstown, Kentucky. Editorial credit: woodsnorthphoto / Shutterstock.com

Part of the fabled Bourbon Trail lies in Bardstown. Known as the "Bourbon Capital of the World," you can visit the Heaven Hill Distillery or Bardstown Bourbon Company and learn about what made this small town achieve such significance. A stroll down My Old Kentucky Home State Park would serve as a great opportunity to find out what inspired Stephen Foster’s song as you get a glimpse into 19th-century Kentucky life. You could also check out the Oscar Getz Museum of Bourbon History and see the artifacts from Prohibition and early distilling. If you are still interested in what else survived the test of time here, the downtown area includes Basilica of St. Joseph Proto-Cathedral — the first Catholic cathedral west of the Allegheny Mountains.

Midway

Midway, Kentucky.
Midway, Kentucky. Editorial credit: Alexey Stiop / Shutterstock.com

Train tracks run directly through the middle of this small town, right along a historic railroad line. It is usually a stopover, but Midway is famous for a number of things, and it is definitely worth a stay. You can grab a meal at a local farm-to-table restaurant like Holly Hill Inn, and there are many equestrian farms for horse lovers to enjoy and bask in the state’s thoroughbred culture. Midway is also famous for Midway University, and, if you time it right (typically late September) you could also enjoy the Midway Fall Festival.

Paducah

Paducah, Kentucky
Paducah, Kentucky

Believed to have been named after the Padouca tribe (a Native American group), this town is home to the National Quilt Museum, where many textile arts can be found from across the globe. Its historic downtown area includes the Paducah Wall to Wall murals, where you can see something of a timeline of the region’s history along the Ohio River. On that note, this place is also known for its Lowertown Arts District, a brilliant neighborhood with galleries and workshops. Paducah has a dedication to the arts and crafts, so much so that it is recognized as a member of the UNESCO Creative Cities Network. The city even hosts the River Discovery Center, an interactive museum that focuses on the importance of the nearby waterways.

Harrodsburg

Harrodsburg, Kentucky.
Harrodsburg, Kentucky. Editorial credit: Scott Woodham Photography / Shutterstock.com

This is Kentucky’s oldest town. Established in 1774, you will find a lot of preserved pioneer sites like Old Fort Harrod State Park here. A good starting point here would be Beaumont Inn, a hotel built in 1845 and converted to an inn around 1919. It's famous for its Southern cuisine, so after a meal there, you may want to head on over to the Mercer County Fair & Horse Show, one of the oldest continuous fairs in the United States. Harrodsburg has a way of preserving Kentucky’s early history, and places like the Shaker Village of Pleasant Hill do that and more. It is a living history museum that preserves the Shaker community’s legacy and can instantly captivate any visitor curious enough to take a look.

Pineville

Chained Rock near Pineville.
Chained Rock near Pineville. Editorial credit: Michele Korfhage / Shutterstock.com

You will find this small town at the base of Pine Mountain in Bell County, and it is usually a stopover or a gateway to Cumberland Gap National Historical Park. But that is not all Pineville can be. Chained Rock is a unique geological attraction there that has been tied to local folklore over the years, and it should be your first stop. You could also check out Bell Theater nearby; the town has a way of keeping its historic venue alive with live performances and film screenings. The landscape itself draws you in. If you can make the climb, the Pine Mountain overlook is worth the effort, so keep your camera charged and ready if you visit Pineville.

Danville

Danville, Kentucky.
Danville, Kentucky

Danville is a name that carries some weight in this state. Known as the birthplace of Kentucky, this site is where the state's first constitution was signed in 1792. In fact, the town also harbors the Constitution Square Historic Site, a museum with replicas of historic buildings. The Great American Brass Band Festival is also hosted here. It is a free event that celebrates brass music with parades and concerts. But if you are more of an art lover than anything else, you will be glad to know that the Norton Center for the Arts regularly brings Broadway performances and national acts to Danville. It is a year-round cultural hub.

Hodgenville

Abraham Lincoln Birthplace National Historical Park in Hodgenville, Kentucky
Abraham Lincoln Birthplace National Historical Park in Hodgenville, Kentucky

This is the birthplace of one of the most prominent historical figures in America: President Abraham Lincoln. So, the first thing to do on these hallowed grounds, naturally, would be to visit the Abraham Lincoln Birthplace National Historical Park and the Lincoln Museum. When the townsfolk are not from celebrating Lincoln Days with reenactments and parades, Hodgenville also houses the LaRue County Courthouse, one of the many sights to see in the town’s historic district. The main square features a bronze statue of a young Lincoln, and the area is conveniently next to Knob Creek, just 10 minutes away, where you can also visit Abraham Lincoln's Boyhood Home.

Berea

The Pinnacles
The Pinnacles

You might never want to leave Berea if you enjoy the outdoors. The Pinnacles offers many hiking routes with breathtaking views of the Appalachian foothills. The town hosts the Festival of Learnshops, where you can learn crafts and skills. It is very hands-on and has some of the friendliest, most helpful people working there. Speaking of which, the Berea Artisan Village District is the center for woodworking, pottery, and weaving demonstrations, so one should stay very active in these parts. The best stop here would take place at the Historic Boone Tavern Hotel and Restaurant; it is run by Berea College and offers insight into sustainable practices that pair with delicious cuisine.

Final Thoughts

It remains a mystery why residents would pay a high price to live crammed in a big city when so many small towns offer not just freedom of movement, but countless captivating features that would dwarf even the largest cities. The name Kentucky — as in Kentucky Fried Chicken (KFC) made it to global fame; now imagine how many unturned stones and hidden gems lie beyond the famous restaurant chain. This state is so rich in history with some of the most incredible landmarks that a stopover could very easily become a destination the next time you plan a trip to the Bluegrass State. With any of the eight most captivating small towns in Kentucky as your starting point, you're well on your way!

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