10 Small Towns in Kentucky to Visit for a Weekend Getaway

A weekend getaway in Kentucky offers a journey through the scenic wonder of Bluegrass State. You can visit historic landmarks like the Boone Trace Marker in Berea, the Historical Society Museum of Hopkins County in Madisonville, or hiking trails like the Bracken Creek Horse and Hiking trails in Augusta—each of these ten small Kentucky towns. Whether you're drawn to cultural richness or outdoor escapades, a unique adventure awaits in these small Kentucky towns. These Kentucky weekend getaways offer a truly unforgettable experience.

Berea

Madison County’s southeastern escape is home to the acclaimed Pinnacles Trails of Berea College Forestry, a haven for walkers and nature enthusiasts and awarded as Kentucky's best hike by Outside magazine. John B. Stephenson Memorial Forest's mile-long Anglin Falls trail unravels a captivating waterfall. Standing tall since 1853, the historic Union Church, or the Boone Trace Marker, marked by Daniel Boone in the late 18th century, is a crucial trail shaping westward expansion, a place to admire the area's history. The Doctor’s Inn Air B&B, or The Greathouse Inn Bed and Breakfast, a lovingly restored 1917 arts and crafts home, offers elegant lodging and warmth. 

Madisonville

Madisonville's western part of the state is home to the historic Governor Ruby Laffoon Cabin—a mid-1800s construction once inhabited by Kentucky's 43rd governor. This influential figure resided in this unique cabin. Cherry Park offers four pickleball courts where you can embrace a leisurely game or relax in the green space. The county's rich history unfolds at the Historical Society of Hopkins County through its vibrant murals, or explore the narratives at the Historical Society Museum of Hopkins County. Consider the Hammack-Moore House on Main Street in downtown Madisonville, offering a range of lodging options.

Harrodsburg

Established in 1774, Harrodsburg is the first permanent English settlement west of the Allegheny Mountains. Home to a full-scale replica of James Harrod's 1774 fort, you can explore the history at Old Fort Harrod State Park. The historic Mansion Museum, the George Rogers Clark Federal Monument, the Lincoln Marriage Temple, and the oldest cemetery west of the Alleghenies are all to discover within the Old Fort Harrod State Park's complex. Enjoy an evening of entertainment by attending a show at the Ragged Edge Community Theatre or the musical notes at Studio G before experiencing exquisite accommodations and a delightful dining experience at the Beaumont Inn. 

Lebanon

The Loretto Motherhouse Heritage Center is a top-tier museum where you can explore the legacy of the Sisters of Loretto, bringing history to life in the Heart of Kentucky. Experience the impact of the Civil War on a self-guided Historic Homes & Landmarks Tour, or learn about the art and techniques of whiskey-making at the Lebanon Branch Distillery. Take a stroll through time at Fiddlers Grove Historic Village to relive early village life on their grounds. Complete your day by resting at the Wildflower Ranch Inn, an 1871-built manor that combines historic attractions with modern luxury.

Henderson

Audubon Mill Park, located in the western part of the state along the Ohio River, invites exploration at the original site of John James Audubon's grist mill. Century-old shade trees adorn the park; visitors can access riverfront views and picnic tables. Sixteen bronze sculptures honoring the naturalist and artist can be found throughout the park. A self-guided tour is available within downtown Henderson to discover these tributes. The historical significance of the Henderson County Public Library, which opened in 1904 and features a beautiful exhibition on local history, can be appreciated. The L&N Bed and Breakfast, a charming 1895 home transformed into a bed and breakfast in the heart of downtown Henderson, is equipped with a balcony view of the Ohio River.

Midway

The Bluegrass Railroad Museum unveils the rich history of central Kentucky, showcasing preserved artifacts from the region's railroad heritage. In the heart of Midway, nature enthusiasts can appreciate the scenic marvel of Walter Bradley Park. The operational Weisenberger Mill, producing various items since 1865, is available for tours. After a day of exploration, you can unwind at the Historic Scottwood Bed & Breakfast, which offers early morning views of horse farms and stunning sunsets. Alternatively, you can choose the Cabin at Elkhorn Ridge Farm for a retreat surrounded by beautiful farmlands.

Pikeville

Pikeville, found in the eastern part of the state within the Appalachian Mountains, provides a variety of cultural experiences. The Appalachian Center for the Arts hosts theater plays, music concerts, and visual arts shows. The Hatfields and McCoys Feud Historic Driving Tour allows you to explore the sites of "the world's most famous feud" on a self-guided journey. Bob Amos Park, surrounded by the scenic Appalachian Mountains, provides an excellent relaxing place. The Overlook Events Center atop the hill is worth visiting for a spectacular view. Lodging options include the Landmark Hotel or the Hatfield and McCoy Lodge.

Greenville

Greenville, found within the hills of western Kentucky, exudes a quaint and relaxed atmosphere. As you meander through the 12-acre Brizendine Brothers Nature Park woodland, you'll come across 'Yogi,' a 7' chainsaw-sculpted bear. Whether you engage in fishing or take in the shoreline views enclosed by 50-foot sandstone bluffs at Lake Malone State Park, nature's beauty envelops you. The historic Muhlenberg Community Theatre Inc. showcases extraordinary exterior architecture, offering a splendid venue to appreciate the fine arts. Greenville's newest lodging addition, the Aloft Greenville Downtown Hotel, provides an unparalleled experience.

Bardstown

Explore Bardstown, Kentucky, renowned as the "Bourbon Capital of the World." Learn about the bourbon legacy at the Heaven Hill Bourbon Experience, which has a tasting center and a museum that recounts the local bourbon story. Uncover the charm of Bardstown's My Old Kentucky Home State Park, where Federal Hill and the Basilica of Saint Joseph Proto-Cathedral showcase the town's beauty. Experience a memorable stay at one of the many exceptional lodging options, such as the Bourbon Manor Bed & Breakfast Inn, a luxurious Antebellum Mansion constructed in 1810, or the authentic mid-century Bardstown Motor Lodge with fire pits and a poolside bar.

Augusta

Augusta, located on the southern bank of the Ohio River, was awarded the title of "Most Picturesque Town in Kentucky” by USA Today. One can experience a weekend retreat at the South Bank Station on the Ohio, a stunning 1880's Historic River Cottage steeped in the nostalgia of yesteryear. The 1811 Augusta Jail in Appelman Park or the history at Baker-Bird Winery, the Oldest Commercial Estate Winery in America, can be enjoyed. Augusta's rich history at the Haley House Museum can be witnessed by walking downtown, or one can venture outdoors to appreciate the scenic marvel along the Bracken Creek Horse and Hiking trails.

A Journey Through Kentucky's Heartland

Your time spent in Kentucky for a weekend getaway promises enticing adventures in the Bluegrass State. It has historic landmarks like the Historic Scottwood Bed & Breakfast in Midway or the Loretto Motherhouse Heritage Center in Lebanon and nature parks like the Brizendine Brothers Nature Park in Greenville. In each of these ten small Kentucky towns, a unique adventure awaits. With their unique blend of natural landmarks, nature parks, and comfortable accommodations, these Kentucky towns promise a weekend getaway that will not disappoint.