Celebrating the Legacy of Shore’s Former Trustees at the Fall 2025 Winslow Trustee Dinner

Service. Leadership. Dedication. Wisdom. Support. Legacy. These are the words that come to mind when we think of Shore trustees and their impact on our school. Fittingly, one of Shore’s beloved traditions is the annual Winslow Trustee Dinner, a special evening to celebrate and share with Shore’s former trustees, the individuals who helped shape the path of this school over generations. The annual event also provides an important opportunity for former trustees to meet current trustees, hear from school leadership, and enjoy the camaraderie. 

With over sixty in attendance, Board of Trustees President Amanda Jackson spoke about the dynamic initiatives underway through Board committees, and highlighted the energy she felt from the Board’s recent day-long retreat focused on Shore’s next strategic plan. “As we enter into Amber’s second year as Head of School, the Shore community is more energized than ever —  not just in spirit, but in action. In just over one year, Amber has launched new programs that prepare our students to meet a complex, changing world with confidence and curiosity. Whether it’s through off-campus experiences, creative technology integration, or student-led service initiatives, the faculty and staff are not simply teaching — they’re inspiring a lifelong love of learning.”

Jackson applauded “the energy, warmth, and drive that Amber shares with our community each day.” And, with a smile, she added, “This woman is tireless! On top of running the school, Amber has also spent these past few weeks at Shore Safari roasting s’mores, doing morning coverage at our new 7:00 a.m. ‘before-school care’ program, showing up at student bus stops when the timing wasn’t quite right, and greeting families along the JV soccer sidelines. She is the leader that Shore needs and deserves.” 

As Bock took the podium, she shared her sincere appreciation for the warm welcome she received into the Shore community, and thanked the current and former trustees for creating “both the emotional and financial momentum for us to lift Shore to a great year.” Indeed, over $200,000 given by current and former trustees fueled new initiatives for Shore students last year, and more opportunities in service, travel, and learning beyond Shore’s campus continue to grow from that success. 

Each member of Shore’s Administrative Team shared an update, covering finances, enrollment, advancement, marketing, secondary school preparation and placement, student support, and alumni success. Bock noted, “Shore is a community where no accomplishment is achieved alone; rather, accomplishments are achieved through the collective talent and drive of capable people working together.”

Bock acknowledged that “thriving schools are incredibly busy places,” and highlighted new initiatives underway this year, including Shore’s new Podcast, athletic enrichment programming options for Lower School students in golf, lacrosse, and soccer, an Upper School golf team, late day tutorial support for Upper School students, a sixth bus route to Melrose, and robust professional development on literacy and AI to keep Shore on the cutting edge of educational excellence.

Bock also shared a glimpse into plans for Shore’s next three to five years. “There are exciting opportunities ahead in the strategic plan: initiatives focused on academic excellence, of course, but also caring for the gem that is our campus — reimagining and enhancing special places at Shore — and broadening our impact as a vibrant community and an educational hub in the North Shore.” 

Throughout the course of the evening, guests reflected on Shore’s longstanding identity and well-known legacy of excellence, and shared excitement for how this is brought to life daily on campus. The ten alumni in attendance, representing both current and former trustees, showed enthusiasm for Shore’s efforts to reach toward the future while staying grounded in its history and traditions.

The leadership, vision, and sustained commitment to Shore’s mission that former trustees provide to the school leave an enduring legacy. Their influence is woven into the fabric of Shore’s growth and success, and their dedication continues to strengthen the bonds that connect past, present, and future Shore families. And most importantly, Shore students thrive in a dynamic learning community that this legacy and support set in motion.