Labor Day weekend marks the conclusion of summer and the start of colorful fall foliage and pleasant weather. Enjoy the holiday with a scenic adventures or a relaxing trip in Kentucky. From big cities to laid-back towns, this breathtaking state offers phenomenal attractions ranging from historic schoolhouses to the Kentucky Derby. Book a stay at one of numerous Kentucky vacation rentals for your upcoming Labor Day weekend getaway. Take a look at the top cities and towns in Kentucky perfect for an autumn weekend trip.
1. Louisville
Louisville is home to the Kentucky Derby, one of the most famous horse races in the United States, and you can start your visit to the town with a tour of Churchill Downs, the track where it takes place. The museum includes information on past winning horses. Scream on a roller coaster or bob up and down on the carousel at Kentucky Kingdom, a local amusement and water park. Kids of all age – even the fully grown kids – love a tour of the Louisville Slugger Museum and Factory with the giant baseball bat out front.
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2. Bowling Green
As a college town, Bowling Green practically bursts with energy. Take a tour of the Historic Railpark and Train Museum. Located in an old railway station, this museum teaches the state’s rich history with the railroad and offers the chance to climb on vintage cars. Kids make a vroom vroom sound as they walk through the National Corvette Museum and see some of the oldest restored cars. Try hiking at the Lost River Cave area and take a tour of this unique cave system.
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3. Elizabethtown
Relax and take life a little slower in Elizabethtown. Surprisingly, this small town has a direct connection to President Abraham Lincoln. It was in this area that his daughter Sarah was born in a charming log cabin. Take advantage of the fall colors by stopping by the Bernheim Arboretum and Research Forest. This area has more than 40 miles of hiking trails for your family to explore. If you’re traveling with grown children, hop on the Bourbon Trail of Kentucky and tour the Jim Beam, Maker’s Mark, and Woodford Reserve distilleries.
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4. Henderson
Along the banks of the Ohio River, Henderson is home to the Southern Cherokee Indian Nation. It’s a great place to learn a little more about this Native American culture. Meander along the hiking paths at the Audubon Museum and Nature Center or the John James Audubon State Park. Both parks are popular for birdwatching and wildlife viewing with trails for all skill levels. Just across the river, you can take a tour of the USS LST-325, a decommissioned tank landing ship from World War II.
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5. Winchester
Winchester is a charming town, where you can spend each evening walking around the quaint downtown area and stopping at the local antique stores, such as the Bentley And Murray and Athens Schoolhouse Antiques. Do a little dance at the Bluegrass Heritage Museum, where you can learn more about this genre’s greatest artists and its rich history. See the glorious fall colors by spending a day hiking in the nearby Daniel Boone National Forest.
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6. Paducah
Book a vacation rental in a town designed by William Clark of the Lewis and Clark Expedition. In fact, 20 blocks of the downtown area are on the National Register of Historic Places. Make sure to stop by the Whitehaven Welcome Center, which is housed inside of a lovely Victorian mansion. Learn more about the art of quilting at the National Quilt Museum, where you can see some amazingly detailed pieces in a medium not always considered art, but truly stunning nonetheless.
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7. Red River Gorge
Breathe in the fresh air and see all the leaves and trees changing colors with a weekend away in Red River Gorge. Explore the river with kayak rentals from Red River Adventure or opt for a canoe if you have younger children. Red River Outdoors offers a guided tour of the area and kayaking tours on the water with a knowledgeable guide to lead the way. See for miles around when you ride a zip line at Red River Gorge Zipline.
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8. Lexington
Lexington offers a full weekend of activities. Start with a visit to the Kentucky Horse Park. This working horse farm has a museum and a tour that includes an up-close visit with the animals. Stay for the daily Parade of Breed Show that displays a variety of horse breeds. This town was the childhood home of the President Abraham Lincoln’s wife, Mary Todd, and you can take a tour of her childhood home. Stop by the airport to learn more about aviation at the Aviation Museum of Kentucky.
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9. Frankfort
As the capital city, Frankfort is fun and educational for families with kids. Arrive early enough on Friday to go inside the stately Kentucky Capitol Building. Afterward, take a tour of the Old Statehouse. It was the third capitol building in the state, and it was built for beauty in the Greek Revival style. Grab your fishing gear for a day at Salato Wildlife Center or spend the day hiking through the area.
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10. Hopskinville
Slow down and take life easy in Hopskinville. Walk around the small downtown area and exchange pleasantries with the locals. Learn more about the local and regional history when you visit the Pennyroyal Area Museum, located in the old post office. Covering 40 acres, the Jeffers Bend Recreation Area offers the chance to look at more than 100 types of plants as you navigate the numerous walking trails.
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