CAS Announces 2023 Principals of the Year

The Connecticut Association of Schools is pleased to announce the winners of the 2023 Principal of the Year Awards.
Congratulations to these outstanding administrators!

  2023 Elementary School Principal of the Year

  2023 Middle School Principal of the Year

  2023 High School Principal of the Year


Dr. Keshia Smith-Davis, principal of Great Plain Elementary School (GPES), has been named the 2023 Elementary School Principal of the Year. Superintendent of Schools Kevin Walston, who nominated her for the award, praises her as a “warm, engaging, articulate and inclusive school administrator who consistently leads by example.”

“I am grateful and truly honored to have been selected as Connecticut’s Elementary Principal of the Year by the Connecticut Association of Schools,” said Smith-Davis upon learning the news. “This could not have been possible without the support of the Great Plain Elementary School’s hardworking students, staff, parents, district leaders, Superintendent Walston, and most of all, my family. I am truly blessed!”

Now in her nineteenth year as GPES principal, Smith-Davis is a celebrated change agent, school culture influencer, instructional innovator, cultivator of positivity and master of parent-community engagement. Thanks to her dedication and transformational leadership, GPES is a 3-time CT School of Distinction and a 2022 National Blue Ribbon Award winner. Says Dr. Kara Quinn Casimiro, assistant superintendent of teaching and learning, “Dr. Smith-Davis is a highly respected and passionately involved instructional leader who is well known for being both tenacious and innovative in her approach, resulting in a sharp narrowing of the achievement gap and acceleration of all student learning at Great Plain School.”

Since assuming the principalship of GPES in 2004, Smith-Davis has led with passion and love to build a school where kindness, compassion and commitment to excellence are cornerstones. She has focused her energy and attention on making GPES the most positive, welcoming place it can be. She implemented the “Choose Love” and “Start with Hello” programs to foster a safe, inclusive, connected school community; she introduced Friday dances to celebrate school successes; and she organized a weekly t-shirt contest to build school spirit and pride. In 2019, GPES was the first school in the nation to receive the Ben’s Bells “Be Kind” award.

Chief of Schools K-8 Christopher Roche describes the climate at GPES as “replete with mutual trust and respect, where all students and staff are cared for and celebrated.” Adds Phyllis Cohen, grade 4 teacher, “Dr. Smith-Davis’ compassion and empathy have created an environment of warmth and benevolence, one in which we all feel safe and secure, functioning as a family that looks out for one another. Her leadership and positive attitude propel us to meet our goals and reach new heights.”

Recognizing that parent engagement and community relations have a powerful impact on student and school success, Smith-Davis has worked tirelessly to build strong, mutually supportive relationships with families and with the greater Danbury community. She leads Principal Forums to have honest, open dialogues with parents and community members; she collaborates with the PTO to host pep rallies, student assemblies and other schoolwide events that showcase and celebrate her students; she partners with local businesses and agencies to bring professionals into the building to engage with students. Says PTO President Roger Chappuis III, “GPES is a relatively small school in our district; however, our outreach to and engagement in our community are unmatched. Dr. Smith-Davis has always emphasized that the best way to succeed as a school is if our community is fully included.”

Keshia-Smith has applied a no-excuses mindset to building a close-knit learning community where all students are expected to perform at high levels and where all stakeholders have a role to play in making that happen. Says Roche, “GPES has incredibly high expectations for ALL students and staff members while working as a team to increase academic outcomes. At GPES, it is ‘all hands on deck,’ creating the tremendous synergy that makes the school a vibrant learning community for all students.” Observes Chappuis, “When a child is in need, it would not be out of context to see our janitor helping that student with lunch. If a child is feeling insecure about something, the staff rally to surround the student with love and support.”


Rachael Caggiano, principal of Derby Middle School (DMS), has been named the 2023 CAS Middle School Principal of the Year. In an impressive show of support, the entire Grade 8 Team of teachers nominated her for the award. Said one staff member, “Rachael is always “students first,” but she invests as much in us as she does in our students. She cares equally about every member of this school community.”

“I am incredibly honored and humbled to receive this recognition,” said Caggiano when notified of her selection. “I am grateful to work with such a dedicated team of educators who are committed to providing our students with a high-quality education and a positive school experience. This award is a testament to our hard work and the incredible students we have the privilege of serving.”

Caggiano has served the Derby public schools since 2011, applying her skills and expertise wherever they have been most needed. She began as a special education teacher at Derby High School before transitioning to a supervisory role for grades 6-12. In 2015, she was appointed assistant principal and athletic director at the high school; and, in 2018, she was selected by a large committee of teachers, parents, board members and community members to lead DMS as its principal. “Principal Caggiano is an exceptional leader who has made a significant impact on the lives of our students, families, and staff,” says Superintendent of Schools Dr. Matthew Conway, Jr.

Caggiano is a highly visible, hands-on administrator with a ‘whatever it takes to help a student’ attitude. At any given moment of the day – and oftentimes night – she is industriously engaged in efforts to make DMS a better place to work and learn. “Her heart and soul are in this school,” says Dr. Michael Rafferty, the district’s director of teaching and learning. “She sees every day as a new opportunity to bring about higher levels of success for her students and staff.”

All who work with Caggiano agree that the hallmark of her success is her ability to establish authentic personal connections with her students. Through her constant encouragement and casual conversations in the hallways, she conveys her genuine interest and investment in their success. “The kids are #1 first and foremost. We need to know their stories,” says Caggiano.

Caggiano’s office is a converted classroom in a busy hallway where students freely roam in and out all day. “It’s a safe space for students,” says Rafferty. “She is the emotional hub of the school and every day students stop by for affirmations and boosts.” Adds the parent of a DMS 8th grader, “Students gravitate to her. She is a like a second mom. She nourishes kids, especially those who might need an extra push.”

Caggiano leads by example, always exhibiting the characteristics that comprise the school’s motto, Together We RISE – Respectful, Independent, Safe, Empowered. “We tell our students to shoot for the stars and our job is to remove any barriers that might be in their way,” says Caggiano. States art teacher Alicia Lombard, “Rachael expects us to RISE. We believe every student can RISE. And we instill that belief in all of our students.” Remarks the parent of two DMS students, “We have risen under Rachael. Our kids are thriving. The entire school community is thriving.”

Two years ago, Caggiano facilitated an opportunity for ten of her staff members to enroll, along with her and Rafferty, in the Harvard Graduate School of Education’s (HGSE) Instructional Leadership Certificate (ILC) program. The enthusiasm and positive learning outcomes of the first cohort of program participants led to a second, district-wide cohort of forty-two participants representing all district schools and content areas. The ongoing excitement of the ILC participants to continue to improve their professional practice spurred the creation of the Derby Live Learning Lab. The in-school learning lab is a physical space where teachers can share ideas and collaborate on problems of practice. It has been a hub of learning, inquiry and exploration for staff and students alike and was featured in a recent article published by the HGSE, “A New Vision for Teacher Collaboration.”


Kristen St. Germain, principal of Wheeler Middle/High School in North Stonington, has been selected as the 2023 CAS High School Principal of the Year. She was nominated for the award by her superintendent, Troy Hopkins. A self-professed “do-er” with an aversion to being idle, St. Germain is known as a passionate and purposeful leader who is deeply committed to providing a pathway to success for every one of her students.

Reacting to the news of her award, St. Germain stated, “I am so honored to receive this award and I share this recognition with all of my Wheeler families, colleagues and students who certainly make coming to work each and every day a privilege. Through my own experiences as an educator, I truly know the value a community has in shaping future generations, and I have been so blessed to have had the support along my own educational journey from my family and friends, teachers and fellow educators, and for that I am most grateful.”

Ask any member of the Wheeler community about St. Germain and the first word to come to mind is “omnipresent.” It is impossible to step into the school building without bumping into St. Germain. She seems to be everywhere at all times. For St. Germain, however, it’s not just about being physically present; it’s about being engaged, being involved and being connected; it’s about doing everything she can to support her staff, students and community. Assistant Principal Allison Reyes says, “This is not a job for Kristen. She is on 24 hours a day. She is there. She is present. She is at every event, connecting and creating trust. She is in classrooms, hallways, the cafeteria, seeing what is happening, addressing issues and always looking for ways to make Wheeler a better place for students and staff.”

A positive, energizing force for change, St.Germain’s compassion and caring are channeled into a warm, nurturing atmosphere where everyone feels valued and validated. Her leadership has helped to foster a sense of community and belonging among all members of the school community, which has led to improved performance and overall wellbeing. “The level of concern she displays for her students and staff is more than any other administrator I have ever worked with,” says social studies teacher Kim Haggerty. Adds Wheeler parent Lisa Mazzella, “The kindness and acceptance she models infuses and inspires others to become better versions of themselves.”

St. Germain has worked with staff to build a cohesive school community which is responsive to the educational needs of all of its students. “We design programs that fit our kids rather than trying to make our kids fit the mold of the traditional student,” says St. Germain. Brett Mastroianni, a parent and member of the North Stonington Board of Selectmen, praises her ability to develop personalized programs and pathways to help her students flourish. “Kristen takes time to get to know her students’ individual needs, desires and motivators, and then helps put them on a path to succeed,” states Mastroianni. Observes Mazzella, “Kristen is a strong advocate for the success of all students and recognizes that there are many paths to success. She is innovative and forward thinking and seeks out any and all opportunities for her students.”

During her nine years as Wheeler principal, St. Germain has introduced a number of programs designed to promote inclusivity, equity and acceptance. One of her proudest accomplishments is the creation of the Eastern Connecticut Conference (ECC) Diversity Council. The Council consists of members from all of the ECC schools, including student athletes, athletic directors, principals and teachers, who plan activities and initiatives to foster a positive, healthy, inclusive climate at all ECC sports events. The Council affords students the opportunity to expand their experience base and have a positive impact beyond their own campus.

St. Germain will represent Connecticut in the National Principal of the Year Award Program sponsored by the National Association of Secondary School Principals (NASSP). She will compete for the national honor along with principals of the year from each of the other forty-nine states, the District of Columbia, the Department of Defense Education Activity, and the Department of State Office of Overseas Schools.

Caggiano, Smith-Davis and St. Germain will be honored by CAS at the “Celebration of Excellence in Educational Leadership” to be held on October 26, 2023, at Saint Clements Castle in Portland.


Principal of the Year Award Program Background and Procedures
The Principal of the Year Program, sponsored annually by the Connecticut Association of Schools, was established in 1984 to bring recognition to the principalship and to spotlight the important role of the principal in shaping the educational environment and experiences of children. The program recognizes outstanding school principals who have succeeded in providing high quality learning opportunities for students. These administrators have demonstrated excellent leadership, commitment to staff and students, service to their communities, and contributions to the overall profession of educational leadership.

Each year nominations are solicited for an Elementary, Middle, and High School Principal of the Year. Nominees must submit a written application which is evaluated by a selection committee consisting of active and retired principals and assistant principals. Site visits are conducted at the schools of the two highest rated candidates at each level (elementary, middle and high). Winners are then chosen based upon the outcome of the site visit as well as the quality of the written application. The three individuals selected for recognition are honored by CAS at an awards dinner in the fall.