Based on the 1924 comic strip created by Harold Gray, the musical follows the adventure of little orphan Annie as she gets adopted by Billionaire Oliver Warbucks for the Christmas holiday. Chosen by secretary Grace Farrell, Annie meets and befriends all the members of the house staff including Drake the butler, Mrs. Pugh, Mrs. Greer, and many more. In a search for her birth parents, she finds herself meeting president FDR and spending some time with his cabinet. Working against her are Ms. Hannigan, the matron at the orphanage, her brother Rooster, and his girlfriend Lily St. Regis. With Warbucks, Annie discovers so much of the world she hadn't discovered before, learns the truth about her parents and finally finds herself a home.

Annie will be performed at the Windsor Club in Waban, Newton.