[4] In 1846, around the age of 29, Chickering moved to Philadelphia, Pennsylvania, where she continued her role in the church teaching Sunday School to young girls.

"[5] Sometime around 1854, Chickering moved back to Dedham, Massachusetts where she spent her days caring for the ill, it was during this time when she decided that her life's work should be toward promoting the good in other people.

[7] In the early 1860s, Chickering visited a friend in Philadelphia, who once a week spent an afternoon with the female prisoners of the Pennsylvania State Penitentiary.

[8] Chickering requested to join her friend on her visit to the Penitentiary one Tuesday afternoon, to help uplift the spirits of the women through prayer and religious teachings.

Chickering observed the cycle repeat itself and its effect on the women, "...and this mournful round is trodden again and again, till a wretched death closes the scene for these victims of misfortune, neglect, and sin.

"[12] From what she had seen first hand in the Dedham Jail, Chickering realized there was desperate need to reform these women so they could lead productive lives once they were released from prison.

Chickering and the matrons also worked to help find the discharged female prisoners secure forms of employment before leaving the Asylum.

[22] The bill for separate prisons for women finally passed 1874, after previously being defeated many times and many signed petitions, Chickering had succeeded in her efforts.

Even at the end of her life, Chickering would not accept praise or take credit for the success of her work in prison reform or the Asylum, as she refused to allow her picture to be hung in the farm house even at the request of the matrons who now ran the facility in Dedham.