Born in Iowa in 1889 and educated there, Eleanor Hobby moved to Hawai‘i in 1914 with her husband, William Hobby, an engineer who had taken a job in Hilo with the Department of Public Works.
There, Eleanor taught school for a year until 1916, when her husband transferred to Honolulu.
In 1919, after three years in Honolulu, Mr. Hobby accepted another position as engineer at Lihu‘e Plantation and the Hobbys moved to Kaua‘i, where Eleanor began her long career as an educator of two generations of Kaua‘i’s school children, until 1954, when she retired.
Her first teaching appointment on Kaua‘i was as one of three teachers assigned to the High School English Standard Annex, which was located on the grounds of Kaua‘i High School and included grades one through eight. (In 1926, the High School English Standard Annex was added to Lihu‘e School in Pua Loke, situated in the area nowadays occupied by a park, government buildings and M. Kawamura Enterprises.)
Mrs. Hobby taught for three years at the High School English Standard Annex, then taught for one year at Lihu‘e School, where the principal was Mrs. Edith Troeller.
She then succeeded Mrs. Dora Ahana for a year as principal of Huleia School, which at that time during the 1920s was a fair-sized school with about 155 pupils. Huleia School was located not far down the dirt road beginning just to the left of the William Hyde Rice Monument at the end of Kipu Road.
From Huleia School, Eleanor served as principal of Makaweli School for four years, followed by 19 years service as principal of ‘Ele‘ele School.
Mrs. Hobby’s last principalship, from 1952 to 1954, was at Lihu‘e School, once again succeeding Mrs. Dora Ahana.
Eleanor and William Hobby had three children: Ruth, William and Richard.