George Woollard was born in 1946 on Cape Cod in Massachusetts. He later lived in Wisconsin where his father, also named George, worked as the director of the Institute of Geophysics. In 1962 the family moved to Honolulu, Hawaii at the invitation of the University of Hawaii where George senior was wanted to set up a new institute of geophysics. George junior finished high school in Honolulu at Punahou Academy and went on to study at Willamette University in Salem, Oregon and the Institute for American Universities in Aix-en-Provence in France. He eventually earned a BA degree in painting and later an MFA degree in printmaking from the University of Hawaii. In 1982 George was awarded an artist's fellowship to pursue his work at the Cite Internationale des Arts in Paris.

Upon completion of his MFA in 1977, George started parallel careers in teaching and in making art. George has given instruction in drawing, painting with watercolor and acrylics, and various forms of printmaking. He has taught classes at the University of Hawaii, Chaminade University, Windward Community College, Kapiolani Community College, and since 1995 at the Art Centre of the Honolulu Academy of Arts. He has also been on the art faculty of Cleveland Institute of Art's program in Lacoste France, in 1992. In addition, George has been directing and teaching artist's workshops both in Hawaii and Europe.

As a professional artist, George is a regular participant in art exhibitions at home and abroad. His work can be found in many public and private collections including the Honolulu Academy of Arts, the Contemporary Museum in Honolulu, the Hawaii State Foundation on Culture and Art, the University of Hawaii, Exxon Corp, The Biblioteque Nationale in Paris, the Laguna Gloria Museum in Austin, Texas, Kaiser Foundation, and Bank of Hawaii.