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The Story of Westport Day School

Westport Day School was founded in 2013 by Dr. Dawn Matera, an experienced educator with a vision for redefining what specialized education could look like. The school’s roots are traced back to A Way to Learn, Dr. Matera’s thriving private tutoring practice, which supported students with learning disabilities and executive function challenges. Her practice quickly gained a reputation for personalized, compassionate instruction and life-changing academic support. 

Before launching Westport Day School, Dr. Matera honed her skills in individualized instruction and curriculum development through years of teaching at respected institutions such as Eagle Hill–Southport (now The Southport School) and Winston Preparatory School in Connecticut. These experiences gave her firsthand insight into the transformative power of personalized education—and the unmet needs that still existed for students who struggled to thrive in traditional settings.

The vision for a therapeutic day school came into focus when Dr. Matera partnered with Dr. Mark Beitel, a Westport clinical psychologist and innovative researcher. Together, they created a school model that blended rigorous academics with evidence-based therapeutic practices. Their shared passion gave rise to Westport Day School: a place where students could find both challenge and support; where learning differences and clinical challenges were met with understanding, and students were empowered to grow emotionally, socially, and intellectually. 

Today, Westport Day School stands as a beacon of possibility for families across Connecticut. What began as a passion project has grown into a State-Approved Special Education Program for the state of Connecticut and a fully accredited academic institution through the Middle States Commission on Higher Education. 

State-Approved Special Education Program

Accredited by the Middle States Commission on Higher Education

Enrolling up to 50 students (Grades 5–12+)

Now approved to enroll up to 50 students in its beautiful and nurturing space, Westport Day School remains steadfast in its mission: 

  • To maintain small class sizes that foster connection and engagement 

  • To invest in highly trained and well-compensated faculty and staff who are valued for their professionalism and expertise 

  • And to provide a transformative placement option for students in grades 5–12+ who deserve to be seen, understood, and inspired 

Every graduate of  Westport Day School carries with them not only academic skills but also a deep understanding of who they are—and the confidence to take on college, career, and life with strength and clarity.