Discover 5 Of The Oldest Cities In Kentucky

Written by Drew Wood
Updated: June 8, 2023
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Though nestled in a quiet part of the country, Kentucky has often been on the front lines of U.S. history. It has been contested ground since before the first Europeans arrived. It then became a theater of conflict between the British and French, as well as the American revolutionaries. Later, it was on the front line of the Civil War. Visiting some of the oldest cities in Kentucky gives you a view of our country’s history. It also inspires hope for its future.

Harrodsburg was honored as the oldest permanent pioneer settlement west of the Appalachians by President Franklin D. Roosevelt.

Oh, and by the way, definitions of “city” vary widely. We’ve chosen to include just places with a population of at least 1,500 people as of the 2020 census. You won’t find any ghost towns on this list, just friendly places ready to welcome you on your next vacation.

Hiking in Fall

Every city in Kentucky is within a short drive of a beautiful natural environment.

©Monkey Business Images/

Kentucky’s Natural Landscape

Climate specialists classify the Kentucky climate as “humid subtropical.” That just means the summers can be really hot and the winters don’t get too cold. With this kind of climate, the state supports a variety of habitats, including grasslands, forests, and wetlands. It’s a stable basis for agriculture and has helped give Kentucky a worldwide reputation for top-class horse breeding. But the state still has plenty of wild spaces left for white-tailed deer, black bears, foxes, and coyotes. Additionally, visitors may spot birds, like bald eagles, ospreys, and peregrine falcons. Anglers will find a wide variety of fish species, such as bass, carp, catfish, perch, pike, and trout.

Galloping race horses in racing competition.

Kentucky is famous for its world-class horse breeding and racing.


1. Harrodsburg, 1774

Harrodsburg, population 9,064, was founded in 1774 by settlers from Pennsylvania. It is the oldest permanent pioneer settlement west of the Appalachians. Daniel Boone’s younger brother, Squire, was one of the original settlers. During the Civil War, Harrodsburg was used as a medical center. Hospitals housed many hundreds of sick and wounded soldiers. In the modern era, Harrodsburg’s economy has been helped by investments by Hitachi and Corning Incorporated. This company supplies glass for iPhones.

If you’d like to visit Harrodsburg, one place worth a look is Old Fort Harrod State Park. It has a replica of the original pioneer fort on the site, a log house, and a cemetery. There are opportunities to hike, fish, or picnic. Rocky Point Manor is a two-story mansion that was once a Civil War hospital. The series Ghost Adventures investigated it for possible paranormal activity in 2011.

Downtown Harrodsburg has shops and museums and the Ragged Edge Theatre with live comedy, musical, and dramatic performances. The area has over 30 miles of horseback riding trails. Kids will enjoy the corn maze and pumpkin patch, with a zipline, wagon rides, and a petting zoo. But above all, don’t forget the Shaker Village of Plesant Hill. It’s the third-largest Shaker community in the country. Shaker architecture, furniture, and interior design are popular to this day for their clean, simple, functional, and elegant design. You might want to redecorate after visiting there!

White fence on horse pasture, Shaker Village of Pleasant Hill, Harrodsburg, Kentucky

The Shaker Village of Pleasant Hill is a restored Shaker community that will impress you with simple and elegant architecture and interior design.

©Danita Delimont/

2. Bardstown, 1780

Bardstown, founded in 1780, was named after the pioneering Bard brothers. It was the first center for Catholicism west of the Appalachians. Also, it became a major center for the production of bourbon whiskey, with a lot of distilleries in the area. It now goes by the nickname “Bourbon Capital of the World.” The population of the city today is 13,567.

History lovers will appreciate that there are about 200 buildings on the National Register of Historic Places in Bardstown’s historic district. A really unique experience in the area is My Old Kentucky Dinner Train. You can enjoy a gourmet meal in a vintage train car on a 37-mile round-trip. My Old Kentucky Home State Park includes Federal Hill, a plantation home that inspired the song “My Old Kentucky Home.” Old Talbott Tavern is another popular attraction. Located on a stagecoach line, its guests included European royalty, Presidents, adventurers like Daniel Boone, and outlaws like Jesse James.

Products Made From Honey

Bardstown is the “Bourbon Capital of the World.” This hot toddy has lemon, bourbon, honey, and spices, to cure sore throats and dull parties.

©Brent Hofacker/

3. Ashland, 1786

Country music star Billy Ray Cyrus filmed his music video for “Achy Breaky Heart” in Ashland.

©Corey Graese, CC BY-SA 4.0 <>, via Wikimedia Commons – License

Ashland, population 21,625, was home to the Adena and Hopewell cultures, and later the Shawnee. In the 1700s Europeans began to settle the area, starting with the Scotch-Irish who moved down the Shenandoah Valley and passed through the Cumberland Gap into what is today Kentucky. In the 1800s iron deposits were discovered there and Ashland became a manufacturing city strategically located at the place where Kentucky, West Virginia, and Ohio meet. Companies like Ashland Oil and Refining Company, the C&O Railroad, and Armco became major pillars of the local economy.

Visitors to Ashland can enjoy hiking and bird-watching in the Jesse Stuart State Nature Preserve, named for a famous Kentucky writer. Central Park has burial mounds of the Adena Native American culture and a log cabin home to the city’s founding family. The Paramount Arts Center is a multidisciplinary performing arts center with concerts, dramas, dance, etc. Country star Billy Ray Cyrus, born and raised near Ashland, filmed his music video for “Achy Breaky Heart” there. Kids will enjoy Malibu Jack’s – a family entertainment center with go-carting, laser tag, miniature golf, an arcade, inflatables, a bowling lane, and an indoor playground for small kids.

4. Versailles, 1792

Versailles was founded in 1792 and named after Versailles, France, in honor of General Lafayette who was a friend of the founding Briscoe family. The pronunciation has become Americanized to “Ver-sails.” Versailles is in the bluegrass region of Kentucky among thoroughbred horse farms. The city is also on Kentucky’s Bourbon Trail which includes whiskey distilleries across the state. The area around Versailles was also one of the leading hemp producers in the state from 1775-1915. The recent liberalization of laws about hemp cultivation and usage is bringing this industry back.

One of the interesting things to do in the area is to stay at the Kentucky Castle, a 10,000-square-foot castle with mysteries and puzzles to solve. The Jack Jouett House is the home of a Revolutionary War hero, nicknamed “The Paul Revere of the South.” He successfully warned Thomas Jefferson and the Virginia legislature about an impending British attack. Sun Valley Farm is a working ranch where you can see the whole process of breeding, training, and racing world-class thoroughbred horses. Nostalgia Station Toy and Train Museum is a fun place to see miniature trains and vintage toys. And in the summer and fall, Versailles has farmers’ markets and orchards with locally-grown fruits and vegetables to buy or pick yourself. Honey, jams and jellies, flowers, pumpkins, Christmas trees – there’s something for every season.

How long do horses live: American Saddlebred

Versailles is the place to go if you’re a horse-lover. These are saddlebred, the oldest American horse breed, or “Kentucky Saddlers.”


5. Williamsburg, 1818

Williamsburg, Kentucky (population 5,326) was founded in 1818 at a strategic location. It’s just 50 miles from Cumberland Gap, a natural division at the midpoint of the Appalachian Mountain range that makes it easier to travel between the east and west. Three freshwater streams meet at Williamsburg, where the Cumberland River is fordable. Coal mining and lumber were valuable sources of income in the area. The Louisville and Nashville Railroad connected Williamsburg to the country’s growing transportation network and helped it to thrive.

The Cumberland Gap National Historical Park is one of the main tourist attractions in the area. There’s a place in the park where you can stand in three states at once: Kentucky, Tennessee, and Virginia. The visitors’ center has a museum with interactive historical exhibits. It also features an auditorium with films about the area’s culture and history and a bookstore. A gift shop sells arts and crafts from Appalachia. Cumberland Falls State Resort Park has a beautiful waterfall called Eagle Falls. It’s truly the “Little Niagara of the South.” Another interesting attraction, 17 miles north of Williamsburg is the Sanders Café & Museum. This is where Colonel Sanders first developed his world-famous Kentucky Fried Chicken recipe in 1937.  

Eagle Falls Kentucky

Eagle Falls in Cumberland Falls State Resort Park has been called the “Little Niagara of the South.”

©Alexey Stiop/

Saddle Up And Hit The Bourbon Trail

If civilization collapses, Kentucky has got you covered. It has horses for transportation, bourbon for medicine, and Shaker building methods. Kentucky also has tools and furniture, old boarding houses, theaters, and stagecoach stops. Come check out the old ways in Kentucky and see what you’ve been missing.

Summary Of 5 Of The Oldest Cities In Kentucky

RankCityDate Founded/Settled

The photo featured at the top of this post is © Denev

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About the Author

Drew Wood is a writer at A-Z Animals focusing on mammals, geography, and world cultures. Drew has worked in research and writing for over 20 years and holds a Masters in Foreign Affairs (1992) and a Doctorate in Religion (2009). A resident of Nebraska, Drew enjoys Brazilian jiu-jitsu, movies, and being an emotional support human to four dogs.

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