Kentucky’s lovely scenery, a mix of rolling hills and horse farms along with the more rugged terrain of state parks like Cumberland Falls, is also home to some of the US’s most interesting historic districts. From its attractive antebellum mansions to its Civil War battlefields and from its quaint Main Streets to its many historic landmarks, Kentucky's small towns offer a unique opportunity for visitors to experience a little of this rich history for themselves.
To find out more about the kind of authentic experiences available in the beautiful "Bluegrass State," explore these small towns that have the best historic districts.
Just 40 miles’ drive south of Kentucky’s largest city, Louisville, and you will find yourself in one of its smallest towns: Bardstown. Given the title of the "Bourbon Capital of the World" for the 11 major distilleries located in the area, Bardstown’s historic downtown area features a variety of well-preserved heritage buildings.
It’s also home to the oldest surviving stagecoach stop in the US, the Old Talbott Tavern. Constructed in 1779 and facing the town’s town square and stunning red-brick Old Courthouse, the tavern is reputedly the world’s oldest bourbon bar and once hosted King Louis-Philippe of France as well as famed American frontiersman Daniel Boone. You can even see evidence of one of its most notorious guests, Jesse James, in the bullet holes the outlaw left behind after firing his gun in anger.
An easy hour drive from downtown Lexington, Danville is often referred to as the "City of Firsts" for being the place where Kentucky's original constitution was drafted in 1792. This fact is celebrated in Constitution Square, a spot that’s considered the birthplace of Kentucky statehood and features a collection of historic buildings, including a replica of the meeting house where constitutional conventions were once held.
Other places of interest include the historic McDowell House Museum, as well as Danville Presbyterian Church, built in the early 1830s in Greek Revival style. Close by, Perryville Battlefield State Historic Site is another must-visit and was the location of the most significant Civil War battle in the state, commemorated each year with re-enactments of the fighting that took place here in 1862.
Set on the banks of the Ohio River, an hour’s drive southeast of Cincinnati, the pretty town of Maysville was once a significant port and gateway to the American West. Maysville Downtown Historic District is the place to start your exploration. Here you will find Phillips' Folly, a three-story brick house built in 1825. In addition, the Russell Theatre, which opened in 1930, staged performances from local legend Rosemary Clooney; the singer, aunt to modern-day film star George Clooney, spent her early childhood in Maysville.
Be sure to take a stroll along the Maysville Riverfront, where you’ll find Limestone Landing, once the docking point for steamboats plying the Ohio River.
Established in 1793 and named after two sisters, Cynthia and Anna Harrison, Cynthiana's entire historic downtown is listed on the National Register of Historic Places and is where you’ll find Rohs Opera House. Constructed in 1871, this elegant building began life as a bank before its transformation into a vaudeville theater and, eventually, a cinema.
Other places to visit in Cynthiana’s historic district include the Harrison County Courthouse, with its impressive clock tower, and the Battle of Cynthiana Museum, which commemorates not one, but two Civil War battles that took place in and around the town in 1862 and 1864, respectively.
Founded in 1827 at the confluence of the Ohio and Tennessee Rivers, the important river town of Paducah has the distinction of being one of only 300 UNESCO Creative Cities worldwide, a title it wears with pride. Visit Paducah’s Lower Town Historic District, and you’ll find a large collection of stunning 19th-century homes and buildings, many now home to art galleries and studios.
This connection to art can also be seen in the town’s iconic Floodwall Murals. Painted on the floodwall built after the devastating 1937 flood, these murals depict key moments in the town's history from its early days to the present time. Other landmarks linked to the town’s creative populace include the Market House Theater, built in 1905, and the National Quilt Museum, which explores the town’s textile arts heritage.
Located in the coal-rich region of western Kentucky, Madisonville tries hard to live up to its claim of being the "Best Town on Earth." While highly subjective, it does rank up there as one of the best historic small towns in Kentucky. The 28 buildings that fall under the umbrella of the Madisonville Commercial Historic District are spread over an area of 11 acres and include the Hopkins County Courthouse, a stately-looking edifice built in 1937 that features attractive Art Deco-inspired styling.
Interested in digging deeper into the region’s history? Check out the Hopkins County Museum and Heritage Center. Housed in two historic buildings, Givens House and Ranney House, it provides a fascinating look at the area's coal mining heritage and the Civil War period.
The oldest town in Kentucky, Harrodsburg was first settled in 1774 and is where you’ll find Morgan Row. Located in the downtown area, these 19th-century brick structures were once used as stores and residences and are among the oldest buildings in the city. Old Fort Harrod State Park is another must-see. A replica of the original fort that was built here in 1775, it’s built on the actual site where pioneers established the first permanent European settlement west of the Alleghenies and features authentic-looking cabins, blockhouses, and a stockade.
Another must-visit is the Shaker Village of Pleasant Hill. The largest restored Shaker community in the world, this 3,000-acre landmark provides a fascinating glimpse into the Shaker way of life. The Beaumont Inn is also worth a look and is Kentucky's oldest family-operated country inn.
The Final Word
As well as its rich history and endless Southern charm, Kentucky is also home to many charming small towns with well-preserved historic districts that are worth exploring. If you do visit these destinations, you’ll be rewarded with an authentic take on the key events, places, and people who have helped shape the state.