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 Christian Martyn as Billy Andrews Kyle Meagher as Paul #1 Daimen Landori-Hoffman as Paul #2 Philip Williams as Thomas Lynde 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
