Any “small town in Kentucky” list cannot be complete without Bardstown. Named “the Most Beautiful Small Town In America” by USA Today, Bardstown has a lot to offer. Slow down and sip your bourbon. You’re in the heart of Bourbon Country, after all! Go for a leisurely stroll in Bernheim Forest, or Bardstown’s historic downtown.
This western Kentucky town is right on the banks of Lake Barkley, and only a short distance from the Land Between the Lakes National Recreation Area. The town offers plenty of options for outdoor activities, but make sure you stop to admire the old tobacco barns dotting the surrounding countryside. Many of them are on the Kentucky Quilt Trail and are decorated with colorful quilt squares.
Berea is best known for its arts and crafts, and is therefore home to many artists and galleries. Be sure you hike the Pinnacles, which offer a ton of natural beauty and stunning views once you’re at the top. Some people even say that on a clear day, you can see buildings that are about 40 miles away in downtown Lexington from the West Pinnacle.
This southwestern Kentucky town is located on the Kentucky-Tennessee border. Guthrie has always been synonymous with railroads, and the town itself is even named after James Guthrie, who was a United State senator and briefly president of the Louisville and Nashville Railroad. Guthrie is also the hometown of poet laureate and Pulitzer Prize winner Robert Penn Warren. You can visit his birthplace, which is now a museum dedicated to his life and accomplishments.
Located near Lake Cumberland, this town offers you the opportunity to relax on a boat or in a quiet lakeside cabin. Go sailing, jet skiing, or partake in any kind of water activity, all while being surrounded by the beauty of Lake Cumberland State Resort Park. If you’re not much of a water person, go on a hike, find a scenic overlook, and watch white clouds roll across the hills.
Pineville is a town tucked in the mountains of eastern Kentucky. Located in between Pine Mountain and the Cumberland River, there is plenty of natural beauty around the town. Pineville is perhaps best known for Chained Rock. Originally just folklore, children were told that a giant, menacing boulder on top of Pine Mountain couldn’t fall and crush the town because it had been chained. That wasn’t true until 1932, when the rock was in fact harnessed by a large chain. You can take a hike to see the Chained Rock, as well as some awesome views of Pineville.
Augusta is a small town that sits on the Ohio River, just 42 miles east of Cincinnati. You would never know a booming metropolis was such a short distance away in this quiet town. Walk along the riverfront and enjoy the scenic views of the waterway. You might even see and old-fashioned steam boat chugging along. Many people don’t realize that George Clooney spent his high school years in Augusta.
This town in southern Kentucky is located right in the middle of Daniel Boone National Forest. It is also home to the Big South Fork Scenic Railway, which will take you 600 feet down into the Big South Fork Gorge. You’ll also stop at the historic Blue Heron Mining Camp, which is a former coal mining community that sits on the banks of the Cumberland River. This town may be located in the middle of a national forest, but it’s also home to some fascinating Kentucky history.
This charming country town is a little less than an hour outside of Louisville, but this agricultural community has less than 1,000 residents. Enjoy the rolling countryside, or visit one of their scenic wineries, including Chuckleberry Farm and Winery and Springhill Winery.
Fredonia is a small community of about 500 people in western Kentucky. This is one of those classic Southern towns with a tight-knit feel where everybody knows your name.
Upton, which is just outside of Elizabethtown, has a total area of 1.5 square miles and 654 residents. The Louisville and Nashville Railroad used to run through Upton, and the town was a target of Confederate General John Hunt Morgan during the Civil War.
This town in southern Kentucky has a quaint city square with a historic courthouse. Stop and get an old-fashioned milkshake at L&R Soda Shop, or purchase homemade breads, pastries, and jellies from the Amish community located along nearby Highway 68-80.
The motto of Wilmore is “small town charm,” and that’s exactly what you’ll get in this town located in Jessamine County. Not far from Wilmore are the Kentucky River Palisades, which are a series of steep limestone cliffs and outcroppings along the Kentucky River. Wilmore is also close to the Shaker Village of Pleasant Hill.
Princeton is a beautiful small town in western Kentucky. Be sure to to check out Big Springs Park, which is a natural spring flowing from a cave in downtown Princeton. Get some country ham at Col. Bill Newsom’s Aged Country Hams, which has been in operation since 1917.