Bailey attended the public schools of Fitchburg, Massachusetts. When he was 17 Bailey started work as an apprentice for the Bellows Falls Gazette. By 1844 Bailey became editor and publisher of the newspaper.[1]
In 1845 Bailey began to study law, first with William C. Bradley in Westminster, Vermont, and later with the firm of Torrey and Wood in Fitchburg.[1]
Bailey served on the Fitchburg, Massachusetts school committee from 1849 to 1854. He was appointed postmaster of Fitchburg on May 3, 1851, and served until May 4, 1853, when his successor was appointed.
Bailey served as member of the Massachusetts house of representatives in 1857. He served in the Massachusetts State Senate 1858–60. Bailey was the Republican Party candidate for congress in Massachusetts' ninth congressional district in the 1860 election.[1]
^ abcdeEmerson, William Andrew (1887), Fitchburg, Massachusetts, Past and Present, Fitchburg, MA: Press of Blanchard & Brown, p. 284, hdl:2027/loc.ark:/13960/t5db8626n