Aerial view of Frankfort, Kentucky.

The Most Picturesque Small Towns In Kentucky

Kentucky, located in the southeastern region of the United States, is known for its geography, ranging from the Appalachian Mountains in the east to the rolling bluegrass region in the central part of the state. Kentucky is notable for its horse racing, particularly the annual Kentucky Derby held at Churchill Downs in Louisville. It is also known for bourbon production, with numerous distilleries scattered throughout the state.

The state is home to picturesque small towns with well-preserved downtown districts, historic sites, and natural scenery. These seven towns are sure to enchant visitors with their hospitality, history, and landscapes.


The Old Talbott Tavern in Bardstown, Kentucky
The Old Talbott Tavern in Bardstown, Kentucky. Editorial credit: Ryan_hoel /

Bardstown, Kentucky, established in 1780, is one of the oldest towns in the state and is often referred to as the "Bourbon Capital of the World." Its history is rooted in the production of bourbon whiskey, which began in the early 19th century and continues to play a significant role in the town's economy and culture.

My Old Kentucky Home State Park includes a historic mansion and park. Visitors can take guided tours of the mansion, which inspired Stephen Foster's famous song. Barton 1792 Distillery is a historic bourbon distillery. Tours and tastings are available for visitors to learn about the bourbon production process and the history of the distillery. The Bourbon Heritage Center is a museum and visitor center dedicated to the history of bourbon whiskey. It has exhibits on the bourbon-making process, the history of bourbon in Kentucky, and the heritage of the local distilleries.


The charming town of Midway, Kentucky
The charming town of Midway, Kentucky. Editorial credit: Alexey Stiop /

Midway, Kentucky, was established in the 1830s as a railroad town. The town's development was closely tied to the railroad, with the first train passing through in 1833. Midway played a role in the transportation of goods and passengers, contributing to the growth of central Kentucky. The town's name reflects its location, being midway between Lexington and Frankfort.

Weisenberger Mill is a historic gristmill located along South Elkhorn Creek. It is a glimpse into Kentucky's milling history and sells locally produced flour and cornmeal. Equus Run Vineyards is a vineyard that has tours and tastings. Outdoor concerts and events are frequently held on the vineyard grounds. Midway's Historic Railroad Depot is a well-preserved train station that reflects the town's railway past. Visitors can appreciate the vintage site and learn about the role of the railroad in Midway's development.


A historic barn near Harrodsburg, Kentucky.
A historic barn near Harrodsburg, Kentucky. Editorial credit: Ken Schulze /

Harrodsburg, Kentucky, established in 1774, is the oldest permanent settlement west of the Allegheny Mountains. Founded by James Harrod, it played a role in the early expansion and development of Kentucky. The town was a focal point for pioneers and settlers moving westward. Harrodsburg's significance is preserved through its well-maintained historic sites and buildings.

Shaker Village of Pleasant Hill is a large restored Shaker community with numerous historic buildings and gardens. Educational exhibits offer insights into the Shaker way of life and their contributions to agriculture and craftsmanship. Old Fort Harrod State Park includes a reconstructed fort that shows life in the 18th century. The park also has a pioneer cemetery and the Lincoln Marriage Temple, where Abraham Lincoln's parents were married. The Beaumont Inn is a historic inn known for its Southern hospitality. Visitors can enjoy historic tours and fine dining.


Boyle county court house in Danville, Kentucky
Boyle County Court House in Danville, Kentucky.

Danville, Kentucky, established in 1783, played a role in the early governance of the state. It is known as the "City of Firsts" for its many pioneering achievements, including hosting the signing of Kentucky's first constitution in 1792. Danville was an important center for education and medicine in the 19th century.

Constitution Square Historic Site is a park that commemorates the signing of Kentucky's first constitution. Visitors can explore log structures and learn about the state's early government. McDowell House Museum is the historic home of Dr. Ephraim McDowell. The museum shows his medical achievements, including the first successful ovarian surgery. Pioneer Playhouse is an outdoor theater that hosts summer performances. The theater is a historic setting.


Woodford county courthouse in downtown Versailles, Kentucky
Woodford County Courthouse in downtown Versailles, Kentucky.

Versailles, Kentucky, was established in 1792 and named after the French city of Versailles in honor of General Lafayette's assistance during the American Revolution. Located in Woodford County, the town has a history rooted in agriculture, particularly horse breeding and bourbon production. Versailles became a prominent center for thoroughbred horse farms.

Jack Jouett House Historic Site is the home of Revolutionary War hero Jack Jouett. Visitors can take guided tours and view exhibits that highlight his contributions to American independence. Pisgah Presbyterian Church is known for its historic architecture and cemetery. The church has been a cornerstone of the community since the early 19th century. Buckley Wildlife Sanctuary is a nature preserve with hiking trails and birdwatching opportunities. Educational programs are available to learn more about local wildlife and conservation efforts.


Skyline of Maysville, Kentucky
Skyline of Maysville, Kentucky. Image credit: Nealparr at the English Wikipedia via Wikimedia Commons.

Maysville, Kentucky, founded in 1787, is a town located along the Ohio River. It played a role in the early settlement of Kentucky and was a major center for the tobacco industry and river trade in the 19th century, which contributed to its economic growth. Maysville's history is reflected in its well-preserved historic districts and buildings.

Old Washington Historic District includes preserved 18th-century buildings and hosts historic tours. Museums within the district look at the area's early history and its role in westward expansion. Kentucky Gateway Museum Center has exhibits on regional history, a miniatures gallery, and a genealogical research library. Visitors can explore artifacts and learn about the cultural heritage of the region. Simon Kenton Memorial Bridge is a historic bridge that spans the Ohio River. It offers views of the river and Maysville's riverfront.


Aerial view of Frankfort, Kentucky.
Aerial view of Frankfort, Kentucky.

Frankfort, Kentucky, established in 1786, is the state capital and holds a significant place in Kentucky's history. The town was strategically chosen for its location along the Kentucky River, which facilitated trade and transportation in the early days. Frankfort's history is marked by its political importance and development as a center for state government. It has been the site of many key events and decisions in Kentucky's history.

Kentucky State Capitol is a historic building that hosts guided tours. Visitors can explore its architecture and learn about the state's legislative process. Liberty Hall Historic Site is a historic mansion with gardens. Guided tours provide insights into early Kentucky history and the lives of its prominent residents. Capital City Museum is dedicated to Frankfort's history. Exhibits cover topics such as politics, bourbon, and local culture.

In Summary

Kentucky is dotted with picturesque small towns worth visiting. Bardstown's bourbon heritage and historic sites, such as My Old Kentucky Home State Park, look at the state's distilling past. Midway's historic railroad depot and picturesque vineyards highlight its small-town atmosphere. Harrodsburg, with its Shaker Village and Old Fort Harrod, preserves the pioneering spirit of early Kentucky settlers. These seven towns exemplify how preserved history creates picturesque settings in Kentucky.

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