Main street of Midway, a small town in Central Kentucky famous of its boutique shops and restaurants. Editorial credit: Alexey Stiop /

The 8 Most Picturesque Small Towns In Kentucky

Called the "Bluegrass State," Kentucky is widely celebrated as home to horse racing, bluegrass music, fried chicken, and of course, Kentucky bourbon. With a geography that ranges from expansive horse pastures to the towering peaks of the Appalachian Mountains, the state is among the most beautiful in the country. If you want a taste of its famous southern charm but are looking for a less urban experience than you would find in Louisville or Lexington, there are many idyllic small towns sure to suit your fancy. 


Harrodsburg Kentucky
Beautiful downtown area of Harrodsburg, Kentucky. Image credit: J. Stephen Conn/Flickr.

Founded in 1774, Harrodsburg is considered the oldest permanent American settlement west of the Allegheny Mountains. The town is steeped in history and features many opportunities for exploration, including the Old Fort Harrod State Park, which has a full-scale replica of the fort built by James Harrod in 1774. Visitors can also explore the Shaker Village of Pleasant Hill, a restored 19th-century Shaker community that is over 3000 acres and features over 30 historic buildings surrounded by picturesque countryside. The town's Main Street is lined with unique shops, galleries, and restaurants, and the surrounding landscape is dotted with local farms and rolling hills.


Maysville, Kentucky
The skyline of Maysville, Kentucky. Image credit: Nealparr via Wikimedia Commons

With its picturesque downtown lined with historic brick buildings, quaint shops, and restaurants, Maysville feels like a step back in time. Located on the Ohio River and surrounded by the steep hills that make up its banks, the city symbolizes the natural beauty of the Appalachian region. It also has all the cultural touchstones of the area, featuring not just the state's oldest bourbon distilleries, The Old Pogue Distillery, but also the National Underground Railroad Museum, so situated due to Maysville's importance in the underground railroad's mission. For more history, check out the 1867 Washington Opera House, which has hosted a variety of performers over the years, including Mark Twain and John Philip Sousa. 


The Old Talbott Tavern in Bardstown
The Old Talbott Tavern in Bardstown. Editorial credit: Ryan_hoel /

"The Bourbon Capital of the World," Bardstown is another gorgeous center of what makes Kentucky special: natural beauty, history, and of course, bourbon whiskey. The city is surrounded by beautiful scenery which only exists in the Appalachians and is particularly striking when autumn turns the vistas into a panorama of orange and gold. The downtown is a little slice of Americana, with over 200 buildings on the National Register of Historic Places. Most famously, the town is home to numerous bourbon distilleries and historic sites, including the Old Talbott Tavern, which has operated since 1779. According to legend, this distillery hosted famous guests such as Abraham Lincoln and Daniel Boone and is riddled with bullet holes left by the outlaw Jesse James. 


A sign welcomes visitors to Cumberland Gap National Historical Park
A sign welcomes visitors to Cumberland Gap National Historical Park in Middlesboro. Editorial credit: William Silver /

Middlesboro is a true hidden gem, a small town situated entirely within a meteorite crater known as the Middleboro Basin. Located in the very south of Kentucky, it is also one of the municipalities that directly adjoins the Cumberland Gap National Historic Park. Surrounded by stunning mountain vistas and lush forests, this historic passageway, once traveled by frontiersmen like Daniel Boone, is now a popular destination for outdoor enthusiasts seeking to hike, camp, and explore the beautiful Appalachian Mountains. The natural beauty of the Cumberland Gap is truly breathtaking. With its rocky outcroppings, rushing streams, and towering trees, it provides a serene escape from the hustle and bustle of everyday life. Middlesboro is the perfect small town to visit for such an experience. 


Main street of Midway, a small town in Central Kentucky famous of its boutique shops and restaurants.
Main street of Midway, a small town in Central Kentucky famous of its boutique shops and restaurants. Editorial credit: Alexey Stiop /

As you stroll down the picturesque Main Street of Midway, Kentucky, you will undoubtedly be transported to a bygone era, where horse-drawn carriages once made their way through town, and the pace of life was slower. The town's scenic beauty is unparalleled, with rolling hills and verdant fields stretching as far as the eye can see, making it a perfect destination for anyone looking to escape the crowds and noise of big city life. Centrally located in Kentucky's Bluegrass region, Midway offers unique opportunities to experience the green rolling hills, the horse farms with white picket fences, and the sprawling estates that dot the landscape, which create that distinct quality of Southern charm. 


Historic commercial buildings in downtown Winchester, Kentucky.
Historic commercial buildings in downtown Winchester, Kentucky. Image credit: Christopher L. Riley, via Wikimedia Commons

The seat of Clark County, Winchester, has all the hallmarks of a charming small town in a Southern state. Surrounded by picturesque farmland and horse pastures, the city exudes warmth and tranquility. The historic downtown, with its brick sidewalks and Victorian-era architecture, invites visitors to wander and explore. Winchester holds the distinction of being the birthplace of the Kentucky staple of beer cheese, a sharp cheese dip flavored with beer and spices. It proudly hosts both the Beer Cheese trail - a series of thirteen beer cheese-themed stops - as well as the annual Beer Cheese Festival, which takes place every June. Whether for a taste of a local delicacy or just for the charm and beauty of one of Kentucky's loveliest towns, Winchester should not be missed. 


Paducah , Kentucky
Historic buildings in the downtown Main Street in Paducah. Editorial credit: Angela N Perryman /

A designated UNESCO Creative City, Paducah embodies the perfect blend of past and present. Situated along the scenic banks of the Ohio River, the city boasts a rich history that can be seen in its beautifully restored Victorian buildings and tree-lined streets. But Paducah is also a hub of modern art and creativity, with a thriving arts district that attracts visitors from all over the world. The riverfront, adorned with public art installations, is a testament to Paducah's commitment to marrying tradition with innovation. Live music, museums, and art centers are ready to enhance the city's natural beauty, making Paducah a true destination for anyone seeking creative inspiration. 


Berea, Kentucky
Aerial view of the scenic countryside around Berea.

For even more creativity, travelers will not want to miss Berea, Kentucky's Folk Arts and Crafts Capital. Witness real working artists practice their craft in varying media and invest in artisan crafts in a plethora of gift shops and galleries. While doing so, you will be surrounded by sculptures, murals, and other publicly displayed art, making the time you spend in Berea a true joy. Of course, as with the other towns on this list, the city is resplendent with both history and natural beauty, and visitors are never far from a hike or an educational experience should they seek one out.  

Kentucky, a land of rolling hills and lush greenery, is where the scent of bourbon mingles with the sound of bluegrass. Its beauty lies not only in its picturesque small towns and quaint horse farms but also in the way its people embrace both the traditions of the past and the promise of the future. It is a place where the natural world and human culture intertwine in surprising and delightful ways, creating a tapestry of sights, sounds, and experiences that is truly one-of-a-kind. 

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