Summary
Kentucky presents a unique opportunity to experience the charm of small towns in the United States, enriched with friendly communities, scenic nature reserves, and distinctive dining and shopping venues. This state, the birthplace of both President Lincoln and Bill Monroe, renowned for its bourbon, offers an array of adventures for travelers seeking exploration in hidden gems.
Beyond charming towns, Kentucky boasts hundreds of miles of national parks, lakes, rivers, and caves for outdoor enthusiasts. While the Kentucky Derby horse race attracts many visitors, the state is an appealing destination year-round. National holidays are accompanied by local celebrations, and traversing the state during spring, summer, and autumn ensures a comprehensive appreciation of Kentucky’s outdoor and indoor offerings.
Each featured small town possesses its unique character and presents a distinctive view of Kentucky. From towns nestled in the Appalachians to those adjacent to historic Daniel Boone country, the listed towns may have modest populations but are rich in history, warmth, and cultural significance.
Here are the top fifteen small towns to discover in Kentucky:
1. Somerset
Engaging in houseboating is a popular activity among Kentucky residents, especially at Lake Cumberland in Somerset. Visitors have the option to rent various sizes of boats suitable for any budget, making it an excellent destination for a water-centric getaway.
Even without houseboating, Somerset offers recreational opportunities along Lake Cumberland’s shores, including fishing, swimming, kayaking, and skiing. Other notable natural attractions encompass the Big South Fork Rivers and a breathtaking sandstone bridge.
Somerset also serves as a strategic base for excursions to the Daniel Boone National Forest, the Big South Fork National River, and a scenic train ride on the Big South Fork Scenic Railway, which traverses the surrounding landscape.
In addition to these adventures, Somerset provides an array of entertainment options, such as a water park, music festivals, drive-in theatres, dining establishments, and museums!
2. Shelbyville
Shelbyville is a noteworthy destination for equestrian enthusiasts. While Louisville, home to the Kentucky Derby, is often associated with major equestrian events, Shelbyville hosts its annual horse show and is recognized for breeding American Saddlebred horses.
Visitors can engage in fruit picking at the Mulberry Orchard, enjoy wine tastings, explore antiques at the Ruby Rooster Antique Mall, and partake in activities at Gallrein Farms, which caters to both children and adults.
A visit to Shelbyville would not be complete without touring the local distilleries found along the “Bourbon Trail.”
3. Bardstown
Bardstown, recognized as the Bourbon Capital of the World, is home to notable distilleries, including Barton 1792, Heaven Hill, and Willett Distillery. It would be prudent to arrange for a designated driver to navigate this small town’s tasting rooms.
When sober, guests can learn about bourbon’s history at the Oscar Getz Museum of Whiskey History, which features exhibits ranging from the pre-Colonial period to Prohibition and beyond.
Additionally, the Civil War Museum offers insights into one of America’s pivotal historical eras, and various heritage tours are available that can provide an overview of significant attractions within a few hours.
Adventurous visitors may enjoy camping at My Old Kentucky Home State Park while searching for the town’s reputed ghostly inhabitants. Experience the bourbon, and immerse yourself in local culture.
4. Rosine
Rosine attracts bluegrass aficionados from around the world, being the birthplace of Bill Monroe, known as the father of bluegrass music. Pilgrims can visit Monroe’s home, venues where he performed, and his final resting place, showcasing family photographs on display.
The Rosine Barn Jamboree served as a venue where Monroe honed his craft; even those averse to bluegrass can appreciate the current ambiance of the stage. Adjacent to this is the Rosine General Store, where locals often play music on the porch.
To further enrich the bluegrass experience, visitors can explore Owensboro to discover more about the genre at the International Bluegrass Music Museum, showcasing a collection of bluegrass memorabilia.
5. Berea
Berea stands out as one of Kentucky’s artistic core areas, drawing diverse painters, musicians, textile designers, and sculptors. It promotes a dynamic environment that fosters creativity through initiatives such as the annual Berea Craft Festival, with ongoing exhibitions at the Kentucky Artisan Center and the Square Gallery.
The town features several historical landmarks, including Berea College, established in 1855 as the first interracial college in the region, alongside numerous historic restaurants, buildings, and private residences.
6. Hodgenville
Hodgenville, recognized as the birthplace of Abraham Lincoln, holds significant historical importance. Those interested in exploring Lincoln’s legacy can traverse the scenic forest trails within the Abraham Lincoln Birthplace National Historical Park and the Abraham Lincoln Boyhood Home, where he received early education. The Lincoln Museum, although modest in size, offers Civil War artifacts, newspaper articles, and wax figures, alongside a bronze statue of President Lincoln situated in the town square.
Hodgenville presents a unique opportunity to reconnect with the past, allowing visitors to gain insight into the life of one of the nation’s most influential leaders within a single day.
7. London
London, Kentucky, serves as an ideal hub for both residents and travelers who are passionate about outdoor recreation. This small town provides access to natural attractions such as the Daniel Boone National Forest, Rockcastle River, Laurel River, and Levi Jackson State Park.
Adventurous individuals can hike along the Sheltowee Trace National Recreation Trail or cycle through the various routes in London-Laurel County. For those seeking some additional excitement, the Wildcat Mountain ATV Park offers a thrilling experience.
The Camp Wildcat Battlefield, a site relatively unchanged since its days of conflict, serves as a historical gem—sure to captivate visitors with interest in reenactments.
8. Pikeville
Pikeville presents a well-rounded opportunity to experience the diverse offerings of Kentucky in one location. Outdoor enthusiasts can explore the breathtaking Appalachian Mountains through horseback riding, hiking, mountain biking, kayaking, or ziplining.
The community is alive with frequent performances at the Jenny Wiley Theatre and the Artists Collaborative Theatre, while country music resonates through the streets—either formally or spontaneously.
History enthusiasts can visit the site of the Hatfield and McCoy feud, a dramatic confrontation between two rival families that shaped a significant part of the region’s heritage.
9. Glasgow
Identified as “A little bit of Scotland in Kentucky,” Glasgow exudes a distinct charm. The town comes alive during its annual Scottish Highland Games, showcasing cultural heritage.
Glasgow offers a gateway to Kentucky’s natural wonders, including Mammoth Cave National Park—ideal for spelunking—and Brigadoon State Nature Reserve. Adventure seekers can partake in hiking, camping, swimming, and myriad outdoor pursuits.
Historical attractions such as the Historic Plaza Theatre, Museum of the Barrens, Veterans Wall of Honor, and Fort Williams provide a glimpse into life during the Civil War era.
10. Murray
Recognized by USA Today as the “Friendliest Small Town in America,” Murray invites visitors to explore its vibrant community and natural beauty.
The town’s harmonious location near Kentucky Lake and the Land Between the Lakes recreation area fosters a relaxed atmosphere for residents and visitors alike. Enjoy a range of activities such as fishing, hiking, kayaking, and wildlife observation, alongside stunning sunsets reflected over tranquil waters.
Additionally, the local economy thrives on boutique shopping and live music events, promoting a welcoming social environment.
11. Greenville
Greenville is a picturesque small town characterized by its well-preserved heritage structures, local boutiques, and an engaged community participating in regular events designed for both locals and visitors. Although accommodation options are limited, the town’s exceptional hospitality encourages repeat visits.
Highlights include the 12-acre forest at Brizendine Brothers Nature Park, a scenic six-mile Rails to Trails walk, and Lake Malone State Park, complemented by a charming gazebo in the city park—ideal for picnicking.
Local theatre, veteran honors, and restaurants serving traditional Kentucky cuisine enhance the rich experience of Greenville.
12. Lebanon
Lebanon represents the core of the Bourbon Belt Trail, a route extending over eighty miles that connects ten bourbon distilleries. The town is home to renowned distilleries such as Maker’s Mark and Limestone Branch, alongside Kentucky Cooperage, a leading bourbon barrel manufacturer.
Lebanon’s vibrant atmosphere is complemented by historical Civil War sites and attractions, including a heritage center, Pope’s Creek Ranch, and the Turtleman museum, dedicated to the local folk hero.
While it may be small, Lebanon offers a myriad of intriguing experiences for visitors.
13. La Grange
La Grange is a unique small town where the number of farm animals may exceed the human population. Visitors can participate in various farm tours that teach about animal care, sustainable farming, and even cooking with local ingredients.
La Grange also has the distinction of being the only town in the United States where a freight train passes through the main street, providing an unusual yet memorable experience.
Couples may enjoy accommodations in charming, vintage B&Bs, away from hectic urban life, with nearby attractions including the Kentucky Derby Museum and lively bluegrass music venues.
14. Maysville
Maysville is characterized by its lively atmosphere, with easy access to the Ohio River and a host of historic sites, dining options, and recreational activities that cater to all types of travelers.
The town’s theaters, such as the Washington Opera House and Russell Theatre, provide engaging performances, while the Kentucky Gateway Museum Center showcases a fascinating miniature collection.
Outdoor adventure is plentiful, featuring zip-lining opportunities, seasonal festivals, and a selection of vibrant local bars, making it evident that Maysville residents embrace a joyful lifestyle.
15. Midway
With a small population of under 2,000, Midway is esteemed for its beautifully preserved architecture, antique shops, wildlife refuges, galleries, and restaurants known for exceptional service.
The town enhances the visitor experience by offering a cellphone walking tour. Tourists can pick up a map at City Hall and access a guided narration detailing the site’s highlights through a phone call. This innovative approach integrates historic exploration with modern technology.
In addition to the town square, visitors can enjoy museums, orchards, vineyards, and even an adventure center for a well-rounded experience in this captivating small town.
