Teacher of the Year
Teacher of the Year 2025
Jennifer Cirino
The Westport Public Schools proudly announces the naming of Westport’s 2025 Teacher of the Year - Jennifer Cirino. Jenn is currently a library media specialist at Staples High School (SHS), and was unanimously chosen for this honor by a selection committee made up of her peers from across the district.
Jenn has successfully served as a library media specialist at SHS since August 2019. Prior to her current role she served as the district’s information technology literacy coordinator for nine years. Throughout her tenure as a Westport teacher, Jenn has worked tirelessly with her colleagues finding unique and innovative ways to provide the best instruction for students.
Nominations for Westport’s Teacher of the Year share inspiring words about the nominees. The names of those making nominations are kept anonymous to allow for objective decisions in the selection process, but this direct quote from Jenn’s nomination captures the essence of why she is the perfect choice for the 2025 Westport Teacher of the Year.
“There are those few people in your life who actually inspire you to be your better self. Jenn does that for me. When she speaks with a student, she is genuinely interested in what they have to say and is so excited to hear their ideas and move them forward. Whether it's technology or getting ideas for a project, Jenn makes these students feel special. She has created a community that thrives within the library. Students who might not ordinarily have found their place yet at Staples, find it there. Students who need a faster horse, find it there.”
What makes Jenn’s selection as Westport’s 2025 Teacher of the Year extra special is that she is a fifth generation Westporter. Her deep connections to the community further enrich what she brings as a teacher to the countless students and staff coming through the Staples High School library.
This year marks the 30th anniversary of the Staples High School state championship in women’s basketball. Jenn was a member of that amazing team. Little did she know then that she would carry forward the skills and experiences as a teammate on the court to her career as a teacher in her hometown.
In Jenn’s reflection on being honored as Westport’s 2025 Teacher of the Year, she wrote, “You don't always notice in the moment, what a profound impact you have on your students. Education changes, but at the end of the day you are the single most important factor to these kids and YOU ARE making a difference, one small step at a time: even with the challenges that come up during the year.” There is no doubt Jenn has carried forward the positive impact so many coaches and teachers made in her life to her role as a teacher today. As such, she is the perfect educator to serve as Westport’s 2025 Teacher of the Year!
For more information on the Connecticut Teacher of the Year Program, please visit The CT Department of Education.