Superintendent's Office

The Superintendent’s Office serves as the primary connection between the elected 10-member Board of Education and the entire Milford Public Schools organization.

Dr. Anna Cutaia, our Superintendent of Schools, is the liaison between these two sectors. She oversees all day-to-day operational activity, instructional programming, and staff management and communicates with the Board frequently to keep everyone informed of all district activity.

In addition, she frequently works with our city officials on a variety of issues and is an eager partner in the many community activities conducted in Milford.

Dr. Cutaia holds the position of Superintendent of Schools in Milford. She began her appointment in Milford on August 1, 2018. She received her Bachelor of Arts degree from Mount St. Mary College in 1991 and a Master’s in education from the University of Southern Mississippi in 1997. While working as an educator for several years, Dr. Cutaia continued her post-graduate studies and received her certificate in the Executive Leadership Program (2007), followed by a Doctorate in Education (2013) from the University of Connecticut.

Dr. Cutaia’s career in education has been a rich tapestry, touching every facet of educational leadership. She began in Myrtle Beach, SC, as a teacher (1991-1998), then transitioned to roles as an assistant principal (1998-2000) and principal (2000-2003). Her journey continued in Connecticut, where she served as the principal of Casimir Pulaski Elementary School in Meriden. During her early years in the state, she also contributed to the Connecticut State Dept. of Education (CSDE) as an educational consultant and adjunct professor at the University of Connecticut and Southern Connecticut State University. Dr. Cutaia's leadership extended to the Fairfield Public School district, where she served six years as the Director of Elementary Education. Before her current role in Milford, she served as the Superintendent of Schools for Regional District 14, working with the communities of Bethlehem and Woodbury.

Throughout her 33 years in the field of education, Dr. Cutaia contributed to helping to strengthen and develop the profession through numerous professional presentations and opportunities to teach. Dr. Cutaia served as an adjunct professor in reading for Southern Connecticut State University in 2013-2014. Since 2015, she has taught for UCONN as an adjunct professor and lead instructor in their Principal Preparation Program. Additionally, she teaches in the Superintendent Certification Program at UCONN and Sacred Heart University. Dr. Cutaia helped establish a Teacher Leader Doctoral Program and is an adjunct professor at Fairfield University.

Dr. Cutaia is involved in many professional and local organizations. Since 2014, she has actively participated in the Superintendent's Network of the Partners for Educational Leadership. She served on the NEAG School of Education Alumni Board at UCONN. She also serves on the local boards of the Milford Chamber of Commerce and the Milford United Way.

Harkening back to her years in teaching, Dr. Cutaia received numerous awards for her exemplary contributions to young people and school communities, including Lakewood Elementary’s Teacher of the Year in 1997. In 2021, Dr. Cutaia's exceptional leadership was recognized when she was named ‘Superintendent of the Year’ by the Connecticut Parent Teacher Association. Additionally, she was recognized with the 2024 Connecticut Arts Administrators Association Arts Advocacy Award. Finally, she was named the 2024 Italian American of the Year by the Milford Columbus Committee. These prestigious awards represent her unwavering commitment to education and significant contributions to the field.

On a personal note, one of her favorite pastimes includes gathering around the dinner table with her family enjoying traditional Sicilian dishes.

You can reach Dr. Cutaia via email here.