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 Glenna Walters as Tillie Boulter Philip Williams as Thomas Lynde Christian Martyn as Billy Andrews Ella Jonas Farlinger as Prissy Andrews Stephen Tracey as Mr. Phillips