On the same day that Garrison met Simeon S. Jocelyn in New York City—Friday, April 12, 1833—Prudence Crandall received a third student at her school, Ann Eliza Hammond. Ann was from Rhode Island, and she joined Crandall as a boarding student. Crandall had met Hammond and her mother in February when she traveled to Providence.
Ann Eliza Hammond’s enrollment as the first black student from another state spurred Crandall’s opponents to quickly test the old vagrancy law. The law allowed town leaders to declare that a person from another state was a burden to the town and order the person to leave or risk paying a fine. Upon failure to pay the fine within ten days, the person would face either immediate expulsion or severe punishment—“he or she should be whipped on the naked body.”83
On Saturday evening, one day after Hammond arrived, Canterbury officials notified Prudence Crandall that they regarded Miss Hammond as a burden to the town. On Sunday, Crandall traveled to Brooklyn to tell Samuel May that she expected the town to serve a writ upon her as the guardian of Miss Hammond and require that she pay the fines.84 “I presume I shall be subjected to that penalty next Friday,” Crandall said. “I think it is best to pay the first fine when demanded. …”85 May told the treasurer of Canterbury that he and the Benson family were willing to post a bond in the amount of ten thousand dollars to protect the town from the cost of any vagrancy on account of students from other states.86
“A written offer of bonds has been presented to the selectmen by Mr. May to secure the town against any damage that shall be done by any of my pupils,” Crandall wrote to Simeon S. Jocelyn. “I presume the bonds will not be accepted by them—this is a day of trial.”87 The unexpectedly small enrollment combined with the ongoing opposition to her school depressed Crandall. “Disappointment seems yet to be my lot,” she wrote on April 17.88 “Very true, I thought many of the high-minded worldly men would oppose the plan, but that Christians would act so unwisely and conduct in a manner so outrageously was a thought distant from my view,” Crandall said. “If this school is crushed by inhuman laws, another I suppose cannot be obtained, certainly one for white scholars can never be taught by me.”89
On Saturday, April 20, Crandall discussed the vagrancy issue with Rev. May, who told her she should not pay any fine. Instead, May said she should take the matter to court. Crandall favored paying the fine and avoiding a legal confrontation, but she told May she would consider challenging the ordinance in court. May also told Crandall he received a letter from a friend in Reading, Massachusetts, inviting Crandall to move her school for black women to their town. Crandall wrote to Simeon S. Jocelyn and asked what he thought of moving her school to Reading, but stressed, “Do not mention this to anyone until we get further information from that town.”90 Crandall was willing to relocate her school but did not want to be misled. She thought Jocelyn would understand and have good advice; he had once believed the people of New Haven would embrace a college for black men.
The sheriff of Windham County served a legal writ upon Ann Eliza Hammond at Crandall’s school on Monday, April 22, 1833. The writ demanded that Hammond appear before attorney George Middleton, a justice of the peace, at the home of Chauncey Bacon on Thursday, May 2, at one o’clock in the afternoon, to answer charges brought by the town. Middleton could order Hammond to pay a fine of $1.67 for the previous week and command her to leave the town or face further fines. The writ also clearly stated that if Hammond refused to pay the fine and refused to leave, she would be “whipped on the naked body not exceeding ten stripes.”91 Word of the sheriff’s visit to the school traveled quickly to Brooklyn and Samuel May.
“I feared they would be intimidated by the actual appearance of the constable, and the imposition of a writ,” May said. “So, on hearing of the above transaction, I went down to Canterbury to explain the matter if necessary; to assure Miss Hammond that the persecutors would hardly dare proceed to such an extremity.”92 May told both Hammond and Crandall that they must not give in to the authorities, that no fines should be paid, and that Hammond must not leave Canterbury. He said that while the possibility of the town carrying out the ultimate punishment in the ordinance—a public whipping—was remote, May advised Hammond to submit to that fate “if they should in their madness inflict it.”93 Sixteen-year-old Ann Eliza Hammond had arrived in Canterbury only a week earlier to enroll in Prudence Crandall’s school. Now a minister from Brooklyn asked Hammond “to bear meekly the punishment” of a public whipping in order to expose their opponents as barbarians. “Every blow they should strike her would resound throughout the land, if not over the whole civilized world,” May said.94 May saw the controversy not only in terms of personal suffering, but also as part of a larger campaign to advance the cause of emancipation. Hammond accepted May’s challenge. “I found her ready for the emergency,” May said, “animated by the spirit of a martyr.”95
Andrew Judson traveled to New York City at the end of April. The purpose of his trip was likely to assist in efforts to capture Garrison. The colonization movement was very popular in New York, and Judson knew he could depend on assistance from those who were offended by Garrison’s attacks on colonization. There were at least two options if Judson succeeded in capturing Garrison: return Garrison to Canterbury to face libel charges, or hand him over to those from the South who hated Garrison and the Liberator. Crandall and her sister Almira worried about Garrison’s safety. “I hope that our friend Garrison will be enabled to escape the fury of his pursuers,” Almira Crandall wrote to Henry Benson. “Our anxieties for him were very great at the time Judson went to New York, as we expected his business was to take Mr. Garrison.”96
Eager to escape to England, Garrison left New York for Philadelphia hoping to board a boat bound for Liverpool, but he arrived too late—the ship had already set sail. Arthur Tappan persuaded Garrison to allow Tappan’s friend Robert Purvis to drive him by horse-drawn carriage to Trenton, New Jersey. While traveling along the Delaware River, Garrison barely escaped a fatal accident.97 A passing steamboat caught Garrison’s attention, and he wanted to see it from a point closer than the road. Purvis accordingly steered the carriage off the road and toward the river. After nearing the edge of a cliff, Purvis turned the carriage back toward the road and stopped. For a few minutes Garrison had an unobstructed view of the steamboat. After the boat passed by, Purvis took the reins and signaled for the horse to pull forward toward the road. Instead, the horse began to back up, moving the carriage closer to the cliff with each step. Realizing the danger and unable to stop the horse, Purvis jumped out of the carriage, expecting Garrison to do the same. Garrison did not move. Purvis shouted, “Sir, if you do not get out instantly, you will be killed.” Garrison finally jumped out the door, just as the horse abruptly stopped with the rear wheel of the carriage precariously balanced on the edge of the cliff.98
From Trenton, Garrison returned to New York City and traveled on to New Haven, where he continued to elude his enemies. He spent a few days with Nathaniel Jocelyn, who finished Garrison’s portrait. Nathaniel’s concern for Garrison’s safety was so great that he painted Garrison not in his studio, but in a room next to the studio and near a side exit, in case Garrison needed to flee.99 As for the portrait, Garrison deemed it a success and called it “a good likeness of the madman Garrison.”100
Garrison traveled once more to New York City, hoping to evade his potential kidnappers and depart for