In 1873, Elmira Montgomery joined her father, Robert Montgomery, and other founders of the Kingdom of the Happy Land as they traveled from Cross Anchor, South Carolina, to the mountains of western North Carolina. The group of about fifty people included many of Elmira’s relatives, such as her aunts and uncles Myrah Montgomery, Wiley and Rachel Bennett, and William and Louella Bobo Montgomery. Her cousin Sarah Bennett, close in age, was among the children traveling with them.

The Federal Census from 1870  lists Elmira in her father, Robert Motgomery's household. Her mother is unknown. The only adult woman present was Caroline Montgomery, who was just 10 years older than Elmira and 28 years younger than Robert—possibly making her Elmira’s sister rather than her mother.

Elmira and Robert are the only members of that household known to have relocated to western North Carolina. Elmira was likely between 8 and 13 when she left Cross Anchor with her father, and was a young adult by the time the Kingdom of the Happy Land property was purchased.

In 1887, around age 20, Elmira sold 40 acres of Happy Land property to her aunt Louella for $25. Likely inherited from her late father, the land was sold at a fraction of its value, suggesting Elmira aimed to keep the property within the family rather than profit from the sale.

In 1900, Elmira was living in Green River Township, Henderson County, with her uncle Wiley Bennett and her aunt Myrah Montgomery (Robert and Wiley’s sister). Also in the home was 11-year-old Lillie Montgomery, listed as Wiley’s niece. Lillie may have been Elmira’s daughter or cousin. The census shows Elmira had been married for 10 years and had four children, with only one surviving. No spouse is listed, and she still carried the Montgomery name. 

Sadie Smathers Patton also mentions a Lily Montgomery in her booklet. According to Patton, Lily Montgomery was a daughter of William and Louella Bobo Montgomery who "died early."

In 1916, the last resident of the Kingdom of the Happy Land, Jerry Casey, died. Community history asserts that Elmira cared for Casey at the Kingdom until he died. 

On the 1920 census, Elmira is listed as still living in Green River Township. She worked as a domestic servant and lived in her employer’s household. She was listed as single, with no mention of children.

By 1930, Elmira lived in Hendersonville with her aunt Rachel Bennett, the widow of Wiley. Elmira, still listed as single and in her sixties, continued working in domestic service for a private family.