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Gary Maestas

Marion, MA

Education Consultant & School Superintendent

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About Gary

Dr. Maestas embarked on his career in education after graduating from New Mexico Highlands University and teaching in the Longmeadow public school systems. During that time, he also worked as a Program Coordinator at Holyoke Community College. After earning a Master's Degree in Education from Springfield College, Dr. Maestas soon began his administrative career as assistant principal at North Brookfield Junior/Senior High School in North Brookfield, Massachusetts.


Dr. Maestas's tenure in the Plymouth school district began after a three-year stint as principal in the Old Rochester Regional school system. Serving as Plymouth's Coordinator of Media and Technology Services, he worked with all K-12 schools in implementing hardware, software, and technology standards into the District curriculum. During this period, Dr. Maestas served as an adjunct professor at Endicott College in Beverly, Massachusetts, and Framingham State College and as a senior visiting lecturer at Bridgewater State College.

Following a brief tenure as Plymouth South Middle School principal, Dr. Maestas was promoted to Assistant Superintendent in 2003. During that time, he received a Certificate of Advanced Graduate Study from Regent University (he earned his Doctor of Education degree from Regent in 2010). Dr. Maestas succeeded Mr. Barry Haskell as Plymouth Schools Superintendent in 2008.


During his thirteen years at the helm, Dr. Maestas has worked extensively with the school committee and local boards to develop innovative programs to benefit youth. Dr. Maestas has also been a facilitator in constructing a new $84 million Plymouth North High School and a $107 million Plymouth South High School project slated to open in September 2017. 


In 2011 and again in 2016, Dr. Maestas took part in the DreamRide, a fundraising bicycle ride from Washington, DC to Plymouth, MA. Over seven days, Dr. Maestas—accompanied by a team of riders, student videographers, bike technicians, and volunteers-- biked eight hours a day, stopping at local schools to spread their message of education and healthier living. The journey also featured video blogs. Dr. Maestas conversed with students back in Plymouth about the journey and developing healthy life habits and prizes to students, including two bicycles at each stop.


In total, DreamRide and DreamRide2 raised a significant amount of money for the Plymouth Education Foundation, a non-profit organization established to support and enhance the education of the students and citizens of the Town of Plymouth.


Retiring in October 2020, Dr. Maestas started an educational consulting organization working with schools internationally supporting educational leadership. In August 2021, he agreed with the Town of Hingham to become their Interim Superintendent until the end of the 2021/2022 school year.


Married, Dr. Maestas resides in Marion with his wife Ruby, and they have three adult children Martin, Gary, and AJ.

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