Some think that "Aunt Mary" was "Aunt Rachel Loehr," the relative of Almon Keefer, an older neighbor boy as the "Aunt Mary." Riley visited her often as a vagrant child escaping his poverty-stricken adolescent home. The Loehr and Riley families visited each other as well. Minnie Belle Mitchell provides an idealized picture of Riley's youth going to Aunt Rachel's as follows:

"...the three boys, Bud, John and Hum with Almon Keefer would go to Aunt Rachel's alone, walking the entire distance, loitering along country roads....cutting through time land, playing games of make-believe, giving Indian and catbird calls and gathering hackberries and haws along the way. But all weariness disappeared when Aunt Rachel's home was reached and they were welcomed...The country home...had its gourd vine climbing to the roof... It had its windless well, its little spring house where the milk and butter and all sorts of good things were kept cool and fresh. There hollyhocks at the windows and a swing hung from an apple tree. And after the children had taken their usual bareback rid on the old mare, slid down he hay stack, and had visited the traps where robber rabbits and foxes were caught...Aunt Rachel would call them to dinner.

The boys recalled the wild scramble to the well for the hasty washing of hands and faces, the "jellies, jams and marmalades," the usual cherry cobbler or custard pie with plenty of milk to drink. The poem is nominally written to Riley's brother, John, which helps to date its first writing. Riley used an original four stanzas for "Old Aunt Mary's" from the letter in his early platform appearances. New stanzas were added over the years. In a special edition of the poem in 1904, the poem was completed with twelve additional stanzas.

Riley's great poetic characters were all "composites." There were actually many "Aunt Mary's." Aunt Mary was a "character type" of warm-hearted persons who cared for children. Possibly a new such person contributed every time Riley revised the poem which was often. Additionally ev ery time an older person died, she seems to have been eulogized by obituary and funeral sermon as the kindly "Aunt Mary" of Riley's poem if Riley had only a remote connection to the decedent.

One version of how the poem "Out to Old Aunt Mary's" happened to be written has Riley and friend, "Haute" Tarkington, later Mrs. Ovid Butler Jameson, preparing to accompany Haute's little brother, Booth, who lived at Indianapolis, on a week-end visit with the grandparents and his Aunt Mary. Sunday came and with it, the prospect of a visit to Aunt Mary but it had to be postponed. On hearing of this disappointment Booth began to cry over the unexpected failure of his plan.

This suggested a theme for the poet, who, with his characteristic genius wrote one of his best poems -"Out to Old Aunt Mary's." The poem was first published in the Indianapolis JOURNAL and later revised. This Mary was Mary Tarkington Alexander and she lived in Greensburg, Indiana. Her portrait shows a warmly "pudgy" faced woman with friendly eyes, wide smile, a close cropped white hair in a matronly gown. She was a person any child wanted to embrace in a hug. Among other candidates of "aunt's" were "blood" aunts in Mooresville and Martinsville, Indiana. The family of Riley's mother, the Marines, were very close. Riley visited their families often as a child, adolescent and in his later years.