Head of School's Welcome

Dear Families,

From the moment I first stepped onto The Country School campus as Head of School and as a parent (now 5th and 8th graders!), I was embraced by a vibrant community defined by warmth, curiosity, and a deep sense of tradition. Since its founding, TCS has remained steadfast in upholding values of care, integrity, and intellectual curiosity—qualities evident in every classroom, every conversation, and every corner of campus life. The Country School is, and always will be, a school grounded in traditional, foundational academics and our graduates reflect this philosophy as they head into the world.

At TCS, the joy and challenge of learning extend far beyond the classroom—to outdoor adventures, artistic expression, and athletic pursuits. As a school family, we are united in our commitment to fostering academic excellence, cultivating strong character, celebrating diversity, and inspiring a lifelong love of learning. These shared values empower our students to reach their fullest potential and become thoughtful, capable leaders of tomorrow. 

For over ninety years, The Country School has been inspiring children to “do their best always.” As Head of School, I am honored to work alongside our exceptional educators and staff to carry this tradition forward. Founded in 1934 by a group of devoted parents and Headmistress Mrs. Dorothy E. Startt, TCS has grown into a thriving Pre-k-8 independent school, serving 330 students from across Maryland’s historic Eastern Shore.

Our Pre-k-8 model is intentional and powerful. It creates a nurturing and dynamic environment where younger students look up to their older peers, and older students grow into compassionate leaders during a pivotal stage in their moral and academic development. Though we continue to innovate—with modern facilities and a forward-thinking faculty—the true strength of TCS lies in its people. It is the relationships we build, the community we foster, and the values we live each day that define who we are. We believe in living our values every day, and pursuing each opportunity with an enduring sense of honesty, respect, responsibility, compassion, generosity, commitment, cooperation, fairness and moral courage. 

As I embark on my second year as a Country School Cougar, I do so with excitement and gratitude knowing all the incredible memories that continue to lie ahead, including a very special year as an 8th Grade parent! I am humbled to be entrusted with the leadership of this great institution, and along with the rest of our faculty and staff, the education of our children. I can not wait to greet you under the bell tower each morning, it is the highlight of each day!

Sincerely, 

Jay Parker, Head of School