Rideout's father, a miller and road contractor, died when Rideout was twelve. Rideout's elder brother, who managed a bank in California, became the support of the family. At school, Rideout's ability caught the attention of his English teacher, Laura Burns, who was a cousin of the distinguished Harvard professor of English, Charles Townsend Copeland. She and Copeland motivated a group of Calais townspeople to lend Rideout the wherewithal to enter Harvard in 1895, where he was the first in his family to attend college. At Harvard, his literary talent came to the fore. Eventually he became Editor-in-Chief of "The Harvard Monthly". His friends at Harvard included William Morrow, William Jones, Raynal Bolling, and Arthur Ruhl. After graduating in 1899 as Class Odist, Rideout was an instructor in the Harvard English department.