Upland Country Day School

Upland Country Day School enrolls about 250 students in pre-school through middle school in Kennett Square, Pennsylvania, in Chester County near the Delaware border. The school is independent and nonsectarian. Its curriculum balances academics with arts and athletics woven into daily instruction rather than treated as separate programs. Latin and Spanish language study begin in the early grades, giving students a linguistic foundation before high school.

Teaching at Upland Country Day School differs from boarding school roles in one essential way: you go home at the end of each day. Faculty teach and coach, then step away from campus. That boundary matters for work-life balance and personal renewal. With fewer than 300 students, you will know families by name and see how your classroom work translates into student growth across years. Teachers here design instruction around individual student strengths while maintaining high academic standards for all learners.

The school expects faculty to encourage intellectual risk-taking and build student persistence through challenging material. Curriculum design carries real weight—teachers shape what gets taught and how, not simply execute mandated lessons. Leadership roles in a school this size influence school culture in visible ways. Faculty retention tends to be strong, which means colleagues stay and relationships deepen.

Upland Country Day School maintains solid financial footing with over $7.6 million in net assets and steady fundraising momentum. Recent leadership hiring reflects ongoing school investment. Day school positions typically include teaching and coaching; specific salary and benefits packages depend on role and experience level.