Helen Maria Holmes was born in Kingston, on September 9, 1865. She graduated from Kingston High School in 1881 aged 15, and from Smith College in 1887. Holmes subsequently pursued graduate studies at Radcliff College and the Massachusetts Agricultural College (now University of Massachusetts at Amherst), where she was one of the first women to attend classes.

She lived at Hillholm, an imposing house built in 1811 by her grandfather Jedediah Holmes Jr. She ran the surrounding farm, located near the present day address of 13 Wapping Road in Kingston for some years: in 1910, the federal census showed her occupation as "florist and grower" and in 1920 as "Proprietor, own farm." In 1921, Hillholm burned to the ground while Holmes was away in Boston.

She enjoyed traveling, art, music, gardening and civic affairs, and spoke fluent French, Italian, and German. From 1889 to 1891, and again from 1896 and 1899, Holmes served as the superintendent of schools for the town of Kingston. Around 1924, she worked at the headquarters of the Maison Internationale in Geneva, Switzerland.

She was an active participant in public life including Old Home Days, garden clubs, community markets, the Plymouth Girls Club and social work at the Plymouth Cordage. She served as the first president of the Jones River Village Club and as a president of the New England Farm and Garden Association. A contemporary referred to her as being a “charming speaker.”

Holmes remained single throughout her lifetime. She died of ovarian cancer at age 73, on November 23,1938, and was buried in the Holmes family plot in Kingston Evergreen Cemetery.