Today there is little known of the man and his life, but The Church of Jesus Christ of Latter-day Saints vital statistics database records that he was born on 15 November 1877 in the town of Fairfield, Franklin county, Vermont. He married Estella W. Goodspeed on 14 September 1913 in Montclair, Essex, New Jersey.

Bailey wrote numerous stories involving animals, similar to the style of another popular children's writer of the time, Thornton W. Burgess (1874-1965). In "The Tale of Freddie Firefly" Freddie is part insect, part human. Other endearing insect characters are Chirpy Cricket, Greenie Grasshopper, Kiddie Katydid, and Jennie Junebug. The well dressed Brownie Beaver, Cuffy Bear, Fatty Coon, and Sandy Chipmunk, among others, populate the charming whimsical tales. Rich in adventure and lessons in responsibility and growing up, they also teach easily understandable information about the animal world. Bailey weaves tales that are enchanting and educational, with references to nursery rhymes and folklore, lushly illustrated by Harry L. Smith.