He soon found employment there with one Mr. Hibbard, whom he served three years and was lodged in a cabin better than that in Kentucky. His family, however, had been so exposed that during the first winter they almost died of sickness, but his employer was kind to him. Mr. Hibbard taught Henson's son Tom, then twelve years of age. Tom's achievements were soon such that instead of reading the Bible to his father to assist him in preaching he taught his father to read. Henson then entered the service of one Mr. Risely, who had experienced more elevation of mind than Mr. Hibbard. With this advantage Henson not only realized more fully than ever the ignorance in which he lived, but became interested in the elevation of his people there, who had been content with the mere making a livelihood rather than solving the economic problems of freedom. A good many, thereafter, agreed to invest their savings in land. In this they had the cooperation of Mr. Risely. Henson set out, therefore, in 1834 to explore the country and finally selected a place for a settlement to the east of Lake St. Clair and Detroit river later called Colchester.
Henson thereafter directed his attention to those whom he had left in bondage. If he felt any compunction of conscience for having conducted the party of Maryland slaves through a free State without making an effort to free them, he made up for that in later years. Addressing an audience of Negroes some years later at Fort Erie, Pennsylvania, he took occasion to remind them of their duty to assist in the emancipation of their fellowmen in the South. In the audience was a young man named James Lightfoot, who had fled from a plantation near Maysville, Kentucky. Seeing his duty as never before, he approached Father Henson to arrange for the rescue of his enslaved kinsmen. Knowing the agony in which he was, Henson undertook the perilous task of bringing them to Canada. Leaving his family alone he traveled on foot through New York, Pennsylvania and Ohio into Kentucky. He had little difficulty in finding the Lightfoots. On presenting them a small token of the loved one, who, they were told, had gone to the land of freedom, they exhibited no little excitement. Unfortunately, however, Lightfoot's parents were so far advanced in years and his sisters had so many children that they could not travel. As the young men, who could have gone, were not anxious to be separated from their loved ones, all declined the invitation to make this effort for freedom at that time, promising to undertake it a year thereafter, if Henson returned for them.
Henson agreed to do so and in the meantime went forty or fifty miles into Bourbon County in the interior of Kentucky in quest of a large party of Negroes who were said to be ready to escape. After a search for about a week he discovered that there were about thirty fugitives collected from various States. With them he started on the return trip to Canada, traveling by night and resting by day. They contrived to cross the Ohio river and reached Cincinnati in three days. There they were assisted and directed to Richmond, Indiana, a settlement of Quakers, who helped them on their way. After a difficult journey of two weeks they reached Toledo and took passage for Canada, which they reached in safety.
Henson then remained on his farm in Canada some months, but when the appointed time for the delivery of the enslaved kinsmen of James Lightfoot arrived, he set out again for Kentucky. He passed through Lancaster, Ohio, where the people were very much excited over a meteoric shower, thinking that the day of judgment had come. Henson thought so too, but believing that he was promoting a righteous cause, he kept on. On arriving at Portsmouth on the Ohio, he narrowly escaped being detected by Kentuckians in the town. He resorted to the stratagem of binding his head with dried leaves in a cloth and pretended to be so seriously afflicted that he could not speak. Arriving at Maysville, he had little difficulty in finding the slaves whom he was seeking. The second person whom he met was Jefferson Lightfoot, the brother of James Lightfoot for whom Henson was making this trip. Saturday night, as usual, was set as the time for the execution of this affair, for the reason that they would not be missed until Monday and would, therefore, have a day ahead. They started from Maysville in a boat, hoping to reach Cincinnati before daylight, but the boat sprang a leak and the party narrowly escaped being drowned. They procured another boat, however, and got within ten miles of Cincinnati before daylight. To avoid being detected, they abandoned the boat and proceeded to walk to Cincinnati, but faced another difficulty when they reached the Miami, which at that point was too deep to be forded. But in going up the river seeking a shallow place they were seemingly led providentially by a cow that waded across before them. As the weather was cold and they were in a state of perspiration on wading through, the youngest Lightfoot was seized with serious contractions, but recovered after receiving such ministrations as could be given on the way. They were assisted in Cincinnati and the next day started on their journey to Canada. They had not gone far before the young Lightfoot became so seriously ill that he had to be carried on a litter, and this became so irksome that he himself begged to be left in the wilderness to die alone rather than handicap the whole party with such good prospects for freedom. With considerable reluctance, they acceded to his request, and sad indeed was the parting. But before they had gone more than two miles on their journey one of the brothers of the sick man suddenly decided to return, as he could not suffer to have his brother die thus in the wilderness, and be devoured by wolves. They returned and found the young man seemingly in a dying condition. They at once decided to resume their journey and had not gone far before they saw a Quaker whose thee and thou led them to believe that he was their friend. They then told him their story, which was sufficient. He immediately returned home, taking them with him. The fugitives remained there for the night and arranged for the boy to remain with the Quaker until he should recover. They were then provided with a sack of biscuit and a supply of meat, with which they set out again for Canada. After proceeding a little further they met a white man, who became helpful to them in escaping the slave hunters who were then on their trail. This man while working for an employer who undertook to punish him had used violence and had to run off. The party, knowing the increasing danger of capture, walked all night, trying to cover the distance of forty miles. At daybreak they reached a wayside tavern near Lake Erie and ordered breakfast. While the meal was in preparation they quickly fell asleep. Just as the breakfast was ready, however, Henson had the peculiar presentiment that some danger was near and that he should at once leave the house. After experiencing some difficulty in persuading the fugitives to leave the tavern quickly they agreed to follow his orders. They had hardly left the tavern when they heard the tramping of the horses of the slave hunters. They hid themselves in some bushes nearby which overlooked the road. The Lightfoots quickly recognized the slave hunters and whispered their names to Henson as they passed by. This was the critical moment of their lives. Had they remained in the house a few minutes longer they would have been apprehended. Their white friend proceeded to the door in advance of the landlord and when asked as to whether he had seen any slaves said that he had, that there were six of them and that they had gone toward Detroit. The slave-hunters at once set out in that direction. The fugitives returned to the house, devoured their breakfast immediately and secured the assistance of the landlord, who hearing their piteous story agreed to take them in his boat to Canada. In the language of Henson, "Their bosoms were swelling with inexpressible joy as they mounted the seats of the boat, ready, eager, to spring forward, that they might touch the soil of the freeman. And when they reached the shore, they danced and wept for joy and kissed the earth on which they first stepped, no longer slaves but freemen."5
Within a short time thereafter the boy whom they had left in dying condition on the way reached them on the free soil of Canada in good health. And Frank Taylor, the master of these fugitives, on recovering from an attack of insanity which apparently resulted from the loss of these slaves was persuaded by his friends to free the remaining members of the Lightfoot family, an act which he finally performed, enabling them after a few years to join their loved ones beyond the borders of the land of the slave. In this way Henson became instrumental in effecting the escape of as many as one hundred and eighteen slaves.6
The next important work was the establishment of the British American Manual Labor Institute in connection with Reverend Hiram Wilson.