Remembering the Roamin’ Man of the Smokies

Gatlinburg’s Wiley Oakley was a self-described “Roamin’ Man.” He used the sobriquet in the titles of quaint books he wrote and published, along with his gifts in self-promotion, as a way to describe his passion for roving amidst steep ridges and deep hollows in his beloved Smokies. While undeniably a compulsive roamin’ man, Oakley was also a sportsman, natural historian, entrepreneur, and unofficial mountain ambassador. 

Ever larger than life, Oakley deserves considerable credit for putting Gatlinburg on the tourism map. Through a combination of far-reaching vision, personal charm, shrewd business sense, and sheer hard work, he figured prominently in turning a sleepy crossroads into a crowded tourist Mecca.

To visit Gatlinburg is to come in contact with this engaging mountain man’s imprint. Fittingly, one of the bustling town’s main roadways bears his name, and no single individual even approaches his historical contributions to this gateway to the Tennessee side of the Great Smoky Mountains National Park. 

Wiley’s lifelong love affair with his native heath found expression in many ways. Early in his career he guided hunters, fishermen, hikers, and naturalists to remote mountain fastnesses. That led to recognition of Gatlinburg’s tourism potential, and he soon founded a store which combined shrewd business sense with tireless promotion of mountain folkways. As the movement for a national park gained steam, leading proponents of its creation turned to him to showcase wonders he had known since boyhood. A genial, gregarious soul of the sort even fellow mountaineers fondly described as a “genuine character,” he was ideally suited for hyping the region’s grandeur.

Oakley was born on September 12, 1885, in Mount LeConte’s shadow, the son of Henry and Elmina Oakley and one of nine children. It was an era when mountain families tended to be quite large and, in due course, he would continue that tradition with his own bustling home filled with children. Wiley grew up close to—and never lost his love for—the land. His family eked out a hardscrabble livelihood through faming, hunting and fishing, supplemented by small but welcome infusions of cash his father earned by serving as Gatlinburg’s postman.

Wiley’s early years were difficult. He had little formal schooling but did acquire basic elements of reading and writing. His mother died when he was small. The two had been especially close, and the grieving boy “thought the pretty white clouds in the sky might be his mother’s flowing white robes.” Seeking solace, young Wiley began wandering rugged terrain near his home. Through exposure to raw nature and his father’s loving tutelage, he became a superb woodsman. That adolescent immersion in nature and mountain folkways would be a defining aspect of his entire life.

Absorbing lessons in woodcraft from his father and Cherokees—like parched ground soaking up a gentle rain—he developed the skills of an accomplished woodsman while simultaneously acquiring knowledge commonly dominated by mountain women. His expertise encompassed harvesting nature’s bounty for food, use of medicinal herbs, exceptional endurance, how to read weather signs, tracking expertise, cooking, and, most of all, survival in the wilds. Oneness with nature became the focal point of his life.

From his early teens onward, young Oakley assumed significant responsibilities in helping put food on the family table. In the forefront of his efforts were fishing for trout and hunting for bears, deer, wild turkey and small game. Those pursuits, performed in solitude, provided him ample time for reflection. Yet for all his love of being alone, he was no misanthrope. 

Exposed to the delights of oral tradition from his youngest years, Oakley absorbed mountain lore like a sponge. In time, he would develop remarkable abilities as a storyteller. Untold thousands of visitors thrilled to rocking-chair tales at his Gatlinburg store. Musically talented, he had a clear, true voice and would be part of one string band or another throughout adulthood. To walk Gatlinburg’s streets and hear the moving refrains of his favorite song, the grand gospel standard “I’ll Fly Away,” was to be within earshot of paradise.

In addition to musical abilities, Oakley possessed ample artistic skills. Among them were painting, wood carving, crafting a wide variety of useful implements, making children’s toys, and whittling whimsical “look-sees.” According to family legend, Wiley did the router work on wooden signs which originally marked the entrance to the Tennessee side of the Park, and he provided primitive yet fetching illustrations for his books. The cover art, featuring silhouettes of him as a mountain hunter, rifle in hand and hound at his side, is particularly impressive.

Oakley’s good-natured ways endeared him to everyone and helped convince locals that his vision of sharing and showcasing the mountains was viable. He believed doing so could provide a livelihood for him, his family, and his neighbors. Over time he garnered a national reputation as a hunting and fishing guide catering to affluent sportsmen. Clients welcomed the fact that Wiley’s guiding sessions involved far more than catching a mess of trout, shooting grouse, or killing a bear. Those who accompanied him found themselves fascinated participants in detailed lessons of practical natural history and enchanted listeners to well-told tales. Long before modern outfitters claimed they were breaking new ground with nature hikes, Wiley Oakley offered them with matchless knowledge and a uniqueness of character.

A cornpone philosopher of the first water, he dispensed mountain wit and wisdom with the sparkling brightness of a mountain stream. Oakley became so well known for his whimsy and commonsense wisdom that he traveled to big cities for storytelling sessions. One has to wonder whether those who underwrote such trips didn’t thing they were making money through using Oakley to promote hillbilly stereotypes reminiscent of those found in the writings of Horace Kephart and Margaret Morley. In truth, it’s probably more accurate to conclude that wily Wiley got the better of the deal.

Oakley guided entrepreneurs such as Henry Ford, journalists like the legendary Ernie Pyle, and when the official movement to create a national park gathered steam, hordes of politicians and scientists. The latter, with their doctoral degrees and ivory-tower mentality, were babes in the woods compared to Oakley. Mesmerized by his personality and astounding practical knowledge of flora and fauna, not to mention exhausted by the way he hiked mile after mile of rugged terrain, they soon recognized him as a local stupor mundi. He pointed out dozens of plants previously unknown to the botanical world, provided their colloquial names, and often described their practical uses.

Soon enough, Oakley became what one visitor described as a “national treasure.” His distinctive voice, redolent of Smokies twang and what is styled Appalachian English, was heard on radio stations across the country. Prior to beginning a tale, Wiley, a fine yodeler, warned his listeners how to discern if a given story might stretch the truth. “If I yodel at the end that’s a signal you don’t have to believe it unless you want to.” Most of his yarns required some enthusiastic yodeling. 

The majority of his tales involved either hunting or fishing, both pursuits lending themselves to considerable gilding of the lily. A typical story was an angling account of his battle with a “big ‘un.”

“One time I went out a-fishin’, and I caught a fish so big that I couldn’t hardly bring it in home, and it wallered me all over the river.” 

He then followed up with a spate of melodious yodeling before describing an experience with a flock of wild turkeys roosting on a limb. According to his account, he fired at the limb rather than one of the birds, splitting it open so that the legs of all the turkeys were caught in the limb. “I got the whole business but I had a time in climbing up the tree to get the turkeys out.” Clearly that particular story demanded especially expressive yodeling. It also attests to why Oakley earned widespread recognition as the “Will Rogers of the South.”

Scrimping and saving whenever he could, and working long hours as a guide and at other endeavors, Oakley eventually managed to buy land and build a home on Gatlinburg’s main street. The home doubled as a gift shop selling his handicrafts, gifts, and eventually, books. Customers loved him and found signs he hung in store windows, such as “Antiques Made to Order,” irresistible.

Sounds of live music often filtered from the store, and weekly during the tourist season a string band performed. There were also frequent impromptu pickin’ and grinnin’ sessions, something he enjoyed almost as much as roamin’. Even in his final years, in declining health because of a long battle with cancer, Oakley loved to listen to his talented son, Harvey, and others play. Inevitably, at some point, he would request the aforementioned “I’ll Fly Away.” Then the group would move seamlessly into other gospel classics such as “Life Is Like a Mountain Railway” and “Will the Circle Be Unbroken?”

During Oakley’s lifetime, Gatlinburg, thanks in no small measure to his tireless promotional efforts, made the transition from a backwoods village without sidewalks or paved streets to a thriving tourist destination. One has to wonder what Oakley would think of the crowded, bustling town as it exists today.

The grand old man of the Tennessee Smokies died on November 18, 1954, and was buried in White Oak Flats Cemetery. There a tombstone fashioned to look like logs from the side of a mountain cabin marks his final resting place. Noted Tennessee politician J. Percy Priest, a longtime friend, delivered the eulogy. He urged the assembled mourners to “raise in the hushed silence of the mountains a simple but rugged memorial to the memory of one who was and is the living spirit of the Great Smoky Mountains.” He praised Wiley’s “unhurried life” and the way in which it was reflected in the serenity of the hills, rock-ribbed and eternal, from which he drew his quiet strength.

Priest likened Wiley’s character to that of the “sturdy and stalwart pines crowning the wind-swept peaks” and reminisced about his “genuine sense of gratitude for the bounties, the blessings, and the teachings of nature and nature’s God.” Priest concluded that in the future whenever family, friends, or visitors to the mountains read his books or gazed on words “chiseled in bronze or marble” (a plaque honoring him was placed before the Gatlinburg Visitor Center on the drive bearing his name), they could take comfort in knowing that “somewhere nearby, roamin’, would be the immortal spirit of Wiley Oakley.”

It was a fine, fitting tribute. Sadly, today many seem unaware of the man except as a name, and have no knowledge of what he meant to Gatlinburg and east Tennessee. Decades have passed since the last performance of an outdoor drama in which one of the central characters was Wiley Oakley. Yet the land Wiley Oakley knew and loved so well is as it was—beautiful, ethereal, and eternal. Hopefully at least an occasional visitor, and even more so residents, pauses to ponder the contributions of this great man of the mountains. 

Nineteenth-century poet Sam Walter Foss once implored, “bring me men to match my mountains.” Wiley Oakley was such a man, a genuine force of nature marvelously matched with his beloved Smokies.