8 Most Scenic Drives in Kentucky

Kentucky's two-lane roads tell stories that weathered billboards and aging gas stations just can't match. Between quiet valleys and limestone cliffs, past bourbon distilleries and historic mills, eight drives in particular capture what makes Kentucky special. As you will see, each of the eight most scenic drives in Kentucky offer their own slice of life in the Bluegrass State, whether you are tracing Daniel Boone's footsteps or watching bison lumber through the very same spots mammoths once roamed.

Wilderness Road Heritage Highway

One of America's earliest migration routes west still draws travelers, though today they come for scenery rather than settlement. This 94-mile stretch between Middlesboro and Berea follows portions of Daniel Boone's historic trail from 1775, winding through mountain passes and along creek beds where pioneers first entered Kentucky's wilderness. The two-hour drive provides peeks at the critical role the Appalachian landscape played in shaping America's westward expansion. The journey's highlight comes early at Cumberland Gap National Historical Park, where three states meet at a natural mountain pass. Here, visitors explore limestone caves and a reconstructed pioneer settlement that brings frontier life into focus. Further north, the Dr. Thomas Walker State Historic Site honors the first explorer to document the gap. The drive ends near Levi Jackson Wilderness Road Park, where a reproduction of McHargue's Mill stands as a working reminder of frontier life — its water wheel turns as visitors hear pings coming from the local blacksmith’s hammer on an anvil.

Country Music Highway

Eastern Kentucky's hills have produced more hit country music artists per capita than anywhere else in America, according to Smithsonian Magazine, and US Route 23 strings their stories together like an old country song. The 144-mile route from Greenup to Whitesburg takes about three hours to travel if you don't stop. Between the strip mines turned wildlife areas and mountain hollows that shaped a uniquely American music style, this drive shows why they call it coal country's Nashville connection. Along the way, the Country Music Highway Museum in Paintsville brings the region's musical heritage to life, with exhibits honoring local legends like Loretta Lynn and Chris Stapleton.

Red River Gorge Scenic Byway

Try not to let its modest 46-mile length fool you — the drive from Stanton to Zachariah packs more natural wonders into each mile than most highways manage in their entire length. This journey through Daniel Boone National Forest shows off Kentucky's most dramatic landscape, where sandstone arches and towering cliffs attract rock climbers from across the country. The adventure starts properly at Nada Tunnel, a narrow, 900-foot-long passage through solid limestone that early loggers blasted with dynamite and carved by hand. From there, the road winds past one natural marvel after another. Sky Bridge looks like a stone walkway across the sky, while Chimney Top Rock offers views clear into the next county. Near the end of the drive, visitors learn how Whistling Arch earned its name. Some locals say the eerie music it makes in the wind is actually the spirits of long-gone mountain dwellers singing.

Lincoln Heritage Scenic Highway

History and bourbon share this 72-mile route from Hodgenville to Danville. The two-hour drive cuts through the heart of Kentucky, where Abraham Lincoln's humble beginnings coexist with America's signature spirit. Rolling pastures crowded with thoroughbred horses give way to rickhouses and aging bourbon barrels, while historic battlefields remind travelers of the price Kentucky paid during the Civil War. The journey begins where Lincoln's story started, at the Abraham Lincoln Birthplace National Historical Park in Hodgenville. A granite and marble memorial building houses a replica of the tiny cabin where the future president was born. Further along, Heaven Hill Bourbon Heritage Center shows how limestone-filtered water and Kentucky's climate create perfect bourbon-making conditions. The drive concludes near Perryville Battlefield State Historic Site, where what is considered Kentucky's largest Civil War battle left its mark on the landscape; today's peaceful fields offering little hint of their violent past.

Boone Creek Scenic Byway

This compact nearly 9-mile loop southeast of Lexington proves that sometimes the best drives are not very long at all. This half-hour route follows limestone walls and waterfalls that helped power the region's early mills and provides glimpses of authentic Kentucky Bluegrass here and there. The historic Grimes Mill anchors the drive's history, its massive stone walls looking almost the same as they did in 1807 when the mill first started grinding local grain and corn. The famous Raven Run Creek and Nature Sanctuary spreads across 734 acres nearby, with trails going through pioneer ruins and near cliffs overlooking the Kentucky River. The nearby Arboretum, State Botanical Garden of Kentucky rounds out the journey as Kentucky's official state botanical garden, giving tourists a look at both the University of Kentucky campus and many of the native plants found across the Bluegrass State.

Cumberland Cultural Heritage Highway

If you like lakes and history, you will love one of the longer drives on our list: the almost 200-mile Cumberland Cultural Heritage Highway; it connects Albany to Jamestown. The cuts through genuine rural southern Kentucky, where lake culture meets small-town life. Farm fields and forests suddenly give way to massive stretches of water, not to mention the many historic sites dotting the quieter sections between towns. Mill Springs Mill, built in 1877 and restored in 1976, still turns its giant water wheel just off the main route; it's reportedly one of the largest of its type in the world. Further along, General Burnside Island State Park — Kentucky's only island state park — attracts boaters and golfers alike to Lake Cumberland's waters and shores. Near the drive's end, Wolf Creek National Fish Hatchery is an unexpected but fascinating stop, the birthplace to millions of rainbow trout before they head to Kentucky's streams and lakes.

US Route 68 (Shakertown to Perryville)

This scenic route is yet another instance of a short drive packing in one memorable story after another. Just about 18-miles long, this 30-minute drive between Shakertown and Perryville captures centuries of Kentucky life. The route puts classic Bluegrass countryside on full display, showing off countless green pastures and historic buildings peeking through ancient trees. Shaker Village of Pleasant Hill is the start — and crown jewel — of the drive, its 34 original 19th-century buildings providing a window into one of America's largest Shaker communities. Exhibits about Shaker life crowd the restored buildings, while herb gardens and workshops keep traditional skills alive and well. Like the Lincoln Heritage Scenic Highway, this route ends at Perryville Battlefield.

Big Bone Lick Scenic Byway

The scenic drive with the oddest name actually tells one of Kentucky's oldest stories. This 22-mile route between Beaverlick and Burlington takes less than an hour to drive but spans thousands of years of natural history. The road follows routes once used by massive Ice Age mammals that were looking for the area's salt licks. In fact, it is not uncommon for drivers to spot their modern descendants: a herd of bison roaming the same grounds. Big Bone Lick State Historic Site anchors the drive's southern end, where salt springs still bubble up along Big Bone Creek. The park's museum displays the massive bones that gave the area its name, while hiking trails lead past grazing bison to prehistoric salt springs. Further down the road, visitors can take in the view from picturesque Rabbit Hash on the banks of the Ohio River, then stop at the Dinsmore Homestead for an authentic look at 1842 farm life. The drive's final stop at Kinman Farm Market in Burlington brings everything full circle, home to many modern farmers still working the same soil that once fed prehistoric giants.

Conclusion

Kentucky's backroads tell stories that interstates just do not have time for these days. From Daniel Boone's forays through the wilderness to the country music stars who grew up in the Kentucky mountains, these scenic drives in Kentucky showcase the Bluegrass State at its most personal and genuine. Whether you have half an hour for the Boone Creek loop or an afternoon to explore the Country Music Highway, each route speaks to a unique piece of this remarkable region. Prehistoric salt licks, Civil War battlefields, bourbon rickhouses, and more — these eight scenic Kentucky drives prove slowing down and taking your time can reap massive rewards.