She documented the daily activities of her life in diaries beginning at the age of 17, which included records of the portraits that she made.

While married Bascom fulfilled the role of a minister's wife, was a teacher, and was active at the local library and in temperance societies.

Bascom worked with a variety of materials, including pastels, pencils, cut paper, and foil.

Some of her initial works were layered pieces of paper that represented the head and neck, clothing, and accessories placed over a background.

Charlotte Streifer Rubinstein, author of American Women Artists: From Early Indian Times to the Present (1982), said that Bascom had a "calm strength of characterization combined with a sensitive feeling for shape, color and texture.

[2][3] Bascom had two older half-sisters from Henshaw's previous marriage to Ruth Sargeant, who was her namesake.

[4] Her father was a veteran of the French and Indian War and during the American Revolution,[5] he was a key leader of the Worcester County Minutemen.

[5] Bascom moved back to her parents’ house[3] and opened a millinery business in Leicester following her husband's death.

[10][3] As a minister's wife, Bascom was busy socializing, recording church events, and visiting the sick.

[13] Clough R. Miles, her stepson, who had lived and studied in the Bascom household, resided with them again when he taught school.

In 1827, Reverend Bascom represented Ashby at the Massachusetts General Court for a three-year period, which took him away from the house when he was in Boston.

[1] In the early 1830s Reverend Bascom's health began to decline and he spent 9 months of the year in Savannah.

[1] Bascom and Susanna Paine were two of 11 or more women who worked as professional itinerant portraitists in the late 18th and early 19th centuries.

[16] Her artistic productivity was facilitated by a way of life that strongly emphasized community as well as family involvement, and was further nurtured by a penchant for travel in New England.Bascom sometimes received no payment for her portraits when they were gifts or people could not afford to pay.

[4] Bascom started making portraits in 1801 by tracing the shadow cast of the sitter by lamp- or candlelight on drawing paper placed on a wall in a dark room.

She began creating collages in 1828 with clothing cut from paper—metal foil was used for buttons, jewelry and eyeglass frames—which were layered on the cut-out of the subject's head and neck.

"Her portrait of Elizabeth Cummings Low (1829) is one such collage composition pasted onto a slate blue ground; the crisp photographic lines are evocative of the shadow-tracing process," according to Lois S. Avigad.