Wooster School

Wooster School, founded in 1926, is a day school in Danbury, Connecticut, located one hour north of New York City. It serves 300 to 500 students in middle and upper school grades. The school has built its reputation on progressive education and remains known regionally and nationally for innovative teaching practices. Its founding mission—"from each according to what he has, to each according to what he needs"—still shapes how faculty recognize each student's individuality and design instruction around real needs rather than uniform pacing.

Teaching at Wooster means real curriculum influence. Faculty design courses, pilot new instructional methods, and shape humanities offerings across grade levels without layers of approval common at larger schools. You teach five days a week, coach or lead activities, and then leave campus. This day-school structure lets teachers maintain lives outside school walls while staying deeply involved in student learning.

Wooster's financial position—net assets over $14 million—supports small class sizes and ongoing professional development. Salaries track independent school norms. Health coverage and retirement contributions are standard. The school invests in faculty growth, not just program overhead. For teachers seeking pedagogical freedom without boarding school residence requirements or rural isolation, Danbury offers suburban access to both school and city.

Upper School humanities and English positions represent the most recent hiring focus. Spanish and other language instruction openings emerge regularly. Administrative and support roles fill as needs arise. Wooster seeks faculty who value progressive methods and want direct input on curriculum and teaching approach.

Teachers drawn to day-school independent education find Wooster's combination of pedagogical autonomy, reasonable commute, and engaged student body compelling. The chance to design your own teaching keeps senior faculty engaged across decades.