Schools
Get To Know Milford Superintendent Of Schools Dr. Anna Cutaia
Cutaia shares her biggest surprise to date, what she's currently working on, and why you might call her the district's biggest cheerleader.

MILFORD, CT — The first thing you notice about Milford's new Superintendent of Schools Dr. Anna Cutaia is how approachable, down-to-earth and happy she is in her own skin. Last week, Cutaia met with the assembled Milford media, which includes yours truly, the Milford Mirror's Jill Dion, and the New Haven Register/Connecticut Post's Pamela McLoughlin.
Cutaia has been on the job in Milford since Aug. 1 after being hired by the Board of Education in the spring to replace Dr. Elizabeth Feser, who retired after leading the district since 2011.
Cutaia held court with the fourth estate in her office for about 45 minutes, where she displayed an abundance of humor, genuine affection for Milford students and the local community. She makes you feel right at home, which is not always the case with top officials, who often view the media the way our current President does.
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"Milford has embraced me, and I am so thankful for that. They've been warm and welcoming. I'm excited for the next chapter," Cutaia said when asked what has impressed her the most about Milford.
"It's been a fantastic novel. I can't wait to read the next chapter," she added.
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Listen and Learn Tour
If you were hoping Cutaia would share at this early juncture all the things she plans to change in the Milford Public Schools you're going to be disappointed. She made it clearly repeatedly that she is in a six month "listening tour" where she is meeting with all different groups of people in Milford and getting their thoughts on the school system.
She said she is eager to hear their input on what they are most proud of, where they believe the school system can grow and what is important for them to know about the organization.
"The first six months are critical and my goal is to understand what our community wants," Cutaia said. "We want to make sure our goals align with what the community wants."
She plans to hold public events in October and November so people can share their opinions of the school system.
Top Impression Of Milford To Date
"The people are proud here and the community supports their schools," Cutaia said.
Cutaia said Milford has 14 schools, 5,600 students and the city is pretty big but the "people see us as a tight community. While large, we work together to do great things for the kids."
She said it's clear parents and students have extreme confidence in the staff, which she called "highly capable and committed team in all of our schools."
Youths Grow Up Even Faster Today
She said as an educator she is committed to improving opportunities that students have and that students are pursuing career opportunities fast.
"We're not going to wait until high school for kids to know what they want to be," Anna said, while saying she wants the schools to offer even more opportunities in science, math and the arts.
She said she also wants to support teachers in their professional growth.
Milford Schools Biggest Cheerleader
Cutaia embraces social media and uses Twitter to show some of the best and lighter moments in the Public Schools. Feel free to follow her at @milfordsuper on Twitter.
If Cutaia isn't in her office at the Parsons Government Center then you're likely to find her in one of the schools. She said her favorite moments are spent face-to-face with students.
"I make it a priority to be in the classroom," Cutaia said. "So many great things are happening here."
Here are some of her most recent tweets:
Taking lessons on some dolphin moves from Flapjack at East Shore Middle @shannan726 pic.twitter.com/hnF2PBEUQF
— Dr. Cutaia (@MilfordSuper) September 27, 2018
So proud to hear Trevanna Kandrach speak with conviction about her support of United Way as she co-Chairs this year’s campaign. @MrBLionPride pic.twitter.com/a5kzixd4Hi
— Dr. Cutaia (@MilfordSuper) September 27, 2018
AP Economics with Milford Teacher of the Year pic.twitter.com/ayR1Jc28fW
— Dr. Cutaia (@MilfordSuper) September 26, 2018
Pumpkin Delight reviewing book trailers developed by students. For the love of reading pic.twitter.com/uodL194KDs
— Dr. Cutaia (@MilfordSuper) September 25, 2018
Her Biggest Surprise
"I wasn't ready for the number of community based organizations that work so well with the school district," Cutaia said, while quickly adding that it's been such an excellent surprise. She said so many groups want to offer assistance and enhance what the Milford Public Schools already does.
"We have so many committed organizations," she added. "...Milford is an extended family."
Her Resume
Cutaia came to Milford with 27 years of professional educational experience, most recently serving as the
Superintendent of Schools for Regional District 14 for the past four years, encompassing the communities of
Bethlehem and Woodbury. Before leading Regional District 14, she served for six years as the Director of
Elementary Education in the Fairfield Public School district.
Cutaia 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, 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.
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, Cutaia moved to Connecticut and served as principal of Casimir Pulaski Elementary School in Meriden. During her early years in Connecticut, 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.
Photo credit: Kathy Bonetti/Milford Public Schools
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