There was always something about the East Coast that Penelope Haddad, who grew up in California, loved. She was obsessed with the Freedom Trail in Boston, walking it with her dad every time they visited. She did her 5th grade state report on Massachusetts, although she mispronounced Worcester “Worchester,” she admitted. 

“I always felt like I belonged here,” said Ms. Haddad. “I was so grateful that I got the opportunity to actually make my home here.” 

Ms. Haddad moved to the Vineyard the summer before 7th grade. Now, six years later, she also belongs at the top of her class as a co-valedictorian of the 2026 graduating class at the regional high school.

The Vineyard was a fresh start for Ms. Haddad and her family, who had been visiting for many summers. In the years before she moved, California was hit hard by wildfires, which made living during the Covid pandemic very claustrophobic. Ms. Haddad’s mom had also undergone treatment for stage 4 breast cancer in California, surviving a terminal diagnosis to attend her daughter’s many graduations. 

“It was a good thing to...live in a new place, on this Island that represented healing for her,” Ms. Haddad said.

A fresh start meant moving away from her childhood friends, giving up the roots she had built in her early years at school. But she started right back into building new ones while attending the West Tisbury School. 

At the regional high school, Ms. Haddad dove headfirst into extracurriculars: she played soccer for three years and hockey for one (a brand new endeavor, because Californians don’t skate), she wrote for the student newspaper and volunteered with Interact Club for causes across the Island. 

She also mentored kids in Big Brothers Big Sisters, volunteered at Windemere and participated in Generations Club, a new high school club that fosters connections between students and older adults.

Next year she will attend Dartmouth College to study sociology on a pre-med track.

“I like to study people,” she said. “I think [sociology] will really help me with a patient-centered look on care in the future, and also just to understand the patients I’m treating better. I don’t want to be locked in a lab.” 

This year, Ms. Haddad led the school as student body president, running meetings for the class representatives and bringing in elected officials to speak to students about government and leadership. 

Ms. Haddad will spend this summer working at the Fish House, a stark transition from her first summer job at Nell MV, a women’s clothing store in Edgartown. She is casual about that change, even if it comes with tuna blood, a lingering scent of fish on her clothes, and an upcoming mandatory de-facing of blue crabs.

“Gnarly stuff,” she said. “But it’s also been a different look at an industry on-Island that I wasn’t aware of, how it carries our Island. It’s definitely given me an appreciation for where our food comes from.” 

On Sunday, at graduation in her valedictorian speech, she will encourage her classmates to embrace the mixed emotions they will encounter next year, the sadness of endings and the joy of beginnings. Things shouldn’t always be so black and white, said Ms. Haddad. 

“I love working in that gray area now,” she said. “I’ve just really been able to trust myself this year, and I’m feeling really confident going into next year.”