Kathleen McEnery Cunningham was my grandmother.

Kathleen McEnery was born in 1885 in Brooklyn, New York, and soon moved to Great Barrington, Massachusetts. She married my grandfather Francis Cunningham and they lived in Rochester, New York.

Here’s a bit of information about my grandfather Frank Cunningham and his family:

In New York City, Kathleen Cunningham studied with Robert Henri, whose teachings were central to the work of the group of artists known as the Ashcan School. She also studied abroad and exhibited two paintings at the controversial 1913 Armory Show in New York City. After her marriage to Rochesterian Francis Cunningham, whose family owned the Cunningham Carriage Factory, she continued painting in a studio off the family's home on 10 South Goodman St., now on the campus of the Rochester Museum and Science Center. Mrs. Cunningham was a member of the Gallery's Board of Managers from 1927 through 1971.

The following biography is from the Archives of AskART:

Kathleen McEnery (Cunningham), painter of figure, portraits and still lives, was born in 1885 and died in Rochester, New York in 1971, having lived there for the last fifty-seven years of her life. She studied at the Pratt Institute in Brooklyn and with Robert Henri at the New York School of Art and also with him in Spain in 1906 and 1908. In 1908, she rented a studio in Paris, and was very productive for several years as a painter. Returning to New York City, she exhibited with well-known artists inclucing Henri, John Sloan, George Bellows, Stuart Davis, Leon Kroll, Edward Hopper, and Andrew Dasburg, as well as at the Pennsylvania Academy of the Fine Arts, in Philadelphia, and the Biennial Exhibition of the Corcoran Gallery, Washington, D.C.
McEnery exhibited two figure paintings in the 1913 Armory Show in New York City. One of those paintings, Going to the Bath is now in the collection of the National Museum of American Art, Smithsonian Institution, Washington, D.C., and appears in Eleanor Tufts' book, American Women Artists: 1830-1930, published by the National Museum of Women in the Arts, Washington, D.C., in 1987. The painting depicts two standing female nudes painted, under Paul Cezanne's influence, in the hard-edged, sculptural style developed, and popular, in America early in the century. The other painting, Dream contrasts a thoughtful woman, nude to the hips, with the bars of a chair behind her.
The extensive stylistic differences between these paintings in the Armory Show and McEnery's earlier Woman in an Ermine Collar, 77 x 38, painted in 1909, now in the collection of the Memorial Art Gallery of the University of Rochester, indicate that the Armory show works must have been painted around 1910-1913. Prior to her influence by modernism, McEnery painted Woman in an Ermine Collar in a subtly blended, romantic-realist style suggesting the influence of John Singer Sargent, William Merritt Chase and even Thomas Eakins. Woman with an Ermine Collar is a quite dark painting of a young woman standing with hand on hip, her dark clothing blending with the black background to effectively spotlight her light collar, white blouse and, secondarily, her face and hands. This painting was given by the artist to her children who, in turn, donated it in 1983 to the Gallery and was exhibited as part of the "Memorial Exhibition: Kathleen McEnery Cunningham," put on by the Memorial Art Gallery in 1972.
In 1914, one year after the Armory Show, McEnery married Frank Cunningham, whose family ran the Cunningham car manufacturing business, eventually raising three children, and for many years, domestic responsibilities competed with her painting activities. From 1927 until 1971, she served on the Memorial Art Gallery Board of Managers of the University of Rochester. She was also a founding faculty member of Rochester's Harley School and belonged to the Chatterbox Club and the Eastman Theater's Corner Club.
An exhibition of sixteen of McEnery's paintings was presented in 2003 by the Hartnett Gallery of the University of Rochester, including still-lives and striking portraits of Eugene Goossens, conductor, and Eddie Murphy, horn player, of the Rochester Philharmonic Orchestra.
Since the artist's death, only two public exhibitions before this had taken place-the 1972 show at the Memorial Art Gallery of the University of Rochester, and in 1987, at the National Museum of Women in the Arts, Washington, D.C.

Peter Hastings Falk (editor). Who Was Who in American Art