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 Philip Williams as Thomas Lynde Kyle Meagher as Paul #1 Christian Martyn as Billy Andrews Ella Jonas Farlinger as Prissy Andrews Brian Tree as Minister Janet Porter as Mrs. Andrews Stephen Tracey as Mr. Phillips Brenda Bazinet as Jeannie