Dr. Bailey received his Bachelor of Arts degree in 1927 from the University of New Brunswick and completed his Master of Arts (1929) and Doctorate (1934) degrees at the University of Toronto, with specialization in ethno-history and aboriginal culture. He was awarded a Royal Society of Canada Fellowship for Research in 1934 to study at the School of Economics and Political Science at the University of London. Following completion of his studies abroad, Dr. Bailey was awarded a Carnegie grant to study British and continental museum administration.
From 1935-1938, Dr. Bailey worked as assistant director and associate curator at the New Brunswick Museum in Saint John. The provincial government funded a chair in history at the University of New Brunswick in 1938, and Dr. Bailey served as the first head of the UNB History Department from 1938-1969.
Dr. Bailey's literary interests led to the founding of the Bliss Carman Society in 1940 and to his co-founding of The Fiddlehead, Canada's oldest literary magazine, in 1945.
From 1946-1959, Dr. Bailey served as Honorary Librarian and Chief Executive Officer of the UNB Library. He worked closely with Lord Beaverbrook during the construction of the wing for the Bonar Law-Bennett Library, which opened in 1951, and Lord Beaverbrook frequently sought Dr. Bailey's advice on books which he purchased or donated to the library.
In addition to his activities as poet, teacher, and librarian, Dr.Bailey served in a variety of administrative positions during a period in which Canadian universities were experiencing rapid growth and were moving towards increased democratization within their governing structures. Dr. Bailey was appointed the first Dean of Arts at UNB and served in this office from 1946-1964, and from 1965-1969, he served as Vice President (Academic) at UNB. Dr. Bailey retired from UNB in 1970 and was appointed Professor Emeritus.
Dr. Bailey has written several books of poetry and scholarly historical and anthropological works. His publications include Songs of the Saguenay and other poems (1927); Tao: A Ryerson Poetry Chap Book (1930); The Conflict of European and Eastern Algonkian Culture 1504-1700: A Study in Canadian Civilization (1937; 1969); Border River (1952); Culture and Nationality: Essays (1972); Thanks for a Drowned Island (1973); Miramichi Lightning (1981); and The Letters of James and Ellen Robb: Portrait of a Fredericton Family in Early Victorian Times (1983). He also served as an editor for the standard Canadian literary reference work, The Literary History of Canada.