Woodcock was born in Winnipeg, Manitoba, but moved with his parents to England at an early age, attending Sir William Borlase's Grammar School in Marlow and Morley College. Though his family was quite poor, Woodcock had the opportunity to go to Oxford University on a scholarship; however, he turned down the chance, because he would have had to acknowledge a religious affiliation. Instead, he took a job as a clerk at the Great Western Railway and it was there that he first became interested in anarchism (specifically libertarian socialism). He was to remain an anarchist for the rest of his life, writing several books on the subject, including Anarchism, the anthology The Anarchist Reader (1977), and biographies of Pierre-Joseph Proudhon, William Godwin, Oscar Wilde and Peter Kropotkin.

It was during these years that he met several prominent literary figures, including T. S. Eliot and Aldous Huxley. He first came to know George Orwell after the two had a public disagreement in the pages of the Partisan Review. Orwell wrote that in the context of a war against Fascism, pacifism was "objectively pro-Fascist". As a pacifist himself, Woodcock took exception to this. Despite this difference, the two met and became good friends. Woodcock later wrote The Crystal Spirit (1966), a critical study of Orwell and his work which won a Governor General's Award.

Woodcock spent World War II working on a farm, as a conscientious objector. At Camp Angel in Oregon, a camp for conscientious objectors, he was a founder of the Untide Press, which sought to bring poetry to the public in an inexpensive but attractive format. Following the war, he returned to Canada, eventually settling in Vancouver, British Columbia. In 1955, he took a post in the English department of the University of British Columbia, where he stayed until the 1970s. 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.

Towards the end of his life, Woodcock became increasingly interested in what he saw as the plight of Tibetans. He travelled to India, studied Buddhism, became friends with the Dalai Lama and established the Tibetan Refugee Aid Society. He and his wife Inge also established Canada India Village Aid, which sponsors self-help projects in rural India. Both organizations exemplify Woodcock's ideal of voluntary cooperation between peoples across national boundaries.

George and Inge also established a program to support professional Canadian writers. 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. The Fund is available to writers of fiction, creative non-fiction, plays, and poetry. The Woodcock's helped create an endowment for the program in excess of two million dollars. The Woodcock Fund program is administered by the Writers’ Trust of Canada and has distributed $772,147 to 164 Canadian writers, as of July 2010.

Woodcock was honoured with several awards, including a Fellowship of the Royal Society of Canada in 1968, the UBC Medal for Popular Biography in 1973 and 1976, and the Molson Prize in 1973. However, he only accepted awards given by his peers, refusing several awards given by the Canadian state, including the Order of Canada. The one exception was the award of the Freedom of the City of Vancouver, which he accepted in 1994.

He is the subject of a biography, The Gentle Anarchist: A Life of George Woodcock by George Fetherling (1998).