Positive feedback for new MVRHS principal Sara Dingledy

New MVRHS principal said she won’t make major changes as she adjusts in her first year at the Island’s high school.

MVRHS Principal Sara Dingledy and other school leaders have been working on ways to continue educating students while school buildings are closed. - MVT file photo

New Martha’s Vineyard Regional High School (MVRHS) Principal Sara Dingledy is off to a great start. Martha’s Vineyard Superintendent of Schools Matt D’Andrea said Ms. Dingledy has received a tremendous amount of positive feedback from school staff, parents, and members of the school committee. Mr. D’Andrea said he is both excited and happy to have Ms. Dingledy as principal, and that he was looking forward to the future.

“She’s someone who has great experience. She’s smart. She’s a visionary leader,” Mr. D’Andrea told The Times. “We have a great staff there, but what’s been lacking is a consistent vision, and she’s going to bring that there and bring the instructional leadership that we need.”

Ms. Dingledy, originally from Connecticut, worked for 17 years in the New York school system. She founded the Westchester Square Academy in 2012 as a part of a New York–based program, New Leaders for New Schools, an initiative for educators to start their own New York City high schools. Previously, Ms. Dingledy was assistant headmaster of the Brooklyn Latin School, a social studies teacher, and one of three founding teachers of the Martin Luther King Jr. High School of Art and Technology.

In an interview with The Times, when asked about the differences between New York and Martha’s Vineyard, Ms. Dingledy said that each culture and community has unique qualities, but a major difference was the “overlap” that is created when the majority of people who work on-Island also live on-Island.

“It’s a community where there’s lots of overlap between parents and employees and board members and support members,” Ms. Dingledy said. “And that’s probably just a function of being on an Island.”


Still early in the school year, Ms. Dingledy said anticipating where to make changes would take time, and that it was a matter of familiarizing herself with the people, systems, and traditions of the high school and Island community. In the future, Ms. Dingledy said, she may look into, revisit, or change certain practices, but at the moment, she’s not planning on making any changes.

“I think that will be driven by the culture and climate here, where there’s already momentum to reexamine certain things that we do,” Ms. Dingledy said. “I’ll certainly empower folks to do that, but I wouldn’t say that there’s something I’m going to take a stand on and change.”

Ms. Dingledy’s policy on cell phones underscores that statement. She does not believe cell phones belong in the classroom setting, and prohibited Westchester Square Academy students from bringing phones to class. For the time being, she has decided to uphold, and to the dismay of some students, enforce an existing rule which states in the student handbook that students can use their cell phones only between classes and during lunch. Cell phones cannot be used during class, in the library, or outside the classroom when classes are in session. Teachers and staff can use their discretion to allow students to use phones for “legitimate purposes” during class time and in the library.

“I don’t think that cell phones belong in schools, or in places where the value is on focus, developing social skills, developing academic skills, and developing impulse-management skills,” Ms. Dingledy said.

What she described as a “longstanding rule” at MVRHS states that students can’t have cell phones during the instructional blocks.

“For instruction, for focus, for plugging into each other, kids can’t have their phones out, and they should not be leaving the room with their phones to walk around the hallways with their earphones,” she said.

The prohibition extends to the use of personal laptops. Ms. Dingledy said the school prefers that students use school-issued laptops because they are properly configured to the high school’s wireless connection. For the nearly 680 students at MVRHS, there are 250 desktop computers in the school, and 300 laptops.

She said MVRHS has limited broadband, and so classroom Internet connections can get disrupted with lots of devices streaming data, especially when the devices are not being used for educational purposes. Ms. Dingledy said that students who have individualized education plans with assistive technology are allowed to use their assigned device, and if a student wishes to bring a personal laptop to school, he or she has to have it configured by the MVRHS technology director.

Community values

One challenge MVRHS students face, Ms. Dingledy said, is that unlike students on the mainland who are able to live at home while attending college, students must leave the Island if they chose to pursue a college education. If students decide to stay on-Island, she said, they’re often choosing to work.

“That, I think, is an enigma,” Ms. Dingledy said. “You have to figure out what path you are steering kids on, how early you start to steer them on that path, and how you make kids who decide that they don’t want to go off-Island still feel successful — like they had a very successful completion of high school — even if they’re forgoing college.”

For adults, Ms. Dingledy said that the importance is instilling in children “values, resilience of character, paths to happiness, sharing gratitude, and learning how to live with each other.” Ultimately, however, it’s up to the child, she said.

“We’re not just teaching kids how to be academic people, we’re teaching kids how to be our neighbors,” Ms. Dingledy said. “They’re going to be your neighbors. They’re either going to work with you or go to college and come back and be your neighbors. I think working to create, own, and perpetuate the values of this community is what a school is responsible for doing.”

Island life

So far, Ms. Dingledy said, the school year was going well and she and her family were settling into the Vineyard. She and her husband, Dan Doyle, have two children — Lucy, 5, and Lorenzo, 3. Her daughter attends the Chilmark School, and her son is in the daycare at Martha’s Vineyard Community Services (MVCS). Mr. Doyle is a geospatial analyst with New York City’s Build It Back Program, a Hurricane Sandy recovery program. He also works part-time for the Martha’s Vineyard Commission (MVC) in their transportation planning department.

Ms. Dingledy is no stranger to Island life. She attended Union College in Schenectady, N.Y., and spent summers on the Vineyard. She lived on the Island for a year in 1994 after she graduated, where she worked as “a not-so-good waitress” at Sandcastles and at Giordano’s.

She said for the past 15 years, she and Mr. Doyle have come to the Island for two weeks in August, and that she and her family had come to visit her uncle, Chuck Wendel of Edgartown, usually once or twice a year.

Ms. Dingledy said the draw to the Island was motivated mostly by family. Although she wasn’t looking for a professional move, Ms. Dingledy and her family were looking for both a place and a community in which they wanted to live and be a part of.

“I think it was a very personal move,” Ms. Dingledy said.

The prospect of living on Martha’s Vineyard became a reality when her uncle read there was an opening for the MVRHS principal job. Ms. Dingledy said there was only one job opportunity for her on the Island, and that was the one.

“So, I think when that came up, it was an enticing idea,” she said.

The opening came after the unexpected departure last August of Gil Traverso, who resigned to take a job in the New Haven, Conn., school district one year into a three-year contract. Former MVRHS Principal Margaret “Peg” Regan, who retired in 2008, filled in for the year.

The school committee reviewed 20 applicants over the course of several months, and Ms. Dingledy was one of three finalists. She was selected as MVRHS principal in January and moved to the Island in July.