Woolson published several volumes, including: Women in American Society (1873); Dress Reform (1874); Browsing Among Books (1881); and George Eliot and Her Heroines (1887).

[2] Her family lived in Windham for four generations, her great-grandfather, Benjamin Goold —a native of Kittery, Maine— having moved there from Portland (then Falmouth) in 1774.

When, at the close of the American Civil War, Mr. Woolson was invited to take charge of the high school of his native city, Concord, New Hampshire, they returned to New England.

[2] For brief periods, Woolson taught her favorite subjects, acting for some months, while in Cincinnati, as Professor of Belles Lettres at the Mount Auburn Young Ladies' Institute; in Haverhill, Massachusetts, as lady principal of the high school; and as assistant in the Concord High School, where, with her husband, she taught for a while the higher mathematics and Latin.

When Portland, Maine celebrated its centennial in 1886, Woolson was unanimously chosen to fill the position of poet, reading a long ode on that occasion.

In 1883–1884, she traveled for 13 months, spending a summer in Ireland, Wales, Scotland and England, also visiting Austria, Hungary, Southern Italy, Spain, and Morocco.