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 Kyle Meagher as Paul #1 Daimen Landori-Hoffman as Paul #2 Joanna Douglas as Miss Muriel Stacy Brian Tree as Minister Deborah Grover as Josephine Barry Ashleigh Stewart as Winifred Rose Brandon Oakes as Aluk Dana Jeffrey as Oqwatnuk Kiawentiio as Ka'kwet