Asa Niles, matching Russell’s progress with loving interest, told Martin Conwell the boy ought to go to Wilbraham Academy.  His own son William was going, and he strongly urged that Charles and Russell Conwell enter at the same time.  It was no light decision for the father to make.  He needed the boys in the work on the farm.  Not only was he unable to help them, but it was a decided loss to let them go.  Long and earnest were the consultations the father and mother held.  The mother, willing to sacrifice herself to the utmost, said, of course, “let them go,” deciding she could earn something to help them along by taking in more sewing.  So it was decided, and in the fall of 1858, Russell and his brother entered the Academy of Wilbraham, a small town about twelve miles east from Springfield.

It was bitter, uphill work.  All the money the two boys had, both to pay their tuition and their board, they earned.  They worked for the near-by farmers.  They spent long days gathering chestnuts and walnuts at a few cents a quart.  They split wood, they did anything they could find to do.  In fact, they worked as hard and as long as though no studies were awaiting to be eagerly attacked when the exhausting labor was finished.  Such tasks interfered with their studies, so that Russell never stood very high in his Academy classes.  Part of the time they lived in a small room on the outskirts of the village, barren of all furniture save the absolutely necessary, and for six weeks at a stretch, lived on nothing but mush and milk.  Their clothes were of the cheapest kind, countrified in cut and make, a decided contrast to those of their fellow students, who came from homes of wealth and refinement It is very easy for outsiders and older heads to talk philosophically of being above such things, but young, sensitive boys feel such a position keenly and none but those who have actually endured such a martyrdom of pride know what they suffer.  It takes the grittiest kind of perseverance to face such slights, to seem not to see the amused glance, not to hear the sneering comment, not to notice the contemptuous shrug.

Such slights Russell endured daily from certain of his classmates, and though he realized fully that the opinion of these was of little value, nevertheless they hurt.  But to the world he stood his ground unflinchingly, even if there were secret heartaches.  He studied hard, and what he studied he learned.  He had his own peculiar way of studying.  Once he was missing from his classes several days.  The teachers reported it to the principal, Dr. Raymond, who investigated.  He found Russell completely absorbed in history and mastering it at a mile-a-minute gait.  Dr. Raymond was wise in the management of boys, especially such a boy as Russell, and he reported to the teachers, “Let him alone.  Conwell is working out his own education, and it isn’t worth while to disturb him.”

His passion for debate and oratory found full scope in the debating societies of the Academy.  These welcomed him with open arms.  He was so quick with his witty repartee, could so readily turn an opponent’s arguments against him, that the nights it was known he would speak, found the “Old Club” hall always crowded to hear “that boy from the country.”