I began even as a boy to realize how wide the world can be for a man of free intelligence.

Around this time he started to write more prolifically producing several travel books and collections of poetry as well as the works on anarchism for which he is best known. The Woodcock Fund which began in 1989 provides financial assistance to writers in mid-book-project who face an unforeseen financial need that threatens the completion of their book. Though his family was quite poor Woodcock had the opportunity to go to Oxford University on a partial scholarship; however he turned down the chance because he would have had to become a member of the clergy.

He is perhaps best remembered elsewhere for writing Anarchism: A History of Libertarian Ideas and Movements (1962) the first post-War history of anarchism. He founded in 1959 the journal Canadian Literature the first academic journal specifically dedicated to Canadian writing.