Scenic, full of Southern charm and rich in history, Kentucky, or the ‘Bluegrass State,’ is home to some of the most beautiful small towns in America. From whats known as the ‘Bourbon capital of the world’ Bardstown, to arty communities like Paducah and Berea, we round up 10 of the state’s most charming towns.
Named one of the ‘most beautiful small towns in America’ by The Rand McNally, picturesque Bardstown is located in the heart of Kentucky’s Bluegrass Region. Known as the ‘Bourbon capital of the world’, Bardstown has the art of distilling the tipple down to a fine art. Some local distilleries date back as far as 1776 and this history is celebrated each September with the annual Kentucky Bourbon Festival. Bardstown is home of My Old Kentucky State Park, which hosts The Stephen Foster Story, a Broadway-style musical about the ‘American father of music’ and composer of Kentucky’s state anthem. The downtown area is a mix of historic buildings, eclectic boutiques and great restaurants.
Berea is located a few miles south of Lexington and is home to a vibrant community of painters, musicians, weavers and other such artisans alongside a number of artsy events including Berea Craft Festival and Berea Celtic Festival. Beautiful downtown Berea is home to several historically significant sites such as Berea College, which is a liberal arts college founded in 1855 and the South’s first interracial and coeducational institute. Another site, Boone Tavern, is a hotel opened in 1909 and listed on the National Register of Historical Places and named after American pioneer and explorer Daniel Boone.
Dating back to 1774, Harrodsburg is the state’s oldest city and home to a smorgasbord of interesting sites relating to its rich history. This includes the Shaker Village of Pleasant Hill, America’s biggest restored Shaker settlement, and Dedman Drugstore which first opened in 1865 and today is home to its original soda fountain, as well as The Kentucky Fudge Company. Take a trip aboard the authentic Dixie Belle paddle steamer and see the scenic Kentucky River Palisades from a unique angle or explore downtown Harrodsburg for its charming and colorful storefronts, unique local crafts and antiques and restaurants serving up good old Southern cuisine.
Designated a UNESCO City of Crafts and Folk Art in 2013, Paducah, also known as Quilt City USA, is a hot spot for quilt and fiber-based artists. It is also home to The National Quilt Museum and the annual QuiltWeek festival. Located on the banks of the Ohio and Tennessee Rivers on the border with Illinois, Paducah is rich in history with 20 blocks of its picturesque downtown district listed on the National Register of Historic Places. Here, you can find stunning examples of 19th century architecture and Lower Town, an arty district and Paducah’s oldest neighborhood, alongside boutiques, antique stores and local indie art galleries.
A certified Kentucky Cultural District, Danville is home to landmarks rich in history and a plethora of art galleries, museums and first rate restaurants. The site of many firsts, Danville’s Constitution Square is the location of the first post office built west of the Alleghany Mountains. The town was also home to pioneering American surgeon Ephraim McDowell, the first physician to perform a successful abdominal surgery. Danville’s beautiful Main Street was bestowed with a Great American Main Street award in 2001 by the National Trust for Historic Preservation and is host to locally owned pubs and stores and the annual Great American Brass Band Festival.
Founded in 1799, Greenville is an idyllic small American town located amidst western Kentucky’s beautiful forests and rolling hills and is renowned for its warm Southern hospitality. Greenville’s picturesque and historic town square is the location of a beautiful Beaux-Arts style courthouse built in 1907 which features the state’s second largest bell tower dome and the biggest pre-fabricated cupola in the whole country. Greenville’s quaint downtown is fast becoming known for its festivals which include Saturdays on the Square, a series of summertime events, and the outdoor art festival Squash & Gobble Arts Bazaar and Fall Festival.
August was listed by noted historian Thomas D. Clark as one of 11 Kentucky treasures that have helped shape the history and culture of the state. The Ohio River town located in northeastern Kentucky was founded in 1797 though as the town grew excavations revealing skeletal remains point to it as an earlier Native American settlement. Today home to just over 1000 people, Augusta is tiny but full of small town charm and its crowning glory is undoubtedly Riverside Drive, which is a scenic spot with picturesque views of the river valley and beautiful 18th and 19th century architecture. It is also home to Augusta’s annual Art in the Garden festival.
Ranked among the 15 Best Places to Live in Kentucky by real estate gurus Movoto, the south central Kentucky town of Glasgow was founded in 1799 and named after the Scottish birthplace of one of its early settlers. The town is home of the Glasgow Highland Games, an annual celebration of Scottish heritage taking place in town for the past 30 years. Glasgow’s location in the Caves, Lakes and Corvettes region close to Mammoth Cave National Park also makes the town a perfect starting point for exploring the state’s natural wonders.
Voted the Friendliest Small Town in America by Rand McNally-USA Today Best of the Road series, Murray is a charming Southern town. Its idyllic location is just a short drive from the stunning Kentucky Lake and the Land Between the Lakes National Recreation Area, which makes it a popular stop off for exploring nature lovers. Murray’s picture-perfect town center is home to several cultural institutions including the Clara M. Eagle Art Gallery at Murray State University and Playhouse in the Park, a community theater housed in a former train depot, and the town’s annual Independence Day celebration Freedom Festival.
Located in the northern reaches of the beautiful Daniel Boone National Forest in northeastern Kentucky, Morehead is a laid back town nestled against the backdrop of the scenic Appalachian Mountain foothills. It has plenty of small town charm and a number of attractions from the historical (including the beautiful Morehead State University established in 1887) to the cosmopolitan (with antique stores and the nearby CCC Trail Vineyard and Winery), and the cultural (with the town’s annual Poppy Mountain Bluegrass Festival). Morehead’s proximity to the breathtakingly beautiful Cave Run Lakes makes it an ideal base for lovers of nature.
KEEN TO EXPLORE THE WORLD?
Connect with like-minded people on our premium trips curated by local insiders and with care for the world
Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.
Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.