06/03/2026
After more than 20 years with Winthrop Public Schools, we celebrate another incredible educator who will be retiring at the end of this school year, Cheryl Paolini. Her journey proves that dreams are worth pursuing no matter how long the path may take.
Ever since she was an elementary school student herself, Cheryl dreamed of becoming a teacher. While the road to the classroom wasn't a direct one, it was filled with purpose, determination, and heart. Cheryl spent 17 years working at Children's Hospital before returning to school to complete her bachelor's degree in Elementary Education and pursue the career she had always envisioned for herself.
When her own children reached school age, Cheryl joined Winthrop Public Schools as an ESP at Fort Banks. She later moved to the ATC when her 1:1 student transitioned to third grade, and the ATC quickly became her second home.
In 2020, during one of the most challenging periods in education, Cheryl stepped into a 4th-grade classroom as a teacher when an unexpected opportunity arose. While many were navigating the uncertainty of the pandemic, Cheryl embraced the challenge with courage and determination, learning Zoom on the fly, adapting lessons for remote learners, and creating a classroom community during a time when connection was needed most.
Two years later, she transitioned into the role of 4th-grade inclusion teacher, where she spent the next four years co-teaching alongside multiple special education teachers and supporting students with compassion, patience, and skill. Cheryl's classroom was always a place where students felt safe, valued, and encouraged to be themselves. Her warmth, sense of humor, and genuine care helped create a learning environment where children could thrive academically and emotionally.
Beyond the classroom, Cheryl has been a wonderful, selfless, caring, and supportive teammate since the moment she walked through the doors at the ATC. She is an incredible colleague, an even better friend, and an even better person. Whether offering a listening ear, lending a helping hand, sharing a laugh, or supporting a colleague through a difficult day, Cheryl has consistently made those around her feel seen, valued, and appreciated. The relationships she has built with staff over the years are a testament to the kind of person she is.
Her impact extends far beyond the walls of the ATC. She has supported generations of students as they grew into successful young adults and had the unique privilege of later seeing many of them walk across the stage as graduates of WHS. One of the most special moments of her career was having the honor of handing diplomas to both of her own children at graduation, a full-circle moment few educators ever experience.
One of the many things that makes Cheryl's story so inspiring is her commitment to lifelong learning. At age 60, she earned her Master's Degree in Elementary Education, proving that growth, perseverance, and personal achievement have no age limit. Her journey serves as a reminder that it's never too late to pursue your passions and make a difference.
As she begins this next chapter, Cheryl is looking forward to spending more time with her growing family, including welcoming grandson #2 this summer. She will be focusing on health and wellness, traveling, and enjoying the freedom that retirement brings.
Cheryl, thank you for your compassion, dedication, resilience, friendship, and the love you poured into the ATC community every single day. Your retirement is truly a huge loss for our school, but your influence, kindness, and legacy will continue to be felt for years to come.
Congratulations on a well-deserved retirement. We wish you endless happiness, good health, and all the adventures this next chapter has in store. You will be deeply missed, but never forgotten ❤️
