You’re a sixth grader. Way back in the fall, shortly after the start of school, you stepped outside your comfort zone, deciding to take a chance on something you’d never tried. Venturing into the unknown was at first terrifying, a feeling that dissipated as it was consumed by the hard work of learning new skills, focusing on the tasks at hand, and absorbing as much of this new world as possible. As winter inched toward spring, the big day approached, and rehearsals ramped up. Characters became fully realized, costumes came together, carefully constructed set pieces began to appear in your practice spaces, and lighting designs took shape. The calendar creeps onward, and, before you know it, the day of the show arrives. It all comes down to this.    

You feel a hum of anticipation in the air, a buzz that intensifies as the house lights dim and spotlights illuminate the stage. Theatergoers shift, settling into their seats, and the actors offstage make the final touches to their costumes, taking a collective deep breath as the room goes silent. After months of hard work—all the rehearsals, set building, costume design, meticulously planned lighting cues—it’s showtime. 

For the last fifteen years, the theatre program at Windward has quietly been elevating itself to the hallmark program it is today: little by little, show by show, student by student. “There was no drama program at Windward when I arrived fifteen years ago,” said Performing Arts Chairperson Betsy Hooper. “At Westchester, we performed in the cafeteria, rehearsing to the sounds of people chopping carrots and bus announcements blaring over the loudspeakers.” In fact, during the first four years of Ms. Hooper’s tenure, there were no provisions or staffing for musical accompaniment of shows, which necessitated some creative problem solving on her part. “I found myself writing scripts with fifty speaking parts,” she explained, “because each child had to have a line or two as there was no option to cast large groups as the chorus. The biggest changes in [Westchester’s] after-school program came when the auditorium was built and we hired Stefano Peña as our musical director. That’s when we began doing musicals and musical revues.” 

Even with its modest beginnings, Windward’s drama program has always adhered to a simple vision: a shared desire to encourage students’ self-expression through art. This perspective shapes everything it produces, as well as creating a safe space for students to express themselves, tap into their creativity, and take artistic risks. 

Windward’s drama program adheres to a simple vision: a shared desire to encourage students’ self-expression through art. 

Aligned with the School’s instructional model, the drama program follows research-based, explicit, systematic techniques grounded in direct instruction. Because theatre is a language-based discipline, it dovetails nicely with the intensive instruction in language arts students receive through their academic coursework. “Drama helps students feel comfortable expressing complex language, builds verbal skills, including reading aloud with expression and memorization, improves reading comprehension, and encourages empathy,” Ms. Hooper said. 

To accommodate the specific needs of our student population, the planning process starts early for each show the drama program presents. “Time, time, time, time. This is the most important element of rehearsal for our kids,” Ms. Hooper explained. Director of Manhattan Drama Program Elly Steiker-Pearl added, “We like to start [the rehearsal process] in the fall and perform in the spring so that there is time for the kids to learn lines, staging, character motivations, etc., without them feeling rushed.” 

This incredibly intentional process pays dividends, both in the finished products—the shows themselves—and in their effects on students’ social and emotional development. 

Taking Risks, Building Confidence  

One of the biggest soft skills that Windward’s drama program espouses is leaning into mistakes. In fact, embracing the notion of fearlessly taking creative risks is a core tenet of the program. One rule, which many artists implicitly understand, is that expecting perfection is a death knell for creativity. Windward’s drama program takes no exception to this rule. Ms. Hooper tells her students, “Don’t be afraid to be wrong. We learn by making mistakes. Really, you don’t learn if everything goes perfectly every time.” In Manhattan, the message is the same. According to Ms. Steiker-Pearl, “I always tell my cast I don’t want a perfect performance. When something goes wrong, how do you adjust? Some of the funniest, most delightful moments happen when kids get back on track after something unexpected occurs on stage.” 

When students feel comfortable trying different approaches without fear of judgment, there is a ripple effect: They are able to lean into vulnerability from a place of psychological safety, which reinforces their decision-making processes, which, in turn, boosts their confidence in themselves. Will Cranch, former co-director of Windward’s Manhattan drama program (who relocated out of state at the end of the 2022-2023 school year), put it simply: “We really emphasize the independence of the students. They get support, but the goal is to have them be independent.”  

And our drama program’s faculty members truly walk the walk embodying this idea; students manage technical aspects of the shows themselves. For example, Manhattan’s production of “Chitty Chitty Bang Bang” in spring 2023 had a fifth grader in the role of props master. Ms. Steiker-Pearl said, "She effectively ran the backstage. Her growth in owning that role was amazing to see.” 

Mr. Cranch added, “She could move to Broadway and do it. Initially she was overwhelmed by everything she had to do, but after some positive reinforcement—‘you’ve got this, you’re doing incredible work’—and talking with the cast about following her instructions, she really shined.” 

This transformation, developing pride in one’s own talents and abilities and a greater fearlessness when it comes to taking risks, is the heart and soul of all Windward’s programs but manifests with beautiful clarity in the drama program. Manhattan Music Director Dan Wilson explained, “Students I teach in an academic setting were completely different kids onstage. It’s so impressive to their other teachers seeing this side of them, seeing them go from being untested to blowing away their teachers and parents.” 

Building a Show  

Giving students adequate preparation time for all that goes into a production is one key ingredient of a successful show, but there are many more factors at play. Planning begins each summer, as the drama program’s faculty members brainstorm for the next year, looking at scripts, selecting a play, and developing a vision for that show. Auditions are held in the fall, with rehearsals starting shortly thereafter. The essentially yearlong process is wholly intentional, to allow students to reach the comfort level with the material that results in the best audience experience.  

For the actors, the first order of business is the decoding work. Ms. Steiker-Pearl noted, “A script is an enormous amount of text for our students.” The goal is to encourage students to eventually view the language through a different lens, as a means of emotional and creative expression. Students explore the way a character’s vocabulary helps define them, or how slang or idioms are reflective of different historical periods or geographical locations. For example, the Westchester drama program presented “Guys and Dolls” in spring 2023, which is set in 1950s-era New York City. Manhattan’s production of “Chitty Chitty Bang Bang” takes place in England in the 1930s. “There's a repeated joke about the slang term bob related to shillings—we had to be clear about what that joke means,” Mr. Cranch explained. This winter, the fifth-grade drama program at Westchester Lower School, directed by Carrie Minio, also put on an era-specific show, a musical revue called “That 60s Show.”  

Next, with the support of faculty members, students dig into the work of developing their characters and understanding their motivations. “This parallels the comprehension work they’re doing in language arts classes from a character perspective,” Ms. Hooper said. 

The next piece is memorization, a process heavily scaffolded for our students, with ample support offered and clear deadlines established. In true Windward fashion, drama program faculty members are patient with students throughout this process, highlighting progress over perfection. “We work with them about what to do when someone forgets a line. How do you get the scene back on track? It’s about working on productive improvisation,” said Assistant Director of Manhattan Drama Program Bradly Valenzuela. 

The musical elements receive the same care and consideration in planning. Music Directors Stefano Peña (Westchester) and Dan Wilson (Manhattan) are keenly aware of the need for maintaining consistency for our students, which translates to creating clear musical cues for actors and helping students understand the link between music and characters’ expression of feelings. “The goals of the music are to enhance the characters’ emotions and teach students about different parts and singing with complex harmonies,” Mr. Peña said. Mr. Wilson added, “We also pay attention to playing the music the exact same way every time so kids know where to come in. Improvising is only for emergencies.” 

Of course, the students working backstage are as critical to each production as those working onstage. Ms. Hooper, who admits her love of theatre is based entirely on backstage work, designed the drama program to ensure that creative non-actors play an important role in each show. Students help paint and design sets, help design and run lighting, and are entirely responsible for being the backstage crew during performances. “That old idea that if a kid wants to participate but doesn’t want to do much, then we should just ‘let them work backstage’ isn’t part of our program,” Ms. Hooper explained. “There is no one in the cast or crew who isn’t working incredibly hard all the time. Putting on a play is demanding work, which is why it’s ultimately so satisfying.” 

In Brief: Ms. Hooper’s Philosophy 

• If something isn’t working, don’t be afraid to start over. Be critical of your own work and be willing to fix it.   

• Don’t be afraid to be wrong. We learn by making mistakes.  

• Practice makes better.  

• Give yourself enough time to complete your task. Don’t rush creative thought. 

• Don’t be scared to try something new.  

• Be openhearted to others so that you can create a community.   

• Collaboration is fun. Work with others—listen to others’ ideas.   

• Drama is life—conflict and resolution are the stuff our lives are made of.   

For our students, the work of producing a play is a labor of love, one that bolsters self-confidence, strengthens peer connections, and expands students’ notions of what they can accomplish when they fully lean into a task. To not only glimpse what is possible but to embody this potential: It is the heart of what we do at Windward.