Robertson first came to the Watauga early in 1770.[17] He had then been married for two years, and had been “learning his letters and to spell” from his well-educated wife; for he belonged to a backwoods family, even poorer than the average, and he had not so much as received the rudimentary education that could be acquired at an “old-field” school.  But he was a man of remarkable natural powers, above the medium height,[18] with wiry, robust form, light-blue eyes, fair complexion, and dark hair; his somewhat sombre face had in it a look of self-contained strength that made it impressive; and his taciturn, quiet, masterful way of dealing with men and affairs, together with his singular mixture of cool caution and most adventurous daring, gave him an immediate hold even upon such lawless spirits as those of the border.  He was a mighty hunter; but, unlike Boon, hunting and exploration were to him secondary affairs, and he came to examine the lands with the eye of a pioneer settler.  He intended to have a home where he could bring up his family, and, if possible, he wished to find rich lands, with good springs, whereto he might lead those of his neighbors who, like himself, eagerly desired to rise in the world, and to provide for the well-being of their children.

To find such a country Robertson, then dwelling in North Carolina, decided to go across the mountains.  He started off alone on his exploring expedition, rifle in hand, and a good horse under him.  He crossed the ranges that continue northward the Great Smokies, and spent the summer in the beautiful hill country where the springs of the western waters flowed from the ground.  He had never seen so lovely a land.  The high valleys, through which the currents ran, were hemmed in by towering mountain walls, with cloud-capped peaks.  The fertile loam forming the bottoms was densely covered with the growth of the primaeval forest, broken here and there by glade-like openings, where herds of game grazed on the tall, thick grass.

Robertson was well treated by the few settlers, and stayed long enough to raise a crop of corn, the stand-by of the backwoods pioneer; like every other hunter, explorer, Indian fighter, and wilderness wanderer, he lived on the game he shot, and the small quantity of maize he was able to carry with him.[19] In the late fall, however, when recrossing the mountain on his way home through the trackless forests, both game and corn failed him.  He lost his way, was forced to abandon his horse among impassable precipices, and finally found his rifle useless owing to the powder having become soaked.  For fourteen days he lived almost wholly on nuts and wild berries, and was on the point of death from starvation, when he met two hunters on horseback, who fed him and let him ride their horses by turns, and brought him safely to his home.