7 Oldest Founded Small Towns to Visit in Kentucky (2024)

To chart the history of Kentucky, you have to go back almost 300 years to when the southern state was originally part of Virginia. Virginia ceded what was then the District of Kentucky to the US in 1792, and the state was born, becoming the 15th in the Union and the first west of the Appalachian Mountains. The new state’s population grew quickly, thanks to key waterways and railroad routes built in the 1800s. As it flourished, Kentucky held onto its heritage, preserving iconic markers of its history in its oldest-founded small towns. These centuries-old communities are now popular destinations in their own right, providing the authentic Kentucky experience in their storybook streets, unique architecture, and southern hospitality.

Harrodsburg

Founded in 1774, Harrodsburg is Kentucky’s oldest town. Its entire downtown, which includes the oldest row houses in the state, is on the National Historic Registry. Those row houses are where you’ll find the Harrodsburg Historical Society, whose museum features exhibits from the pioneer era, the Civil War, and World War II.

For a glimpse of Harrodsburg’s early beginnings, visit the Old Fort Harrod State Park. The park contains a full-scale replica of the original fort, built by James Harrod in 1774, with cabins and homes lifted straight from the pages of history. Also on site are the Matheny-Taylor House, built in 1810, the George Rogers Clark Federal Monument, and the Lincoln Marriage Temple, the tiny log cabin where Abraham Lincoln’s parents were married in 1806.

Bardstown

Kentucky’s second oldest town, Bardstown, was settled in 1780. Nine years later, the local Baptist minister created the first batch of bourbon, earning the town its nickname as ‘the bourbon capital of the world’. Trace the history of the signature spirit at the Oscar Getz Museum of Whiskey History, where you’ll see unique exhibits, including Abraham Lincoln’s liquor license.

Try the local bourbon for yourself at Old Talbott Tavern, a historic saloon that’s been welcoming weary travelers since the 1700s. Rumored to be the oldest stagecoach stop in America, the tavern is said to have served Daniel Boone, President Andrew Jackson, and Abraham Lincoln.

A visit to Bardstown isn’t complete without a stroll around its most famous landmark, the 1818 Federal Hill mansion at My Old Kentucky Home State Park. A 1,300-acre plantation was built by the Rowan family and is now a museum, golf course, and campground.

West Point

Formally established in 1796, West Point is a historic rivertown on the banks of the Ohio River just south of Louisville. To fully appreciate the beauty and history of this quaint town, visit Fort Duffield Park & Civil War Historic Site. Positioned high above West Port, the park offers incredible views of the town, the river, and the rolling hills of southern Indiana beyond. Take an afternoon to wander around the park, which contains 10 miles of scenic hiking and biking trails and the remnants of Fort Duffield, built in 1861. Enjoy more beautiful scenery along the Tioga Falls National Recreation Trail, a 2-mile loop that follows a 150-year-old wagon roadbed to the stunning Tioga Falls.

Hodgenville

Birthplace of the 16th President, Hodgenville, founded in 1836, is the home of the Abraham Lincoln Birthplace National Historic Park. The site was established in 1916 and covers 344 acres of beautiful parkland, an imposing neo-classical temple commemorating Lincoln’s centennial, and a replica of the log cabin where he was born.

Downtown, in the Hodgenville Historic District, there’s more to discover about this legendary figure at the Lincoln Museum, which includes Civil War exhibits and memorabilia. The Museum has also created a self-guided walking tour for those looking to explore downtown Hodgenville on foot, maps can be downloaded from the museum’s website and the tour takes about an hour to complete.

Maysville

Originally called Limestone, Maysville is a picturesque town on the Ohio River that can be traced back to the 1700s. It counts Daniel Boone and Davy Crockett among its earliest visitors. Visit the Kentucky Gateway Museum Center to learn about some of the people who have passed through the area over the centuries, from pioneers and runaway enslaved people to modern-day movie stars such as Rosemary Clooney. The museum contains 33 dioramas, over 4,000 regional artifacts, and a fine arts gallery.

The Maysville area is also known for its historic covered bridges. Relics of the bygone Civil War era, there are only 13 of these unique structures left in Kentucky, 7 of which are within driving distance of Maysville. You can pick up a self-guided driving tour from the Maysville Tourist Office, located in the 1886 Cox Building in the heart of the historic district. Walking around downtown, you’ll notice some striking artwork. These are the famed Maysville murals, 12 paintings that depict important stories in the town’s history, from its origins as a hunting ground for Shawnee Native Americans to the contribution of the local tobacco industry.

Newport

Just across the Ohio River from Cincinnati lies the scenic river town of Newport. Founded in 1795, this lively community has the second-largest historic district in Kentucky. Known as the East Row, the area has a dazzling collection of elegant Victorian homes, as well as stunning examples of Italianate, American FourSquare, and Queen Anne architecture.

Just a few blocks from East Row is Newport’s busy waterfront. Here, you’ll find the Purple People Bridge, the longest bridge in the country that joins two states. After seeing the river from the bridge, see it from the water with BB Riverboats, which runs sightseeing cruises from Newport Landing. If all that sightseeing has made you thirsty, head to New Riff Whiskey Distillery for a sample of Kentucky’s famous spirit. A popular stop on the Kentucky Bourbon Trail Craft Tour, the distillery offers a range of tours in its historic building so you can see firsthand the nuts and bolts of whiskey production, from grain to barrel.

Winchester

Founded in 1792, the small town of Winchester in northeastern Kentucky is crammed with historically significant sites. Stop by the Bluegrass Heritage Museum, housed in the historic Guerrant Mission Clinic and Hospital downtown, to see exhibits detailing the area’s Civil War history, agriculture industry, and the key figures who helped build the town.

Although little remains of the original fort at the Civil War Fort at Boonesboro, this is still worth a visit for its spectacular views over Winchester and the Kentucky River valley. The fort is one of the stops on the scenic Civil War Driving Tour, which guides visitors around the area’s historical sites, including homes, fortifications, and battlefields.

A short drive out of town takes you into the Daniel Boone National Forest, a highlight of which is the stunning Red River Gorge. Boone himself apparently explored the gorge in the late 1700s. Today, it's known for its incredible climbing and hiking thanks to its unique rock formations and diverse terrain.

A visit to Kentucky means walking in the well-trod footsteps of legendary pioneers, leaders of the emancipation movement, past presidents, and Civil War heroes. The state’s beautiful small towns have seen a lot of history, their streets changing with the times as Kentucky evolved from a discarded piece of Virginia to a hub of heritage, art, culture, and outdoor attractions. Sip genuine Kentucky Bourbon at the oldest stagecoach stop in America, see where Abraham Lincoln was born, and wander around Civil War forts — the past comes alive in Kentucky’s historic small towns.

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