Terrence Olivo

Terrence “Terry” Olivo, of Central Valley, NY, passed away peacefully on May 26, 2026, surrounded by the love of his family. He was a devoted husband, father, grandfather, educator, mentor, and friend whose greatest joy in life was the people he loved.

Born in Poughkeepsie, New York, Terry was the only child of Anthony and Roberta Olivo. He carried throughout his life a deep sense of loyalty, responsibility, and devotion to family. Above all else, Terry was a loving husband to Elizabeth Olivo, a proud and devoted father to Erin and Craig Olivo, and a deeply cherished grandfather to Sydney, Ian, and Grady. Family was the center of his life. He gave his love, energy, attention, and unwavering support freely and generously to those he cared about, and his presence made the people around him feel valued, protected, and deeply loved.

Terry dedicated more than four decades of his life to public education and educational leadership. Over a distinguished 47-year career, he served students, teachers, administrators, and communities throughout the Mid-Hudson region with integrity, wisdom, and compassion. He began his career as a history teacher in the Highland Central School District before becoming Assistant Superintendent for Personnel in the Monroe-Woodbury Central School District in 1979. In 1989, he was named Superintendent of Schools for Monroe-Woodbury, a role he held until his retirement in 2004.

Even in retirement, Terry’s commitment to education and public service continued. In 2007, he accepted an invitation to serve Orange-Ulster BOCES as Chief Operating Officer during the agency’s search for a new District Superintendent and remained in that role until 2013. He also served as Director of Research for the Mid-Hudson School Study Council and was a member of the Coordinating Council for the Orange County System of Care.

A graduate of Marist College, Terry earned a Bachelor’s degree in Social Studies Education, followed by a Master’s degree in Educational Administration and a Certificate in Advanced Studies in School District Administration from SUNY New Paltz.

Terry was widely respected for his leadership, vision, and dedication to public education. He was recognized by the Times Herald-Record as one of the Thirty Most Influential People in the Mid-Hudson region in both 2003 and 2004. In 2010, he received the Mid-Hudson School Study Council and SUNY New Paltz Educational Leadership Award in recognition of his outstanding contributions to education. Throughout his career, he was a sought-after speaker and mentor to educators and school leaders across the region.

Yet for all of his accomplishments, Terry will be remembered most for the way he showed up for the people he loved - fully present, deeply caring, endlessly supportive, and devoted beyond measure. His family was his pride and purpose, and the legacy he leaves behind lives not only in the schools and communities he helped shape, but in the countless lives he touched with his kindness, guidance, and love.

He will be deeply missed and forever remembered by his family, friends, colleagues, and all who had the privilege of knowing him.

A wake will be held on Friday, May 29th, from 4-8pm at Flynn Funeral & Cremation Memorial Centers, 139 Stage Road, Monroe, NY 10950.

A Funeral Mass will be held at 10 am on Saturday, May 30th, at St. Patrick's RC Church, 26 Hunter Street, Highland Mills, NY 10930.

Final Funeral Arrangements have been entrusted to Brendan T. Flynn, Thomas F. Flynn, and Megan Morales, Directors and Certified Cremation Specialists of Flynn Funeral & Cremation Memorial Centers, Inc.