Born in Saskatchewan in 1946, Woolfitt moved to Toronto in 1965 to study at York University. While exploring the local art scene, Woolfitt learned about Colour Field painting. An introduction to the works of Mark Rothko, Morris Louis, Hans Hofmann and Jules Olitski sparked his interest in non-objective subject matter, and his foray into painting began.

In 1972 he founded the Woolfitt’s School of Contemporary Painting, where he taught until 1979. In 1978 he established Woolfitt’s Fine Art Supplies, an international distributor of artist materials which he managed until it was sold in 2014. In 2017, he founded The modern.toronto, a museum dedicated to the exhibition of non-objective painting and sculpture.

Woolfitt has had 25 solo exhibitions and more than 15 group exhibitions in Canada, Japan, Thailand and Chelsea, New York. Most recently a major solo exhibition of abstract drawings at the Art Gallery of Ontario. His paintings are in numerous museum, corporate and private collections internationally. In Canada his work can be found in collections at the MacLaren Art Centre, Hart House at the University of Toronto, the Remai Modern and The Robert McLaughlin Gallery.