Bailey served in the Vermont Senate from 1894 to 1896, and was a member of the committees on education, railroads, and the state prison, as well as a joint committee that examined unexpected spending increases on the prison. He was also appointed a member of the state Fish and Game Commission in 1894, and he served until 1900. As a Fish and Game commissioner, Bailey was credited with management improvements at the state fish hatchery, and was also selected to oversee construction of a dam at the outlet of Lake Morey in Fairlee. He was a member of the Vermont Republican State Committee from 1894 to 1904.
