Dr. James Weiss

Dr. James Weiss passed away on August 10, 2025 . He was 78 years old. Born in Meriden, Connecticut on June 21, 1947, he was the son of Dr. Arthur and Gladys Weiss. From an early age, he displayed a passion for education, attending Benjamin Franklin Elementary School and Lincoln Middle School in Meriden. He graduated from Northfield-Mount Hermon School and Colgate University, later earning advanced degrees from the University of Hartford, the University of Connecticut, and the University of Bridgeport.

In 1978, Dr. Weiss returned to his roots as principal of Benjamin Franklin Elementary School, where he served until 1985. His journey in education spanned more than four decades and reflected a lifelong commitment to equity, innovation, and public service.

He began his professional career in 1969 with the National Teacher Corps, teaching in Hattiesburg, Mississippi, and later at the Connecticut Correctional Institution in Cheshire. His path took him through various teaching and administrative roles in Connecticut before assuming leadership positions as superintendent in the Sanborn Regional School District and School Administrative Unit #21 in New Hampshire.

In 2005, Dr. Weiss became Superintendent of Schools for Martha’s Vineyard Public Schools, a role he held with distinction until his retirement in 2015. His tenure was marked by initiatives that enriched the Island’s educational landscape: launching an honors Algebra program at the middle school level, championing STEM programming at the high school, founding the Bridge Program to support students on the autism spectrum, and helping implement a certified nursing assistant track within the high school's Career and Technical Education offerings. Beyond academics, he fostered strong ties with the community as President of the Cape Cod Community College Graduate Board and as an engaged member of the YMCA of Martha’s Vineyard, the Dukes County Health Council, and the Youth Task Force.

His dedication extended beyond the classroom. Dr. Weiss was instrumental in expanding affordable health insurance coverage for public employees in both New Hampshire and Massachusetts. He served as board member and longtime president of the New Hampshire Municipal Health Insurance Trust and later on, the board of the Cape Cod Municipal Health Group. He also contributed to regional philanthropy through his work with the Peter and Elizabeth C. Tower Foundation, the Martha’s Vineyard Community Foundation, and MV Youth.

Dr. Weiss made his home in Oak Bluffs. He was predeceased by his beloved son, Joel. He is survived by his daughter-in-law Nicole of New Hampshire, his sister, Susan Miller of Delray Beach, Florida and his nephew, Alan Miller of Setauket, NY. A member of the Falmouth Jewish Congregation, Dr. Weiss will be remembered for his boundless dedication to education, his thoughtful leadership, and his enduring belief in the power of community.

Services will be held at Chapman Funerals and Cremations located at Edgartown Road in Oak Bluffs on Thursday, August 14 at 2:00pm officiated by Rabbi Zinn.

In his memory, donations may be made to the Martha's Vineyard Community Foundation Scholarship Fund, 4C Cournoyer Rd., Box 243, West Tisbury, MA 02575.