Guest Stars Helen Johns as Mrs. Eliza Barry Jonathan Holmes as Mr. William Barry Kyla Matthews as Ruby Gillis Jacob Ursomarzo as Moody Spurgeon Lia Pappas-Kemps as Jane Andrews Jacob Horsley as Charlie Sloane Miranda McKeon as Josie Pye Ryan Kiera Armstrong as Minnie May Barry Glenna Walters as Tillie Boulter Daimen Landori-Hoffman as Paul #2 Christian Martyn as Billy Andrews Philip Williams as Thomas Lynde Kyle Meagher as Paul #1 Ella Jonas Farlinger as Prissy Andrews Brian Tree as Minister Janet Porter as Mrs. Andrews Stephen Tracey as Mr. Phillips David Ingram as Mr. Harmon Andrews Trenna Keating as Mrs. Pye Cara Ricketts as Mary Lacroix