Drive These 4 Kentucky Byways This Fall

Kentucky’s history and culture are as multifaceted as the bourbon it’s so well known for. The state is the birthplace of President Abraham Lincoln and was the site of a handful of significant Civil War battles. It’s home to the Kentucky Derby and a renowned thoroughbred industry. It gave rise to some of country music’s brightest stars, and its location along the western edge of the Appalachian Mountains makes it a place of natural beauty. Explore all of this by following Kentucky’s National Scenic Byways, including these four routes.

Country Music Highway
U.S. Route 23 carries quite the tune in Kentucky. Winding along the eastern edge of the state, the roadway became part of the 144.1-mile Country Music Highway National Scenic Byway in 2002 thanks to the prevalence of stars who hail from this region surrounded by the peaks and valleys of the Appalachian Mountains. 

“There’s a lot of mountain soul in all the artists that come from here, and you can hear it in the music,” says Joe Campbell, executive director at Mountain Arts Center in Prestonsburg.

In Ashland, near the northern end of the route, the art deco Paramount Theatre built in 1931 served as a movie theater until 1972, when it became the Paramount Arts Center, a 1,400-plus seat concert venue. The Paramount helped launch the careers of Ashland natives Wynonna and Naomi Judd, and Billy Ray Cyrus, who is from nearby Greenup County. (The music video for Cyrus’ “Achy Breaky Heart” was filmed at the theater in the early 1990s.) Today, acts such as Trace Adkins and The Marshall Tucker Band take the Paramount stage. 

Learn about the Judds, Cyrus and more at the U.S. 23 Country Music Highway Museum in Paintsville, about 60 miles southeast of Ashland. The museum features instruments and other artifacts across 14 exhibits from country music royalty who called this part of Kentucky home. Check out stage wardrobe worn by Chris Stapleton, Ricky Skaggs and other artists, Loretta Lynn’s guitar and one of the Judds’ gold records. 

The 1,044-seat Mountain Arts Center in Prestonsburg, located about 15 miles southeast of Paintsville, hosts nationally touring acts that play bluegrass, gospel, rock and country. (Lynn, Cyrus, Stapleton and more all played here over the years.) The center is also home to Billie Jean Osborne’s Kentucky Opry, which performs at the venue on a regular basis.

For an encore, stop in Pikeville along the last leg of the byway to check out an infamous bit of Kentucky history. The town played host to part of the feud between the Hatfields and the McCoys. Today, you can visit a museum, grave sites and more related to the dust-up between the two families. 

Explore More
For more information about the Country Music Highway, visit nsbfoundation.com. 

Paramount Arts Center
paramountartscenter.com

U.S. 23 Country Music Highway Museum 
facebook.com/countrymusichighwaymuseum

Mountain Arts Center
macarts.com

Lincoln Heritage Scenic Highway
Delve into two of Kentucky’s most well-known exports — Abraham Lincoln and bourbon — on the 71.2-mile Lincoln Heritage Scenic Highway. While Illinois is known as the Land of Lincoln, the 16th U.S. President was born in Kentucky in 1809, and this byway that follows U.S. Routes 31E and 150 winds you through the region he called home. There’s also a bit of bourbon along the way to keep things interesting. 

Found among the steep, conical hills (also known as knobs) in this part of the state, travelers can visit the Abraham Lincoln Birthplace National Historical Park’s Birthplace Unit, which features a reconstructed cabin meant to emulate the one Lincoln was born in. It’s protected from the elements by the Memorial Building, a Beaux-Arts-style structure completed in 1911.

In downtown Hodgenville, the Lincoln Museum’s exhibits include a dozen room-sized dioramas depicting Lincoln’s life, from his birth to his assassination at Ford’s Theatre. The diorama depicting the assassination includes a duplicate of the chair he was sitting in during the play.

“He sacrificed his life to keep this country together and to end slavery,” says Rob Thurman, assistant director at the Lincoln Museum. “We’re just very proud that his starting point is right here in Hodgenville.”

For a taste of Kentucky history, head 26 miles northeast to the Heaven Hill Bourbon Experience in Bardstown, which provides a smooth opportunity to learn the state’s bourbon backstory and sample some of the goods. Located along Kentucky’s Bourbon Trail, the roughly 21,000-square-foot destination features exhibits on the history of both the spirit and the distillery, which makes brands such as Elijah Craig, Evan Williams, Old Fitzgerald and more. Don’t miss out on the tasting and tour experiences. 

Just north of Perryville, about 36 miles east along U.S. 150, sits Perryville Battlefield State Historic Site, the location of a Civil War battle that resulted in the Union maintaining control of the border state, according to park manager Bryan Bush. Visitors can retrace the progress of the Oct. 8, 1862, battle, hike more than 17 miles of trails and visit the on-site museum.  

“Lincoln once said, ‘I’d hope to have God on my side, but I must have Kentucky,’” Bush says.

Explore More
For more information about the Lincoln Heritage Scenic Highway, visit nsbfoundation.com.  

Abraham Lincoln Birthplace National Historical Park
nps.gov/abli

Lincoln Museum
lincolnmuseum-ky.org

Heaven Hill Bourbon Experience
heavenhilldistillery.com

Perryville Battlefield State Historic Site
parks.ky.gov

Old Frankfort Pike Historic and Scenic Byway
Kentucky’s first formal horse-racing track was built in Lexington in 1789, three years before the Bluegrass State was admitted to the Union. Saddle up and explore thoroughbred history on the 15.5-mile Old Frankfort Pike Historic and Scenic Byway. Lined with limestone walls, wooden fences and fields dotted with grazing horses, you won’t want to race by any of these stops. 

In Lexington, McConnell Springs Park offers a natural space with nearly 2 miles of trails, interesting topographical water features and an education center with exhibits. 

A little over 2 miles west, before the roundabout that circles a statue of famed Triple Crown winner Secretariat, pull into the Old Frankfort Pike Scenic Overlook. Aside from providing a slightly elevated view of Secretariat midstride, signs detail the history of the area and provide a perfect starting gate for the horse farms farther down the road. 

“When you’re driving Old Frankfort Pike, the trees form a canopy, and it’s an experience you don’t get in many other places,” says Shannon Castagnola, stallion season and public sales director at Airdrie Stud, a thoroughbred farm in Midway. “You can feel the history of these farms.”

Join the ranks of Bing Crosby and Queen Elizabeth II when you visit the 1,000-acre Darby Dan Farm. The farm hosted both notables during its history, and some scenes from the 2010 movie “Secretariat” were filmed here. Visitors can take a tour of the property, which has produced six Kentucky Derby winners (four of them from when it was called Idle Hour Stock Farm in the first half of the 20th century). 

Home to 2023 Kentucky Derby winner, Mage, Airdrie Stud is another horse farm with a long history that predates its 1972 founding. The land the 2,500-acre farm now occupies used to be part of Woodburn Stud horse farm, where the thoroughbred breed originated in the U.S. in the 19th century. Today, visitors can tour the farm, see (and maybe feed peppermint to) stallions, mares and foals, and learn about the history of the farm and thoroughbred horse breeding. 

“The lifestyle of a major stud farm is incredibly special, and we want to be able to share that,” says Castagnola, who leads the tours.

Explore More
For more information about the Old Frankfort Pike Historic and Scenic Byway, visit nsbfoundation.com. 

McConnell Springs Park
lexingtonky.gov

Old Frankfort Pike Scenic Overlook
oldfrankfortpike.org

Airdrie Stud
airdriestud.com

Darby Dan Farm
darbydan.com

Wilderness Road Heritage Highway
In the 1770s, frontiersman Daniel Boone helped chart a path through the Cumberland Gap, providing a westward route across the Appalachian Mountains. Today, visitors can tread where America’s legendary explorer did on the 93.8-mile Wilderness Road Heritage Highway, which evolved from Boone’s original path and follows Kentucky Route 229 and U.S. Route 25. 

“Driving the Wilderness Road shows you the real beauty of Kentucky,” says Todd Finley, executive director of the Kentucky Artisan Center in Berea at the northern end of the route. 

Straddling three states (Kentucky, Virginia and Tennessee) at the southern end of the scenic byway, Cumberland Gap National Historical Park consists of 14,000 acres of land that once served as a passage to the west. The park features 85 miles of trails, a multilevel cave with guided tours and the Hensley Settlement, a preserved, early 20th century mountaintop outpost. 

About 54 miles north in the town of London, Levi Jackson Wilderness State Park features McHargue’s Mill, a working watermill built in 1939. (The millstones used to build the mill were brought along the Wilderness Road in 1805.) Don’t miss the park’s campground and museum.

From there, head 22 miles north to the Renfro Valley Entertainment Center in Mount Vernon. The destination’s New Barn Theatre offers a 1,500-seat venue that hosts touring acts ranging from classic country to rock to bluegrass to southern gospel. The stage at the standing-room-only Old Barn Theatre has hosted live music since 1939. The entertainment center also has a recreational vehicle campground on-site.

The Kentucky Artisan Center at Berea near the northern end of the route isn’t your average roadside stop. The center’s gallery-like atmosphere is thanks to the works of art made by nearly 1,200 Kentucky artisans. Visitors can find paintings, pottery and wood-carved kids toys — all made in Kentucky. 

“It’s very important to us that we support our arts and craftsmen so that we can keep these traditions alive,” Finley says.

Once you’ve browsed the artists’ wares, enjoy Kentucky-made ice cream on the patio before getting back on the road. 

Explore More
For more information about the Wilderness Road Heritage Highway, visit nsbfoundation.com.

Cumberland Gap National Historical Park
nps.gov/cuga

Levi Jackson Wilderness State Park
levijacksonpark.com

Renfro Valley Entertainment Center
renfrovalley.com

Kentucky Artisan Center
kentuckyartisancenter.ky.gov