High school to look for new principal 

Sara Dingledy, Martha’s Vineyard Vineyard Regional High School (MVRHS) principal for the past nine years, will be stepping down for a role in the district’s front office.

Dingledy hasn’t told The Times the specific reasons she is leaving this post for a new one, but district administrators and school committee members said that she applied for a position that was recently created, and that she is a good fit for the role.

With news of her departure from the high school, officials praised Dingledy as a stabilizing presence for the high school throughout her tenure. She came onboard after a tumultuous time — some six principals had served, with a few in interim positions, over a five-year period, according to Superintendent of Schools Richie Smith. 

Smith said that she led the high school through that period, and described the MVRHS principal position as the hardest job in the district during a public meeting last week.

“She really stabilized things,” Smith said. “Sara has been in the most challenging job,” he added, noting that her front-facing position came with a lot of difficulty. Smith’s job as superintendent is tough, he told school committee members, but hers may be the toughest.

Dingledy’s new role, the first of its kind in the district — curriculum, instruction, and operations coordinator — was created by the All-Island School Committee recently as a way to improve management across the local public schools. 

The new job was posted online on May 5, and seven prospective individuals applied, all off-Island aside from Dingledy. After Dingledy was interviewed by Smith, he appointed her and started preparing for the transition. 

The focus for the new position, according to Smith, is to help students who are moving from grade to grade, specifically jumping between elementary to middle school and middle to high school. For some school committee members, the issue has been a hurdle for the district, with elementary schools with different standards and diverse student bodies merging into the high school. 

Amy Houghton, chair of the All-Island School Committee, said she believes the new role speaks to Dingledy’s strengths. Her power as an educator, Houghton said, is in her ability to move forward with potentially positive initiatives no matter the popularity. 

Houghton cited Dingledy’s handling of remote learning during the COVID pandemic, her “Phones Away” program — where students must put their phone into a locked case during school hours — and her standardized assessments of teachers. 

“While [these initiatives] might not have been popular when they were put in place, she stuck with it, and I think that is her strength,” Houghton said. “She’s really strong on standards. She’s very strong on making sure that people are meeting the mark, and making sure they get the support they need when they’re not.”

Michael Watts, a former school committee member from Tisbury, also said that the new role is a good match for Dingledy. “Her analytical skills in that space are really powerful, and I think she will serve the district really, really well in that role,” he said. 

Smith echoed the school committee members’ points. “I believe Sara will bring a keen understanding of curriculum, instruction, and assessment, and data-focused analytical skills,” the superintendent said at the school committee meeting, “and [will] also be a support to Martha’s Vineyard Public Schools Assistant Superintendent Megan Farrell in identifying operational efficiencies and improvements that are key for, I believe, our instructional success moving forward.” 

High school performance reviews from the state have had at least one rough spot over the past few years under Dingledy’s leadership. In 2023, the state Department of Education listed MVRHS as in need of intervention. In Massachusetts, if a school doesn’t meet 95 percent attendance in any one category or subcategory, the state flags the school as being a school in need of intervention. At the time, Dingledy said that there were eight students who did not attend the MCAS test in 10th grade, and that’s why the school was labeled with that designation.

The high school, in the most recent results that came out last September, has been recognized as having made “moderate progress toward targets,” and is no longer in need of state assistance. 

The search for a new principal is expected to start right away, with the school committee and Smith conducting interviews with prospective applicants shortly. Smith said they’ll first look to current administrators in order to find the best suited to fill the role.

“We won’t make the move unless we find somebody who will really support the school well,” Smith said. “Sara won’t leave until we find a more than adequate … person to take on the leadership role there.”

Asked if the timing was poor with the high school undergoing a major project to build a new school building or make significant renovations, Smith said that Dingledy will still be within the district, and will help in the process. Had she been leaving the district, he might have been more worried.

“She’s still around, and I intend to have her as a resource for the project and supporting the new principal,” the superintendent said. “I don’t think it will detract from her ability to be there for the project.

“I’m super-happy with the leadership in our schools,” Smith told the school committee last week. “So I’m not going to settle on somebody in this high school position, I assure you.”

Dingledy chose not to comment for this story.