The portraits of Aaron Willard’s two oldest children, Aaron Jr. and Nancy, were painted in 1804 by the Boston artist John Ritto Penniman.

Penniman is known for his early decorative and ornamental painting, early landscapes and city views, and literary and religious scenes. Some of his best-known works include a miniature still life of shells painted on a chest of drawers commissioned in 1809 by Salem merchant Elias Hasket Derby from the Boston cabinetmaker Thomas Seymour; a scene of Meetinghouse Hill in Roxbury painted in 1799, commissioned by Aaron Willard, one of the many craftsmen who lived and worked in the neighborhood; and The Last Supper, painted in 1812 for the chancel of Boston's Old North of Church. The carved and gilded frames for these portraits are attributed to John Dogged. (An entry for 16 frames sold to John Ritto Penniman is included in a January 1804 Doggett daybook.)

Both portraits are dated 1804. The front right bottom corners of the painting also bear a note in paint, stating the age of the sitter (see the detail) as “Aged 20 Y. 7 M” for Aaron and “18 years and 7 months of age” for Nancy. Interestingly enough, the painter himself must be around same age at that time, and knew both Aaron and his sister Nancy very well, since he was an ornamental painting apprentice next door to their father’s workshop. He also painted clock faces for the Willard’s manufacturing and had just established his own studio next to them and across from John Doggett- a famous gilder and frame maker, who was also a long-term friend.

The portraits of Aaron Jr. and Nancy were sold, thus ending almost two centuries of family ownership. Aaron Jr. and Nancys portraits returned to the "family" when they were purchased by Willard House and Clock Museum in 1991 from an antique dealer near Philadelphia.