Row of Victorian-era Buildings of La Grange, Kentucky

These Historic Towns in Kentucky Are Worth Exploring

Not only is Kentucky considered one of the most attractive states in the USA, it also just so happens to be one of the most interesting historically. The 15th state to be admitted to the Union, an event that took place on June 1st, 1792, the “Bluegrass State” opened up to settlers big time with the establishment of the Wilderness Road just four years later. These settlements quickly grew, most initially sustained by farming due to the region's fertile soils.

Fast forward 230 years and these communities across Kentucky are now microcosms of the state’s rich culture and history, each just waiting to be explored. From Harrodsburg, the oldest town in the Bluegrass State, to charming Hodgenville, famous as the birthplace of Abraham Lincoln, each of these seven towns in Kentucky is rich in history and boasts unique attractions that make them perfect places to visit for those seeking to learn more about American life and culture​​​​​​​​​​.


The beautiful downtown area of Harrodsburg, Kentucky.
The beautiful downtown area of Harrodsburg, Kentucky. Image credit J. Stephen Conn via Flickr.

Established in 1774, Harrodsburg has the distinction of being Kentucky's oldest town and the first permanent English settlement west of the Allegheny Mountains. The town's history is intricately tied to the American Revolutionary War as well as the westward expansion as the early settlers arrived, a period that is commemorated at Old Fort Harrod State Park. This reconstruction of the original fort built by James Harrod and his company of pioneers is plenty of fun to explore and features replica blockhouses, cabins, and even a stockade.

Another must-visit site is the Shaker Village of Pleasant Hill. This restored 19th-century Shaker community is spread over 3,000 acres and is the largest of its kind in the world and offers unique insights into the Shaker way of life – a lifestyle known for its simplicity, craftsmanship, and communal living. Visitors can explore the well-preserved original buildings, take part in hands-on workshops, and even enjoy traditional Shaker music and dance performances. If you can make a weekend of it, the Beaumont Inn, a historic bed and breakfast, offers traditional Southern hospitality and cuisine in a lovely setting.


Town square in Hodgenville, Kentucky
Town square in Hodgenville, Kentucky, USA. Image credit: Jamie, via Wikimedia Commons.

Hodgenville, an hour’s drive south from the state’s largest city of Louisville, was founded in 1836 and holds a significant place in American history as the birthplace of Abraham Lincoln, the 16th President of the United States. Related attractions in Hodgenville include the Abraham Lincoln Birthplace National Historical Park, which encompasses two separate farms: Sinking Spring Farm, where Lincoln was born; and Knob Creek Farm, where he spent his early childhood. The birthplace site features a replica of the original cabin where his birth occurred and serves as a poignant reminder of Lincoln's humble beginnings. The park's visitor center offers informative exhibits about Lincoln's family and life in Kentucky.

Another noteworthy site is the Lincoln Museum located in Hodgenville's town square. The museum showcases a diverse collection of Lincoln memorabilia, including original manuscripts, campaign artifacts, and personal items, as well as dioramas depicting key moments in his life, from his Kentucky childhood to his presidency. Visit the town square to see a bronze statue of young Abraham Lincoln, a popular spot for photographs.


Frankfort, Kentucky, town skyline on the Kentucky River at dusk
Frankfort, Kentucky, town skyline on the Kentucky River at dusk

The fourth smallest state capital in the United States, Frankfort is also one of the most picture-perfect. Set on the banks of the Kentucky River, Frankfort was founded in 1786 and boasts many interesting landmarks that appeal equally to sightseers as they do history enthusiasts. Leading the pack is the Kentucky Old State Capitol Building, built in Greek Revival style in 1830 and in use until 1910. Tours of the interior are recommended and provide a look at the building’s famous self-supporting staircase and displays regarding key events in Kentucky's legislative history.

Another important site is the Kentucky Old Governor's Mansion. Located near the current (and extremely photogenic) Capitol Building, this historic home was built in 1798 in classic Federal style and provides a glimpse into the state's early political history. The Kentucky Historical Society is another must-visit and houses an extensive collection of artifacts and exhibits detailing the state’s fascinating past. Also worthy of a visit are the Kentucky Military History Museum, housed in the State Arsenal; and the Salato Wildlife Education Center, popular for its native flora and fauna.

La Grange

Train rolling along Main Street in La Grange, Kentucky.
Train rolling along Main Street in La Grange, Kentucky. Image credit Morgan via Wikimedia Commons.

Just 25 miles northeast of Louisville, La Grange is home to one of the most attractive Main Streets in Kentucky. In addition to its pleasing old architecture, here visitors gawk at the unusual yet nostalgic sight of a train running directly through the town center. You can learn more about this unique feature at the La Grange Railroad Museum & Learning Center, which provides insights into the town's rich railroad history and is a must-visit for train enthusiasts.

The downtown area is certainly fun to explore and boasts plenty of well-preserved 19th and early 20th-century buildings that now house an array of boutique shops, art galleries, and restaurants. Here you’ll find the Oldham County History Center with its interesting exhibits relating to prominent townsfolk down the decades as well as displays relating to the Underground Railroad. Outdoor enthusiasts should explore the nearby Morgan Conservation Park with its hiking trails and picturesque scenery. If you’re in town on the third Saturday in July, be sure to attend the Oldham County Day Festival with its parades, crafts, food, and music.


Downtown London, Kentucky.
Downtown London, Kentucky. Image credit: w.marsh via Wikimedia Commons.

Originally a stop on the Wilderness Road and named after the capital of Great Britain, London, KY, was founded in 1826 and was to feature prominently in the Civil War, most notably at the site of the Camp Wildcat Battlefield, where one of the first Union victories occurred. Today, this historic site allows visitors to explore the battleground via a network of trails, an especially fun experience during re-enactment events held each October.

Interested in nature? London serves as the gateway to the Daniel Boone National Forest, a sprawling 708,000-acre site that’s popular for hiking, camping, fishing, and rock climbing, as well as wildlife spotting. Another notable attraction is the Levi Jackson Wilderness Road Park with its replica pioneer camp and mill, nature trails, and picnic areas. For a little quirky fun, the World Chicken Festival is held each September and celebrates local culture and history, as well, of course, as Colonel Sanders and his famous deep-fried chicken recipe.


Home of Bluegrass Music, Rosine.
Home of Bluegrass Music, Rosine. Image credit: Don Sniegowski/Flickr.

Despite having a population of only around 100 souls, Rosine has a surprising array of fun things to do for visitors. The town’s biggest claim to fame is as the birthplace of Bill Monroe, the "Father of Bluegrass Music" who was born here in 1911. Since his passing in 1996, Rosine has become a place of pilgrimage for bluegrass fans with the Bill Monroe Homeplace being especially important. Now fully restored, visitors can explore the childhood home of this music legend and learn about his early life and influences.

Another must-visit, the Bill Monroe Museum opened in 2018 and showcases a wide array of memorabilia related to Monroe's life and career, including instruments, costumes, and personal items, and serves as an educational and cultural center, celebrating the history and impact of bluegrass music. Other fun stuff to do in this quaint small Kentucky town includes participating in the Rosine Barn Jamboree, held on Friday nights between April and December and featuring live bluegrass music performances; and the Jerusalem Ridge Festival, a bluegrass festival held in September that draws fans and musicians from across the globe.   


Historic buildings in Maysville, Kentucky.
Historic buildings in Maysville, Kentucky.

Last but by no means least on this list, Maysville’s location along the Ohio River makes it a wonderful day trip destination from places like Cincinnati (an hour’s drive) or Lexington (a 90-minute drive). The entirety of Maysville’s historic downtown area is listed on the National Register of Historic Places and boasts a range of architectural styles from Federal to Victorian and includes significant buildings like the Mason County Courthouse (1844) and the Russell Theatre (1928).  

The Kentucky Gateway Museum Center is a must-visit and features three unique attractions in one: the KSB Miniature Collection, the Regional History Museum, and the Genealogy & Research Library. The 19th-century Washington Opera House in nearby Old Washington is another fun-to-visit attraction and hosts theater productions and concerts. Finish up at Maysville River Park for great views, a picnic, and fishing.

The Last Word

For a most memorable Kentucky experience, these small towns each offer a fascinating glimpse into the heart and soul of the Bluegrass State. From Harrodsburg's historical heritage to Hodgenville's presidential legacy, Frankfort's political landmarks to La Grange's unique railroad charm, and Rosine's musical roots to Maysville's architectural beauty, these attractive towns offer plenty of fun and are great to explore for those looking to experience small-town Kentucky.  

  1. Home
  2. Places
  3. Cities
  4. These Historic Towns in Kentucky Are Worth Exploring

More in Places