British-born Violet Cherrington spent most of her working life (1922-52) as Principal of Bishop Spencer College, a Church of England school for girls in St John's, Newfoundland. This article focuses on her as a woman, educator and national subject in Canadian history, and it is written as three accounts rather than a single narrative. The first account is based on texts that were mostly written by Cherrington in the 1920s and 1930s when Newfoundland was a British Dominion and then recolonised in 1933. The second account uses texts from the 1940s and 1950s and thus it covers Cherrington's retirement and death as well as Newfoundland's conversion from British colony to Canadian province. The final account focuses on texts including a walking tour, encyclopedia entry and novel that write Cherrington and Bishop Spencer College into the historical imagination to the present day. The interplay between texts and contexts means that some aspects of Cherrington's life and work are illuminated while others are downplayed in each time period. In essence, the article produces several images of Cherrington's working life as a woman, educator and national subject from the 1920s to contemporary times.