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]