A Full-Circle Moment for Oakwood Alumni

Full-circle moments are precious, and when they involve Oakwood alumni, they reflect the enduring connections that define the Oakwood community. One such moment recently brought together alumni whose paths were shaped by shared experiences and a lasting commitment to service.

Alia Insignares, Class of 2017, was a sophomore when she was inspired to create a Service Learning trip for the high school. Providing students with the opportunity to envision and implement their own ideas is a hallmark of Oakwood’s educational ethos, and Alia exemplifies this spirit. She designed Oakwood’s first service-focused trip to Costa Rica in 2016—an experience that has since become legendary for its popularity and enduring tradition.

Creating a legacy at the age of 16 is remarkable. Even more impressive is the impact that legacy continues to have nearly a decade later, particularly for Arianna Vasquez, Class of 2012, who will be a beneficiary of Alia’s founding work during the upcoming Service Learning trip to Peru. Along with her partner, Oakwood Math teacher Chris Hashem, Arianna will serve as a chaperone for the 2026 international trip.

Serendipity played a role in bringing this story full circle, and the opportunity to celebrate it was not missed. A New Year’s dinner brought these alumni together for the first time. Also in attendance was Alia’s partner, Liam Hamilton, who—like Chris—hails from New England, creating an easy connection and shared ties to Oakwood. Chris teaches AP Calculus, AP Statistics, Honors Algebra II, and an Engineering elective, and also coaches Varsity Boys and Girls Soccer. Liam, an entrepreneur and language app developer, has contributed to Oakwood’s French program, where Level III students piloted his learning tool and provided thoughtful feedback. Students appreciated having their voices heard, and Liam valued their insights.

While it is difficult to quantify the joy these moments bring, Oakwood School is deeply grateful for the lasting relationships formed within its community. These full-circle connections are a powerful reminder of the impact of an Oakwood education and the bonds that continue to grow long after graduation.