Guest Stars Kyla Matthews as Ruby Gillis Lia Pappas-Kemps as Jane Andrews Jacob Ursomarzo as Moody Spurgeon Miranda McKeon as Josie Pye Jacob Horsley as Charlie Sloane Glenna Walters as Tillie Boulter Christian Martyn as Billy Andrews Kyle Meagher as Paul #1 Daimen Landori-Hoffman as Paul #2 Ella Jonas Farlinger as Prissy Andrews Joanna Douglas as Miss Muriel Stacy Janet Porter as Mrs. Andrews David Ingram as Mr. Harmon Andrews Trenna Keating as Mrs. Pye Cara Ricketts as Mary Lacroix