The 2026 Middle School Play, Charlie and the Chocolate Factory, was performed on May 7 and 8 in the Stainton Hall Lecture Center. Directed by the Upper School’s Brett Sirolly ’26 and Catherine Vincent ’26, the play was written by Richard R. George and adapted from the beloved book by Roald Dahl.

Well-known for celebrating the power of imagination and championing virtue over vice, Pennington’s staging of this classic tale boasted a cast of over twenty students from Grades 6 through 8, as well as dozens of tech and costume crew helpers from both the Middle and Upper Schools. Teacher of English and History Jane Wilson served as the play advisor and costume co-director. 

In their program note, student co-directors Brett and Cat shared that when choosing which play to stage, “We wanted to land on a show that would be lighthearted and cheerful.” The larger than life Willy Wonka, described by the directors as a “wacky chocolate maker,” was played by eighth-grader Grady Meader, and the vivid purple of his costuming was reflected in the aprons of the many Oompa-Loompas bustling about the factory.

“This production started as a creative dream and a mess of whiteboard sketches,” explained Cat and Brett, “and we are beyond proud of how much everyone involved helped our vision grow. We wouldn’t trade the experience of working on this play and with these students for all the Wonka chocolate in the world.”