Guest Stars Helen Johns as Mrs. Eliza Barry Jonathan Holmes as Mr. William Barry 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 Kyle Meagher as Paul #1 Daimen Landori-Hoffman as Paul #2 Joanna Douglas as Miss Muriel Stacy Deborah Grover as Josephine Barry Ashleigh Stewart as Winifred Rose Araya Mengesha as Elijah Hanford
