Ann Shepard was born and raised near St. Andrews, Scotland. She moved to Canada in 1968 after marrying and completing university. In high school, Ann hated knitting, but as her mother and grandmother would knit gifts for Ann’s children, she took it up once again. She started with simple cushion covers and patterns. From there, she learned to knit full sweaters and more complex patterns. Traditionally, each family had a specific pattern that would distinguish themselves from other families. This inspires Ann to always be trying new knitting patterns. Like her mother and grandmother, Ann simply gifted away her beautiful knitting, until Stefi McLean, a local potter, encouraged her to sell her sweaters. She's been part of the gallery from its humble beginnings. She even named the Whistle Stop Gallery through a contest.