Boasting a culture that is part Midwest, part Southern, Kentucky somehow combines the best of both worlds. The 15th state to join the Union has a mind-bending scenery that is a small price to pay for giving up the ocean. A tour of the Bluegrass State will see you at one time meandering through the high ridges and lush, cascading valleys in the east—at another gazing over the monadnocks, the beautiful knob-shaped hills in the west. In the middle of the state is the Bluegrass region that lends Kentucky its nickname. Named for the unique grass that grows there, this part of the state will see you gasping at the many hills, caves, sinkholes, and springs abundant in the region. A road trip is the best way to take in Kentucky's diverse landscape. For those who want to experience this pleasure-filled respite, these are the best road trips in the state.
AA Highway From Grayson To Newport
This route is an under-the-radar secret that is choke-full of awesome views just about every step of the way. It is mile after mile of beautiful greenery, quiet, calming scenes, and relatively low traffic. This stretch should take you about two hours, many times more, because of the number of times you will need to pull over and cast your eyes over the landscape. This short stretch is not overly twisty. However, it has sections that bestow the feel of driving in the middle of some beautiful forest—because of the abundance of evergreens on either side of the road. Also, some sections of this road feature raised, cliff-like sides that give drivers the impression of cutting right through the middle of low, rolling hills.
The Lincoln Heritage Scenic Byway
Named for one of the most beloved American presidents, the Lincoln Heritage Scenic Byway is a picturesque 72-mile stretch that will not fail to impress a Kentucky explorer. Whether one will want to set foot on Lincoln's Boyhood Home at Knob Creek, where the man who would sign the Emancipation Proclamation lived from when he was two and a half to when he was nearly eight, climb up the balcony of Abbey of Gethsemani and gasp at the awesome views in what is the oldest Trappist monastery in the United States (Trappists are known for their fascinating practice of silence) —or step back into history at the Old Bardstown Village to explore the largest collection of Civil War Artifacts of the Western Theater in America, this road trip has you covered. And that is not to mention the Bourbon Trail. For a state that is home to America's official native spirit, and which once produced up to 95% of the product, the Bourbon Trail will be an exciting eye-opener.
Woodlands Trace National Scenic Byway
With some snacks, a good playlist, and a little gasoline, a road trip that takes you through the Woodlands Trace National Scenic Byway will be quite an adventure. Known simply as "the Trace," this adventure begins from Grand Rivers, an idyllic, waterfront town that is stunningly perched on both Kentucky Lake and Lake Barkley— and goes right through to the Volunteer State, as Tenessee is known. Running in a north-south direction, this charmer is 43 miles long and will make you think you are in the middle of the Amazon Forest—hence the official designation. Since this trip goes through the Land Between the Lakes National Recreation Area, you will want to briefly pull over, catch a glimpse of the enclosed bison and elk, and inhale the heart-ravishing scenery around.
Elk Creek Winery Loop
Going through Owenton and Middleton and tons of other places few people will be able to spot on a map, the Elk Creek Winery Loop is another trip that is among the most underappreciated in the country. This is a loop, which means it starts and ends at about the same place. In this case, the adventure will start and end at the tiny town of Pewee Valley, a charmer that alluringly combines quaintness and quietness — and located about 18 miles west of Louisville, Kentucky. This trip will take you through US 60, US 127, and I 265 and features panoramic views of rolling hills and cascading valleys. Then again, this drive involves a Highway 227 section that is impossibly curvy and which may make you think you're negotiating some curves in California. To reward yourself, you'll need to enjoy a glass of some Cabernet Sauvignon at the Elk Creek Vineyards in Owenton. The whole trip takes about 120 miles.
William Shakespeare might have had this road in mind when he wrote centuries ago that "brevity is the soul of wit." Well, this Kentucky road trip is short, just about 4.5 miles. Yet what it packs in that fleeting stretch is a delicious visual feast — longer roads cannot hold a candle to. But first, take note that this is a backroad— the quintessential "road less traveled." This means you should expect some beautiful countryside scenery without the rush and traffic of a busy highway. Peel your eyes for massive trees. Kentucky is home to the most diverse hardwood species in the United States—except Florida. Also, since this trip involves the town of Lexington, known as the Horse Capital of the World, expect to see the many horses that roam the rolling hills encircling the town. Then again, one of the most talked-about buildings in the state is on this route— the Kentucky Castle.
Mammoth Cave Parkway
No one will pass up the chance to set foot in what is regarded as the longest cave system on the globe. An intricate labyrinth that boats 400 miles of dark, subterranean trails and miles more that have never been explored, Mammoth Cave is a world-famous Kentucky highlight that defies superlatives. Well, it turns out that the trip to Mammoth Cave may just be as stunning as the caves themselves. Mammoth Parkway comprises parts of Kentucky Routes 70 and 255 and features some of the best vistas in the area. For an unforgettable experience, you may need to try out the Green River Ferry, a popular car ferry that runs across the Green River. Then again, it will almost be criminal to miss Doyel Valley Overlook, a spot from which you can gasp at the park's breathtaking landscape spread across.
The Wilderness Road Heritage Highway
Transversing a distance of just under 100 miles, the Wilderness Road Heritage Highway is often a top contender for the most picturesque road trip in Kentucky. Goosebumps will start to set in from the section around Middlesboro near the Tennessee-Kentucky border— and constantly maintain their heart-ravishing burst for mile after mile of the entire journey all the way to Berea, the Folk Arts & Crafts Capital of Kentucky. Phenomenal views await at Cumberland Gap, Pine Mountain State Resort Park, and the Levi Jackson Wilderness State Park. Though you will want to pull over after every mile, you should not particularly miss the McHargues Mill located within the Levi Jackson Wilderness State Park. Also, a one-hour stop at the Kentucky Music Hall of Fame should be a must, especially if your love for country music runs deep and wide.
Home to the largest elk herd east of the Mississippi River, the Bluegrass State boasts other exciting features. Its landscape, for instance, is awesome and diverse, traveling the gamut from the knob-shaped hills in the west to the wave-like ridges and lush, cascading valleys in the east. Needless to say, it is this panoramic drama that often makes for a memorable road trip. To experience the best of Kentucky, one of the country's top three producers of hardwood, find a good playlist and place your car tires on the Lincoln Heritage Scenic Byway or, alternatively, the other six options we have highlighted—that we believe are the most scenic in Kentucky.