Three Chester staff honored by Mid-Hudson School Study Council

Congratulations to the three outstanding Chester Union Free School District employees who were recognized by the Mid-Hudson School Study Council (MHSSC) for their exceptional contributions to education during its recent Excellence in Education Awards during their October 29 ceremony. This year's recipients are Jennifer Cuomo, Dennis Lepre, and Rachel Loftus. Their dedication, leadership, and unwavering commitment to Chester students and school community are inspiring, and these well-deserved honors reflect the exceptional work they do each and every day in service to everyone who is part of the Chester Union Free School District (CUFSD).

Jennifer Cuomo received the Excellence in Pupil Personnel Award. 

As a middle school Guidance Counselor since 2004, Ms. Cuomo has attended to the academic, social, and emotional needs of Chester students and their families with compassion, professionalism, and skill. Her caring approach creates an environment of trust and open communication, which is evident not only in her interactions with students, but with her colleagues as well. 

Whether working with established Chester Academy students or consulting with rising 5th graders, Ms. Cuomo collaborates closely with teachers and administrators to identify every student’s strengths and their academic needs, and advocates for the supports that suit them best. Her keenness in learning about and addressing every child this way helps foster confidence, excitement, and a sense of belonging.

Ms. Cuomo takes great pride in celebrating student accomplishments, organizing and leading recognition ceremonies such as honor roll acknowledgments, Middle School Awards Night, and 8th Grade Moving Up. She also plays a central role in school-wide assemblies, classroom guidance lessons, Fun Fridays for 6th graders, and countless family engagement activities.

Chester is also proud of Ms. Cuomo for the impact she makes not only within our district but across the county. She serves on the countywide Critical Incident Stress Management Team, a trusted group of professionals who provide support when districts face challenging moments, helping school communities regain a sense of stability. Her leadership extends even further; last year, she planned, coordinated, and oversaw the countywide Red Ribbon Week Kickoff Ceremony hosted at Chester. Her passion, attention to detail, and commitment to student well-being were evident in every aspect of the event.

“The numerous and varied demands on school counselors are significant. They require flexibility, compassion, and the ability to respond to crises, all while maintaining a steady focus on long-term student growth and success,” said Catherine O’Hara, CUFSD Superintendent of Schools. “Jen is the heartbeat of our middle school. Her compassion, advocacy, and commitment ensure every student feels seen, supported, and empowered.  Her leadership, tireless advocacy, and positive influence make her an invaluable member of our school community.” 

Dennis Lepre received the Excellence in Support Services Award. 

Mr. Lepre first joined the Chester school community in 2022 as the district’s Tax Collector. It wasn’t long before he began taking on extended responsibilities in the district’s critical, behind-the-scenes data management. Having since assumed the additional title of Data Clerk, Mr.  Lepre collaborates closely with our Director of Technology & Data Management, and his ongoing efforts have established him as a truly indispensable part of our district’s operations. 

Among Chester’s guiding goals and objectives is a steadfast focus on innovative, data-driven, and career-connected learning. Mr. Lepre provides reports on student performance that directly support that goal, and his capacity to compile complex data and turn it into actionable steps is a significant benefit of our students and our faculty alike. 

Mr. Lepre’s glowing professional reputation in the district is second only to his reputation for being an exceedingly positive force in any situation. Known for his quick wit and good humor, his colleagues know that Mr. Lepre will bring positivity to every setting. He is the kind of co-worker who is always willing to lend a hand to any department in need, or offer solutions to issues outside of what would be considered his official daily responsibilities. Whether crunching numbers to being an enthusiastic guest judge in a culinary class, Mr. Lepre has always brought bottomless energy and a can-do spirit to everything he’s involved with. 

“Dennis exemplifies what it means to serve with a positive mindset, perseverance, and problem-solving skills. His support touches nearly every area of our district, from teachers and administrators to students and families,” said Ms. O’Hara. “People like Dennis remind us that leadership is not always about being in the spotlight, but about lifting others up and strengthening the systems at work behind the scenes.”

Rachel Loftus received the Excellence in Administration Award. 

Ms. Loftus first came to Chester as a Special Education teacher in 2010 and has served the district in various leadership roles since. She currently serves as Assistant Superintendent of Pupil Personnel Services & Human Resources. The role combines two critical areas of responsibility, and she has demonstrated extraordinary leadership in both, overseeing the full scope of special education services for the district, while also providing comprehensive support to teachers and staff. 

Ms. Loftus has fostered a passionate collaborative environment wherein staff enthusiastically step forward to take on new responsibilities, feel encouraged to contribute innovative solutions, and lead initiatives that fall under her direction. 

As a tireless advocate for students with special needs, Ms. Loftus has overseen the development and implementation of IEP and 504 plans for more than 300 students across all grade levels. She has advanced professional development initiatives that promote social-emotional well-being, including PBIS and the Choose Love program at the elementary level. She also spearheaded Chester’s participation in Special Olympics, stepping in as a coach herself, revitalized special education services by expanding the ICT model at the elementary school, and supported the initiation of MTSS districtwide.

Always working hard toward our district goals, Ms. Loftus has developed professional development opportunities for our faculty that promote social-emotional well-being. These include, but are not limited to, the PBIS and the Choose Love program, as well as spearheading Chester’s participation in the Special Olympics. There is a deep respect for Ms. Loftus across the district and greater community, for her guidance, expertise, and student-centered vision.  Most recently, she has been working with the Orange County Department of Health to establish a partnership that will bring on-site services to Chester for students whose needs extend beyond in-house supports. This collaboration aims to ensure equitable access to care and reflects her commitment to removing barriers so that all students can succeed.

“Rachel has been driving positive change for Chester students, their families, and our staff for 15 years. She is held in the highest esteem by our administration, faculty, and staff alike,” said Ms. O’Hara. “She is a leader who champions innovative practices that elevate student learning and strengthen our school community. Her steady leadership and ability to manage the demands of her position with clarity and purpose reflect the depth of her skill and dedication. It is an honor to nominate such exceptional candidates for recognition.”

Congratulations Ms. Cuomo, Mr. Lepre, and Ms. Loftus! And thank you for all you do for Chester students, families, faculty and staff.