School superintendent announces retirement

Updated October 1st.

In the midst of a regular meeting last Thursday evening, Superintendent of Schools Richie Smith announced his plans to retire at the end of this school year, a move that came as a surprise to some members of the committee.

The All-Island School Committee assembly started as any other, with a slideshow and update, but energy peaked when Smith discussed his next steps. He read from a retirement letter where he thanked committee members and expressed his hope for their forward movement. 

“As some of you may know … my intention is to retire at the end of this school year,” Smith said to a dozen members before him. “I’ve had the honor of working with the most talented and caring school staff, school committee members, and community members that I’ve ever known. I’ve been blessed to create lasting relationships with our dedicated students and their families, who have provided me with the inspiration for my daily work.”

Smith said he and his wife, Melissa, will be moving to Southwest Virginia to support her parents and provide help through some health challenges they’re facing. “The personal side of things is really outweighing the ability for us to stay,” he said. 

School committee members reached by The Times expressed gratitude for Smith’s long tenure in education on the Island. “Thank you for all that you’ve done,” committee chair Amy Houghton said at Thursday’s meeting. “For the students and the staff, and everyone else.”

Smith’s retirement will be effective June 30, 2026, which happens to be the 25-year mark for him as an educator on the Island. He started as a counselor at the Tisbury School and moved up the ranks over the decades, culminating in the superintendency appointment in 2022. 

The year he was assigned to the position, high school officials were dealing with legal tensions due to contentious disagreement over sports turf material, and teachers were actively protesting their contracts, arguing for higher wages that matched the cost of living. Smith navigated those tides with other administrators and the backing of the school committee. Eventually, the turf issue was mostly resolved, and one item of discourse came full circle just this year: Teachers were afforded cost-of-living salary increases in their most recent contracts. 

Smith cited a deep love for the Island and the community here. He and his wife raised two sons in Oak Bluffs, where he was previously the principal of the public school and Melissa was, and still is, an English Language Arts teacher. He remembered cherished mornings when the family would all drive to the school together — the parents to work, and their sons to their classes. “This has become our home,” Smith added. 

Some issues Smith tackled during his three-year tenure as superintendent of all Martha’s Vineyard public schools were rising socioeconomic challenges, housing insecurity, and wealth inequality for students and their families. He pushed for regionalization efforts and for more resources for an increasingly culturally and ethnically diverse student body. 

“We have faced many challenges, and celebrated our students’ growth and achievement as we continue to build a school system that prioritizes care over students through equity and opportunity,” Smith said. 

This year, Smith appointed a new high school principal, Sean Mulvey (who just started a one-year term), after former principal Sara Dingledy announced her plan to resign and take up an administrative position in the central school district office this past May. The Chilmark school, Edgartown school, and Oak Bluffs school have also seen new principals in the last two years.

Smith was one of the school officials who dealt with the Tisbury school building project, and has been helping to lead the charge on the upcoming — and highly anticipated — high school building project.

According to the committee, the high school building project will be unaffected by Smith’s plans to retire, and it will move forward despite the change. Smith said he and his wife are planning to return to the Island, and said he could see himself continuing to support the project, even just as a public member of the community. He added that the renovation is an extremely important one for the health and well-being of the staff and students at the high school. 

“This building is needed. I’ll carry that when I’m no longer in the school system,” Smith said. “There’s never a good time to leave … But I come back to the feeling that this is the right decision.”

Some school committee members cited appreciation for the timing of Smith’s retirement — they have a year to search for a replacement, and were given ample opportunity to prepare. “I believe he’s put the district in a very good position,” school committee member Robert Lionette said in an interview. 

After his announcement at the meeting, committee members spoke out about Smith’s accomplishments and how grateful they’ve been for his efforts over the years for the public school system on the Vineyard.