The Eastern Shore of Maryland lay very close to the free state of Pennsylvania. Escape might not appear too formidable an undertaking. Distance, however, was not the chief trouble. The nearer the lines of a slave state were to the borders of a free state, the more vigilant were the slavers. At every ferry was a guard, on every bridge sentinels, in every wood patrols and slave-hunters. Hired kidnappers also infested the borders. Nor did reaching a free state mean freedom for the slave. Wherever caught they could be returned to slavery. And their second lot would be far worse than the first! Slaveholders constantly impressed upon their slaves the boundlessness of slave territory and their own limitless power. Frederick and his companions had only the vaguest idea of the geography of the country. “Up North” was their objective. They had heard of Canada, they had heard of New York, they had heard of Boston. Of what lay in between they had no thoughts at all. After many long discussions they worked out their plan for escape. On the Saturday night before the Easter holidays they would take a large canoe owned by a Mr. Hamilton, launch out into Chesapeake Bay and paddle with all their might for its head, a distance of about seventy miles. On reaching this point they would turn the canoe adrift and bend their steps toward the north star until they reached a free state. This plan had several excellent points. On the water they had a chance of being thought fishermen, in the service of a master; hounds could not track them; and over Easter their absence might not be noted. On the other hand, in bad weather the waters of the Chesapeake are rough, and there would be danger in a canoe, of being swamped by the waves. Furthermore, the canoe would soon be missed; and, if absent slaves were suspected of having taken it, they would be pursued by some fast-sailing craft out of St. Michaels. They prepared for one quite possible emergency. Any white man, if he pleased, was authorized to stop a Negro on any road and examine and arrest him. Many a freeman, being called upon by a pack of ruffians to show his free papers, presented them, only to have the hoodlums tear them up, seize the victim and sell him to a life of endless bondage. The week before their intended start, Frederick wrote a pass for each of the party, giving him permission to visit Baltimore during the Easter holidays. He signed them with the initials of William Hamilton, tobacco planter whose place edged on the bay and whose canoe they had planned to take. The pass ran after this manner: This is to certify that I, the undersigned, have given the bearer, my servant John, full liberty to go to Baltimore to spend the Easter holidays. Near St. Michaels, Talbot Co., Md. W. H.