Deborah Neal Caldwell

WINSLOW – Deborah Neal Caldwell, 76, passed away peacefully on the evening of Dec. 28, 2025, surrounded by loved ones. Debby was born on August 27, 1949, in Boston, Mass.

As the oldest of four daughters born to Max Neal and Jane Neal (Arterburn), Debby grew up in Bedford, Mass., attending local schools and graduating from Bedford High School in 1967. Following high school, Debby graduated from the University of Bridgeport, and later obtained a Masters in Education from the University of Maine at Orono.

Debby began a devoted career in elementary education in 1977 at the Corrina Elementary School as a second grade teacher. Several years later, she took a position at Newport Elementary as a K-4 Special Education Teacher. Through the course of a career spanning over three decades with MSAD 48, Debby built a reputation as a patient, dedicated educator with an ability to tailor an approach to addressing each student’s individual needs. Here, she also built many close friendships that extended far beyond her time in the classroom.

Debby enjoyed a lifelong passion for the outdoors, and could often be found bicycling, hiking and kayaking on East Pond. Summers were spent making frequent trips to Acadia with her kids Matt and Andy, and tending numerous gardens. In the process of working through the loss of her younger son in 2008, Debby developed renewed deep faith in Jesus Christ and took comfort in the hope of everlasting life. She volunteered extensively with women’s ministries and the Celebrate Recovery ministry, both in Hampden and at Faith Evangelical Free Church in Waterville. She was very committed to the Faith Church community, and enjoyed mentoring younger believers.

When Debby moved to the Waterville area, she took on a new role as Grammy, which she eagerly embraced. She was named “Dee Debby” by her oldest granddaughter Elyse, a name that sticks to this day. Two little girls to pour love into really was a dream come true, and she thrived in the role. She will forever be remembered for her creative and elaborate games of make-believe and dress up, and fostering the girl’s love of nature.

A celebration of life will be held at Faith Evangelical Free Church in Waterville on Saturday, Jan. 10, 2026 at 10:30 a.m., with a reception to be held after.

In lieu of flowers, the family asks that donations be directed to Debby’s favorite charities Compassion International, or to

Faith Church Women’s Retreat Scholarship

in Debby’s name