Happily, his academic course was not long interrupted by this migration, for Canandaigua Academy, which offered unusual advantages, was within easy reach from his new home. Under the wise instruction of Professor Henry Howe, he began the study of Latin and Greek; and by his own account made "considerable improvement," though there is little evidence in his later life of any acquaintance with the classics. He took an active part in the doings of the literary societies of the academy, distinguishing himself by his readiness in debate. His Democratic proclivities were still strong; and he became an ardent defender of Democracy against the rising tide of Anti-Masonry, which was threatening to sweep New York from its political moorings. Tradition says that young Douglass mingled much with local politicians, learning not a little about the arts and devices by which the Albany Regency controlled the Democratic organization in the State. In this school of practical politics he was beyond a peradventure an apt pupil.

A characteristic story is told of Douglass during these school days at Canandaigua.[[15]] A youngster who occupied a particularly desirable seat at table had been ousted by another lad, who claimed a better right to the place. Some one suggested that the claimants should have the case argued by counsel before a board of arbitration. The dispossessed boy lost his case, because of the superior skill with which Douglass presented the claims of his client. "It was the first assertion of the doctrine of squatter sovereignty," said the defeated claimant, recalling the incident years afterward, when both he and Douglas were in politics.

Douglass was now maturing rapidly. His ideals were clearer; his native tastes more pronounced. It is not improbable that already he looked forward to politics as a career. At all events he took the proximate step toward that goal by beginning the study of law in the office of local attorneys, at the same time continuing his studies begun in the academy. What marked him off from his comrades even at this period was his lively acquisitiveness. He seemed to learn quite as much by indirection as by persevering application to books.[[16]]

In the spring of 1833, the same unrest that sent the first Douglass across the sea to the new world, seized the young man. Against the remonstrances of his mother and his relatives, he started for the great West which then spelled opportunity to so many young men. He was only twenty years old, and he had not yet finished his academic course; but with the impatience of ambition he was reluctant to spend four more years in study before he could gain admission to the bar. In the newer States of the West conditions were easier. Moreover, he was no longer willing to be a burden to his mother, whose resources were limited. And so, with purposes only half formed and with only enough money for his immediate needs, he began, not so much a journey, as a drift in a westerly direction, for he had no particular destination in view.[[17]]

After a short stay in Buffalo and a visit to Niagara Falls and the battle ground of Chippewa, the boy took a steamboat to Cleveland, where happily he found a friend in Sherlock J. Andrews, Esquire, a successful attorney and a man of kindly impulses. Finding the city attractive and the requirements for the Ohio bar less rigorous, Douglass determined to drop anchor in this pleasant port. Mr. Andrews encouraged him in this purpose, offering the use of his office and law library. In a single year Douglass hoped to gain admission to the bar. With characteristic energy, he began his studies. Fate ruled, however, that his career should not be linked with the Western Reserve. Within a few days he was prostrated by that foe which then lurked in the marshes and lowlands of the West—foe more dreaded than the redman—malarial typhoid. For four weary months he kept his bed, hovering between life and death, until the heat of summer was spent and the first frosts of October came to revive him. Urgent appeals now came to him to return home; but pride kept him from yielding. After paying all his bills, he still had forty dollars left. He resolved to push on farther into the interior.[[18]]

He was far from well when he took the canal boat from Cleveland to Portsmouth on the Ohio river; but he was now in a reckless and adventurous mood. He would test his luck by pressing on to Cincinnati. He had no well-defined purpose: he was in a listless mood, which was no doubt partly the result of physical exhaustion. From Cincinnati he drifted on to Louisville, and then to St. Louis. His small funds were now almost all spent. He must soon find occupation or starve. His first endeavor was to find a law office where he could earn enough by copying and other work to pay his expenses while he continued his law studies. No such opening fell in his way and he had no letters of introduction here to smooth his path. He was now convinced that he must seek some small country town. Hearing that Jacksonville, Illinois, was a thriving settlement, he resolved to try his luck in this quarter. With much the same desperation with which a gambler plays his last stake, he took passage on a river boat up the Illinois, and set foot upon the soil of the great prairie State.[[19]]

A primitive stage coach plied between the river and Jacksonville. Too fatigued to walk the intervening distance, Douglass mounted the lumbering vehicle and ruefully paid his fare. From this point of vantage he took in the prairie landscape. Morgan County was then but sparsely populated. Timber fringed the creeks and the river bottoms, while the prairie grass grew rank over soil of unsuspected fertility. Most dwellings were rude structures made of rough-hewn logs and designed as makeshifts. Wildcats and wolves prowled through the timber lands in winter, and game of all sorts abounded.[[20]] As the stage swung lazily along, the lad had ample time to let the first impression of the prairie landscape sink deep. In the timber, the trees were festooned with bitter-sweet and with vines bearing wild grapes; in the open country, nothing but unmeasured stretches of waving grass caught the eye.[[21]] To one born and bred among the hills, this broad horizon and unbroken landscape must have been a revelation. Weak as he was, Douglass drew in the fresh autumnal air with zest, and unconsciously borrowed from the face of nature a sense of unbounded capacity. Years afterward, when he was famous, he testified, "I found my mind liberalized and my opinions enlarged, when I got on these broad prairies, with only the heavens to bound my vision, instead of having them circumscribed by the little ridges that surrounded the valley where I was born."[[22]] But of all this he was unconscious, when he alighted from the stage in Jacksonville. He was simply a wayworn lad, without a friend in the town and with only one dollar and twenty-five cents in his pocket.[[23]]

Jacksonville was then hardly more than a crowded village of log cabins on the outposts of civilized Illinois.[[24]] Comfort was not among the first concerns of those who had come to subdue the wilderness. Comfort implied leisure to enjoy, and leisure was like Heaven,—to be attained only after a wearisome earthly pilgrimage. Jacksonville had been scourged by the cholera during the summer; and those who had escaped the disease had fled the town for fear of it.[[25]] By this time, however, the epidemic had spent itself, and the refugees had returned. All told, the town had a population of about one thousand souls, among whom were no less than eleven lawyers, or at least those who called themselves such.[[26]]

A day's lodging at the Tavern ate up the remainder of the wanderer's funds, so that he was forced to sell a few school books that he had brought with him. Meanwhile he left no stone unturned to find employment to his liking. One of his first acquaintances was Murray McConnell, a lawyer, who advised him to go to Pekin, farther up the Illinois River, and open a law office. The young man replied that he had no license to practice law and no law books. He was assured that a license was a matter of no consequence, since anyone could practice before a justice of the peace, and he could procure one at his leisure. As for books, McConnell, with true Western generosity, offered to loan such as would be of immediate use. So again Douglass took up his travels. At Meredosia, the nearest landing on the river, he waited a week for the boat upstream. There was no other available route to Pekin. Then came the exasperating intelligence, that the only boat which plied between these points had blown up at Alton. After settling accounts with the tavern-keeper, he found that he had but fifty cents left.[[27]]

There was now but one thing to do, since hard manual labor was out of the question: he would teach school. But where? Meredosia was a forlorn, thriftless place, and he had no money to travel. Fortunately, a kind-hearted farmer befriended him, lodging him at his house over night and taking him next morning to Exeter, where there was a prospect of securing a school. Disappointment again awaited him; but Winchester, ten miles away, was said to need a teacher. Taking his coat on his arm—he had left his trunk at Meredosia—he set off on foot for Winchester.[[28]]