Kentucky Road Trip: Bluegrass to Pennyroyal

Trod by Daniel Boone in the 1700s, central Kentucky evolved from raw wilderness to a land of gentility, where local folk became wealthy by raising thoroughbred horses and producing fine whiskey.

Keeneland Race Course
Get a look behind the scenes at the exciting pounding hooves of racehorses at Keeneland Race Course, near Lexington.

Route Details
Length: About 270 miles, plus side trips.

When to go: Popular year-round.

Ferries: At the Green River in Mammoth Cave National Park, two ferries run on a regular basis.

Not to be missed: The Stephen Foster Story (a musical biography performed outdoors), Bardstown.

Nearby attractions: Mary Todd Lincoln House, Lexington. Fort Boonesborough State Park, southeast of Lexington. Land Between the Lakes Recreation Area, west of Hopkinsville.

Visitor center: Mammoth Cave National Park, near Cave City, KY.

Further information: Kentucky Department of Travel, 500 Mero Street, 22nd Floor, Frankfort, KY 40601; tel. 502-564-4930,

Trod by Daniel Boone in the 1700s, central Kentucky evolved from raw wilderness to a land of gentility, where local folk became wealthy by raising thoroughbred horses and producing fine whiskey. Indeed, Kentucky was virtually made for these two treasures: its ancient beds of limestone enrich the native bluegrass (making the bones of the horses that graze on it especially strong) and sweeten the waters of the pristine streams used to produce prized Kentucky bourbon.

1. Lexington
This gracious city is bedecked with such antebellum gems as Ashland, a Federal-style mansion built by statesman Henry Clay, and the Hunt-Morgan House, dating from the early 1800s. But the main delight here is the countryside, where the fastest thoroughbreds and standardbreds in America graze on meadows of bluegrass behind white wooden fences. For a firsthand look at the business of horses, stop at Keeneland Race Course, a traditional track complete with shade trees and grandstand. Or spend an afternoon at Kentucky Horse Park, where displays on 1,200 sprawling acres celebrate the noble equus.

Head out of town on Rte. 68, a charming road edged with ancient stone walls, gabled horse barns (some as fancy as French chateaus), and seemingly endless fields of burley tobacco. The road crosses the Kentucky River Gorge, where the river flows between palisades of white limestone. Farther along, the route passes through lush, rolling farmland punctuated by stands of walnuts and oaks.

2. Shaker Village of Pleasant Hill
The plain yellow and white buildings of Shaker Village (also known as Shakertown) are set on verdant, oak-studded hills in the little town of Pleasant Hill. This was once home to some 500 Shakers, a 19th-century religious order and community known for its agricultural skills, ritualistic dancing, and dedication to a simple life apart from the bustle of the world. Though the Shakers are long gone (the last died in 1923), their spirit lives on at this former home — now a museum complete with crafts demonstrations, guides in Shaker dress, and such examples of their handiwork as flat brooms and wooden clothespins (original Shaker inventions). Visitors are welcome to spend the night in one of the old communal buildings, where the clean, bright rooms are sparsely decorated with handwoven rugs and simple wooden furniture.

3. Harrodsburg
Virgin forests and abundant game lured James Harrod to this area in 1774. Here, some 250 miles from the nearest town, he built the first permanent white settlement west of the Alleghenies. The original fort is gone, but a replica with two-story blockhouses and dirt floors conveys a vivid sense of frontier housing. In summer people in pioneer-style costumes (women wear gathered skirts and white pin-on aprons) demonstrate such frontier crafts as rug weaving, blacksmithing, and broom making. Next to the fort, the fieldstone markers of the original graveyard are scattered in a grove of trees.

To view another side of Harrodsburg, visit the venerable Beaumont Inn (originally built as a finishing school for girls). Here, amid flowered carpets, antique furniture, and curtains of Brussels lace, you can sample such local culinary delights as hickory-smoked country ham, spoon bread, and General Robert E. Lee orange-lemon cake.

4. Danville
In Danville, a short jaunt down Rte. 127, you’ll find the state’s first college, first log post office, and first law school — hence the sobriquet City of Firsts. West of town Kentucky’s bloodiest battle in the entire Civil War unfolded on a hot autumn day in 1862, when thirsty Confederate troops came across Union soldiers who were guarding a nearly dry creek. Cannonfire and screams filled the air as 40,000 men played out a gory battle that, when the smoke cleared, left some 7,500 dead and marked a fatal loss of initiative for the South. A trail winds across the battlefield (now a serene parkland), and a museum showcases rifles, cannons, musket balls, uniforms, canteens, and other Civil War memorabilia.

5. Springfield
The drive rolls west on Rte. 150, past fields of hay and corn and farmhouse gardens overflowing with lilies, and jogs into the handsome village of Springfield. Southwest of Springfield, a scenic detour via Rtes. 152 and 49 passes through picturesque fields to the village of Loretto. Here a cluster of rustic red-shuttered buildings perched along the banks of a stream comprise the family-run Maker’s Mark Distillery. For nearly two centuries it has made some of the finest, smoothest bourbon in the world. Inside the stillhouse, where the pungent smell of sour mash fills the air, you can dip your finger into the cypress vat and taste the bubbling brew, then watch as the copper still transforms the mix into bourbon. Local law forbids sampling the finished product, though other tippling opportunities abound at the many inns that line the streets of Bardstown, the next stop on the drive, located in a nearby “wet” county.

6. Bardstown
Visiting Bardstown on a tour of the Western Frontier in 1797, the French king Louis Philippe found a city replete with elegant homes, posh inns, and reputable learning institutions — a description that still rings true. In 1852, composer Stephen Foster vacationed with his relatives at Federal Hill, a gracious plantation house that inspired him to write the ballad “My Old Kentucky Home.” Today visitors are guided by women in hoop skirts who call attention to priceless heirlooms, rare old portraits — and the patriotism of Foster’s uncle. The mansion’s ceilings are 13 feet high, its brick walls are 13 inches thick, and each flight of stairs has 13 steps — all in zealous tribute to the numerical count of America’s original states.

Before heading south on Rte. 31E, explore the charming downtown district, where you’ll find weathered brick houses on tree-shaded streets, the first cathedral built west of the Alleghenies (it was dedicated in 1819), and the Oscar Getz Museum of Whiskey History.

7. Hodgenville
Rte. 31E meanders through deep woods and past the boyhood home of Abraham Lincoln: a reconstructed log cabin beside rippling Knob Creek marks the site. A few miles farther the drive enters the town of Hodgenville, a virtual theme park celebrating Lincoln. A bronze statue overlooks the town square; the Lincoln Museum is brimming with exhibits and memorabilia; and on Saturdays a “Lincoln Jamboree” is held. South of town, at the Abraham Lincoln Birthplace National Historic Site, you can visit the temple-like monument of granite and pink marble that enshrines the crumbling log cabin in which the great president is said to have been born in 1809.

8. Crystal Onyx Cave
Rambling south on Rte. 31E, the drive enters the region called the Pennyroyal — named for an herb but renowned as the locale of some of the world’s most amazing caves. Beyond tourist-oriented Cave City, which is full of flashing neon signs, two stops in particular are worth your while: Crystal Onyx Cave, a labyrinth of rare onyx columns; and Horse Cave (also known as Hidden River Cave) in the city of Horse Cave. John Muir noted that in hot weather “the cold air that issues from its fern-clad lips” could cool everyone in town.

9. Mammoth Cave National Park
Follow signs to the East Entrance of Mammoth Cave National Park, where some 4,000 years ago woodland Indians discovered the fern-draped mouth of Mammoth Cave, whose
ceilings sparkle with delicate white gypsum crystals. What must have amazed the Indians was the cavern’s sheer enormity: large rooms and wide corridors go on underground for miles and miles.

Little did these Indians know that they were the first to explore one of the most extensive cave systems in the world. (Its charted passages meander more than 350 miles in darkness beneath the hills, and countless others remain unexplored.) Sometime around the birth of Christ, the Indians abandoned Mammoth Cave, and it fell into obscurity until 1797. Then, according to legend, a hunter tracking a wounded bear he had shot stumbled across the opening. After this serendipitous discovery, stories spread around the globe about the natural caverns, and soon its corridors were filled with curious visitors. Weddings and balls were held in the cave’s enormous rooms.

Today a variety of tours are offered by the National Park Service ranging from a quarter-mile stroll to a five-mile belly-crawling, body-squeezing trek (a warm coat is recommended for the former, and kneepads are required for the latter). One tour includes a stop at the Snowball Room, where the ceiling dazzles with frostlike nodules of gypsum.

An assortment of creatures have over the millennia adapted to the cave’s environment. Colorless, eyeless fish and blind crayfish haunt the waters of Echo River. Other creatures include spiders, beetles, and cave crickets. The cave is constantly expanding in size as its water dissolves the stone and carves the caverns ever deeper down into the earth.

10. Duncan Hines Scenic Byway
Continuing through Mammoth Cave National Park, the drive hops across the Green River by ferry, entering an area of wild backcountry. Sunlight filters to the forest floor through a thick canopy of maples, beeches, sycamores, oaks, and hickories, and the forest is filled with chirping songbirds. Here the seasons are exquisitely portrayed, beginning in spring and summer with a colorful procession of blooming dogwoods, redbud trees, and wildflowers. In the fall blazing reds and golds ignite the foliage. But only in winter, when the ground is barren and all the leaves are gone, can you see the craggy layers of limestone — along with all their sinkholes, streams, and fissures oozing with icy water.

Continuing north out of Mammoth Cave National Park, the drive follows the well-marked Duncan Hines Scenic Byway past lofty ridges, deep valleys, and outcroppings. At the southern tip of Nolin River Lake, the byway veers north to Bee Spring, then west and south through such charmingly named villages as Sunfish, Sweeden, and Windyville. As you continue along this series of country lanes, follow the byway signs all the way into the town of Bowling Green.

11. Bowling Green
George and Robert Moore, two brothers, donated land to found this town on a bend in the Barren River in 1798. According to lore, it was named in honor of Bowling Green Square in New York City. Today Bowling Green is a blend of the old and the new, from the elegant 1872 Italianate home known as River View at Hobson Grove, to the recently founded National Corvette Museum, a tribute to the American sports car, manufactured here in Bowling Green by General Motors. The museum features classic Corvettes spanning the years since 1953, when the first model rolled off the assembly line.

12. Jefferson Davis Monument
The drive follows Rte. 68 through the town of Russellville, whose collection of historic edifices includes the old Southern Bank Building, robbed by outlaw Jesse James in 1868. A few miles farther, a tall white obelisk — bearing a remarkable resemblance to the Washington Monument in the nation’s capital — towers 351 feet above the surrounding farmland. Located in the little town of Fairview, the structure signals local sympathy for Jefferson Davis, first and only president of the Confederate States of America, who was born here in 1808 and stayed loyal to the Southern cause all his life. An elevator to the top of the monument takes you to a sweeping vista of barns, silos, and farmhouses scattered across an appealing patchwork of fertile fields.

Farther along on Rte. 68, the road enters the old-time world of the Amish (watch for their horse-drawn carriages), where roadside stands offer freshly harvested beans, peaches, tomatoes, and corn.

13. Hopkinsville
One of Kentucky’s larger cities, with a population of some 30,000, Hopkinsville has long been a leading market for tobacco. In recent years factories have thrived here as well, producing everything from truck frames, textiles, and flour to springs and bowling balls. In its distant past Hopkinsville was a stop on the infamous Trail of Tears. Cherokee Indians who did not survive the grueling trek are memorialized at the Trail of Tears Commemorative Park.

For a look at more of the town’s past, stop by the Pennyroyal Area Museum on East Ninth Street. Its exhibits (including Edgar Cayce, known even after death as one of the world’s greatest psychics; Indian lore; Civil War mementos; pioneer furnishings; and old farm tools) seem to be borrowings from the most intriguing attics in southwestern Kentucky.

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