[4] Sherwood may have received her earliest training in art from her mother; a sketchbook dating to 1873 was in the hands of family members in 1987.

Among her earliest works were illustrations for publications such as Harper's Magazine, and in 1880 she won the $1,000 first prize in a competition to design a Christmas card for Louis Prang & Company.

In 1884–1885 the women attended classes at the Académie Julian in Paris;[2] Sherwood's instructor there was Tony Robert-Fleury.

The Rockwell Centre for American Visual Studies cites this as a surprisingly early illustration of a girl reading.

Her work was also exhibited in the Palace of Fine Arts at the Fair[6] She accepted commissions once more in 1918 to provide support for her family, and continued painting watercolors for much of her career.