 Bowles attended Springfield High School; Phillips Academy, in Andover, Massachusetts; and Harvard, from which he graduated in 1912 after having served as business manager of "The Harvard Crimson".After working a year at "The Republican", he spent two years as circulation manager of the Philadelphia, Pennsylvania "Public Ledger", then two years with the "Springfield Daily News", his family's weekday-evening paper.After two years with the US Marine Corps during World War I, he became publisher of his family newspapers, which also included the "Morning Union", and Sunday's "The Springfield Union and Republican".