[2][3] Her mother, May Rowed, was William Montgomery's younger second wife and a former student of the Melbourne National Gallery of Victoria School.
Although marriage reduced her time for artwork, May Montgomery stayed in direct contact with many of the major women artists of Edwardian Melbourne, including Josephine Muntz Adams, Jessie Traill, Dora Wilson, Violet Teague, Lillian White and the Sri-Lankan Australian artist Isabel van Stavern.
She also painted oriental style flowerpieces and designed costumes for amateur theatricals, fancy dress balls and tableaux, including fundraising events during World War One for the Victorian Artist Society.
Towards the end of the 1930s she began attending George Bell's classes at his Burke Street school, although his teaching did not impact greatly on her artmaking until the later 1940s.
She established a studio in the Olderfleet buildings with Lucy Newell which became an important meeting place for many young artists in Melbourne including Treania Smith, Constance Coleman, Marna Pestell and Geoff Jones.
She became increasingly aligned with George Bell and his oppositional stance to the emerging expressionist and free-er aesthetic seen among the most radical Melbourne artists.
She was an enthusiastic and assiduous student and for most of the "homework" assignments that Bell set, Montgomery produced fully developed artworks, rather than sketches and provisional studies.
She painted in Victorian alps with Lucy Newell and Mollie Hill,[12] who was based at Bright, both friends from the National Gallery School, camping in stockmen's and cross-country skier's huts.
The new building of the Lyceum Club in Ridgeway Place Melbourne, designed by Ellison Harvie and completed in 1959 included a large mural by Montgomery of Magnolias.
During the postwar years Montgomery worked alongside and was friend of many of the major classical modernists of the 1950s including Dorothy Mary Braund, Nancy Grant, Guelda Pyke, Constance Stokes, Eveline Syme (part of whose studio contents she inherited), Geoff Jones, Frances Derham, Barbara Brash and Mary Cecil Allen.
[16] In 1989 her work, along with that of other Bell pupils, Maidie McGowan and Marjorie Woolcock, toured to three Victorian regional galleries in the Form and Flowers Exhibition.
[18] Recently works have been acquired by other public collections including Ballarat, Bendigo, Geelong, the State Library of Victoria (gift of the Montgomery family) and the National Gallery of Australia (prints).