Principal Dingledy finds balance 


Molly Baldino

Mrs. Dingledy talks with English as a Second Language teacher Mr. Foley during passing time in the hallway.

Martha’s Vineyard Regional High School (MVRHS) Principal Sara Dingledy juggles the responsibilities of motherhood with her job charting a vision for the larger school community. Throughout her four years at the helm of the high school, Mrs. Dingledy has developed strong connections with students, faced many day-to-day challenges, and learned to leave time for herself and her family.

Principal Dingledy has had to balance the need to provide administrative stability after years of high turnover with the risk that her policies would be perceived as too strict. According to senior Bella Giordano, a teacher’s assistant in the MVRHS Restorative Justice Office, the students’ perception of Principal Dingledy has become more positive over time. “Her seemingly strict nature caught people off-guard, and led most to assume the worst. However, it is clear that after her work here at the school, perceptions have drastically changed,” she said. 

Mrs. Dingledy likes to schedule her morning so that she has time to circulate through the building and interact with students and faculty. She said, “I like to keep myself free for flex block, because I like to be out there circulating. I try and get into at least two or three classrooms to do visits and give people feedback on what’s going on in classrooms.”

Ms. Dingledy’s duties also extend to welcoming incoming students throughout the year, and she meets with guidance counselors and teachers in order to coordinate this process. “[This semester] we have about six or seven. I think two are arriving from Jamaica, and the rest are arriving from Brazil. We set up empty classes for English as a Second Language teachers to teach at the beginning of the year, because in January, there’s always an influx of kids arriving from Brazil when their school year ends,” said Principal Dingledy. 

An ongoing area of focus for Mrs. Dingledy’s administrative team is identifying at-risk students and intervening early in order to provide support. Dingledy said, “We really review where kids are, each kid. We run data and look at attendance, grade performance, and how they’re doing in terms of tardies, lates, write-ups, that sort of thing. I don’t think people understand that we try and be proactive, to pick things out early. So when things happen, and kids fail, we are genuinely surprised that we haven’t already considered them.”

Vice Principal Jeremy Light thinks that Dingledy has fully grown into her role of being a successful principal. He said, “Mrs. Dingledy greatly exemplifies what it means to give respect when it is earned. The lasting bonds she has created with the students are formed on the mutualistic principles of respect, care, and growth,” he said. “She has brought stability and consistency to the school.” 

After school ends, Principal Dingledy’s day continues. Afternoons may include taking her daughter, Lucy, to horseback riding, cooking dinner for her family, negotiating dinner options with her son Lorenzo, riding her Peloton bike to decompress, and checking email one last time before bed. 

In her role, Mrs. Dingledy values the importance of looking ahead to the future. When asked what her ongoing goals are, Mrs. Dingledy said, “Having a good, positive school culture. [The senior class] are a great group, so it has set a good tone that I hope other classes will follow.”