When a friend, knowing that I’m a history buff, suggested that I develop a list of Kentucky’s 10 most notable historic sites and ride my bicycle to visit them, I was more than ready to pack my saddlebag and begin pedaling. Narrowing a list of possible sites to 10 was no easy task. Dozens of places in Kentucky have histories that have impacted our state and nation in exceptional and significant ways.
At this point, I hope readers will take a minute to develop their own lists and then see how their 10 sites compare to the ones I settled on.
CUMBERLAND GAP
There’s no better place to start than at the beginning, and there’s nothing more directly associated with the beginning of Kentucky’s settlement and eventual statehood than the Cumberland Gap. My bike ride began at the Cumberland Gap National Historical Park, a mile south of Middlesboro on the borders of Kentucky, Tennessee and Virginia. The park and its 2,440-foot-high Pinnacle Overlook provide magnificent views of the seemingly endless wilderness that was 18th-century travelers’ first sight of Kentucky.
Why Selected as a Most Notable Historic Site? The Cumberland Gap is a natural 800-foot “notch” in the Appalachian Mountain range. From 1775 to 1810, 300,000 Irish, Scottish, German and English immigrants journeyed hundreds of miles from the East Coast. They could enter Kentucky only because they were able to pass through the Cumberland Gap. From here, they traveled northward over the Wilderness Road to carve out their homesteads and begin new lives as farmers, builders, craftsmen, shopkeepers, entrepreneurs and distillers.
This huge migration was the beginning of the Commonwealth. Kentucky became a state in 1792. By 1810, an amazing 10 percent of the nation’s entire population had passed through the Cumberland Gap. It’s safe to say that our Commonwealth would look vastly different today had the Cumberland Gap not made it possible for our ancestors to settle Kentucky.
Interesting Tidbit: More than half the population of central Kentucky can trace their family trees back to 18th-century European immigrants who passed through the Cumberland Gap to establish their homes in America.
PERRYVILLE CIVIL WAR BATTLEFIELD
The journey from the Cumberland Gap to the Boyle County town of Perryville and the Perryville Civil War Battlefield State Historic Site took me through the dense wilderness of the Daniel Boone National Forest and to places such as Baileys Switch, Mount Victory, Woodstock, Dog Walk, Crab Orchard and Stanford. Pedaling 12 miles per hour and with occasional stops, I soaked up the natural beauty and refreshing wonder of Kentucky’s rustic, wooded countryside. It was a long trip, so my bike and I were good and ready to reach the battlefield, located a couple of miles northwest of Perryville.
The 5-hour Battle of Perryville took place on Oct. 8, 1862. Involved were 22,000 Union and 16,000 Confederate soldiers, with 899 Union and 532 Confederate troops dying during the conflict. Thousands more were wounded.The Perryville Battlefield Historic Site maintains a digital database of more than 5,800 of the battle’s 7,607 combat casualties.
Why Selected: The Battle of Perryville, the largest and bloodiest Civil War battle fought in Kentucky, was instrumental in determining the Civil War’s outcome. A year before, President Abraham Lincoln had written to his generals: “We must win Kentucky. If Kentucky goes, so will Missouri and Maryland. All will be lost.” After the battle, the Confederate Army retreated to Tennessee, enabling Union forces to retain control of Kentucky and go on to win the war.
Every October, a re-enactment is carried out featuring authentic weaponry, clothing and campsites; and there are demonstrations of infantry, artillery and cavalry. As many as 3,800 re-enactors commemorate the battle on what is widely considered to be one of the best-preserved battlefields of the Civil War.
Interesting Tidbit: Two hundred-fifty horses were involved in the Battle of Perryville, mostly used to pull supply wagons and cannons. Horses were targeted and many were killed because both sides realized how essential they were to the war’s logistics.
SHAKER VILLAGE OF PLEASANT HILL
Northeast of Harrodsburg is the picturesque Shaker Village of Pleasant Hill. This one-time religious community—a part of the United Society of Believers in Christ’s Second Appearance—was active from 1805 to 1910, claiming at its peak more than 500 members, 5,000 acres of land and 25 miles of stone fences. It was one of 20 Shaker communities in the United States. Following its decline and abandonment, a preservationist effort was begun in 1961. As a result, Shaker Village has become a popular tourist and conference destination with overnight lodging in original Shaker buildings, a first-class dining venue, a conference center and 37 miles of scenic trails for hikers, horseback riders and cyclists.
Why Selected: Shaker Village was the largest and longest-lasting religious communal society in American history. According to Aaron Genton, Shaker Village’s collections manager, the 34 buildings of Shaker Village constitute the largest private collection of 19th-century structures in the country.
Most people know about the Shakers’ unique worship practice, a merging of spirit and body that manifested itself through physical activity, such as dancing and, at its most enthusiastic, vigorous shaking. Genton told me that the Shakers created these motions as spiritual exercises to help them humble themselves before God and to underscore their belief that all members of the community were spiritual equals. This, in turn, gave rise to other Shaker beliefs that were progressive for their time, such as their outspoken advocacy for gender and racial equality.
Interesting Tidbit: Unlike the Mennonites and Amish with whom they are sometimes confused, the Shakers were technologically advanced and were early adopters of new techniques and tools. They practiced selective livestock breeding and scientific agriculture, and were the first to create a municipal water system, develop a powered grain elevator, install water pumps in their kitchens, and invent a horse-powered washing machine.
OLD OSCAR PEPPER DISTILLERY
It’s a challenging but truly awesome 35-mile bike ride from Pleasant Hill to the Old Oscar Pepper Distillery—now Woodford Reserve—located off U.S. 60 between Versailles and I-64. Given that there are more barrels of aging bourbon in storage in Kentucky (7.5 million) than there are residents (4.5 million), a distillery needed to be on my list of historic sites.
Why Selected: There’s a long history of bourbon-making on the Woodford Reserve site that goes back to 1812, when Elijah and Sarah Pepper selected a 350-acre tract alongside Glenn’s Creek and began farming and distilling. The first distillery building that was erected in 1838 as well as the log homestead of the Pepper family still stand.
The distillery grew under three generations of the Pepper family. The expertise of Scotsman James Crow, master distiller under Oscar Pepper from 1833-1855, is credited for bringing revolutionary scientific methods, such as sour-mash fermentation, to bourbon-making processes. In 1872, the Pepper family sold the business. Following Prohibition, during which warehouses were emptied and sealed (1920-34), the Brown-Forman Corporation resumed production at the site and, in 1996, created a new distillery as well as a tourism destination.
Interesting Tidbit: According to Katie Farley, Woodford Reserve’s media manager, the distillery “uses the same iron-free, limestone-filtered water that Elijah Pepper drew from Glenn’s Creek in 1812.” Woodford Reserve does not use water directly from the creek, of course, but instead pumps water from five underground springs 95 feet below the surface before they feed into Glenn’s Creek. When I asked if this supply of water will ever run out, Farley replied that “the original Pepper Spring has been ample and healthy for more than 200 years. We do not anticipate it ever running dry.”
CAVE HILL CEMETERY
The next stop was Cave Hill Cemetery, a national cemetery spread over 296 acres of picturesque rolling hills in the middle of Louisville. Cave Hill is known for its exquisite works of monumental art that mark the gravesites of 136,000 Kentuckians.
Following a morning walk through Cave Hill (bicycles are not permitted on the cemetery’s 16 miles of roadways), I readily agreed when Cave Hill President Gwen Mooney described the cemetery as “an outdoor museum, a historical treasure, a scenic retreat and a peaceful final resting place” for the more than 600 who are interred there every year.
Why Selected: Moving from one gravesite to the next at Cave Hill is like taking a stroll through our state’s history. Visitors are able to view the burial sites of Muhammad Ali, Colonel Harland Sanders, George Rogers Clark, and Mildred and Patty Hill (composers of the song “Happy Birthday”), Civil War soldiers from both sides, and others who made lasting contributions to our state’s history and culture. The interment of Ali in 2016 turned Cave Hill into one of Louisville’s most popular tourist sites.
Established in 1848, Cave Hill brought the concept of rural, garden-style cemetery landscape architecture to Kentucky. The property originally was a farm with a cave that ran 246 feet into a hillside, located at the far east end of Broadway Street, away from the bustle of city life. In the mid-19th century, prior to the era of large municipal parks, it was common for large cities to promote a cemetery as a green oasis and pastime destination. People would go to stroll, picnic and meditate. Recognizing the trend, the city of Louisville hired a landscape engineer to design a cemetery with winding pathways, trees and shrubs, waterfowl, tranquil vistas and spring-fed lakes, all peacefully located among the farm’s rolling hills. This became Cave Hill.
Interesting Tidbit: In addition to being a burial ground, Cave Hill is a magnificent arboretum with more than 600 species of trees and shrubs, including 20 trees that are the largest of their kind in Kentucky. Cave Hill employs a horticulturist, two arborists and a maintenance staff of 50 who care for the grounds.
CHURCHILL DOWNS
Nothing matches being in a crowd of 160,000-plus people screaming like crazy as 20 of the world’s best 3-year-old Thoroughbred racehorses charge down the homestretch in the Kentucky Derby at Churchill Downs racecourse in south Louisville. I can’t speak for the horses, but there’s nothing in the human experience that’s comparable!
Why Selected: Churchill Downs has hosted the Kentucky Derby, the Commonwealth’s most iconic sporting event and the world’s most famous race for 3-year old Thoroughbreds, since its first running in 1875. That makes the Kentucky Derby at Churchill Downs the longest continually run major sporting event in America.
Horse racing in Kentucky dates back to the late 1700s. The founding of Churchill Downs began in 1872, when Col. Meriwether Lewis Clark Jr. traveled to England, where he attended the Epsom Derby. This sparked Clark’s dream of creating a comparable horse-racing spectacle in America.
Upon his return to Louisville, Clark developed a racetrack that became known as Churchill Downs because it was constructed on land that Clark leased from his uncles, John and Henry Churchill. A crowd of 10,000 was present for Churchill Downs’ opening day on May 17, 1875. The famous twin spires grandstand was constructed in 1895, when the tradition of adorning the Derby winner with a garland of roses also began.
Interesting Tidbit: In the early 1900s, the Kentucky State Fair was held at Churchill Downs. During those years, the fair featured the popular but odd spectacle of two locomotives being intentionally crashed head-on in the infield.
MY OLD KENTUCKY HOME
Visiting Bardstown and My Old Kentucky Home is always a delightful experience. The town’s residents are history-aware and hospitable. More importantly, there’s a lot to see in this town of 13,000. Nothing generates as much nostalgia as touring the antebellum My Old Kentucky Home mansion and the gorgeous gardens surrounding it.
Why Selected: My Old Kentucky Home, for generations, has held a special place in the hearts of Kentuckians and is one of the most iconic 19th-century homes in the country. It also inspired Stephen Foster’s song “My Old Kentucky Home,” an important musical composition in American history due to its influence on the 19th-century abolitionist movement.
The original structure that would become a mansion in 1818 was built in 1798 on a 1,200-acre plantation named Federal Hill and owned by U.S. Sen. John Rowan and his wife, Ann Lytle. The Commonwealth of Kentucky purchased Federal Hill from the Rowan family in 1923 and renamed it My Old Kentucky Home. When the Rowans owned Federal Hill, it was the center of Kentucky’s political, cultural and social life.
Interesting Tidbit: During his time as owner of the Federal Hill mansion, John Rowan killed Bardstown’s town doctor in a duel. Rowan was absolved of any wrongdoing when it was determined that all rules of dueling had been followed. This, however, led the Kentucky legislature to pass a law that is still upheld today and requires state officials, attorneys, public notaries and school board members to promise in their oaths that they have never fought in a duel.
ABBEY OF GETHSEMANI
After enjoying lunch at Bardstown’s iconic 18th-century Talbott Tavern, I headed south to the Abbey of Our Lady of Gethsemani. While pedaling the 12 picturesque miles through wooded, gently rolling countryside, I found myself wondering what a delegation of French monks might have been thinking back in 1848 when, guided by Louisville Bishop Benedict Joseph Flaget, they made this same trip to explore a location for their new outpost in America. They decided to settle on a tract of land that had been named Gethsemani by the Sisters of Loretto, from whom it was purchased.
Why Selected: A Trappist monastery, Gethsemani is the oldest continuously operating monastery in the U.S. For 170 years, the monks there have exemplified religious devotion. World-renowned monk, theologian and writer Thomas Merton resided there from 1941 until his death in 1968.
Forty monks live at Gethsemani, ranging in age from 33 to 95. They lead disciplined lives of prayer, meditation, sacred reading and work. In addition to worship and contemplation, every able-bodied monk has a job. Some tend the monastery’s large vegetable garden and greenhouse, three prepare the monks’ meals, a few oversee the monastery’s Retreat House program that hosts 5,000 guests each year, others administer the operations, and many are involved in producing the monastery’s popular fudge and fruitcake. Last year, the monks sold 90,000 pounds of fruitcake and 60,000 pounds of fudge.
Monastic life is intentionally lived as separate from the world. Monks are not permitted to leave Gethsemani, even for a short time, without the Abbot’s permission. One monk has not been away in 55 years. When I asked if monks believe that their life at Gethsemani makes the world a better place, Brother Paul Quenon told me, “Yes, by faith, we do. We’re like healthy trees. We purify the air by being what we are. Gethsemani witnesses to another way of being in the world, to show there are choices that can be made in the interest of deeper values.”
Interesting Tidbit: Monks at Gethsemani are allowed to talk during the day but observe silence at meals and in their rooms. I don’t know if this means that they can’t talk to themselves! The day begins when the “rising bell” is rung at 3 a.m., and monks gather to sing the Office of Vigils with psalms and readings. Each day ends with evening prayers. Monks are in bed by 8 p.m. There are no TVs, radios or personal phones at the monastery, but monks can write and receive letters and have access to newspapers and a 40,000-book library.
LINCOLN BIRTHPLACE
My next stop was the Abraham Lincoln Birthplace National Historical Park outside Hodgenville in LaRue County. The park is located on the site where the Lincoln family lived and President Lincoln was born in 1809. The centerpiece of this historic site is a stately granite-and-marble memorial that contains a replica of the one-room log cabin in which Lincoln was born. The memorial is the most impressive structure of its kind in Kentucky. It would be difficult to climb the 56 steps leading to it (one step for each year of Lincoln’s life) without feeling a sense of awe, gratitude and pride.
Why Selected: The memorial celebrates the life and legacy of Kentucky’s most famous son and America’s most highly regarded president. Dedicated in 1911, it was the nation’s first memorial to honor Lincoln. It was paid for by contributions from 100,000 private donors, many of whom were schoolchildren whose average gift was 31 cents.
In late 1808, Thomas and a pregnant Nancy Hanks Lincoln moved from nearby Elizabethtown to a farm south of Hodgenville. Like most families who settled on the Kentucky frontier in the early 1800s, the Lincolns didn’t have much money. But according to Park Ranger Natalie Barber, “they weren’t considered poor because it was mostly a cashless economy and the Lincolns built self-sufficient lives around the area’s natural resources.” They used chestnut trees to build and heat their home, cleared land to raise vegetables, hunted game, and made their own furniture and clothes. A nearby spring provided an ample supply of fresh water.
Interesting Tidbit: Two months after moving to their farm, the Lincolns welcomed their second child. They named him Abraham, after his grandfather. Years later, Nancy Lincoln’s cousin, Dennis Hanks, recalled learning that “the Lincolns had a baby at thur house, so I jest run all the way over. I rickolect when I held the little feller in my arms his mother said, ‘Be keerful with him, Dennis.’ I sort o’ swung him back and forth; a little to peart, I reckon, fur with the talkin’ and the shakin’ he soon begun to cry and then I handed him over to Auntie who was standin’ close by. ‘Auntie,’ sez I, ‘he’ll never come to much,’ fur I’ll tell you he wuz the puniest, cryin’est little youngster I ever saw.”
MAMMOTH CAVE
Biking south from Hodgenville to Cave City took me past my “most favorite in all the world” general store—the Amish-owned R&S Grocery and Bakery on Ky. 31W between Munfordville and Horse Cave—and into the gorgeous, densely forested Mammoth Cave National Park, the final stop on my trip.
Why Selected: With 405 miles of mapped caves, vast chambers and subterranean passageways, Mammoth Cave is by far the world’s longest known cave system. New parts are still being discovered, and there seems to be no end in sight! It’s also a UNESCO World Heritage Site and a Biosphere Reserve.
When I asked park guides how Mammoth Cave was formed, they told me that an ancient sea covered the center of our continent around 325 million years ago. This created a 600-foot crust of soluble limestone, which was then covered by a sandstone-and-shale cap that was deposited by an ancient river. Eventually, the sea and river disappeared, and natural forces eroded the cap until about 10 million years ago, when cracks and holes began to expose the limestone. Rainwater worked its way underground and hollowed out the cave as we know it today. During the next 10 million years, natural forces will continue to shape Mammoth Cave, which will eventually erode, collapse and break down into a series of canyons.
Interesting Tidbit: Mammoth Cave National Park is one of our nation’s oldest and most popular tourist attractions. Last year, more than 2 million guests visited the park, and 587,853 of them took one of the cave’s guided tours. According to Dave Wyrick, Mammoth Cave chief of interpretation, guided tours have been offered for more than 200 years. Stephen Bishop, an enslaved African American, was the cave’s first tour guide back in 1816.
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After enjoying a Kentucky Hot Brown at Mammoth Cave’s Green River Grill, I began to pedal for home. I was feeling fortunate that I was able to visit 10 amazing places of historic significance that have helped shaped our Commonwealth and nation. These sites are different from one another, but all have a lot to teach us. There is so much more to know about these remarkable locales than the few words I’ve written are able to express. Each is wonderfully staffed and maintained, provides an up-to-date website, offers dining or picnic facilities, and operates an information center, museum and gift shop. Plus, they are located in Kentucky’s most picturesque places. Be sure to visit them. You will learn a lot about Kentucky.