Pickersgill, widowed at the age of 29, became successful enough in her flag making business, that, in 1820, she was able to buy the house that she had been renting in Baltimore, and later became active in addressing social issues, such as housing and employment for disadvantaged women. From 1828 to 1851, she was president of the Impartial Female Humane Society which had been founded in 1802, incorporated in 1811, and helped impoverished families with school vouchers for children and employment for women. Under Pickersgill's leadership, this organization built a home for aged women and later added an Aged Men's Home which was built adjacent to it. These, more than a century later, evolved into the Pickersgill Retirement Community of Towson, Maryland which opened in 1959.