EVEN FOR THE LATE EIGHTEENTH century, David Crockett did not have a typical adolescence. His journey into manhood commenced in the autumn of 1799, when he set out with Cheek, again bound for the state of Virginia. This trip was intended as a cooling-off period to give the angry John Crockett time to calm down and forgive David’s trespasses, in particular his dropping out of school after less than a week of attending classes. David originally had no intention of being gone so long. Before he finally did come home, in the spring of 1802, John Crockett, unsure if his prodigal son was even still alive, had forgiven David.

The party left on a crisp fall morning. Jesse Cheek’s small band of drovers included one of David’s brothers as well as one of Cheek’s brothers. They took the well-used route east out of Tennessee into northern Virginia, with stops along the way at Abingdon, Lynchburg, and Charlottesville.1 After flanking the Blue Ridge Mountains, they passed through Chester Gap, obscured by hanging clouds of morning fog as thick as wood smoke. They then moved on to the heart of the Shenandoah Valley. Their final stop was Front Royal, chartered in 1788 and often called “Hell Town” due to the glut of strong drink and comely women readily available for rough mountaineers and travelers off the Shenandoah River.2 It is not known if David or any of his fellow drovers partook of either the liquor or the women, as randy cowhands were known to do seventy-five years later in the cattle towns of Kansas.

David had no plans to tarry long in the same country where his grandfather David Crockett and other family had once lived before crossing over the mountains to what became Tennessee. After Cheek sold the herd to a local buyer, David and the other Cheek brother started back home in advance of the others, including David’s brother. With but one horse available for their return trip, David and his traveling companion agreed that they would share the steed equally so one of them would not have to walk more than the other. It was a failed plan. After three days on the road, David found that the Cheek brother hardly ever gave up his perch on the saddle.3 Unwilling to continue with someone so contrary, the footsore Crockett felt he would be better off looking for alternative transportation and, with four dollars of pay in his pocket, struck out on his own.

Crockett purchased a few provisions and had resumed his journey back to Tennessee when he encountered Adam Myers, a teamster hauling a wagonload of goods. Myers, from Greene County, Tennessee, where David was born, seemed “a jolly good fellow.”4He proposed that Crockett reverse directions and go with him to his delivery destination in Gerrardstown, Virginia, now West Virginia, and then immediately return to Tennessee.

“On a little reflection, I determined to go back with him, which I did; and we journeyed on slowly as wagons commonly do, but merrily enough.” As the wagon slowly bumped down the road, Crockett concluded that he had made the right decision. “I often thought of home, and, indeed, wished bad enough to be there; but when I thought of the school-house and Kitchen, my master, and the race with my father, and the big hickory he carried, and of the fierceness of the storm of wrath that I had left him in, I was afraid to venture back; for I knew my father’s nature so well, that I was certain his anger would hang on him like a turkle [sic, turtle] does to a fisherman’s toe, and, if I went back in a hurry, he would give me the devil in three or four ways.”5

Just two days out on the eastbound trip, Crockett and Myers encountered the rest of the original Jesse Cheek drovers on their way home. The other Crockett son tried his best to talk David into going back to their family. Crockett’s brother “pressed him hard” and came up with several persuasive arguments, such as “the pleasure of meeting my mother, and my sisters, who all loved me dearly.”6 David came close to yielding and even shed tears, an uncharacteristic behavior for such an adventurous young man, but when the thought of that “promised whipping” came to mind, he finally “determined that make or break, hit or miss, I would just hang on to my journey, and go ahead with the waggoner.”

Crockett and Myers accordingly pressed on to Gerrardstown. After unloading the shipment, Myers tried to find some cargo to take back to Tennessee and learned that the closest goods available were to the southeast in Alexandria, near the new city of Washington. Crockett opted to stay in Gerrardstown and find temporary work until Myers returned with the back load.

Crockett hired on as a laborer with John Gray, a local farmer who in 1787 had helped lay out Gerrardstown with David Gerrard, whose father, John Gerrard, not only gave the village its name but also served as pastor of the first Baptist church west of the Blue Ridge Mountains. John Gray was Scottish to his fingertips, but he was willing to shell out twenty-five cents a day in wages to the young Scots-Irish hireling who plowed the grain fields as well as any man. “I continued working for him until the waggoner got back, and for a good time afterwards, as he continued to run his team back and forward, hauling to and from Baltimore.”7

In the spring of 1800, Crockett had put aside enough money to purchase some decent clothing and decided to take time off and sport his new wardrobe. Myers was bringing a wagonload of flour to Baltimore, so Crockett joined him and gave the teamster his remaining savings of about seven dollars to tuck away for safekeeping. The leisurely wagon ride from Virginia into Maryland was uneventful until they reached Ellicott’s Mills, just outside Baltimore. Founded by Quakers, this bustling town built on seven hills on the banks of the Patapsco River had one of the largest merchant mills in the nation—the place where Myers was to deliver the barrels of flour that filled his wagon.

“Here I got into the wagon for the purpose of changing my clothing, not thinking that I was in any danger; but while I was in there we were met by some wheel-barrow men, who were working on the road, and the horses took a scare and away they went, like they had seen a ghost,”8 Crockett later wrote. When the spooked horses bolted, the wagon tongue and both axletrees snapped, tossing Crockett and several heavy wooden barrels out in the road. David was shaken up but somehow avoided being “ground up fine as ginger.” He spoke of the incident years later in his autobiography as a member of Congress when he wrote, “[But] this proved to me, that if a fellow is born to be hung, he will never drown; and, further, that if he is born for a seat in Congress, even flour barrels can’t make a mash of him.”

His determination and body intact, Crockett helped Myers with the flour unloading, and the broken runaway wagon was hauled to a Baltimore shop for repairs. Over the couple of days they had to wait, Crockett sported his new clothes and explored the city, and that included going to the busy wharf to see the big sailing ships. The curious youngster stepped aboard one of the vessels, and the ship’s captain told him that he was in need of another crewman and inquired of Crockett if he would be interested in a voyage to London. Crockett jumped at the chance, and when he was asked about his parents, he explained that they lived hundreds of miles away in Tennessee and that he was on his own. Crockett admitted that by then “I had become pretty well weaned away from home, and I cared but little where I was, or where I went, or what become of me.”9

After reaching an agreement with the captain, Crockett hurried back to tell Myers and get both his clothes and the stash of money. Myers refused to give Crockett either and vowed that he would confine the young man and take him back to Tennessee. Unable to board the ship without his most precious belongings, David continued on with Myers. Over the next several days, as they traveled once again down the road, Myers kept a constant watch on the boy and several times threatened him with his wagon whip.10 At last, Crockett saw an opening and being “resolved to leave him at all hazards,” he managed to get his clothing and sneak away but “without a farthing of money to bear my expenses.”

As usual, Crockett’s luck held, and after going just a few miles, he came upon yet another teamster, “as resolute as a tiger.” They struck up a conversation, and when Crockett began crying and spoke of his plight and the treatment he had received, the new acquaintance became angry and pronounced Myers “a scoundrel, and many other hard names.”11 Coincidentally, this man was named Henry Myers, but he was from Pennsylvania, not related in any way to the Tennessee Myers. David and the man backtracked and found Adam Myers. “You damn’d rascal, you have treated this boy badly,” Henry Myers bellowed.12 The trembling Adam Meyers confessed that he had already spent David’s seven dollars and promised to pay it back to him when he got to Tennessee. That satisfied Crockett. He persuaded his champion to leave the other Meyers alone and they departed.

The new duo traveled together for several days. When they reached a point where they had to part ways, the older man took up a collection from some other “waggoners” at a roadhouse and handed Crockett three dollars to help tide him over until he found more work.13 That grubstake got Crockett as far Christiansburg, Virginia. The seat of government for Montgomery County, this town had been established in 1776 and named for William Christian, a famed Indian fighter and brother-in-law of Patrick Henry. When Crockett first came to town, the legend was already being told of Daniel Boone coming to the area for an extended visit and getting in trouble with the law for failing to pay a loan he took out to purchase supplies for his axemen blazing the Wilderness Trail.14

Shortly after arriving in Christiansburg, Crockett hired on for a month of hard farmwork with James Caldwell for one shilling a day. After that, he bounded himself to Elijah Griffith, a Christiansburg hatter.15 In exchange for his room and board and a chance to learn the hatter’s trade, Crockett agreed to work for Griffith for a four-year term of service. He joined the other journeymen and apprentices at the shop, hopeful that he may have found a trade that would earn him the decent living he yearned for. Hatmaking had become a viable business on the frontier, with wagonloads of hats leaving Virginia for Tennessee and returning with furs and pelts, maple syrup, feathers, and peach brandy.

Unfortunately for David, not every hatter succeeded. After only eighteen months of learning the trade, Crockett rose one morning to learn that he was once more out of work. His employer had become so far behind with his debts that he packed up in the middle of the night and left the country.16 Broke and without gainful employment, Crockett for a time hired on at John Snider’s Hattery Shop, which enabled him to pull together the money needed to return to Tennessee. Life on the open road had been a useful teacher, but home and hearth beckoned. In the late winter of 1802, Crockett “cut out for home.”17

He had barely started the journey when he faced the frigid crossing of the white-capped New River at the point where it connects with the Little River, ten miles south of Christiansburg.18 Try as he might, Crockett was not able to convince any of the ferryboat operators to take him across. They all told him that it was far too dangerous for anyone to attempt a crossing until the stormy weather abated and the winds died down. He eventually found someone who reluctantly agreed to lend him a canoe. Using rope to secure his bundle of clothes and belongings in the canoe, he pushed off into the choppy water.

“When I got out fairly on the river, I would have given the world, if it had belonged to me, to have been back on shore,”19 Crockett recalled of that treacherous crossing. “But there was no time to lose now, so I just determined to do the best I could, and the devil take the hindside.” After much struggle, he was able to turn the canoe into the swift waters and then paddled with all his might upstream for about two miles until the current carried him across. “When I struck land, my canoe was about half full of water, and I was as wet as a drowned rat. But I was so much rejoiced, that I scarcely felt the cold, though my clothes were frozen on me.”

Desperate to get warm, Crockett had to hike at least three miles before coming to a house where he could find comfort and dry his frozen clothing by the fire. The youngster also accepted a quaff of spirits, or, as he explained, “I took ‘a leetle of the creator [critter],’—that warmer of the cold, and cooler of the hot—and it made me feel so good that I concluded it was like the negro’s rabbit, ‘good any way.’”20 After the river crossing, Crockett proceeded home to Tennessee. While passing through Sullivan County, he was surprised to find his brother, who had gone with him so long before, at the start of the Cheek cattle drive. After a good visit and rest, Crockett left on the final leg of his journey.

He arrived at the Crockett Tavern late one evening. There were several wagons pulled up and what appeared to be a considerable company of guests inside. Instead of bursting through the door, David simply inquired if there was an empty bed for him. It was assumed that he was another paying guest, and he was told that he could stay the night. He found a place on a bench and spoke as little as possible. “I had been gone so long, and had grown so much, that the family did not at first know me,” Crockett wrote. “And another, and perhaps a stronger reason was, they had no thought or expectation of me, for they all long had given me up for lost.”21

At last everyone was called to supper. David joined the family and other guests at the long table. In only an instant the new tavern guest was identified. David’s sister Betsy had been staring at him ever since his arrival. Suddenly she sprang to her feet and ran to his side. The ecstatic girl seized David around the neck and exclaimed, “Here is my lost brother!”22 Almost thirty-four years later, when working with Thomas Chilton on the Narrative, Crockett had trouble describing his exact feelings at that moment.

“The joy of my sisters and my mother, and indeed of all the family, was such that it humbled me, and made me sorry that I hadn’t submitted to a hundred whippings, sooner than cause so much affliction as they had suffered on my account.” Crockett also noted, probably with a sly grin, that due to his increased age and enhanced size at the time of his homecoming, “together with the joy of my father, occasioned by my unexpected return,” there would not be any more dreaded whippings. He was right.

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