Jeremy Light to head Oak Bluffs School

MVRHS assistant principal Jeremy Light, shown here during the high school's 2022 Class Night event, will be Oak Bluffs School's next principal. —Eunki Seonwoo

Jeremy Light has been named new principal of the Oak Bluffs School, to take effect after he completes the school year as assistant principal of the Martha’s Vineyard Regional High School.

Other officials will also step into new leadership roles in what has been a high-turnover year at Vineyard public schools, putting stress on teachers and administrators. 

District Superintendent Richie Smith announced Light’s appointment at Thursday’s all-Island school committee meeting.

“There are some mixed feelings — all celebratory for Jeremy — feeling like he’s deserved this position, but also knowing that’s an important position that we need to fill at the high school,” Smith said.

“I’m really excited,” Light told The Times on Friday, though he said that leaving the high school feels “really bittersweet.”

“I’m ready for a new challenge,” he added.

Light and his family already have strong connections to the Oak Bluffs School. His wife Danielle teaches sixth-grade math there, and his daughter is enrolled there. Light’s son just graduated.

Light said he wants to foster a climate of trust at his new school.

He will take over on July 1 from retiring Principal Megan Farrell, who announced her retirement in April. 

At Edgartown School, John Stevens will serve as interim principal. He currently is assistant superintendent. Debbie Debettencourt will serve under Stevens as assistant principal. 

In April, Principal Shelley Einbinder announced her retirement effective July 1, and Assistant Principal MaryAnn Bartlett resigned effective June 30.

Kate Squire has been named Chilmark School principal. She currently teaches fourth grade at Concord Public Schools. In October, Principal Susan Stevens announced her retirement.

“We’ve had a lot of administrative changes,” Smith said at Thursday’s meeting. “I feel very optimistic about the changes that we have made.”


  1. Congratulations Jeremy.
    Best Wishes on your next adventure in Oak Bluffs.
    “Proud to Be from OB”!!!! I can hear it now.

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