[5] There, she met the artists Anna Page Scott, Ida C. Haskell, Susan J. Moody, and Pauline Dohn Rudolph ("Lena").

Surviving family correspondence sheds light on Stanley's experiences, including details on other artists' methodologies and critiques she received from her instructors.

In the summer of 1888, Stanley traveled to Rijsoord, a small, isolated town in the Netherlands, with a group of friends and classmates that included Ida C. Haskell, Pauline Dohn Randolph, Alice Kellogg, and Page Scott.

In May 1889, Stanley's painting, Au commencement et à al fin, was selected for exhibition at the Paris Salon, and in June, she returned to Rijsoord for the summer along with many of her classmates.

She continued to produce works over the next several years and exhibited at the National Academy of Design, The Boston Art Club, and the Society of Washington Artists.

In June 1895, at her brother David's graduation from West Point Military Academy, Stanley met Lieutenant Willard Ames Holbrook, whom she would later marry.

Due to her husband's position in the army, Stanley and her family frequently moved, including to Chickamauga, Georgia (1898), Cuba (1898), and Fort Stevens, Oregon (1899).

On February 25, 1907,[1] at 42 years of age, Anna Stanley died of pneumonia at her home in Chester, leaving behind her husband and two sons.