Wolstenholme studied at the Nova Scotia College of Art and Design (NSCAD) between 1982 and 1986 and re-enrolled in 1989.[3] After completing her Master of Fine Arts degree at the State University of New York, she returned to NSCAD in 1996 to teach.[3]
In 1997, Wolstenholme toured the rock festival Lilith Fair, with her long-time friend, Sarah McLachlan.[3] Colleen had co-written a song on McLachlan's album Surfacing and earned a gold record.[3]