Superintendent of Schools

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. Anna 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, followed by a Master’s degree 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), both from the University of Connecticut. 

Dr. Cutaia’s career path has touched every segment of the educational leadership spectrum.  She started her career in Myrtle Beach, SC, where she served as a teacher (1991-1998), an assistant principal (1998-2000), and principal (2000-2003).  In 2003, Dr. Cutaia moved to Connecticut and served as principal of Casimir Pulaski Elementary School in Meriden.  During her early years in Connecticut, Dr. Cutaia also worked with the Connecticut State Dept. of Education (CSDE) as an educational consultant and as an adjunct professor at the University of Connecticut and Southern Connecticut State University.  Dr. Cutaia served for six years as the Director of Elementary Education in the Fairfield Public School district.  Prior to coming to Milford, she served as the Superintendent of Schools for Regional District 14 for four years, encompassing the communities of Bethlehem and Woodbury. 

Dr. Cutaia has also served as an adjunct professor in the area of 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.

Dr. Cutaia is involved in many professional and local organizations.  Since 2014, she has been an active participant of the Superintendent's Network of the Connecticut Center for School Change and is a member of the College Board Connecticut Advisory Committee.  She is a member of 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.  

You can reach Dr. Cutaia via email at 

You can also follow her on Twitter - @MilfordSuper.